NP-MRD: Showing NP-Card for Mollemycin A (NP0012613)

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Record Information

Version

1.0

Created at

2021-01-05 21:57:30 UTC

Updated at

2024-04-19 09:30:36 UTC

NP-MRD ID

NP0012613

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Mollemycin A

Provided By

NPAtlas

Description

2-[6-Ethyl-2-hydroxy-5-(2-hydroxy-2-methylbutanoyl)oxan-2-yl]-N-[(6R,7S,10S,13S,14S,21R,24S)-10-ethyl-6,9,23-trihydroxy-29-{[(2S,4S,5R,6S)-5-{[(2S,4S,5R,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-24-(methoxymethyl)-6-methyl-2,8,11,15,22,25-hexaoxo-13-(propan-2-yl)-12-oxa-3,9,16,17,23,26,27-heptaazatetracyclo[24.4.0.0³,⁷.0¹⁶,²¹]Triacont-29-en-14-yl]-2-hydroxypropanimidic acid belongs to the class of organic compounds known as cyclic glycodepsipeptides. These are peptidomimetic containing a glycodepisipeptide backbone that lies in a cyclic moiety. Mollemycin A is found in Streptomyces. It was first documented in 2014 (PMID: 24611932). Based on a literature review very few articles have been published on 2-[6-ethyl-2-hydroxy-5-(2-hydroxy-2-methylbutanoyl)oxan-2-yl]-N-[(6R,7S,10S,13S,14S,21R,24S)-10-ethyl-6,9,23-trihydroxy-29-{[(2S,4S,5R,6S)-5-{[(2S,4S,5R,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-24-(methoxymethyl)-6-methyl-2,8,11,15,22,25-hexaoxo-13-(propan-2-yl)-12-oxa-3,9,16,17,23,26,27-heptaazatetracyclo[24.4.0.0³,⁷.0¹⁶,²¹]Triacont-29-en-14-yl]-2-hydroxypropanimidic acid.

Structure

MOL SDF PDB SMILES InChI

Mollemycin A
  Mrv1652301052122572D          

 91 97  0  0  0  0            999 V2000
   -3.5249   -4.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7887   -5.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0981   -4.5572    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4295   -3.8017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2292   -4.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4976   -2.9795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2951   -2.1798    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8438   -1.4891    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1928   -0.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5854   -0.2568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1928   -0.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5854   -0.2568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8438   -1.4891    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2951   -2.1798    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    3.3198   -2.9114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4295   -3.8017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0981   -4.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9010   -8.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7210   -7.9717    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0525   -7.2162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5697   -8.8180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0355  -10.8123    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.0506   -6.0435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4508   -0.9303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4508   -0.9303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2382   -1.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3855   -1.5896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8452   -0.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2864   -0.0108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4039   -1.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9046   -0.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.0403   -1.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5396   -2.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.8571   -2.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3564   -3.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8585   -1.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1760   -2.3037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3592   -0.8865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.0149   -1.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7764   -1.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8600   -0.2309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9408   -1.6084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4522   -0.0591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0506   -1.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7154   -2.3370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3371   -1.0747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
 30 29  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  1  0  0  0
 33 37  1  1  0  0  0
 38 37  1  6  0  0  0
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 39 40  1  0  0  0  0
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 55 56  1  0  0  0  0
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 19 66  1  0  0  0  0
  8 67  1  6  0  0  0
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 89 91  1  0  0  0  0
 59  3  1  0  0  0  0
 16 11  1  0  0  0  0
 28 23  1  0  0  0  0
 35 30  1  0  0  0  0
 43 38  1  0  0  0  0
 56 52  1  0  0  0  0
 77 72  1  0  0  0  0
M  END

Mollemycin A
  Mrv1652301052122572D          

 91 97  0  0  0  0            999 V2000
   -3.5249   -4.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7887   -5.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0981   -4.5572    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4295   -3.8017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2292   -4.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4976   -2.9795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2951   -2.1798    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8438   -1.4891    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1928   -0.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5854   -0.2568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1928   -0.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5854   -0.2568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8438   -1.4891    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2951   -2.1798    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4976   -2.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3198   -2.9114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4295   -3.8017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0981   -4.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5867   -5.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4067   -5.1312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2495   -3.7109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5638   -6.5515    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7438   -6.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9010   -8.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7210   -7.9717    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0525   -7.2162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2097   -8.6365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5697   -8.8180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0583   -9.4828    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7269  -10.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2155  -10.9031    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0355  -10.8123    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3668  -10.0568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8783   -9.3920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1868   -9.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5240  -11.4771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8840  -11.6586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0640  -11.7493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5925   -7.4885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0012613

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1OC(O)(CCC1C(=O)C(C)(O)CC)C(C)(O)C(=O)N[C@H]1[C@@H](OC(=O)[C@H](CC)N(O)C(=O)[C@H]2N(CC[C@@]2(C)O)C(=O)C2C=C(CNN2C(=O)[C@H](COC)N(O)C(=O)[C@H]2CCCNN2C1=O)O[C@H]1C[C@H](OC)[C@H](O[C@H]2C[C@H](OC)[C@H](O)[C@H](C)O2)[C@H](C)O1)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C59H96N8O24/c1-14-34-54(75)90-45(29(4)5)43(62-55(76)58(10,79)59(80)20-19-33(38(15-2)91-59)48(69)56(8,77)16-3)52(73)64-35(18-17-22-60-64)51(72)67(82)37(28-83-11)50(71)65-36(49(70)63-23-21-57(9,78)47(63)53(74)66(34)81)24-32(27-61-65)88-41-26-40(85-13)46(31(7)87-41)89-42-25-39(84-12)44(68)30(6)86-42/h24,29-31,33-47,60-61,68,77-82H,14-23,25-28H2,1-13H3,(H,62,76)/t30-,31-,33?,34-,35+,36?,37-,38?,39-,40-,41-,42-,43-,44+,45-,46+,47+,56?,57+,58?,59?/m0/s1

> <INCHI_KEY>
RJMAMONPIIYLDD-XUEXKZAKSA-N

> <FORMULA>
C59H96N8O24

> <MOLECULAR_WEIGHT>
1301.449

> <EXACT_MASS>
1300.653746003

> <JCHEM_ACCEPTOR_COUNT>
25

> <JCHEM_ATOM_COUNT>
187

> <JCHEM_AVERAGE_POLARIZABILITY>
132.92878004392446

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[6-ethyl-2-hydroxy-5-(2-hydroxy-2-methylbutanoyl)oxan-2-yl]-N-[(6R,7S,10S,13S,14S,21R,24S)-10-ethyl-6,9,23-trihydroxy-29-{[(2S,4S,5R,6S)-5-{[(2S,4S,5R,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-24-(methoxymethyl)-6-methyl-2,8,11,15,22,25-hexaoxo-13-(propan-2-yl)-12-oxa-3,9,16,17,23,26,27-heptaazatetracyclo[24.4.0.0^{3,7}.0^{16,21}]triacont-29-en-14-yl]-2-hydroxypropanamide

> <ALOGPS_LOGP>
0.37

> <JCHEM_LOGP>
-1.0356776830000005

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.868450588925697

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.265094279473612

> <JCHEM_PKA_STRONGEST_BASIC>
3.897592878965768

> <JCHEM_POLAR_SURFACE_AREA>
413.53000000000003

> <JCHEM_REFRACTIVITY>
334.6237999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[6-ethyl-2-hydroxy-5-(2-hydroxy-2-methylbutanoyl)oxan-2-yl]-N-[(6R,7S,10S,13S,14S,21R,24S)-10-ethyl-6,9,23-trihydroxy-29-{[(2S,4S,5R,6S)-5-{[(2S,4S,5R,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-13-isopropyl-24-(methoxymethyl)-6-methyl-2,8,11,15,22,25-hexaoxo-12-oxa-3,9,16,17,23,26,27-heptaazatetracyclo[24.4.0.0^{3,7}.0^{16,21}]triacont-29-en-14-yl]-2-hydroxypropanamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-JAN-21   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Mollemycin A                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-JAN-21         0                                  
HETATM    1  C   UNK     0      -6.580  -8.654   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.206  -9.349   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.916  -8.507   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.535  -7.096   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -6.028  -7.475   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -4.662  -5.562   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -4.284  -4.069   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.442  -2.780   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.227  -1.834   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.959  -0.479   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      -0.770  -1.334   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -1.540   0.000   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       2.227  -1.834   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.959  -0.479   0.000  0.00  0.00           O+0
HETATM   19  N   UNK     0       3.442  -2.780   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       4.284  -4.069   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.662  -5.562   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.197  -5.435   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0       4.535  -7.096   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       3.916  -8.507   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.828  -9.748   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.359  -9.578   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.978  -8.168   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       6.066  -6.927   0.000  0.00  0.00           N+0
HETATM   29  O   UNK     0       7.271 -10.819   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.653 -12.229   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.122 -12.399   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.503 -13.809   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.415 -15.050   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.946 -14.881   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       7.565 -13.470   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       7.858 -16.121   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.797 -16.460   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       5.709 -17.701   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.090 -19.111   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.002 -20.352   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       7.533 -20.183   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       8.151 -18.773   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       7.239 -17.532   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       9.682 -18.603   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       8.445 -21.424   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       5.384 -21.763   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       3.853 -21.932   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       2.973 -13.979   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       2.354 -15.389   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       2.873  -9.640   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       3.819 -10.855   0.000  0.00  0.00           O+0
HETATM   52  N   UNK     0       1.519 -10.373   0.000  0.00  0.00           N+0
HETATM   53  C   UNK     0       2.230 -11.739   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       1.150 -12.837   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -0.228 -12.149   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       0.000 -10.626   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      -1.519 -10.373   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      -1.961 -11.281   0.000  0.00  0.00           O+0
HETATM   59  N   UNK     0      -2.873  -9.640   0.000  0.00  0.00           N+0
HETATM   60  O   UNK     0      -3.819 -10.855   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0      -0.768 -13.591   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0      -1.230 -12.017   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0       5.694  -3.450   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0       5.864  -1.920   0.000  0.00  0.00           O+0
HETATM   65  C   UNK     0       7.274  -1.301   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0       4.575  -1.737   0.000  0.00  0.00           O+0
HETATM   67  N   UNK     0      -4.575  -1.737   0.000  0.00  0.00           N+0
HETATM   68  C   UNK     0      -6.045  -2.196   0.000  0.00  0.00           C+0
HETATM   69  O   UNK     0      -6.320  -2.967   0.000  0.00  0.00           O+0
HETATM   70  C   UNK     0      -7.178  -1.153   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      -6.135  -0.020   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      -8.221  -2.286   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      -9.155  -1.062   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0     -10.683  -1.260   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0     -11.275  -2.681   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0     -10.341  -3.905   0.000  0.00  0.00           C+0
HETATM   77  O   UNK     0      -8.813  -3.708   0.000  0.00  0.00           O+0
HETATM   78  C   UNK     0     -10.933  -5.327   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0      -9.999  -6.551   0.000  0.00  0.00           C+0
HETATM   80  C   UNK     0     -12.803  -2.879   0.000  0.00  0.00           C+0
HETATM   81  O   UNK     0     -13.395  -4.300   0.000  0.00  0.00           O+0
HETATM   82  C   UNK     0     -13.737  -1.655   0.000  0.00  0.00           C+0
HETATM   83  C   UNK     0     -12.513  -0.720   0.000  0.00  0.00           C+0
HETATM   84  C   UNK     0     -14.961  -2.590   0.000  0.00  0.00           C+0
HETATM   85  C   UNK     0     -16.383  -1.997   0.000  0.00  0.00           C+0
HETATM   86  O   UNK     0     -14.672  -0.431   0.000  0.00  0.00           O+0
HETATM   87  O   UNK     0      -7.356  -3.002   0.000  0.00  0.00           O+0
HETATM   88  O   UNK     0      -8.311  -0.110   0.000  0.00  0.00           O+0
HETATM   89  C   UNK     0      -5.694  -3.450   0.000  0.00  0.00           C+0
HETATM   90  C   UNK     0      -6.935  -4.362   0.000  0.00  0.00           C+0
HETATM   91  C   UNK     0      -6.229  -2.006   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   59                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   89                                                  
CONECT    8    7    9   67                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   12   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   66                                                  
CONECT   20   19   21   63                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   28                                                  
CONECT   24   23   25   50                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27   23                                                       
CONECT   29   26   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   48                                                  
CONECT   33   32   34   37                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34   30                                                       
CONECT   36   34                                                            
CONECT   37   33   38                                                       
CONECT   38   37   39   43                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   46                                                  
CONECT   41   40   42   45                                                  
CONECT   42   41   43   44                                                  
CONECT   43   42   38                                                       
CONECT   44   42                                                            
CONECT   45   41                                                            
CONECT   46   40   47                                                       
CONECT   47   46                                                            
CONECT   48   32   49                                                       
CONECT   49   48                                                            
CONECT   50   24   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53   56                                                  
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56   61   62                                             
CONECT   56   55   57   52                                                  
CONECT   57   56   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57   60    3                                                  
CONECT   60   59                                                            
CONECT   61   55                                                            
CONECT   62   55                                                            
CONECT   63   20   64                                                       
CONECT   64   63   65                                                       
CONECT   65   64                                                            
CONECT   66   19                                                            
CONECT   67    8   68                                                       
CONECT   68   67   69   70                                                  
CONECT   69   68                                                            
CONECT   70   68   71   72   88                                             
CONECT   71   70                                                            
CONECT   72   70   73   87   77                                             
CONECT   73   72   74                                                       
CONECT   74   73   75                                                       
CONECT   75   74   76   80                                                  
CONECT   76   75   77   78                                                  
CONECT   77   76   72                                                       
CONECT   78   76   79                                                       
CONECT   79   78                                                            
CONECT   80   75   81   82                                                  
CONECT   81   80                                                            
CONECT   82   80   83   84   86                                             
CONECT   83   82                                                            
CONECT   84   82   85                                                       
CONECT   85   84                                                            
CONECT   86   82                                                            
CONECT   87   72                                                            
CONECT   88   70                                                            
CONECT   89    7   90   91                                                  
CONECT   90   89                                                            
CONECT   91   89                                                            
MASTER        0    0    0    0    0    0    0    0   91    0  194    0
END

View in JSmol

Synonyms

Value

Source

Generator

Chemical Formula

C₅₉H₉₆N₈O₂₄

Average Mass

1301.4490 Da

Monoisotopic Mass

1300.65375 Da

IUPAC Name

2-[6-ethyl-2-hydroxy-5-(2-hydroxy-2-methylbutanoyl)oxan-2-yl]-N-[(6R,7S,10S,13S,14S,21R,24S)-10-ethyl-6,9,23-trihydroxy-29-{[(2S,4S,5R,6S)-5-{[(2S,4S,5R,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-24-(methoxymethyl)-6-methyl-2,8,11,15,22,25-hexaoxo-13-(propan-2-yl)-12-oxa-3,9,16,17,23,26,27-heptaazatetracyclo[24.4.0.0^{3,7}.0^{16,21}]triacont-29-en-14-yl]-2-hydroxypropanamide

Traditional Name

2-[6-ethyl-2-hydroxy-5-(2-hydroxy-2-methylbutanoyl)oxan-2-yl]-N-[(6R,7S,10S,13S,14S,21R,24S)-10-ethyl-6,9,23-trihydroxy-29-{[(2S,4S,5R,6S)-5-{[(2S,4S,5R,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-13-isopropyl-24-(methoxymethyl)-6-methyl-2,8,11,15,22,25-hexaoxo-12-oxa-3,9,16,17,23,26,27-heptaazatetracyclo[24.4.0.0^{3,7}.0^{16,21}]triacont-29-en-14-yl]-2-hydroxypropanamide

CAS Registry Number

Not Available

SMILES

CCC1OC(O)(CCC1C(=O)C(C)(O)CC)C(C)(O)C(=O)N[C@H]1[C@@H](OC(=O)[C@H](CC)N(O)C(=O)[C@H]2N(CC[C@@]2(C)O)C(=O)C2C=C(CNN2C(=O)[C@H](COC)N(O)C(=O)[C@H]2CCCNN2C1=O)O[C@H]1C[C@H](OC)[C@H](O[C@H]2C[C@H](OC)[C@H](O)[C@H](C)O2)[C@H](C)O1)C(C)C

InChI Identifier

InChI=1S/C59H96N8O24/c1-14-34-54(75)90-45(29(4)5)43(62-55(76)58(10,79)59(80)20-19-33(38(15-2)91-59)48(69)56(8,77)16-3)52(73)64-35(18-17-22-60-64)51(72)67(82)37(28-83-11)50(71)65-36(49(70)63-23-21-57(9,78)47(63)53(74)66(34)81)24-32(27-61-65)88-41-26-40(85-13)46(31(7)87-41)89-42-25-39(84-12)44(68)30(6)86-42/h24,29-31,33-47,60-61,68,77-82H,14-23,25-28H2,1-13H3,(H,62,76)/t30-,31-,33?,34-,35+,36?,37-,38?,39-,40-,41-,42-,43-,44+,45-,46+,47+,56?,57+,58?,59?/m0/s1

InChI Key

RJMAMONPIIYLDD-XUEXKZAKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 900 MHz, C2D6OS, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
1H_1H NMR	[¹H, ¹H] NMR Spectrum (2D, 900 MHz, CDCl3, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 900 MHz, C2D6OS, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 900 MHz, CDCl3, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 900 MHz, C2D6OS, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 900 MHz, CDCl3, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 900 MHz, C2D6OS, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 900 MHz, CDCl3, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 226 MHz, CDCl3, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 900 MHz, C2D6OS, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 900 MHz, CDCl3, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
1H_1H NMR	[¹H, ¹H] NMR Spectrum (2D, 900 MHz, C2D6OS, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 900 MHz, CDCl3, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 900 MHz, C2D6OS, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 226 MHz, CDCl3, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 900 MHz, C2D6OS, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
1H_1H NMR	[¹H, ¹H] NMR Spectrum (2D, 900 MHz, C2D6OS, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 900 MHz, CDCl3, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 900 MHz, CDCl3, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces		24611932

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic glycodepsipeptides. These are peptidomimetic containing a glycodepisipeptide backbone that lies in a cyclic moiety.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Depsipeptides

Direct Parent

Cyclic glycodepsipeptides

Alternative Parents

Substituents

Cyclic glycodepsipeptide
Macrolide lactam
Alpha-amino acid ester
N-acyl-alpha amino acid or derivatives
Macrolactam
Macrolide
O-glycosyl compound
Disaccharide
Glycosyl compound
Alpha-amino acid or derivatives
Acyloin
1,2-diazinane
Oxane
Pyrrolidine
Tertiary alcohol
Tertiary carboxylic acid amide
Alpha-hydroxy ketone
Carboxamide group
Carboxylic acid ester
Carboxylic acid hydrazide
Hemiacetal
Hydroxamic acid
Ketone
Lactam
Lactone
Secondary carboxylic acid amide
Secondary alcohol
Monocarboxylic acid or derivatives
Polyol
Carboxylic acid derivative
Acetal
Dialkyl ether
Oxacycle
Azacycle
Ether
Organoheterocyclic compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic oxide
Organopnictogen compound
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	0.37	ALOGPS
logP	-1	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.27	ChemAxon
pKa (Strongest Basic)	3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	25	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	413.53 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	334.62 m³·mol⁻¹	ChemAxon
Polarizability	132.93 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

NPAtlas ID

2021

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

30974157

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102230378

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Raju R, Khalil ZG, Piggott AM, Blumenthal A, Gardiner DL, Skinner-Adams TS, Capon RJ: Mollemycin A: an antimalarial and antibacterial glyco-hexadepsipeptide-polyketide from an Australian marine-derived Streptomyces sp. (CMB-M0244). Org Lett. 2014 Mar 21;16(6):1716-9. doi: 10.1021/ol5003913. Epub 2014 Mar 11. [PubMed:24611932 ]

Showing NP-Card for Mollemycin A (NP0012613)

MOL for NP0012613 (Mollemycin A)

3D MOL for NP0012613 (Mollemycin A)

3D SDF for NP0012613 (Mollemycin A)

3D-SDF for NP0012613 (Mollemycin A)

PDB for NP0012613 (Mollemycin A)

3D PDB for NP0012613 (Mollemycin A)

SMILES for NP0012613 (Mollemycin A)

INCHI for NP0012613 (Mollemycin A)

Structure for NP0012613 (Mollemycin A)

3D Structure for NP0012613 (Mollemycin A)