NP-MRD: Showing NP-Card for (6s,7s,9z,12r)-12-[(2s,4e,6r,7r,9r)-7,9-dihydroxy-4,6-dimethyldec-4-en-2-yl]-7,9-dimethyl-2-oxo-1-oxacyclododec-9-en-6-yl (2e,4e,6e,8e,10e,12s,13s,15s)-12,13,15-trihydroxy-4,6,10-trimethylhexadeca-2,4,6,8,10-pentaenoate (NP0278755)

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Record Information

Version

1.0

Created at

2022-09-09 03:53:59 UTC

Updated at

2022-09-09 03:53:59 UTC

NP-MRD ID

NP0278755

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6s,7s,9z,12r)-12-[(2s,4e,6r,7r,9r)-7,9-dihydroxy-4,6-dimethyldec-4-en-2-yl]-7,9-dimethyl-2-oxo-1-oxacyclododec-9-en-6-yl (2e,4e,6e,8e,10e,12s,13s,15s)-12,13,15-trihydroxy-4,6,10-trimethylhexadeca-2,4,6,8,10-pentaenoate

Description

Mycolactone B belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. (6s,7s,9z,12r)-12-[(2s,4e,6r,7r,9r)-7,9-dihydroxy-4,6-dimethyldec-4-en-2-yl]-7,9-dimethyl-2-oxo-1-oxacyclododec-9-en-6-yl (2e,4e,6e,8e,10e,12s,13s,15s)-12,13,15-trihydroxy-4,6,10-trimethylhexadeca-2,4,6,8,10-pentaenoate is found in Mycobacterium ulcerans. It was first documented in 2019 (PMID: 32091711). Based on a literature review a significant number of articles have been published on Mycolactone B (PMID: 31425525) (PMID: 31295000) (PMID: 31174850) (PMID: 30860179).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092205542D          

 53 53  0  0  1  0            999 V2000
   -3.5724    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   11.1375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   11.5500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   12.7875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7158   12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   13.6125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868   14.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   14.8500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4302   15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   15.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    8.6625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    7.8375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    7.4250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5737    6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.7171    7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    9.0750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    8.6625    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  1  0  0  0
  5 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  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  6  0  0  0
 43 45  1  0  0  0  0
 45 46  1  6  0  0  0
 45 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  6  0  0  0
 26 51  1  0  0  0  0
 51 52  1  6  0  0  0
 51 53  1  0  0  0  0
  2 53  1  0  0  0  0
M  END

     RDKit          3D

123123  0  0  0  0  0  0  0  0999 V2000
    1.8658    0.5669   -1.7471 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6670    1.6303   -1.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9625    1.4246   -0.9542 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7450    1.7922    0.8026 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5572    0.5702    0.5062 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9237   -0.7471    0.6731 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5181    0.7225   -0.5984 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7706   -0.1449   -0.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7301   -1.5876   -0.4375 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8982    0.5353   -0.4204 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2464    0.0407   -0.2705 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.8992    0.5672    1.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6816   -1.3067   -0.6307 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4802   -2.3354    0.2356 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2356   -1.3402   -0.8551 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6456   -2.6537   -1.4362 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.1289   -2.6776   -1.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1799   -3.7637   -0.7529 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1458    1.8246    2.0201 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8758    1.2643    3.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6700    1.0077    4.0890 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4075    0.8829    3.4392 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5484    1.7365    2.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3442    1.0787    1.9890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4204    2.2610    1.4549 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8639    1.8468    1.8534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4406    2.1093    3.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8087    2.7312    3.9236 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5767    1.1117    2.4754 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.9908   -0.4113    1.7245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7973   -0.7254    2.9075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5336   -0.7530    0.5359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8699   -1.3080    0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.7065   -2.1695   -0.9695 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -11.1390   -2.3859   -2.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4627   -2.9577   -2.5388 C   0  0  2  0  0  0  0  0  0  0  0  0
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  -13.3074   -1.8329   -3.1455 C   0  0  1  0  0  0  0  0  0  0  0  0
  -14.6253   -2.2693   -3.3450 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3467   -0.6826   -2.1649 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.1703    0.4767   -2.7108 C   0  0  2  0  0  0  0  0  0  0  0  0
  -13.5819    0.9783   -3.9917 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2066    1.5178   -1.7561 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5725    2.3859    0.0060 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4676    3.3151   -0.6109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9224    2.8064   -0.5254 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.8479    0.6899   -1.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9855    0.5897    0.8411 H   0  0  0  0  0  0  0  0  0  0  0  0
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   11.5490    0.0883    1.9223 H   0  0  0  0  0  0  0  0  0  0  0  0
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   11.0951   -2.1499    1.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.7678   -1.0838    0.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.5227    0.0145    3.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
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 49116  1  0
 50117  1  0
M  END


  Mrv1652309092205542D          

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    1.4289    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4289    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    8.6625    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
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  9 10  1  0  0  0  0
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 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  1  0  0  0
  5 20  1  0  0  0  0
 20 21  1  0  0  0  0
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 26 51  1  0  0  0  0
 51 52  1  6  0  0  0
 51 53  1  0  0  0  0
  2 53  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0278755

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](O)C[C@@H](O)[C@H](C)\C=C(/C)C[C@H](C)[C@H]1C\C=C(C)/C[C@H](C)[C@H](CCCC(=O)O1)OC(=O)\C=C\C(\C)=C\C(\C)=C\C=C\C(\C)=C\[C@H](O)[C@@H](O)C[C@H](C)O

> <INCHI_IDENTIFIER>
InChI=1S/C44H70O9/c1-28(13-11-14-29(2)25-39(48)40(49)27-37(10)46)21-30(3)18-20-44(51)52-41-15-12-16-43(50)53-42(19-17-31(4)22-34(41)7)35(8)24-32(5)23-33(6)38(47)26-36(9)45/h11,13-14,17-18,20-21,23,25,33-42,45-49H,12,15-16,19,22,24,26-27H2,1-10H3/b14-11+,20-18+,28-13+,29-25+,30-21+,31-17-,32-23+/t33-,34+,35+,36-,37+,38-,39+,40+,41+,42-/m1/s1

> <INCHI_KEY>
WKTLNJXZVDLRTJ-PCNYYULESA-N

> <FORMULA>
C44H70O9

> <MOLECULAR_WEIGHT>
743.035

> <EXACT_MASS>
742.501983834

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
123

> <JCHEM_AVERAGE_POLARIZABILITY>
87.36318084007496

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6S,7S,9Z,12R)-12-[(2S,4E,6R,7R,9R)-7,9-dihydroxy-4,6-dimethyldec-4-en-2-yl]-7,9-dimethyl-2-oxo-1-oxacyclododec-9-en-6-yl (2E,4E,6E,8E,10E,12S,13S,15S)-12,13,15-trihydroxy-4,6,10-trimethylhexadeca-2,4,6,8,10-pentaenoate

> <JCHEM_LOGP>
6.4509314039999985

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.580888609254803

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.584436646260283

> <JCHEM_PKA_STRONGEST_BASIC>
-2.545385313567307

> <JCHEM_POLAR_SURFACE_AREA>
153.74999999999997

> <JCHEM_REFRACTIVITY>
219.49580000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(6S,7S,9Z,12R)-12-[(2S,4E,6R,7R,9R)-7,9-dihydroxy-4,6-dimethyldec-4-en-2-yl]-7,9-dimethyl-2-oxo-1-oxacyclododec-9-en-6-yl (2E,4E,6E,8E,10E,12S,13S,15S)-12,13,15-trihydroxy-4,6,10-trimethylhexadeca-2,4,6,8,10-pentaenoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.668  16.170   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335  16.940   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335  18.480   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001  19.250   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001  20.790   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335  21.560   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335  23.100   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.668  20.790   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.002  21.560   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -9.336  20.790   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.002  23.100   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -9.336  23.870   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -10.669  23.100   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -9.336  25.410   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -8.002  26.180   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0     -10.669  26.180   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -10.669  27.720   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -12.003  28.490   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -9.336  28.490   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.667  21.560   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.334  20.790   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.000  21.560   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.334  19.250   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.000  18.480   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.000  16.940   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.334  16.170   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.334  14.630   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.000  13.860   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.000  12.320   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.334  14.630   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.667  13.860   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.001  14.630   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.001  16.170   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.335  13.860   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.668  14.630   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.668  16.170   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.002  13.860   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.336  14.630   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      10.669  13.860   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      12.003  14.630   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      12.003  16.170   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      13.337  13.860   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      14.670  14.630   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      14.670  16.170   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      16.004  13.860   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      16.004  12.320   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      17.338  14.630   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      18.672  13.860   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      20.005  14.630   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      18.672  12.320   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      -2.667  16.940   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -2.667  18.480   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -4.001  16.170   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   53                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   20                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    5   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   51                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48                                                            
CONECT   51   26   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51    2                                                       
MASTER        0    0    0    0    0    0    0    0   53    0  106    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₄H₇₀O₉

Average Mass

743.0350 Da

Monoisotopic Mass

742.50198 Da

IUPAC Name

(6S,7S,9Z,12R)-12-[(2S,4E,6R,7R,9R)-7,9-dihydroxy-4,6-dimethyldec-4-en-2-yl]-7,9-dimethyl-2-oxo-1-oxacyclododec-9-en-6-yl (2E,4E,6E,8E,10E,12S,13S,15S)-12,13,15-trihydroxy-4,6,10-trimethylhexadeca-2,4,6,8,10-pentaenoate

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H](O)C[C@@H](O)[C@H](C)\C=C(/C)C[C@H](C)[C@H]1C\C=C(C)/C[C@H](C)[C@H](CCCC(=O)O1)OC(=O)\C=C\C(\C)=C\C(\C)=C\C=C\C(\C)=C\[C@H](O)[C@@H](O)C[C@H](C)O

InChI Identifier

InChI=1S/C44H70O9/c1-28(13-11-14-29(2)25-39(48)40(49)27-37(10)46)21-30(3)18-20-44(51)52-41-15-12-16-43(50)53-42(19-17-31(4)22-34(41)7)35(8)24-32(5)23-33(6)38(47)26-36(9)45/h11,13-14,17-18,20-21,23,25,33-42,45-49H,12,15-16,19,22,24,26-27H2,1-10H3/b14-11+,20-18+,28-13+,29-25+,30-21+,31-17-,32-23+/t33-,34+,35+,36-,37+,38-,39+,40+,41+,42-/m1/s1

InChI Key

WKTLNJXZVDLRTJ-PCNYYULESA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Mycobacterium ulcerans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Mycolactone
Diterpenoid
Diterpene lactone
Macrolide
Long chain fatty alcohol
Fatty alcohol
Fatty acid ester
Fatty acyl
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	6.45	ChemAxon
pKa (Strongest Acidic)	13.58	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.75 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	219.5 m³·mol⁻¹	ChemAxon
Polarizability	87.36 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

58163695

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102372899

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Guenin-Mace L, Ruf MT, Pluschke G, Demangel C: Mycolactone: More than Just a Cytotoxin.. 2019. [PubMed:32091711 ]
Fraga AG, Trigo G, Murthy RK, Akhtar S, Hebbur M, Pacheco AR, Dominguez J, Silva-Gomes R, Goncalves CM, Oliveira H, Castro AG, Sharma U, Azeredo J, Pedrosa J: Antimicrobial activity of Mycobacteriophage D29 Lysin B during Mycobacterium ulcerans infection. PLoS Negl Trop Dis. 2019 Aug 19;13(8):e0007113. doi: 10.1371/journal.pntd.0007113. eCollection 2019 Aug. [PubMed:31425525 ]
Gehringer M, Mader P, Gersbach P, Pfeiffer B, Scherr N, Dangy JP, Pluschke G, Altmann KH: Configurationally Stabilized Analogs of M. ulcerans Exotoxins Mycolactones A and B Reveal the Importance of Side Chain Geometry for Mycolactone Virulence. Org Lett. 2019 Aug 2;21(15):5853-5857. doi: 10.1021/acs.orglett.9b01947. Epub 2019 Jul 11. [PubMed:31295000 ]
Aydin F, Sun R, Swanson JMJ: Mycolactone Toxin Membrane Permeation: Atomistic versus Coarse-Grained MARTINI Simulations. Biophys J. 2019 Jul 9;117(1):87-98. doi: 10.1016/j.bpj.2019.05.012. Epub 2019 May 21. [PubMed:31174850 ]
Singh A, William McBride JH, Govan B, Pearson M: Survey of local fauna from endemic areas of Northern Queensland, Australia for the presence of Mycobacterium ulcerans. Int J Mycobacteriol. 2019 Jan-Mar;8(1):48-52. doi: 10.4103/ijmy.ijmy_168_18. [PubMed:30860179 ]
LOTUS database [Link]

Showing NP-Card for (6s,7s,9z,12r)-12-[(2s,4e,6r,7r,9r)-7,9-dihydroxy-4,6-dimethyldec-4-en-2-yl]-7,9-dimethyl-2-oxo-1-oxacyclododec-9-en-6-yl (2e,4e,6e,8e,10e,12s,13s,15s)-12,13,15-trihydroxy-4,6,10-trimethylhexadeca-2,4,6,8,10-pentaenoate (NP0278755)

MOL for NP0278755 ((6s,7s,9z,12r)-12-[(2s,4e,6r,7r,9r)-7,9-dihydroxy-4,6-dimethyldec-4-en-2-yl]-7,9-dimethyl-2-oxo-1-oxacyclododec-9-en-6-yl (2e,4e,6e,8e,10e,12s,13s,15s)-12,13,15-trihydroxy-4,6,10-trimethylhexadeca-2,4,6,8,10-pentaenoate)

3D MOL for NP0278755 ((6s,7s,9z,12r)-12-[(2s,4e,6r,7r,9r)-7,9-dihydroxy-4,6-dimethyldec-4-en-2-yl]-7,9-dimethyl-2-oxo-1-oxacyclododec-9-en-6-yl (2e,4e,6e,8e,10e,12s,13s,15s)-12,13,15-trihydroxy-4,6,10-trimethylhexadeca-2,4,6,8,10-pentaenoate)

3D SDF for NP0278755 ((6s,7s,9z,12r)-12-[(2s,4e,6r,7r,9r)-7,9-dihydroxy-4,6-dimethyldec-4-en-2-yl]-7,9-dimethyl-2-oxo-1-oxacyclododec-9-en-6-yl (2e,4e,6e,8e,10e,12s,13s,15s)-12,13,15-trihydroxy-4,6,10-trimethylhexadeca-2,4,6,8,10-pentaenoate)

3D-SDF for NP0278755 ((6s,7s,9z,12r)-12-[(2s,4e,6r,7r,9r)-7,9-dihydroxy-4,6-dimethyldec-4-en-2-yl]-7,9-dimethyl-2-oxo-1-oxacyclododec-9-en-6-yl (2e,4e,6e,8e,10e,12s,13s,15s)-12,13,15-trihydroxy-4,6,10-trimethylhexadeca-2,4,6,8,10-pentaenoate)

PDB for NP0278755 ((6s,7s,9z,12r)-12-[(2s,4e,6r,7r,9r)-7,9-dihydroxy-4,6-dimethyldec-4-en-2-yl]-7,9-dimethyl-2-oxo-1-oxacyclododec-9-en-6-yl (2e,4e,6e,8e,10e,12s,13s,15s)-12,13,15-trihydroxy-4,6,10-trimethylhexadeca-2,4,6,8,10-pentaenoate)

3D PDB for NP0278755 ((6s,7s,9z,12r)-12-[(2s,4e,6r,7r,9r)-7,9-dihydroxy-4,6-dimethyldec-4-en-2-yl]-7,9-dimethyl-2-oxo-1-oxacyclododec-9-en-6-yl (2e,4e,6e,8e,10e,12s,13s,15s)-12,13,15-trihydroxy-4,6,10-trimethylhexadeca-2,4,6,8,10-pentaenoate)

SMILES for NP0278755 ((6s,7s,9z,12r)-12-[(2s,4e,6r,7r,9r)-7,9-dihydroxy-4,6-dimethyldec-4-en-2-yl]-7,9-dimethyl-2-oxo-1-oxacyclododec-9-en-6-yl (2e,4e,6e,8e,10e,12s,13s,15s)-12,13,15-trihydroxy-4,6,10-trimethylhexadeca-2,4,6,8,10-pentaenoate)

INCHI for NP0278755 ((6s,7s,9z,12r)-12-[(2s,4e,6r,7r,9r)-7,9-dihydroxy-4,6-dimethyldec-4-en-2-yl]-7,9-dimethyl-2-oxo-1-oxacyclododec-9-en-6-yl (2e,4e,6e,8e,10e,12s,13s,15s)-12,13,15-trihydroxy-4,6,10-trimethylhexadeca-2,4,6,8,10-pentaenoate)

Structure for NP0278755 ((6s,7s,9z,12r)-12-[(2s,4e,6r,7r,9r)-7,9-dihydroxy-4,6-dimethyldec-4-en-2-yl]-7,9-dimethyl-2-oxo-1-oxacyclododec-9-en-6-yl (2e,4e,6e,8e,10e,12s,13s,15s)-12,13,15-trihydroxy-4,6,10-trimethylhexadeca-2,4,6,8,10-pentaenoate)

3D Structure for NP0278755 ((6s,7s,9z,12r)-12-[(2s,4e,6r,7r,9r)-7,9-dihydroxy-4,6-dimethyldec-4-en-2-yl]-7,9-dimethyl-2-oxo-1-oxacyclododec-9-en-6-yl (2e,4e,6e,8e,10e,12s,13s,15s)-12,13,15-trihydroxy-4,6,10-trimethylhexadeca-2,4,6,8,10-pentaenoate)