NP-MRD: Showing NP-Card for (1s,4e,5'r,6r,6'r,7s,8r,10s,11r,12r,14r,15r,16s,18e,20e,22s,25s,27s,28r,29s)-22-ethyl-7,11,15-trihydroxy-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 (NP0322394)

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Record Information

Version

2.0

Created at

2022-09-12 01:08:29 UTC

Updated at

2022-09-12 01:08:29 UTC

NP-MRD ID

NP0322394

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4e,5'r,6r,6'r,7s,8r,10s,11r,12r,14r,15r,16s,18e,20e,22s,25s,27s,28r,29s)-22-ethyl-7,11,15-trihydroxy-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 C 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,11r,12r,14r,15r,16s,18e,20e,22s,25s,27s,28r,29s)-22-ethyl-7,11,15-trihydroxy-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 diastatochromogenes. (1s,4e,5'r,6r,6'r,7s,8r,10s,11r,12r,14r,15r,16s,18e,20e,22s,25s,27s,28r,29s)-22-ethyl-7,11,15-trihydroxy-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 2015 (PMID: 25849761). Based on a literature review a small amount of articles have been published on Oligomycin C (PMID: 26565618) (PMID: 34119221) (PMID: 35921248) (PMID: 26883908).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122203082D          

 55 57  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  1  0  0  0  0  0  0  0  0  0
   19.0076    1.6092    0.0000 C   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  2  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
    8.3376    3.2024    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7551    3.7866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1348    3.4149    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  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 36 35  1  6  0  0  0
 36 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
  3 41  1  0  0  0  0
 39 42  1  1  0  0  0
 43 42  1  6  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  1  0  0  0
 46 48  1  0  0  0  0
 48 49  1  1  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 50 52  1  6  0  0  0
 48 53  1  0  0  0  0
 43 53  1  0  0  0  0
 43 54  1  0  0  0  0
 36 54  1  0  0  0  0
 54 55  1  1  0  0  0
M  END

     RDKit          3D

129131  0  0  0  0  0  0  0  0999 V2000
    2.8128    5.5870   -0.1897 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1264    4.8209   -1.2745 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8464    1.8884   -0.7435 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -6.2375    1.6184   -0.2527 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.2851    2.2661   -1.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.3484   -0.3572   -1.4469 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.8144   -1.8302    1.0050 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6443   -2.1883    2.3218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1553   -3.0215    0.1227 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.4528   -3.6654    0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9967   -3.9357    0.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0631   -4.9483    0.8211 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7187    2.9489    0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9561    0.4680    1.8457 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3824    0.4219    2.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3453    0.2267    1.0529 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7705   -1.2204    1.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
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 38104  1  0
M  END


  Mrv1652309122203082D          

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   14.2245    0.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   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
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   10.2999    2.2465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.8707    0.6533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.4909    1.0251    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   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
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 43 54  1  0  0  0  0
 36 54  1  0  0  0  0
 54 55  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0322394

> <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@H](C)[C@H](O)[C@@H](C)C\C=C\C=C\1)[C@H]2C

> <INCHI_IDENTIFIER>
InChI=1S/C45H74O10/c1-12-35-17-15-13-14-16-26(3)39(48)30(7)41(50)32(9)43(52)33(10)42(51)31(8)40(49)27(4)18-21-38(47)53-44-29(6)36(20-19-35)54-45(34(44)11)23-22-25(2)37(55-45)24-28(5)46/h13-15,17-18,21,25-37,39-40,43-44,46,48-49,52H,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+,37-,39-,40+,43-,44+,45-/m1/s1

> <INCHI_KEY>
CMMLZMMKTYEOKV-WQRPUZJHSA-N

> <FORMULA>
C45H74O10

> <MOLECULAR_WEIGHT>
775.077

> <EXACT_MASS>
774.528198583

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
129

> <JCHEM_AVERAGE_POLARIZABILITY>
87.49995579945406

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4E,5'R,6R,6'R,7S,8R,10S,11R,12R,14R,15R,16S,18E,20E,22S,25S,27S,28R,29S)-22-ethyl-7,11,15-trihydroxy-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>
8.273005607666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.426403753488213

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.943636543086743

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5454300947629065

> <JCHEM_POLAR_SURFACE_AREA>
159.82

> <JCHEM_REFRACTIVITY>
217.75080000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4E,5'R,6R,6'R,7S,8R,10S,11R,12R,14R,15R,16S,18E,20E,22S,25S,27S,28R,29S)-22-ethyl-7,11,15-trihydroxy-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_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-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      35.481   3.004   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      33.592   1.120   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      35.080   1.517   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      34.680   0.030   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      36.168   0.426   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      34.279  -1.457   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      35.366  -2.547   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      32.791  -1.854   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      32.390  -3.341   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      31.703  -0.763   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      32.104   0.724   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      30.215  -1.160   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      29.815  -2.647   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      29.128  -0.069   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      29.529   1.418   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      27.640  -0.466   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      27.239  -1.953   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      26.552   0.625   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      25.064   0.228   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      23.977   1.319   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      24.378   2.806   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      22.489   0.922   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      21.401   2.013   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      21.802   3.500   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      23.290   3.896   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      20.715   4.590   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      21.115   6.077   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      22.603   6.474   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      19.227   4.194   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      18.826   2.707   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      18.425   1.220   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      16.937   0.823   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      15.850   1.913   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      14.362   1.517   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      16.250   3.400   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      15.163   4.491   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      15.564   5.978   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      14.476   7.068   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      17.052   6.374   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      17.738   3.797   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      19.913   1.616   0.000  0.00  0.00           C+0
HETATM   55  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   41                                                  
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                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37   54                                                  
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   42                                                  
CONECT   40   39   41                                                       
CONECT   41   40    3                                                       
CONECT   42   39   43                                                       
CONECT   43   42   44   53   54                                             
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49   53                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50                                                            
CONECT   53   48   43                                                       
CONECT   54   43   36   55                                                  
CONECT   55   54                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  114    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₅H₇₄O₁₀

Average Mass

775.0770 Da

Monoisotopic Mass

774.52820 Da

IUPAC Name

Not Available

Traditional Name

Not Available

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@H](C)[C@H](O)[C@@H](C)C\C=C\C=C\1)[C@H]2C

InChI Identifier

InChI=1S/C45H74O10/c1-12-35-17-15-13-14-16-26(3)39(48)30(7)41(50)32(9)43(52)33(10)42(51)31(8)40(49)27(4)18-21-38(47)53-44-29(6)36(20-19-35)54-45(34(44)11)23-22-25(2)37(55-45)24-28(5)46/h13-15,17-18,21,25-37,39-40,43-44,46,48-49,52H,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+,37-,39-,40+,43-,44+,45-/m1/s1

InChI Key

CMMLZMMKTYEOKV-WQRPUZJHSA-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 diastatochromogenes	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
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic ketone
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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

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

78430752

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

134687984

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Salim AA, Tan L, Huang XC, Cho KJ, Lacey E, Hancock JF, Capon RJ: Oligomycins as inhibitors of K-Ras plasma membrane localisation. Org Biomol Chem. 2016 Jan 14;14(2):711-715. doi: 10.1039/c5ob02020d. [PubMed:26565618 ]
Bhadani RV, Gajera HP, Hirpara DG, Kachhadiya HJ, Dave RA: Metabolomics of extracellular compounds and parasitic enzymes of Beauveria bassiana associated with biological control of whiteflies (Bemisia tabaci). Pestic Biochem Physiol. 2021 Jul;176:104877. doi: 10.1016/j.pestbp.2021.104877. Epub 2021 May 21. [PubMed:34119221 ]
Bilyk O, Oliveira GS, de Angelo RM, Almeida MO, Honorio KM, Leeper FJ, Dias MVB, Leadlay PF: Enzyme-Catalyzed Spiroacetal Formation in Polyketide Antibiotic Biosynthesis. J Am Chem Soc. 2022 Aug 17;144(32):14555-14563. doi: 10.1021/jacs.2c03313. Epub 2022 Aug 3. [PubMed:35921248 ]
Han S, Pham TV, Kim JH, Lim YR, Park HG, Cha GS, Yun CH, Chun YJ, Kang LW, Kim D: Structural Analysis of the Streptomyces avermitilis CYP107W1-Oligomycin A Complex and Role of the Tryptophan 178 Residue. Mol Cells. 2016 Mar;39(3):211-6. doi: 10.14348/molcells.2016.2226. Epub 2016 Feb 16. [PubMed:26883908 ]
Han S, Pham TV, Kim JH, Lim YR, Park HG, Cha GS, Yun CH, Chun YJ, Kang LW, Kim D: Functional characterization of CYP107W1 from Streptomyces avermitilis and biosynthesis of macrolide oligomycin A. Arch Biochem Biophys. 2015 Jun 1;575:1-7. doi: 10.1016/j.abb.2015.03.025. Epub 2015 Apr 4. [PubMed:25849761 ]
LOTUS database [Link]

Showing NP-Card for (1s,4e,5'r,6r,6'r,7s,8r,10s,11r,12r,14r,15r,16s,18e,20e,22s,25s,27s,28r,29s)-22-ethyl-7,11,15-trihydroxy-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 (NP0322394)

MOL for NP0322394 ((1s,4e,5'r,6r,6'r,7s,8r,10s,11r,12r,14r,15r,16s,18e,20e,22s,25s,27s,28r,29s)-22-ethyl-7,11,15-trihydroxy-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 NP0322394 ((1s,4e,5'r,6r,6'r,7s,8r,10s,11r,12r,14r,15r,16s,18e,20e,22s,25s,27s,28r,29s)-22-ethyl-7,11,15-trihydroxy-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 NP0322394 ((1s,4e,5'r,6r,6'r,7s,8r,10s,11r,12r,14r,15r,16s,18e,20e,22s,25s,27s,28r,29s)-22-ethyl-7,11,15-trihydroxy-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 NP0322394 ((1s,4e,5'r,6r,6'r,7s,8r,10s,11r,12r,14r,15r,16s,18e,20e,22s,25s,27s,28r,29s)-22-ethyl-7,11,15-trihydroxy-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 NP0322394 ((1s,4e,5'r,6r,6'r,7s,8r,10s,11r,12r,14r,15r,16s,18e,20e,22s,25s,27s,28r,29s)-22-ethyl-7,11,15-trihydroxy-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 NP0322394 ((1s,4e,5'r,6r,6'r,7s,8r,10s,11r,12r,14r,15r,16s,18e,20e,22s,25s,27s,28r,29s)-22-ethyl-7,11,15-trihydroxy-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 NP0322394 ((1s,4e,5'r,6r,6'r,7s,8r,10s,11r,12r,14r,15r,16s,18e,20e,22s,25s,27s,28r,29s)-22-ethyl-7,11,15-trihydroxy-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 NP0322394 ((1s,4e,5'r,6r,6'r,7s,8r,10s,11r,12r,14r,15r,16s,18e,20e,22s,25s,27s,28r,29s)-22-ethyl-7,11,15-trihydroxy-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 NP0322394 ((1s,4e,5'r,6r,6'r,7s,8r,10s,11r,12r,14r,15r,16s,18e,20e,22s,25s,27s,28r,29s)-22-ethyl-7,11,15-trihydroxy-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 NP0322394 ((1s,4e,5'r,6r,6'r,7s,8r,10s,11r,12r,14r,15r,16s,18e,20e,22s,25s,27s,28r,29s)-22-ethyl-7,11,15-trihydroxy-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)