ChemComp-EFO: Oligomycin A

Basic information

• Entry: Database: PDB chemical components / ID: EFO
• Name: Name: Oligomycin A; Synonyms: (1R,4E,5'S,6S,6'S,7R,8S,10R,11R,12S,14R,15S,16R,18E,20E,22R,25S,27R,28S,29R)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2R)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-3',4',5',6'-tetrahydro-3H,9H,13H-spiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2'-pyran]-3,9,13-trione
• Comment: antibiotic*YM

Chemical information

Composition

Formula: C₄₅H₇₄O₁₁ / Number of atoms: 130 / Formula weight: 791.062 / Formal charge: 0

Others

4f4s

Type: NON-POLYMER / PDB classification: HETAIN / Three letter code: EFO / Ideal coordinates details: Corina / Model coordinates PDB-ID: 4F4S

History

Create component	May 23, 2012
Modify synonyms	Mar 13, 2021

• External links: UniChem / ChemSpider / BindingDB / ChEBI / ChEMBL / Metabolights / PubChem / PubChem_TPharma / SureChEMBL / Wikipedia search / Google search

Details

SMILES

• ACDLabs 12.01: O=C2C(O)(C)C(O)C(C)CC=CC=CC(CC)CCC3OC1(OC(C(CC1)C)CC(O)C)C(C)C(OC(=O)C=CC(C)C(O)C(C(=O)C(C)C(O)C2C)C)C3C
• CACTVS 3.370: CC[CH]1CC[CH]2O[C]3(CC[CH](C)[CH](C[CH](C)O)O3)[CH](C)[CH](OC(=O)C=C[CH](C)[CH](O)[CH](C)C(=O)[CH](C)[CH](O)[CH](C)C(=O)[C](C)(O)[CH](O)[CH](C)CC=CC=C1)[CH]2C
• OpenEye OEToolkits 1.7.6: CCC1CCC2C(C(C(C3(O2)CCC(C(O3)CC(C)O)C)C)OC(=O)C=CC(C(C(C(=O)C(C(C(C(=O)C(C(C(CC=CC=C1)C)O)(C)O)C)O)C)C)O)C)C

SMILES CANONICAL

• CACTVS 3.370: 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
• OpenEye OEToolkits 1.7.6: CC[C@@H]\1CC[C@H]2[C@H]([C@H]([C@@H]([C@]3(O2)CC[C@@H]([C@@H](O3)C[C@@H](C)O)C)C)OC(=O)/C=C/[C@@H]([C@H]([C@@H](C(=O)[C@@H]([C@H]([C@@H](C(=O)[C@]([C@H]([C@@H](C/C=C/C=C1)C)O)(C)O)C)O)C)C)O)C)C

InChI

• InChI 1.03: 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-/m0/s1

InChIKey

• InChI 1.03: MNULEGDCPYONBU-AWJDAWNUSA-N

SYSTEMATIC NAME

• ACDLabs 12.01: (1R,4E,5'S,6S,6'S,7R,8S,10R,11R,12S,14R,15S,16R,18E,20E,22R,25S,27R,28S,29R)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2R)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-3',4',5',6'-tetrahydro-3H,9H,13H-spiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2'-pyran]-3,9,13-trione
• OpenEye OEToolkits 1.7.6: (1S,4R,5E,5'S,6'S,7E,10R,11S,12R,14S,15R,16R,18S,19R,20S,21E,25R,26S,27R,29R)-4-ethyl-5',10,12,14,16,18,20,26,29-nonamethyl-11,12,15,19-tetrakis(oxidanyl)-6'-[(2R)-2-oxidanylpropyl]spiro[24,28-dioxabicyclo[23.3.1]nonacosa-5,7,21-triene-27,2'-oxane]-13,17,23-trione

PDB entries

Showing all 5 items

PDB-3wgv:
Crystal structure of a Na+-bound Na+,K+-ATPase preceding the E1P state with oligomycin

PDB-4f4s:
Structure of the yeast F1Fo ATPase c10 ring with bound oligomycin

PDB-4wq0:
Crystal structure of cytochrome P450 CYP107W1 from Streptomyces avermitilis in complex with Oligomycin A

PDB-5bps:
Structure of the yeast F1FO ATPase C10 ring with oligomycin A

PDB-6cp5:
Monomer yeast ATP synthase Fo reconstituted in nanodisc with inhibitor of oligomycin bound generated from focused refinement.