NP-MRD: Showing NP-Card for oligomycin b (NP0175579)

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Record Information

Version

2.0

Created at

2022-09-03 13:04:54 UTC

Updated at

2022-09-03 13:04:54 UTC

NP-MRD ID

NP0175579

Secondary Accession Numbers

None

Natural Product Identification

Common Name

oligomycin b

Description

Oligomycin 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. oligomycin b is found in Streptomyces diastatochromogenes and Streptomyces griseolus. oligomycin b was first documented in 2003 (PMID: 12902194). Based on a literature review a significant number of articles have been published on Oligomycin B (PMID: 26565618) (PMID: 32804955) (PMID: 27354061) (PMID: 26672111) (PMID: 25300113) (PMID: 21784985).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032215042D          

 57 59  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309032215042D          

 57 59  0  0  1  0            999 V2000
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   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
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   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
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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
   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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   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
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    9.8707    0.6533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0735    0.4409    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.8589   -0.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0617   -0.5681    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    9.7174    2.8307    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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 32 33  2  0  0  0  0
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  3 42  1  0  0  0  0
 40 43  1  6  0  0  0
 44 43  1  1  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
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 53 54  1  0  0  0  0
 44 54  1  0  0  0  0
 54 55  2  0  0  0  0
 44 56  1  0  0  0  0
 37 56  1  0  0  0  0
 56 57  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0175579

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1CC[C@H]2O[C@]3(O[C@H](C[C@H](C)O)[C@H](C)CC3=O)[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/C45H72O12/c1-12-33-17-15-13-14-16-25(3)42(52)44(11,54)43(53)31(9)40(51)30(8)39(50)29(7)38(49)24(2)18-21-37(48)55-41-28(6)34(20-19-33)56-45(32(41)10)36(47)22-26(4)35(57-45)23-27(5)46/h13-15,17-18,21,24-35,38,40-42,46,49,51-52,54H,12,16,19-20,22-23H2,1-11H3/b14-13+,17-15+,21-18+/t24-,25+,26-,27+,28+,29-,30-,31-,32-,33-,34-,35-,38+,40+,41+,42-,44+,45+/m1/s1

> <INCHI_KEY>
QPRQJOHKNJIMGN-UXAQBZNTSA-N

> <FORMULA>
C45H72O12

> <MOLECULAR_WEIGHT>
805.059

> <EXACT_MASS>
804.502377758

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
129

> <JCHEM_AVERAGE_POLARIZABILITY>
89.53981559699659

> <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,27R,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-3,3',9,13-tetrone

> <ALOGPS_LOGP>
4.40

> <JCHEM_LOGP>
7.164952319333333

> <ALOGPS_LOGS>
-5.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.703234370150629

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.26445725439405

> <JCHEM_PKA_STRONGEST_BASIC>
-2.545446684249253

> <JCHEM_POLAR_SURFACE_AREA>
197.11999999999998

> <JCHEM_REFRACTIVITY>
219.65660000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.31e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oligomycin B

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-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      34.878   3.868   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      35.388   1.955   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  O   UNK     0      18.425   1.220   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      16.937   0.823   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      16.537  -0.664   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      15.048  -1.060   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      14.648  -2.547   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      13.961   0.030   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      15.850   1.913   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      14.362   1.517   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      16.250   3.400   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      17.738   3.797   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      18.139   5.284   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      19.913   1.616   0.000  0.00  0.00           C+0
HETATM   57  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   56                                                  
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   56                                             
CONECT   45   44   46                                                       
CONECT   46   45   47   51                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48                                                            
CONECT   51   46   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   54                                                       
CONECT   54   53   44   55                                                  
CONECT   55   54                                                            
CONECT   56   44   37   57                                                  
CONECT   57   56                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  118    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₅H₇₂O₁₂

Average Mass

805.0590 Da

Monoisotopic Mass

804.50238 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC[C@H]1CC[C@H]2O[C@]3(O[C@H](C[C@H](C)O)[C@H](C)CC3=O)[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/C45H72O12/c1-12-33-17-15-13-14-16-25(3)42(52)44(11,54)43(53)31(9)40(51)30(8)39(50)29(7)38(49)24(2)18-21-37(48)55-41-28(6)34(20-19-33)56-45(32(41)10)36(47)22-26(4)35(57-45)23-27(5)46/h13-15,17-18,21,24-35,38,40-42,46,49,51-52,54H,12,16,19-20,22-23H2,1-11H3/b14-13+,17-15+,21-18+/t24-,25+,26-,27+,28+,29-,30-,31-,32-,33-,34-,35-,38+,40+,41+,42-,44+,45+/m1/s1

InChI Key

QPRQJOHKNJIMGN-UXAQBZNTSA-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
Streptomyces griseolus	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
Alcohol
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

macrolide (CHEBI:7751 )
oligomycin (CHEBI:7751 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.4	ALOGPS
logP	7.16	ChemAxon
logS	-5.2	ALOGPS

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

16735941

KEGG Compound ID

C11312

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281900

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 ]
Chakraborty M, Mahmud NU, Muzahid ANM, Rabby SMF, Islam T: Oligomycins inhibit Magnaporthe oryzae Triticum and suppress wheat blast disease. PLoS One. 2020 Aug 17;15(8):e0233665. doi: 10.1371/journal.pone.0233665. eCollection 2020. [PubMed:32804955 ]
Dame ZT, Islam MT, Helmke E, von Tiedemann A, Laatsch H: Oligomycins and pamamycin homologs impair motility and induce lysis of zoospores of the grapevine downy mildew pathogen, Plasmopara viticola. FEMS Microbiol Lett. 2016 Aug;363(16):fnw167. doi: 10.1093/femsle/fnw167. Epub 2016 Jun 27. [PubMed:27354061 ]
Vlodavsky E, Palzur E, Shehadeh M, Soustiel JF: Post-traumatic cytotoxic edema is directly related to mitochondrial function. J Cereb Blood Flow Metab. 2017 Jan;37(1):166-177. doi: 10.1177/0271678X15621068. Epub 2015 Dec 15. [PubMed:26672111 ]
Danilenko AN, Bibikova MV, Spiridonova IA: [Determination of oligomycins hydrophobicity parameters]. Antibiot Khimioter. 2014;59(3-4):3-6. [PubMed:25300113 ]
Adebiyi A, McNally EM, Jaggar JH: Vasodilation induced by oxygen/glucose deprivation is attenuated in cerebral arteries of SUR2 null mice. Am J Physiol Heart Circ Physiol. 2011 Oct;301(4):H1360-8. doi: 10.1152/ajpheart.00406.2011. Epub 2011 Jul 22. [PubMed:21784985 ]
Grover GJ, Malm J: Pharmacological profile of the selective mitochondrial F1F0 ATP hydrolase inhibitor BMS-199264 in myocardial ischemia. Cardiovasc Ther. 2008 Winter;26(4):287-96. doi: 10.1111/j.1755-5922.2008.00065.x. [PubMed:19035880 ]
Jackson JG, Thayer SA: Mitochondrial modulation of Ca2+ -induced Ca2+ -release in rat sensory neurons. J Neurophysiol. 2006 Sep;96(3):1093-104. doi: 10.1152/jn.00283.2006. Epub 2006 Jun 7. [PubMed:16760347 ]
Quayle JM, Turner MR, Burrell HE, Kamishima T: Effects of hypoxia, anoxia, and metabolic inhibitors on KATP channels in rat femoral artery myocytes. Am J Physiol Heart Circ Physiol. 2006 Jul;291(1):H71-80. doi: 10.1152/ajpheart.01107.2005. Epub 2006 Feb 17. [PubMed:16489108 ]
Yi FX, Bird IM: Pregnancy-specific modulatory role of mitochondria on adenosine 5'-triphosphate-induced cytosolic [Ca2+] signaling in uterine artery endothelial cells. Endocrinology. 2005 Nov;146(11):4844-50. doi: 10.1210/en.2005-0414. Epub 2005 Jul 28. [PubMed:16055429 ]
Moerman KL, Chai CL, Waring P: Evidence that the lichen-derived scabrosin esters target mitochondrial ATP synthase in P388D1 cells. Toxicol Appl Pharmacol. 2003 Aug 1;190(3):232-40. doi: 10.1016/s0041-008x(03)00189-3. [PubMed:12902194 ]
LOTUS database [Link]

Showing NP-Card for oligomycin b (NP0175579)

MOL for NP0175579 (oligomycin b)

3D MOL for NP0175579 (oligomycin b)

3D SDF for NP0175579 (oligomycin b)

3D-SDF for NP0175579 (oligomycin b)

PDB for NP0175579 (oligomycin b)

3D PDB for NP0175579 (oligomycin b)

SMILES for NP0175579 (oligomycin b)

INCHI for NP0175579 (oligomycin b)

Structure for NP0175579 (oligomycin b)

3D Structure for NP0175579 (oligomycin b)