NP-MRD: Showing NP-Card for Macrolactin A (NP0025556)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2021-06-19 17:38:56 UTC

Updated at

2021-06-29 23:50:35 UTC

NP-MRD ID

NP0025556

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Macrolactin A

Provided By

JEOL Database JEOL Logo

Description

Macrolactin A is found in Bacillus sp. PP19-H3. It was first documented in 2015 (PMID: 26544726). Based on a literature review very few articles have been published on (3Z,5Z,8S,9Z,11Z,14S,16R,17Z,19Z,24R)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one (PMID: 27071303) (PMID: 27792158) (PMID: 33808737) (PMID: 33184304) (PMID: 32944805) (PMID: 32673673).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119393D          

 63 63  0  0  0  0            999 V2000
    1.8073    5.0934   -2.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7079    3.5793   -2.7373 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2505    3.0935   -2.8455 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6072    3.4071   -1.6068 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5198    2.2507   -1.1811 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7414    1.1165   -0.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5125    0.9124    0.7407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0090    1.7433    1.8080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2067    1.6037    2.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2206    0.5309    2.1197 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3808    1.1555    1.5720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6109   -0.2028    3.4095 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6607   -1.3113    3.2138 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8910   -0.7650    2.7313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2262   -2.4590    2.2850 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0293   -3.2122    2.8033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8314   -3.4056    2.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4137   -2.9240    0.9328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2150   -3.1135    0.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9903   -3.8414    0.8867 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1667   -5.0199    0.1003 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2935   -3.0075    0.8645 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6861   -2.5163   -0.5091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0032   -1.2705   -0.8949 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1388   -0.1190   -0.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0687    1.1736   -0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7325    1.6916   -1.7363 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7470    1.0621   -2.7791 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3334    2.9819   -1.5839 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8591    5.3991   -2.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3185    5.6092   -3.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3633    5.4375   -1.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2560    3.2997   -3.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2567    2.0137   -3.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2182    3.5477   -3.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0144    3.6987   -0.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2337    4.2780   -1.8373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2634    2.6340   -0.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0871    1.8736   -2.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2916    0.4168   -1.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1181    0.0787    1.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3392    2.5346    2.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4739    2.3132    3.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8539   -0.1823    1.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0646    1.7060    0.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0427    0.5288    4.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7167   -0.6182    3.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8887   -1.7330    4.2006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6645    0.0060    2.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0592   -3.1701    2.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0871   -2.0859    1.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1819   -3.6682    3.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1136   -3.9957    2.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1469   -2.3668    0.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0867   -2.6983   -0.6440 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8375   -4.1762    1.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2990   -5.4581    0.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1150   -3.6395    1.2246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1870   -2.1766    1.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6724   -3.2868   -1.2819 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2054   -1.1202   -1.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3302   -0.3287    1.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1903    1.9352    0.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0  0  0  0
 24 25  1  0  0  0  0
 12 10  1  0  0  0  0
 10  9  1  0  0  0  0
 25 26  2  0  0  0  0
  9  8  2  0  0  0  0
 20 22  1  0  0  0  0
  8  7  1  0  0  0  0
 26 27  1  0  0  0  0
  7  6  2  0  0  0  0
 18 19  2  0  0  0  0
 13 14  1  0  0  0  0
 27 29  1  0  0  0  0
 10 11  1  0  0  0  0
 22 23  1  0  0  0  0
  6  5  1  0  0  0  0
 17 16  2  0  0  0  0
 20 21  1  0  0  0  0
 17 18  1  0  0  0  0
  5  4  1  0  0  0  0
 16 15  1  0  0  0  0
  4  3  1  0  0  0  0
 23 24  2  0  0  0  0
 27 28  2  0  0  0  0
 15 13  1  0  0  0  0
 29  2  1  0  0  0  0
  3  2  1  0  0  0  0
 19 20  1  0  0  0  0
  2  1  1  0  0  0  0
 17 53  1  0  0  0  0
 18 54  1  0  0  0  0
 19 55  1  0  0  0  0
 20 56  1  1  0  0  0
 22 58  1  0  0  0  0
 22 59  1  0  0  0  0
 23 60  1  0  0  0  0
 24 61  1  0  0  0  0
 25 62  1  0  0  0  0
 26 63  1  0  0  0  0
 16 52  1  0  0  0  0
 15 50  1  0  0  0  0
 15 51  1  0  0  0  0
 13 48  1  1  0  0  0
 12 46  1  0  0  0  0
 12 47  1  0  0  0  0
 10 44  1  6  0  0  0
  9 43  1  0  0  0  0
  8 42  1  0  0  0  0
  7 41  1  0  0  0  0
  6 40  1  0  0  0  0
 14 49  1  0  0  0  0
 11 45  1  0  0  0  0
  5 38  1  0  0  0  0
  5 39  1  0  0  0  0
 21 57  1  0  0  0  0
  4 36  1  0  0  0  0
  4 37  1  0  0  0  0
  3 34  1  0  0  0  0
  3 35  1  0  0  0  0
  2 33  1  6  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
M  END

     RDKit          3D

 63 63  0  0  0  0  0  0  0  0999 V2000
    1.8073    5.0934   -2.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7079    3.5793   -2.7373 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2505    3.0935   -2.8455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6072    3.4071   -1.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5198    2.2507   -1.1811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7414    1.1165   -0.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5125    0.9124    0.7407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0090    1.7433    1.8080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2067    1.6037    2.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2206    0.5309    2.1197 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3808    1.1555    1.5720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6109   -0.2028    3.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6607   -1.3113    3.2138 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8910   -0.7650    2.7313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2262   -2.4590    2.2850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0293   -3.2122    2.8033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8314   -3.4056    2.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4137   -2.9240    0.9328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2150   -3.1135    0.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9903   -3.8414    0.8867 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1667   -5.0199    0.1003 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2935   -3.0075    0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6861   -2.5163   -0.5091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0032   -1.2705   -0.8949 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1388   -0.1190   -0.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0687    1.1736   -0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7325    1.6916   -1.7363 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7470    1.0621   -2.7791 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3334    2.9819   -1.5839 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8591    5.3991   -2.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3185    5.6092   -3.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3633    5.4375   -1.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2560    3.2997   -3.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2567    2.0137   -3.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2182    3.5477   -3.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0144    3.6987   -0.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2337    4.2780   -1.8373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2634    2.6340   -0.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0871    1.8736   -2.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2916    0.4168   -1.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1181    0.0787    1.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3392    2.5346    2.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4739    2.3132    3.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8539   -0.1823    1.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0646    1.7060    0.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0427    0.5288    4.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7167   -0.6182    3.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8887   -1.7330    4.2006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6645    0.0060    2.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0592   -3.1701    2.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0871   -2.0859    1.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1819   -3.6682    3.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1136   -3.9957    2.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1469   -2.3668    0.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0867   -2.6983   -0.6440 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8375   -4.1762    1.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2990   -5.4581    0.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1150   -3.6395    1.2246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1870   -2.1766    1.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6724   -3.2868   -1.2819 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2054   -1.1202   -1.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3302   -0.3287    1.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1903    1.9352    0.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 24 25  1  0
 12 10  1  0
 10  9  1  0
 25 26  2  0
  9  8  2  0
 20 22  1  0
  8  7  1  0
 26 27  1  0
  7  6  2  0
 18 19  2  0
 13 14  1  0
 27 29  1  0
 10 11  1  0
 22 23  1  0
  6  5  1  0
 17 16  2  0
 20 21  1  0
 17 18  1  0
  5  4  1  0
 16 15  1  0
  4  3  1  0
 23 24  2  0
 27 28  2  0
 15 13  1  0
 29  2  1  0
  3  2  1  0
 19 20  1  0
  2  1  1  0
 17 53  1  0
 18 54  1  0
 19 55  1  0
 20 56  1  1
 22 58  1  0
 22 59  1  0
 23 60  1  0
 24 61  1  0
 25 62  1  0
 26 63  1  0
 16 52  1  0
 15 50  1  0
 15 51  1  0
 13 48  1  1
 12 46  1  0
 12 47  1  0
 10 44  1  6
  9 43  1  0
  8 42  1  0
  7 41  1  0
  6 40  1  0
 14 49  1  0
 11 45  1  0
  5 38  1  0
  5 39  1  0
 21 57  1  0
  4 36  1  0
  4 37  1  0
  3 34  1  0
  3 35  1  0
  2 33  1  6
  1 30  1  0
  1 31  1  0
  1 32  1  0
M  END


  Mrv1652306192119393D          

 63 63  0  0  0  0            999 V2000
    1.8073    5.0934   -2.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7079    3.5793   -2.7373 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2505    3.0935   -2.8455 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6072    3.4071   -1.6068 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5198    2.2507   -1.1811 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7414    1.1165   -0.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5125    0.9124    0.7407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0090    1.7433    1.8080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2067    1.6037    2.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2206    0.5309    2.1197 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3808    1.1555    1.5720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6109   -0.2028    3.4095 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6607   -1.3113    3.2138 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8910   -0.7650    2.7313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2262   -2.4590    2.2850 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0293   -3.2122    2.8033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8314   -3.4056    2.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4137   -2.9240    0.9328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2150   -3.1135    0.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9903   -3.8414    0.8867 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1667   -5.0199    0.1003 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2935   -3.0075    0.8645 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6861   -2.5163   -0.5091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0032   -1.2705   -0.8949 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1388   -0.1190   -0.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0687    1.1736   -0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7325    1.6916   -1.7363 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7470    1.0621   -2.7791 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3334    2.9819   -1.5839 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8591    5.3991   -2.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3185    5.6092   -3.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3633    5.4375   -1.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2560    3.2997   -3.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2567    2.0137   -3.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2182    3.5477   -3.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0144    3.6987   -0.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2337    4.2780   -1.8373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2634    2.6340   -0.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0871    1.8736   -2.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2916    0.4168   -1.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1181    0.0787    1.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3392    2.5346    2.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4739    2.3132    3.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8539   -0.1823    1.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0646    1.7060    0.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0427    0.5288    4.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7167   -0.6182    3.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8887   -1.7330    4.2006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6645    0.0060    2.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0592   -3.1701    2.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0871   -2.0859    1.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1819   -3.6682    3.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1136   -3.9957    2.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1469   -2.3668    0.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0867   -2.6983   -0.6440 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8375   -4.1762    1.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2990   -5.4581    0.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1150   -3.6395    1.2246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1870   -2.1766    1.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6724   -3.2868   -1.2819 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2054   -1.1202   -1.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3302   -0.3287    1.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1903    1.9352    0.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0  0  0  0
 24 25  1  0  0  0  0
 12 10  1  0  0  0  0
 10  9  1  0  0  0  0
 25 26  2  0  0  0  0
  9  8  2  0  0  0  0
 20 22  1  0  0  0  0
  8  7  1  0  0  0  0
 26 27  1  0  0  0  0
  7  6  2  0  0  0  0
 18 19  2  0  0  0  0
 13 14  1  0  0  0  0
 27 29  1  0  0  0  0
 10 11  1  0  0  0  0
 22 23  1  0  0  0  0
  6  5  1  0  0  0  0
 17 16  2  0  0  0  0
 20 21  1  0  0  0  0
 17 18  1  0  0  0  0
  5  4  1  0  0  0  0
 16 15  1  0  0  0  0
  4  3  1  0  0  0  0
 23 24  2  0  0  0  0
 27 28  2  0  0  0  0
 15 13  1  0  0  0  0
 29  2  1  0  0  0  0
  3  2  1  0  0  0  0
 19 20  1  0  0  0  0
  2  1  1  0  0  0  0
 17 53  1  0  0  0  0
 18 54  1  0  0  0  0
 19 55  1  0  0  0  0
 20 56  1  1  0  0  0
 22 58  1  0  0  0  0
 22 59  1  0  0  0  0
 23 60  1  0  0  0  0
 24 61  1  0  0  0  0
 25 62  1  0  0  0  0
 26 63  1  0  0  0  0
 16 52  1  0  0  0  0
 15 50  1  0  0  0  0
 15 51  1  0  0  0  0
 13 48  1  1  0  0  0
 12 46  1  0  0  0  0
 12 47  1  0  0  0  0
 10 44  1  6  0  0  0
  9 43  1  0  0  0  0
  8 42  1  0  0  0  0
  7 41  1  0  0  0  0
  6 40  1  0  0  0  0
 14 49  1  0  0  0  0
 11 45  1  0  0  0  0
  5 38  1  0  0  0  0
  5 39  1  0  0  0  0
 21 57  1  0  0  0  0
  4 36  1  0  0  0  0
  4 37  1  0  0  0  0
  3 34  1  0  0  0  0
  3 35  1  0  0  0  0
  2 33  1  6  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025556

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])\C([H])=C(\[H])/C(/[H])=C([H])\C([H])([H])[C@]([H])(O[H])C([H])([H])[C@@]([H])(O[H])\C([H])=C(\[H])/C(/[H])=C([H])\C([H])([H])C([H])([H])C([H])([H])[C@]([H])(OC(=O)\C([H])=C(\[H])/C(/[H])=C([H])\C1([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H34O5/c1-20-13-7-3-2-4-8-16-22(26)19-23(27)17-11-5-9-14-21(25)15-10-6-12-18-24(28)29-20/h2,4-6,8-12,14,16,18,20-23,25-27H,3,7,13,15,17,19H2,1H3/b4-2-,10-6-,11-5-,14-9-,16-8-,18-12-/t20-,21-,22+,23+/m1/s1

> <INCHI_KEY>
XXDIJWSZFWZBRM-CJPCAZISSA-N

> <FORMULA>
C24H34O5

> <MOLECULAR_WEIGHT>
402.531

> <EXACT_MASS>
402.240624195

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
44.96971542676518

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3Z,5Z,8S,9Z,11Z,14S,16R,17Z,19Z,24R)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one

> <ALOGPS_LOGP>
3.93

> <JCHEM_LOGP>
3.5133448379999987

> <ALOGPS_LOGS>
-4.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.386664363309027

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.629219062823093

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5775923958996727

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
123.47909999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.49e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3Z,5Z,8S,9Z,11Z,14S,16R,17Z,19Z,24R)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 63 63  0  0  0  0  0  0  0  0999 V2000
    1.8073    5.0934   -2.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7079    3.5793   -2.7373 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2505    3.0935   -2.8455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6072    3.4071   -1.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5198    2.2507   -1.1811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7414    1.1165   -0.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5125    0.9124    0.7407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0090    1.7433    1.8080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2067    1.6037    2.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2206    0.5309    2.1197 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3808    1.1555    1.5720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6109   -0.2028    3.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6607   -1.3113    3.2138 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8910   -0.7650    2.7313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2262   -2.4590    2.2850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0293   -3.2122    2.8033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8314   -3.4056    2.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4137   -2.9240    0.9328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2150   -3.1135    0.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9903   -3.8414    0.8867 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1667   -5.0199    0.1003 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2935   -3.0075    0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6861   -2.5163   -0.5091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0032   -1.2705   -0.8949 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1388   -0.1190   -0.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0687    1.1736   -0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7325    1.6916   -1.7363 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7470    1.0621   -2.7791 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3334    2.9819   -1.5839 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8591    5.3991   -2.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3185    5.6092   -3.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3633    5.4375   -1.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2560    3.2997   -3.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2567    2.0137   -3.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2182    3.5477   -3.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0144    3.6987   -0.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2337    4.2780   -1.8373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2634    2.6340   -0.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0871    1.8736   -2.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2916    0.4168   -1.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1181    0.0787    1.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3392    2.5346    2.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4739    2.3132    3.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8539   -0.1823    1.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0646    1.7060    0.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0427    0.5288    4.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7167   -0.6182    3.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8887   -1.7330    4.2006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6645    0.0060    2.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0592   -3.1701    2.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0871   -2.0859    1.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1819   -3.6682    3.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1136   -3.9957    2.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1469   -2.3668    0.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0867   -2.6983   -0.6440 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8375   -4.1762    1.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2990   -5.4581    0.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1150   -3.6395    1.2246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1870   -2.1766    1.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6724   -3.2868   -1.2819 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2054   -1.1202   -1.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3302   -0.3287    1.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1903    1.9352    0.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 24 25  1  0
 12 10  1  0
 10  9  1  0
 25 26  2  0
  9  8  2  0
 20 22  1  0
  8  7  1  0
 26 27  1  0
  7  6  2  0
 18 19  2  0
 13 14  1  0
 27 29  1  0
 10 11  1  0
 22 23  1  0
  6  5  1  0
 17 16  2  0
 20 21  1  0
 17 18  1  0
  5  4  1  0
 16 15  1  0
  4  3  1  0
 23 24  2  0
 27 28  2  0
 15 13  1  0
 29  2  1  0
  3  2  1  0
 19 20  1  0
  2  1  1  0
 17 53  1  0
 18 54  1  0
 19 55  1  0
 20 56  1  1
 22 58  1  0
 22 59  1  0
 23 60  1  0
 24 61  1  0
 25 62  1  0
 26 63  1  0
 16 52  1  0
 15 50  1  0
 15 51  1  0
 13 48  1  1
 12 46  1  0
 12 47  1  0
 10 44  1  6
  9 43  1  0
  8 42  1  0
  7 41  1  0
  6 40  1  0
 14 49  1  0
 11 45  1  0
  5 38  1  0
  5 39  1  0
 21 57  1  0
  4 36  1  0
  4 37  1  0
  3 34  1  0
  3 35  1  0
  2 33  1  6
  1 30  1  0
  1 31  1  0
  1 32  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       1.807   5.093  -2.585  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.708   3.579  -2.737  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.251   3.094  -2.845  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.607   3.407  -1.607  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.520   2.251  -1.181  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.741   1.117  -0.566  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.513   0.912   0.741  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.009   1.743   1.808  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.207   1.604   2.397  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.221   0.531   2.120  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.381   1.155   1.572  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.611  -0.203   3.410  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.661  -1.311   3.214  0.00  0.00           C+0
HETATM   14  O   UNK     0      -5.891  -0.765   2.731  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.226  -2.459   2.285  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.029  -3.212   2.803  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.831  -3.406   2.228  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.414  -2.924   0.933  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.215  -3.114   0.356  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.990  -3.841   0.887  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.167  -5.020   0.100  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.293  -3.007   0.865  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.686  -2.516  -0.509  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.003  -1.270  -0.895  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.139  -0.119  -0.034  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.069   1.174  -0.390  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.732   1.692  -1.736  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.747   1.062  -2.779  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.333   2.982  -1.584  0.00  0.00           O+0
HETATM   30  H   UNK     0       2.859   5.399  -2.557  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.319   5.609  -3.417  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.363   5.438  -1.645  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.256   3.300  -3.646  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.257   2.014  -3.030  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.218   3.548  -3.727  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.014   3.699  -0.752  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.234   4.278  -1.837  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.263   2.634  -0.474  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.087   1.874  -2.040  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.292   0.417  -1.271  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.118   0.079   1.045  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.339   2.535   2.140  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.474   2.313   3.179  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.854  -0.182   1.378  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.065   1.706   0.832  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.043   0.529   4.107  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.717  -0.618   3.890  0.00  0.00           H+0
HETATM   48  H   UNK     0      -4.889  -1.733   4.201  0.00  0.00           H+0
HETATM   49  H   UNK     0      -5.665   0.006   2.167  0.00  0.00           H+0
HETATM   50  H   UNK     0      -5.059  -3.170   2.203  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.087  -2.086   1.266  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.182  -3.668   3.783  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.114  -3.996   2.794  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.147  -2.367   0.353  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.087  -2.698  -0.644  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.838  -4.176   1.917  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.299  -5.458   0.056  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.115  -3.640   1.225  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.187  -2.177   1.570  0.00  0.00           H+0
HETATM   60  H   UNK     0       2.672  -3.287  -1.282  0.00  0.00           H+0
HETATM   61  H   UNK     0       3.205  -1.120  -1.955  0.00  0.00           H+0
HETATM   62  H   UNK     0       3.330  -0.329   1.017  0.00  0.00           H+0
HETATM   63  H   UNK     0       3.190   1.935   0.374  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2   29    3    1   33                                             
CONECT    3    4    2   34   35                                             
CONECT    4    5    3   36   37                                             
CONECT    5    6    4   38   39                                             
CONECT    6    7    5   40                                                  
CONECT    7    8    6   41                                                  
CONECT    8    9    7   42                                                  
CONECT    9   10    8   43                                                  
CONECT   10   12    9   11   44                                             
CONECT   11   10   45                                                       
CONECT   12   13   10   46   47                                             
CONECT   13   12   14   15   48                                             
CONECT   14   13   49                                                       
CONECT   15   16   13   50   51                                             
CONECT   16   17   15   52                                                  
CONECT   17   16   18   53                                                  
CONECT   18   19   17   54                                                  
CONECT   19   18   20   55                                                  
CONECT   20   22   21   19   56                                             
CONECT   21   20   57                                                       
CONECT   22   20   23   58   59                                             
CONECT   23   22   24   60                                                  
CONECT   24   25   23   61                                                  
CONECT   25   24   26   62                                                  
CONECT   26   25   27   63                                                  
CONECT   27   26   29   28                                                  
CONECT   28   27                                                            
CONECT   29   27    2                                                       
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    2                                                            
CONECT   34    3                                                            
CONECT   35    3                                                            
CONECT   36    4                                                            
CONECT   37    4                                                            
CONECT   38    5                                                            
CONECT   39    5                                                            
CONECT   40    6                                                            
CONECT   41    7                                                            
CONECT   42    8                                                            
CONECT   43    9                                                            
CONECT   44   10                                                            
CONECT   45   11                                                            
CONECT   46   12                                                            
CONECT   47   12                                                            
CONECT   48   13                                                            
CONECT   49   14                                                            
CONECT   50   15                                                            
CONECT   51   15                                                            
CONECT   52   16                                                            
CONECT   53   17                                                            
CONECT   54   18                                                            
CONECT   55   19                                                            
CONECT   56   20                                                            
CONECT   57   21                                                            
CONECT   58   22                                                            
CONECT   59   22                                                            
CONECT   60   23                                                            
CONECT   61   24                                                            
CONECT   62   25                                                            
CONECT   63   26                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  126    0
END

RDKit          3D

63 63  0  0  0  0  0  0  0  0999 V2000
    1.8073    5.0934   -2.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7079    3.5793   -2.7373 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2505    3.0935   -2.8455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6072    3.4071   -1.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5198    2.2507   -1.1811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7414    1.1165   -0.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5125    0.9124    0.7407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0090    1.7433    1.8080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2067    1.6037    2.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2206    0.5309    2.1197 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3808    1.1555    1.5720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6109   -0.2028    3.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6607   -1.3113    3.2138 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8910   -0.7650    2.7313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2262   -2.4590    2.2850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0293   -3.2122    2.8033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8314   -3.4056    2.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4137   -2.9240    0.9328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2150   -3.1135    0.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9903   -3.8414    0.8867 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1667   -5.0199    0.1003 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2935   -3.0075    0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6861   -2.5163   -0.5091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0032   -1.2705   -0.8949 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1388   -0.1190   -0.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0687    1.1736   -0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7325    1.6916   -1.7363 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7470    1.0621   -2.7791 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3334    2.9819   -1.5839 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8591    5.3991   -2.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3185    5.6092   -3.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3633    5.4375   -1.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2560    3.2997   -3.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2567    2.0137   -3.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2182    3.5477   -3.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0144    3.6987   -0.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2337    4.2780   -1.8373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2634    2.6340   -0.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0871    1.8736   -2.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2916    0.4168   -1.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1181    0.0787    1.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3392    2.5346    2.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4739    2.3132    3.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8539   -0.1823    1.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0646    1.7060    0.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0427    0.5288    4.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7167   -0.6182    3.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8887   -1.7330    4.2006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6645    0.0060    2.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0592   -3.1701    2.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0871   -2.0859    1.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1819   -3.6682    3.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1136   -3.9957    2.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1469   -2.3668    0.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0867   -2.6983   -0.6440 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8375   -4.1762    1.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2990   -5.4581    0.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1150   -3.6395    1.2246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1870   -2.1766    1.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6724   -3.2868   -1.2819 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2054   -1.1202   -1.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3302   -0.3287    1.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1903    1.9352    0.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 24 25  1  0
 12 10  1  0
 10  9  1  0
 25 26  2  0
  9  8  2  0
 20 22  1  0
  8  7  1  0
 26 27  1  0
  7  6  2  0
 18 19  2  0
 13 14  1  0
 27 29  1  0
 10 11  1  0
 22 23  1  0
  6  5  1  0
 17 16  2  0
 20 21  1  0
 17 18  1  0
  5  4  1  0
 16 15  1  0
  4  3  1  0
 23 24  2  0
 27 28  2  0
 15 13  1  0
 29  2  1  0
  3  2  1  0
 19 20  1  0
  2  1  1  0
 17 53  1  0
 18 54  1  0
 19 55  1  0
 20 56  1  1
 22 58  1  0
 22 59  1  0
 23 60  1  0
 24 61  1  0
 25 62  1  0
 26 63  1  0
 16 52  1  0
 15 50  1  0
 15 51  1  0
 13 48  1  1
 12 46  1  0
 12 47  1  0
 10 44  1  6
  9 43  1  0
  8 42  1  0
  7 41  1  0
  6 40  1  0
 14 49  1  0
 11 45  1  0
  5 38  1  0
  5 39  1  0
 21 57  1  0
  4 36  1  0
  4 37  1  0
  3 34  1  0
  3 35  1  0
  2 33  1  6
  1 30  1  0
  1 31  1  0
  1 32  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₄O₅

Average Mass

402.5310 Da

Monoisotopic Mass

402.24062 Da

IUPAC Name

(3Z,5Z,8S,9Z,11Z,14S,16R,17Z,19Z,24R)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one

Traditional Name

(3Z,5Z,8S,9Z,11Z,14S,16R,17Z,19Z,24R)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])\C([H])=C(\[H])/C(/[H])=C([H])\C([H])([H])[C@]([H])(O[H])C([H])([H])[C@@]([H])(O[H])\C([H])=C(\[H])/C(/[H])=C([H])\C([H])([H])C([H])([H])C([H])([H])[C@]([H])(OC(=O)\C([H])=C(\[H])/C(/[H])=C([H])\C1([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C24H34O5/c1-20-13-7-3-2-4-8-16-22(26)19-23(27)17-11-5-9-14-21(25)15-10-6-12-18-24(28)29-20/h2,4-6,8-12,14,16,18,20-23,25-27H,3,7,13,15,17,19H2,1H3/b4-2-,10-6-,11-5-,14-9-,16-8-,18-12-/t20-,21-,22+,23+/m1/s1

InChI Key

XXDIJWSZFWZBRM-CJPCAZISSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Bacillus sp. PP19-H3	JEOL database	Nagao, T., et al, J. Antibiotics 54, 333 (2001)

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.93	ALOGPS
logP	3.51	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	14.63	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	123.48 m³·mol⁻¹	ChemAxon
Polarizability	44.97 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101716361

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li W, Tang XX, Yan X, Wu Z, Yi ZW, Fang MJ, Su X, Qiu YK: A new macrolactin antibiotic from deep sea-derived bacteria Bacillus subtilis B5. Nat Prod Res. 2016 Dec;30(24):2777-2782. doi: 10.1080/14786419.2016.1155576. Epub 2016 Apr 13. [PubMed:27071303 ]
Yan X, Zhou YX, Tang XX, Liu XX, Yi ZW, Fang MJ, Wu Z, Jiang FQ, Qiu YK: Macrolactins from Marine-Derived Bacillus subtilis B5 Bacteria as Inhibitors of Inducible Nitric Oxide and Cytokines Expression. Mar Drugs. 2016 Oct 26;14(11). pii: md14110195. doi: 10.3390/md14110195. [PubMed:27792158 ]
Fakhri S, Yarmohammadi A, Yarmohammadi M, Farzaei MH, Echeverria J: Marine Natural Products: Promising Candidates in the Modulation of Gut-Brain Axis towards Neuroprotection. Mar Drugs. 2021 Mar 19;19(3). pii: md19030165. doi: 10.3390/md19030165. [PubMed:33808737 ]
Riyanti, Balansa W, Liu Y, Sharma A, Mihajlovic S, Hartwig C, Leis B, Rieuwpassa FJ, Ijong FG, Wagele H, Konig GM, Schaberle TF: Selection of sponge-associated bacteria with high potential for the production of antibacterial compounds. Sci Rep. 2020 Nov 12;10(1):19614. doi: 10.1038/s41598-020-76256-2. [PubMed:33184304 ]
Salazar F, Ortiz A, Sansinenea E: A Strong Antifungal Activity of 7-O-Succinyl Macrolactin A vs Macrolactin A from Bacillus amyloliquefaciens ELI149. Curr Microbiol. 2020 Nov;77(11):3409-3413. doi: 10.1007/s00284-020-02200-2. Epub 2020 Sep 17. [PubMed:32944805 ]
Sapkota M, Gao M, Li L, Yang M, Shrestha SK, Choi H, Soh Y: Macrolactin A protects against LPS-induced bone loss by regulation of bone remodeling. Eur J Pharmacol. 2020 Sep 15;883:173305. doi: 10.1016/j.ejphar.2020.173305. Epub 2020 Jul 14. [PubMed:32673673 ]
Kim EN, Gao M, Choi H, Jeong GS: Marine Microorganism-Derived Macrolactins Inhibit Inflammatory Mediator Effects in LPS-Induced Macrophage and Microglial Cells by Regulating BACH1 and HO-1/Nrf2 Signals through Inhibition of TLR4 Activation. Molecules. 2020 Feb 4;25(3). pii: molecules25030656. doi: 10.3390/molecules25030656. [PubMed:32033079 ]
Helaly SE, Hamad Z, El Sayed MA, Abdel-Motaal FF, Nassar MI, Ito SI, Stadler M: Bacillus methylotrophicus ASWU-C2, a strain inhabiting hot desert soil, a new source for antibacterial bacillopyrone, pyrophen, and cyclopeptides. Z Naturforsch C J Biosci. 2018 Dec 19;74(1-2):55-59. doi: 10.1515/znc-2018-0093. [PubMed:30864389 ]
Chen L, Heng J, Qin S, Bian K: A comprehensive understanding of the biocontrol potential of Bacillus velezensis LM2303 against Fusarium head blight. PLoS One. 2018 Jun 1;13(6):e0198560. doi: 10.1371/journal.pone.0198560. eCollection 2018. [PubMed:29856856 ]
Liu Q, Ren P, Liu Y, Qin W, Li H, Li W: Exploration of the Glycosyltransferase BmmGT1 from a Marine-Derived Bacillus Strain as a Potential Enzyme Tool for Compound Glycol-Diversification. J Microbiol Biotechnol. 2018 Jun 28;28(6):931-937. doi: 10.4014/jmb.1802.02008. [PubMed:29847868 ]
Jin J, Hwang K, Joo JD, Han JH, Kim CY: Combination therapy of 7-O-succinyl macrolactin A tromethamine salt and temozolomide against experimental glioblastoma. Oncotarget. 2017 Dec 14;9(2):2140-2147. doi: 10.18632/oncotarget.23295. eCollection 2018 Jan 5. [PubMed:29416760 ]
Jin J, Choi SH, Lee JE, Joo JD, Han JH, Park SY, Kim CY: Antitumor activity of 7-O-succinyl macrolactin A tromethamine salt in the mouse glioma model. Oncol Lett. 2017 May;13(5):3767-3773. doi: 10.3892/ol.2017.5918. Epub 2017 Mar 27. [PubMed:28529591 ]
Souris C, Misale A, Chen Y, Luparia M, Maulide N: From Stereodefined Cyclobutenes to Dienes: Total Syntheses of Ieodomycin D and the Southern Fragment of Macrolactin A. Org Lett. 2015 Sep 18;17(18):4486-9. doi: 10.1021/acs.orglett.5b02149. Epub 2015 Sep 9. [PubMed:26349917 ]
Noh K, Kang PsiW: Calculation of a First-In-Man Dose of 7-O-Succinyl Macrolactin A Based on Allometric Scaling of Data from Mice, Rats, and Dogs. Biomol Ther (Seoul). 2017 Nov 1;25(6):648-658. doi: 10.4062/biomolther.2016.192. [PubMed:28274094 ]
Regmi SC, Park SY, Kim SJ, Banskota S, Shah S, Kim DH, Kim JA: The Anti-Tumor Activity of Succinyl Macrolactin A Is Mediated through the beta-Catenin Destruction Complex via the Suppression of Tankyrase and PI3K/Akt. PLoS One. 2015 Nov 6;10(11):e0141753. doi: 10.1371/journal.pone.0141753. eCollection 2015. [PubMed:26544726 ]
Nagao, T., et al. (2001). Nagao, T., et al, J. Antibiotics 54, 333 (2001). J. Antibiotics.

Showing NP-Card for Macrolactin A (NP0025556)

MOL for NP0025556 (Macrolactin A)

3D MOL for NP0025556 (Macrolactin A)

3D SDF for NP0025556 (Macrolactin A)

3D-SDF for NP0025556 (Macrolactin A)

PDB for NP0025556 (Macrolactin A)

3D PDB for NP0025556 (Macrolactin A)

SMILES for NP0025556 (Macrolactin A)

INCHI for NP0025556 (Macrolactin A)

Structure for NP0025556 (Macrolactin A)

3D Structure for NP0025556 (Macrolactin A)