NP-MRD: Showing NP-Card for (1s,4e,5'r,6r,6'r,7s,8r,10s,11s,12r,14s,15r,16s,18e,20e,22s,25r,27s,28r,29s)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2s)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione (NP0197420)

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Record Information

Version

2.0

Created at

2022-09-04 15:40:47 UTC

Updated at

2022-09-04 15:40:47 UTC

NP-MRD ID

NP0197420

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4e,5'r,6r,6'r,7s,8r,10s,11s,12r,14s,15r,16s,18e,20e,22s,25r,27s,28r,29s)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2s)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione

Description

Oligomycin A 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. (1s,4e,5'r,6r,6'r,7s,8r,10s,11s,12r,14s,15r,16s,18e,20e,22s,25r,27s,28r,29s)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2s)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione is found in Streptomyces albidoflavus, Streptomyces avermitilis, Streptomyces coelicolor, Streptomyces diastaticus, Streptomyces diastatochromogenes, Streptomyces griseolus and Streptomyces libani. (1s,4e,5'r,6r,6'r,7s,8r,10s,11s,12r,14s,15r,16s,18e,20e,22s,25r,27s,28r,29s)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2s)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione was first documented in 2021 (PMID: 34043357). Based on a literature review a significant number of articles have been published on oligomycin A (PMID: 33993959) (PMID: 33951287) (PMID: 33918382) (PMID: 33872751) (PMID: 36032127) (PMID: 35964468).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042217402D          

 56 58  0  0  1  0            999 V2000
   12.3235    4.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9061    3.6804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6915    2.8838    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.4887    3.0962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0712    2.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8684    2.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4510    2.1403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2481    2.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8307    1.7686    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.6161    0.9720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6279    1.9810    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.8425    2.7776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2104    1.3968    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.9577    1.0471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6846    2.0720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9958    0.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7930    0.8127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5784    0.0161    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.3756    0.2285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3637   -0.7805    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.9463   -1.3647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5666   -0.9930    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.3519   -1.7896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9840   -0.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1986    0.3878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1868   -0.6212    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.9722   -1.4178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6043   -0.0370    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.8189    0.7595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8071   -0.2495    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.5925   -1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2245    0.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4273    0.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8448    0.7064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0594    1.5030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0476    0.4940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4650    1.0782    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.6797    1.8748    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.4769    2.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0971    2.4589    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.3117    3.2555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1089    3.4680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2999    2.2465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0853    1.4499    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.8707    0.6533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0735    0.4409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4909    1.0251    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6938    0.8127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7056    1.8217    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1230    2.4058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3258    2.1934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1112    1.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7433    2.7776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5027    2.0341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6679    0.8658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.4532    0.0692    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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  6  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 37 36  1  6  0  0  0
 37 38  1  0  0  0  0
 38 39  1  6  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
  3 42  1  0  0  0  0
 40 43  1  6  0  0  0
 44 43  1  6  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  1  0  0  0
 47 49  1  0  0  0  0
 49 50  1  1  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  1  6  0  0  0
 49 54  1  0  0  0  0
 44 54  1  0  0  0  0
 44 55  1  0  0  0  0
 37 55  1  0  0  0  0
 55 56  1  1  0  0  0
M  END

     RDKit          3D

130132  0  0  0  0  0  0  0  0999 V2000
   -1.8684    5.1915   -0.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3377    4.7903    0.8767 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1914    4.3813    2.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6432    5.1715    1.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3025    4.8838    0.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0279    3.8210   -0.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0424    3.2198    0.8067 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4393    3.3304    0.2268 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3245    4.0777   -1.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0622    2.0048   -0.0633 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3496    1.8417   -1.4354 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3828    1.8606    0.6531 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1902    1.7306    2.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2552    2.9055    0.3987 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0779    0.6046    0.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0840    0.6187   -0.4532 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4848   -0.6979    0.5985 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1875   -1.3207    1.7849 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6487   -1.6492   -0.5649 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9484   -2.0501   -0.7344 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6780   -2.8274   -0.4181 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3531   -4.0288   -1.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3620   -2.5206   -1.0098 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2818   -1.8008   -1.9735 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1132   -3.0808   -0.4444 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3249   -4.5317   -0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9046   -2.7944   -1.2389 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.3169   -3.9385   -2.0038 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1972   -4.4869   -3.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0082   -3.4904   -2.5612 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6922   -0.5129    0.3586 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.6356    0.4168    1.0464 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5683    1.8537    0.5811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2481    2.5235    0.9264 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4641   -0.6339    0.0431 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8776    0.3632   -1.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1965   -0.0226   -1.6185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2428    0.0282   -0.4773 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.4444   -0.7532   -0.9130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6280   -0.3491    0.7845 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.3614   -0.8280    1.9520 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6364    4.9384   -1.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3362    4.4948   -1.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0211    3.3558   -1.8921 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2734    2.1117   -1.6375 H   0  0  0  0  0  0  0  0  0  0  0  0
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 38102  1  1
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 39105  1  0
M  END


  Mrv1652309042217402D          

 56 58  0  0  1  0            999 V2000
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   14.5925   -1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.4273    0.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.0594    1.5030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.0971    2.4589    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.3117    3.2555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.2999    2.2465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0853    1.4499    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.8707    0.6533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0735    0.4409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4909    1.0251    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6938    0.8127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7433    2.7776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5027    2.0341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6679    0.8658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.4532    0.0692    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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
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 34 35  2  0  0  0  0
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  3 42  1  0  0  0  0
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 51 52  1  0  0  0  0
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 44 55  1  0  0  0  0
 37 55  1  0  0  0  0
 55 56  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0197420

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1CC[C@H]2O[C@@]3(CC[C@@H](C)[C@@H](C[C@H](C)O)O3)[C@H](C)[C@@H](OC(=O)\C=C\[C@@H](C)[C@H](O)[C@@H](C)C(=O)[C@@H](C)[C@H](O)[C@@H](C)C(=O)[C@@](C)(O)[C@H](O)[C@@H](C)C\C=C\C=C\1)[C@H]2C

> <INCHI_IDENTIFIER>
InChI=1S/C45H74O11/c1-12-34-17-15-13-14-16-27(4)42(51)44(11,53)43(52)32(9)40(50)31(8)39(49)30(7)38(48)26(3)18-21-37(47)54-41-29(6)35(20-19-34)55-45(33(41)10)23-22-25(2)36(56-45)24-28(5)46/h13-15,17-18,21,25-36,38,40-42,46,48,50-51,53H,12,16,19-20,22-24H2,1-11H3/b14-13+,17-15+,21-18+/t25-,26-,27+,28+,29+,30-,31-,32-,33-,34-,35-,36-,38+,40+,41+,42-,44+,45-/m1/s1

> <INCHI_KEY>
MNULEGDCPYONBU-WMBHJXFZSA-N

> <FORMULA>
C45H74O11

> <MOLECULAR_WEIGHT>
791.076

> <EXACT_MASS>
790.523113203

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
130

> <JCHEM_AVERAGE_POLARIZABILITY>
89.12300624357297

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4E,5'R,6R,6'R,7S,8R,10S,11S,12R,14S,15R,16S,18E,20E,22S,25R,27S,28R,29S)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2S)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione

> <JCHEM_LOGP>
7.447626754666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.70521012616219

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.264529805973504

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5454300947629065

> <JCHEM_POLAR_SURFACE_AREA>
180.04999999999995

> <JCHEM_REFRACTIVITY>
219.22780000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
oligomycin A

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      23.004   7.961   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.091   6.870   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.691   5.383   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.179   5.780   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      26.266   4.689   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.754   5.086   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.842   3.995   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      30.330   4.392   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      31.417   3.301   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      31.017   1.814   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      32.905   3.698   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      33.306   5.185   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      33.993   2.607   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      35.388   1.955   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      34.878   3.868   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      33.592   1.120   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      35.080   1.517   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      34.680   0.030   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      36.168   0.426   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      34.279  -1.457   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      35.366  -2.547   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      32.791  -1.854   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      32.390  -3.341   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      31.703  -0.763   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      32.104   0.724   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      30.215  -1.160   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      29.815  -2.647   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      29.128  -0.069   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      29.529   1.418   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      27.640  -0.466   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      27.239  -1.953   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      26.552   0.625   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      25.064   0.228   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      23.977   1.319   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      24.378   2.806   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      22.489   0.922   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      21.401   2.013   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      21.802   3.500   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      23.290   3.896   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      20.715   4.590   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      21.115   6.077   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      22.603   6.474   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      19.227   4.194   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      18.826   2.707   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      18.425   1.220   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      16.937   0.823   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      15.850   1.913   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      14.362   1.517   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      16.250   3.400   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      15.163   4.491   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      13.675   4.094   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      13.274   2.607   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      12.587   5.185   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      17.738   3.797   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      19.913   1.616   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      19.513   0.129   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   42                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   38   55                                                  
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   43                                                  
CONECT   41   40   42                                                       
CONECT   42   41    3                                                       
CONECT   43   40   44                                                       
CONECT   44   43   45   54   55                                             
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   50   54                                                  
CONECT   50   49   51                                                       
CONECT   51   50   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51                                                            
CONECT   54   49   44                                                       
CONECT   55   44   37   56                                                  
CONECT   56   55                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  116    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₅H₇₄O₁₁

Average Mass

791.0760 Da

Monoisotopic Mass

790.52311 Da

IUPAC Name

(1S,4E,5'R,6R,6'R,7S,8R,10S,11S,12R,14S,15R,16S,18E,20E,22S,25R,27S,28R,29S)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2S)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione

Traditional Name

oligomycin A

CAS Registry Number

Not Available

SMILES

CC[C@H]1CC[C@H]2O[C@@]3(CC[C@@H](C)[C@@H](C[C@H](C)O)O3)[C@H](C)[C@@H](OC(=O)\C=C\[C@@H](C)[C@H](O)[C@@H](C)C(=O)[C@@H](C)[C@H](O)[C@@H](C)C(=O)[C@@](C)(O)[C@H](O)[C@@H](C)C\C=C\C=C\1)[C@H]2C

InChI Identifier

InChI=1S/C45H74O11/c1-12-34-17-15-13-14-16-27(4)42(51)44(11,53)43(52)32(9)40(50)31(8)39(49)30(7)38(48)26(3)18-21-37(47)54-41-29(6)35(20-19-34)55-45(33(41)10)23-22-25(2)36(56-45)24-28(5)46/h13-15,17-18,21,25-36,38,40-42,46,48,50-51,53H,12,16,19-20,22-24H2,1-11H3/b14-13+,17-15+,21-18+/t25-,26-,27+,28+,29+,30-,31-,32-,33-,34-,35-,36-,38+,40+,41+,42-,44+,45-/m1/s1

InChI Key

MNULEGDCPYONBU-WMBHJXFZSA-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
Streptomyces albidoflavus	LOTUS Database	35616633
Streptomyces avermitilis	LOTUS Database	35616633
Streptomyces coelicolor	LOTUS Database	35616633
Streptomyces diastaticus	LOTUS Database	35616633
Streptomyces diastatochromogenes	LOTUS Database	35616633
Streptomyces griseolus	LOTUS Database	35616633
Streptomyces libani	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

Macrolide
Ketal
Acyloin
Oxane
Tertiary alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Cyclic ketone
Secondary alcohol
Carboxylic acid ester
Lactone
Ketone
Oxacycle
Acetal
Polyol
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Organooxygen compound
Carbonyl group
Aldehyde
Alcohol
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

oligomycin (CHEBI:28285 )

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	7.45	ChemAxon
pKa (Strongest Acidic)	12.26	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	180.05 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	219.23 m³·mol⁻¹	ChemAxon
Polarizability	89.12 Å³	ChemAxon
Number of Rings	3	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

C00038213

Chemspider ID

10308285

KEGG Compound ID

C11311

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281899

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Omelchuk OA, Malyshev VI, Medvedev MG, Lysenkova LN, Belov NM, Dezhenkova LG, Grammatikova NE, Scherbakov AM, Shchekotikhin AE: Stereochemistries and Biological Properties of Oligomycin A Diels-Alder Adducts. J Org Chem. 2021 Jun 18;86(12):7975-7986. doi: 10.1021/acs.joc.1c00296. Epub 2021 May 27. [PubMed:34043357 ]
Xiao L, Niu HJ, Qu TL, Zhang XF, Du FY: Streptomyces sp. FX13 inhibits fungicide-resistant Botrytis cinerea in vitro and in vivo by producing oligomycin A. Pestic Biochem Physiol. 2021 Jun;175:104834. doi: 10.1016/j.pestbp.2021.104834. Epub 2021 Mar 27. [PubMed:33993959 ]
Wang Q, Lu X, Yang H, Yan H, Wen Y: Redox-sensitive transcriptional regulator SoxR directly controls antibiotic production, development and thiol-oxidative stress response in Streptomyces avermitilis. Microb Biotechnol. 2021 May 5. doi: 10.1111/1751-7915.13813. [PubMed:33951287 ]
Vestergaard M, Roshanak S, Ingmer H: Targeting the ATP Synthase in Staphylococcus aureus Small Colony Variants, Streptococcus pyogenes and Pathogenic Fungi. Antibiotics (Basel). 2021 Apr 2;10(4). pii: antibiotics10040376. doi: 10.3390/antibiotics10040376. [PubMed:33918382 ]
Scherbakov AM, Sorokin DV, Omelchuk OA, Shchekotikhin AE, Krasil'nikov MA: Glucose starvation greatly enhances antiproliferative and antiestrogenic potency of oligomycin A in MCF-7 breast cancer cells. Biochimie. 2021 Jul;186:51-58. doi: 10.1016/j.biochi.2021.04.003. Epub 2021 Apr 16. [PubMed:33872751 ]
Conejeros I, Lopez-Osorio S, Zhou E, Velasquez ZD, Del Rio MC, Burgos RA, Alarcon P, Chaparro-Gutierrez JJ, Hermosilla C, Taubert A: Glycolysis, monocarboxylate transport, and purinergic signaling are key events in Eimeria bovis-induced NETosis. Front Immunol. 2022 Aug 11;13:842482. doi: 10.3389/fimmu.2022.842482. eCollection 2022. [PubMed:36032127 ]
Chen B, Zhou X, Yang L, Zhou H, Meng M, Zhang L, Li J: A Cuproptosis Activation Scoring model predicts neoplasm-immunity interactions and personalized treatments in glioma. Comput Biol Med. 2022 Sep;148:105924. doi: 10.1016/j.compbiomed.2022.105924. Epub 2022 Aug 8. [PubMed:35964468 ]
Iriondo MN, Etxaniz A, Varela YR, Ballesteros U, Hervas JH, Montes LR, Goni FM, Alonso A: LC3 subfamily in cardiolipin-mediated mitophagy: a comparison of the LC3A, LC3B and LC3C homologs. Autophagy. 2022 Dec;18(12):2985-3003. doi: 10.1080/15548627.2022.2062111. Epub 2022 Apr 13. [PubMed:35414338 ]
Cores A, Carmona-Zafra N, Martin-Camara O, Sanchez JD, Duarte P, Villacampa M, Bermejo-Bescos P, Martin-Aragon S, Leon R, Menendez JC: Curcumin-Piperlongumine Hybrids with a Multitarget Profile Elicit Neuroprotection in In Vitro Models of Oxidative Stress and Hyperphosphorylation. Antioxidants (Basel). 2021 Dec 24;11(1):28. doi: 10.3390/antiox11010028. [PubMed:35052532 ]
Wu L, Liu J, Tian X, Groleau RR, Feng B, Yang Y, Sedgwick AC, Han HH, Wang Y, Wang HM, Huang F, Bull SD, Zhang H, Huang C, Zang Y, Li J, He XP, Li P, Tang B, James TD, Sessler JL: Dual-Channel Fluorescent Probe for the Simultaneous Monitoring of Peroxynitrite and Adenosine-5'-triphosphate in Cellular Applications. J Am Chem Soc. 2022 Jan 12;144(1):174-183. doi: 10.1021/jacs.1c07954. Epub 2021 Dec 21. [PubMed:34931825 ]
Tian S, Fu L, Zhang J, Xu J, Yuan L, Qin J, Zhang W: Identification of a DNA Methylation-Driven Genes-Based Prognostic Model and Drug Targets in Breast Cancer: In silico Screening of Therapeutic Compounds and in vitro Characterization. Front Immunol. 2021 Oct 20;12:761326. doi: 10.3389/fimmu.2021.761326. eCollection 2021. [PubMed:34745136 ]
Alonso JM, Escobar-Peso A, Palomino-Antolin A, Diez-Iriepa D, Chioua M, Martinez-Alonso E, Iriepa I, Egea J, Alcazar A, Marco-Contelles J: Privileged Quinolylnitrones for the Combined Therapy of Ischemic Stroke and Alzheimer's Disease. Pharmaceuticals (Basel). 2021 Aug 27;14(9):861. doi: 10.3390/ph14090861. [PubMed:34577561 ]
Li X, Tian R, Wang L, Xu C, Wu H, Liu L, Huang C: Oligomycin A promotes radioresistance in HT29 colorectal cancer cells and its mechanisms. Zhong Nan Da Xue Xue Bao Yi Xue Ban. 2021 Feb 28;46(2):113-120. doi: 10.11817/j.issn.1672-7347.2021.200063. [PubMed:33678646 ]
LOTUS database [Link]

Showing NP-Card for (1s,4e,5'r,6r,6'r,7s,8r,10s,11s,12r,14s,15r,16s,18e,20e,22s,25r,27s,28r,29s)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2s)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione (NP0197420)

MOL for NP0197420 ((1s,4e,5'r,6r,6'r,7s,8r,10s,11s,12r,14s,15r,16s,18e,20e,22s,25r,27s,28r,29s)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2s)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione)

3D MOL for NP0197420 ((1s,4e,5'r,6r,6'r,7s,8r,10s,11s,12r,14s,15r,16s,18e,20e,22s,25r,27s,28r,29s)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2s)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione)

3D SDF for NP0197420 ((1s,4e,5'r,6r,6'r,7s,8r,10s,11s,12r,14s,15r,16s,18e,20e,22s,25r,27s,28r,29s)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2s)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione)

3D-SDF for NP0197420 ((1s,4e,5'r,6r,6'r,7s,8r,10s,11s,12r,14s,15r,16s,18e,20e,22s,25r,27s,28r,29s)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2s)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione)

PDB for NP0197420 ((1s,4e,5'r,6r,6'r,7s,8r,10s,11s,12r,14s,15r,16s,18e,20e,22s,25r,27s,28r,29s)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2s)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione)

3D PDB for NP0197420 ((1s,4e,5'r,6r,6'r,7s,8r,10s,11s,12r,14s,15r,16s,18e,20e,22s,25r,27s,28r,29s)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2s)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione)

SMILES for NP0197420 ((1s,4e,5'r,6r,6'r,7s,8r,10s,11s,12r,14s,15r,16s,18e,20e,22s,25r,27s,28r,29s)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2s)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione)

INCHI for NP0197420 ((1s,4e,5'r,6r,6'r,7s,8r,10s,11s,12r,14s,15r,16s,18e,20e,22s,25r,27s,28r,29s)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2s)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione)

Structure for NP0197420 ((1s,4e,5'r,6r,6'r,7s,8r,10s,11s,12r,14s,15r,16s,18e,20e,22s,25r,27s,28r,29s)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2s)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione)

3D Structure for NP0197420 ((1s,4e,5'r,6r,6'r,7s,8r,10s,11s,12r,14s,15r,16s,18e,20e,22s,25r,27s,28r,29s)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2s)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione)