NP-MRD: Showing NP-Card for Yanuthone B (NP0003478)

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Record Information

Version

1.0

Created at

2020-12-09 00:43:03 UTC

Updated at

2021-07-15 16:46:31 UTC

NP-MRD ID

NP0003478

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Yanuthone B

Provided By

NPAtlas

Description

[(1S)-2,5-dioxo-6-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-7-oxabicyclo[4.1.0]Hept-3-en-3-yl]methyl acetate belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Yanuthone B is found in Aspergillus niger. It was first documented in 2000 (PMID: 11031048). Based on a literature review very few articles have been published on [(1S)-2,5-dioxo-6-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-7-oxabicyclo[4.1.0]Hept-3-en-3-yl]methyl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117473D          

 61 62  0  0  0  0            999 V2000
   -7.6313   -1.2071    3.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3953   -1.1785    1.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6948   -0.1740    0.9676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8407   -2.2843    1.0421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6262   -2.2352   -0.3660 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7074   -1.1080   -0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0382   -0.0766   -1.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1220    0.9994   -1.6649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4846    2.1622   -2.0171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6633    0.7831   -1.5106 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7318    1.9413   -1.6136 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.7725    2.2803   -3.7097 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9399    1.2364   -2.1698 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.3006    0.7009    0.3763 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7065    1.7089    1.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.3502   -1.7513    2.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.7569   -1.6649    3.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9736    2.6028   -0.7226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0466    1.0875   -0.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8119    2.0115   -4.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2369    0.5295   -2.9738 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
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M  END

     RDKit          3D

 61 62  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242117473D          

 61 62  0  0  0  0            999 V2000
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   -7.3953   -1.1785    1.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0842   -0.9436    2.3270 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2350   -1.0975    1.7585 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5633   -0.6878    0.3860 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3502   -1.7513    2.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1984   -0.4290   -2.1206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2658   -0.3909   -0.7290 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3834   -1.0998   -0.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1600   -1.6896    1.0172 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.7569   -1.6649    3.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1504   -3.1606   -0.7479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5634   -2.0464   -0.9140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0220   -0.0452   -1.8785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9231    2.6029   -2.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9736    2.6028   -0.7226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0466    1.0875   -0.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1120    1.7937   -4.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6337    3.3489   -3.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8119    2.0115   -4.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2369    0.5295   -2.9738 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6176    2.1095   -2.2577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4426   -0.2454   -0.6866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9158    1.4166   -0.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9479   -0.5283   -1.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4020    2.0431    2.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3875    2.6380    0.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8047    1.2971    1.8201 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3116    1.1987    0.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9188   -0.4396   -0.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0363   -1.1665    1.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5726    0.4570    2.6087 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0364   -1.3302    3.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0769   -1.3111   -0.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6764   -0.8706    0.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4351    0.3675    0.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3304   -1.4445    2.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2793   -1.4210    3.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2535   -2.8436    2.5065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2910   -0.4464   -0.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  3  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 10 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28  6  1  0  0  0  0
 27 10  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  5 33  1  0  0  0  0
  5 34  1  0  0  0  0
  7 35  1  0  0  0  0
 11 36  1  0  0  0  0
 11 37  1  0  0  0  0
 12 38  1  0  0  0  0
 14 39  1  0  0  0  0
 14 40  1  0  0  0  0
 14 41  1  0  0  0  0
 15 42  1  0  0  0  0
 15 43  1  0  0  0  0
 16 44  1  0  0  0  0
 16 45  1  0  0  0  0
 17 46  1  0  0  0  0
 19 47  1  0  0  0  0
 19 48  1  0  0  0  0
 19 49  1  0  0  0  0
 20 50  1  0  0  0  0
 20 51  1  0  0  0  0
 21 52  1  0  0  0  0
 21 53  1  0  0  0  0
 22 54  1  0  0  0  0
 24 55  1  0  0  0  0
 24 56  1  0  0  0  0
 24 57  1  0  0  0  0
 25 58  1  0  0  0  0
 25 59  1  0  0  0  0
 25 60  1  0  0  0  0
 27 61  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0003478

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C(=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])C(=C(/[H])C([H])([H])C([H])([H])C(=C(/[H])C([H])([H])[C@@]12O[C@]1([H])C(=O)C(=C([H])C2=O)C([H])([H])OC(=O)C([H])([H])[H])\C([H])([H])[H])\C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O5/c1-16(2)8-6-9-17(3)10-7-11-18(4)12-13-24-21(26)14-20(15-28-19(5)25)22(27)23(24)29-24/h8,10,12,14,23H,6-7,9,11,13,15H2,1-5H3/b17-10+,18-12+/t23-,24+/m1/s1

> <INCHI_KEY>
ZNJXRPDYPGYTCI-YFQICCSESA-N

> <FORMULA>
C24H32O5

> <MOLECULAR_WEIGHT>
400.515

> <EXACT_MASS>
400.22497413

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
46.15120625688716

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1S,6R)-2,5-dioxo-6-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-7-oxabicyclo[4.1.0]hept-3-en-3-yl]methyl acetate

> <ALOGPS_LOGP>
4.64

> <JCHEM_LOGP>
4.999130345333331

> <ALOGPS_LOGS>
-5.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.714955909519254

> <JCHEM_PKA_STRONGEST_BASIC>
-4.345125139275441

> <JCHEM_POLAR_SURFACE_AREA>
72.97

> <JCHEM_REFRACTIVITY>
115.85149999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.80e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,6R)-2,5-dioxo-6-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-7-oxabicyclo[4.1.0]hept-3-en-3-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 61 62  0  0  0  0  0  0  0  0999 V2000
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   -6.6262   -2.2352   -0.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7074   -1.1080   -0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0382   -0.0766   -1.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1220    0.9994   -1.6649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4846    2.1622   -2.0171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6633    0.7831   -1.5106 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7318    1.9413   -1.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3507    1.5232   -1.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4637    1.6794   -2.3913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7725    2.2803   -3.7097 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9399    1.2364   -2.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1345    0.6304   -0.7998 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5520    0.2044   -0.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3006    0.7009    0.3763 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7065    1.7089    1.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7318    0.2238    0.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8238   -0.3719    1.8761 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0842   -0.9436    2.3270 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2350   -1.0975    1.7585 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5633   -0.6878    0.3860 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3502   -1.7513    2.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1984   -0.4290   -2.1206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2658   -0.3909   -0.7290 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3834   -1.0998   -0.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1600   -1.6896    1.0172 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.5446   -1.8030    3.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.5634   -2.0464   -0.9140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0220   -0.0452   -1.8785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9231    2.6029   -2.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9736    2.6028   -0.7226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0466    1.0875   -0.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1120    1.7937   -4.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6337    3.3489   -3.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8119    2.0115   -4.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2369    0.5295   -2.9738 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6176    2.1095   -2.2577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4426   -0.2454   -0.6866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9158    1.4166   -0.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9479   -0.5283   -1.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4020    2.0431    2.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3875    2.6380    0.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8047    1.2971    1.8201 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3116    1.1987    0.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9188   -0.4396   -0.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0363   -1.1665    1.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5726    0.4570    2.6087 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0364   -1.3302    3.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0769   -1.3111   -0.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6764   -0.8706    0.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4351    0.3675    0.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3304   -1.4445    2.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2793   -1.4210    3.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2535   -2.8436    2.5065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2910   -0.4464   -0.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  1
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  3
 23 24  1  0
 23 25  1  0
 10 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28  6  1  0
 27 10  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  5 33  1  0
  5 34  1  0
  7 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 14 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 21 52  1  0
 21 53  1  0
 22 54  1  0
 24 55  1  0
 24 56  1  0
 24 57  1  0
 25 58  1  0
 25 59  1  0
 25 60  1  0
 27 61  1  1
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -7.631  -1.207   3.132  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.395  -1.179   1.646  0.00  0.00           C+0
HETATM    3  O   UNK     0      -7.695  -0.174   0.968  0.00  0.00           O+0
HETATM    4  O   UNK     0      -6.841  -2.284   1.042  0.00  0.00           O+0
HETATM    5  C   UNK     0      -6.626  -2.235  -0.366  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.707  -1.108  -0.642  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.038  -0.077  -1.419  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.122   0.999  -1.665  0.00  0.00           C+0
HETATM    9  O   UNK     0      -5.485   2.162  -2.017  0.00  0.00           O+0
HETATM   10  C   UNK     0      -3.663   0.783  -1.511  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.732   1.941  -1.614  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.351   1.523  -1.436  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.464   1.679  -2.391  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.773   2.280  -3.710  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.940   1.236  -2.170  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.135   0.630  -0.800  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.552   0.204  -0.594  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.301   0.701   0.376  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.707   1.709   1.281  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.732   0.224   0.528  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.824  -0.372   1.876  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.084  -0.944   2.327  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.235  -1.097   1.759  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.563  -0.688   0.386  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.350  -1.751   2.551  0.00  0.00           C+0
HETATM   26  O   UNK     0      -3.198  -0.429  -2.121  0.00  0.00           O+0
HETATM   27  C   UNK     0      -3.266  -0.391  -0.729  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.383  -1.100  -0.059  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.160  -1.690   1.017  0.00  0.00           O+0
HETATM   30  H   UNK     0      -7.745  -0.159   3.465  0.00  0.00           H+0
HETATM   31  H   UNK     0      -8.545  -1.803   3.307  0.00  0.00           H+0
HETATM   32  H   UNK     0      -6.757  -1.665   3.636  0.00  0.00           H+0
HETATM   33  H   UNK     0      -6.150  -3.161  -0.748  0.00  0.00           H+0
HETATM   34  H   UNK     0      -7.563  -2.046  -0.914  0.00  0.00           H+0
HETATM   35  H   UNK     0      -7.022  -0.045  -1.879  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.923   2.603  -2.475  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.974   2.603  -0.723  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.047   1.087  -0.501  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.112   1.794  -4.457  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.634   3.349  -3.774  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.812   2.011  -4.064  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.237   0.530  -2.974  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.618   2.110  -2.258  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.443  -0.245  -0.687  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.916   1.417  -0.053  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.948  -0.528  -1.270  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.402   2.043   2.070  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.388   2.638   0.727  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.805   1.297   1.820  0.00  0.00           H+0
HETATM   50  H   UNK     0       5.312   1.199   0.468  0.00  0.00           H+0
HETATM   51  H   UNK     0       4.919  -0.440  -0.324  0.00  0.00           H+0
HETATM   52  H   UNK     0       4.036  -1.167   1.965  0.00  0.00           H+0
HETATM   53  H   UNK     0       4.573   0.457   2.609  0.00  0.00           H+0
HETATM   54  H   UNK     0       6.036  -1.330   3.397  0.00  0.00           H+0
HETATM   55  H   UNK     0       7.077  -1.311  -0.398  0.00  0.00           H+0
HETATM   56  H   UNK     0       8.676  -0.871   0.180  0.00  0.00           H+0
HETATM   57  H   UNK     0       7.435   0.368   0.149  0.00  0.00           H+0
HETATM   58  H   UNK     0       9.330  -1.444   2.176  0.00  0.00           H+0
HETATM   59  H   UNK     0       8.279  -1.421   3.615  0.00  0.00           H+0
HETATM   60  H   UNK     0       8.254  -2.844   2.506  0.00  0.00           H+0
HETATM   61  H   UNK     0      -2.291  -0.446  -0.239  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   33   34                                             
CONECT    6    5    7   28                                                  
CONECT    7    6    8   35                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   26   27                                             
CONECT   11   10   12   36   37                                             
CONECT   12   11   13   38                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13   39   40   41                                             
CONECT   15   13   16   42   43                                             
CONECT   16   15   17   44   45                                             
CONECT   17   16   18   46                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   47   48   49                                             
CONECT   20   18   21   50   51                                             
CONECT   21   20   22   52   53                                             
CONECT   22   21   23   54                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   55   56   57                                             
CONECT   25   23   58   59   60                                             
CONECT   26   10   27                                                       
CONECT   27   26   28   10   61                                             
CONECT   28   27   29    6                                                  
CONECT   29   28                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    5                                                            
CONECT   34    5                                                            
CONECT   35    7                                                            
CONECT   36   11                                                            
CONECT   37   11                                                            
CONECT   38   12                                                            
CONECT   39   14                                                            
CONECT   40   14                                                            
CONECT   41   14                                                            
CONECT   42   15                                                            
CONECT   43   15                                                            
CONECT   44   16                                                            
CONECT   45   16                                                            
CONECT   46   17                                                            
CONECT   47   19                                                            
CONECT   48   19                                                            
CONECT   49   19                                                            
CONECT   50   20                                                            
CONECT   51   20                                                            
CONECT   52   21                                                            
CONECT   53   21                                                            
CONECT   54   22                                                            
CONECT   55   24                                                            
CONECT   56   24                                                            
CONECT   57   24                                                            
CONECT   58   25                                                            
CONECT   59   25                                                            
CONECT   60   25                                                            
CONECT   61   27                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  124    0
END

RDKit          3D

61 62  0  0  0  0  0  0  0  0999 V2000
   -7.6313   -1.2071    3.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3953   -1.1785    1.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6948   -0.1740    0.9676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8407   -2.2843    1.0421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6262   -2.2352   -0.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7074   -1.1080   -0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0382   -0.0766   -1.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1220    0.9994   -1.6649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4846    2.1622   -2.0171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6633    0.7831   -1.5106 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7318    1.9413   -1.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3507    1.5232   -1.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4637    1.6794   -2.3913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7725    2.2803   -3.7097 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9399    1.2364   -2.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1345    0.6304   -0.7998 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5520    0.2044   -0.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3006    0.7009    0.3763 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7065    1.7089    1.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7318    0.2238    0.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8238   -0.3719    1.8761 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0842   -0.9436    2.3270 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2350   -1.0975    1.7585 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5633   -0.6878    0.3860 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3502   -1.7513    2.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1984   -0.4290   -2.1206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2658   -0.3909   -0.7290 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3834   -1.0998   -0.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1600   -1.6896    1.0172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7448   -0.1591    3.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5446   -1.8030    3.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7569   -1.6649    3.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1504   -3.1606   -0.7479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5634   -2.0464   -0.9140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0220   -0.0452   -1.8785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9231    2.6029   -2.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9736    2.6028   -0.7226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0466    1.0875   -0.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1120    1.7937   -4.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6337    3.3489   -3.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8119    2.0115   -4.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2369    0.5295   -2.9738 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6176    2.1095   -2.2577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4426   -0.2454   -0.6866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9158    1.4166   -0.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9479   -0.5283   -1.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4020    2.0431    2.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3875    2.6380    0.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8047    1.2971    1.8201 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3116    1.1987    0.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9188   -0.4396   -0.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0363   -1.1665    1.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5726    0.4570    2.6087 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0364   -1.3302    3.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0769   -1.3111   -0.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6764   -0.8706    0.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4351    0.3675    0.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3304   -1.4445    2.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2793   -1.4210    3.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2535   -2.8436    2.5065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2910   -0.4464   -0.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  1
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  3
 23 24  1  0
 23 25  1  0
 10 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28  6  1  0
 27 10  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  5 33  1  0
  5 34  1  0
  7 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 14 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 21 52  1  0
 21 53  1  0
 22 54  1  0
 24 55  1  0
 24 56  1  0
 24 57  1  0
 25 58  1  0
 25 59  1  0
 25 60  1  0
 27 61  1  1
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
[(1S)-2,5-Dioxo-6-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-7-oxabicyclo[4.1.0]hept-3-en-3-yl]methyl acetic acid	Generator

Chemical Formula

C₂₄H₃₂O₅

Average Mass

400.5150 Da

Monoisotopic Mass

400.22497 Da

IUPAC Name

[(1S,6R)-2,5-dioxo-6-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-7-oxabicyclo[4.1.0]hept-3-en-3-yl]methyl acetate

Traditional Name

[(1S,6R)-2,5-dioxo-6-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-7-oxabicyclo[4.1.0]hept-3-en-3-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C\CC12O[C@@H]1C(=O)C(COC(C)=O)=CC2=O

InChI Identifier

InChI=1S/C24H32O5/c1-16(2)8-6-9-17(3)10-7-11-18(4)12-13-24-21(26)14-20(15-28-19(5)25)22(27)23(24)29-24/h8,10,12,14,23H,6-7,9,11,13,15H2,1-5H3/b17-10+,18-12+/t23-,24?/m1/s1

InChI Key

ZNJXRPDYPGYTCI-YFQICCSESA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aspergillus niger	NPAtlas	11031048

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Cyclohexenone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

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	4.64	ALOGPS
logP	5	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	16.71	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	72.97 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	115.85 m³·mol⁻¹	ChemAxon
Polarizability	46.15 Å³	ChemAxon
Number of Rings	2	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

NPAtlas ID

NPA007617

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78440189

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21775835

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bugni TS, Abbanat D, Bernan VS, Maiese WM, Greenstein M, Van Wagoner RM, Ireland CM: Yanuthones: novel metabolites from a marine isolate of Aspergillus niger. J Org Chem. 2000 Oct 20;65(21):7195-200. doi: 10.1021/jo0006831. [PubMed:11031048 ]

Showing NP-Card for Yanuthone B (NP0003478)

MOL for NP0003478 (Yanuthone B)

3D MOL for NP0003478 (Yanuthone B)

3D SDF for NP0003478 (Yanuthone B)

3D-SDF for NP0003478 (Yanuthone B)

PDB for NP0003478 (Yanuthone B)

3D PDB for NP0003478 (Yanuthone B)

SMILES for NP0003478 (Yanuthone B)

INCHI for NP0003478 (Yanuthone B)

Structure for NP0003478 (Yanuthone B)

3D Structure for NP0003478 (Yanuthone B)