AFB

1,6,7,8,9,11A,12,13,14,14A-DECAHYDRO-1,13-DIHYDROXY-6-METHYL-4H-CYCLOPENT[F]OXACYCLOTRIDECIN-4-ONE

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is present as a standalone ligand in 3 entries

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Chemical Component Summary
Name	1,6,7,8,9,11A,12,13,14,14A-DECAHYDRO-1,13-DIHYDROXY-6-METHYL-4H-CYCLOPENT[F]OXACYCLOTRIDECIN-4-ONE
Synonyms	BREFELDIN A
Identifiers	(1R,2R,3E,7S,11E,13S,15S)-2,15-dihydroxy-7-methyl-6-oxabicyclo[11.3.0]hexadeca-3,11-dien-5-one
Formula	C₁₆ H₂₄ O₄
Molecular Weight	280.359
Type	NON-POLYMER
Isomeric SMILES	C[C@H]1CCC\C=C\[C@@H]2C[C@@H](C[C@H]2[C@@H](\C=C\C(=O)O1)O)O
InChI	InChI=1S/C16H24O4/c1-11-5-3-2-4-6-12-9-13(17)10-14(12)15(18)7-8-16(19)20-11/h4,6-8,11-15,17-18H,2-3,5,9-10H2,1H3/b6-4+,8-7+/t11-,12+,13-,14+,15+/m0/s1
InChIKey	KQNZDYYTLMIZCT-KQPMLPITSA-N

Chemical Details
Formal Charge	0
Atom Count	44
Chiral Atom Count	5
Bond Count	45
Aromatic Bond Count	0

Drug Info: DrugBank

DrugBank ID	DB07348
Name	Brefeldin A
Groups	experimental
Description	A metabolite from Penicillium brefeldianum that exhibits a wide range of antibiotic activity.
Synonyms	Decumbin Synergisidin Brefeldin A Ascotoxin (+)-brefeldin A Nectrolide Cyanein
Categories	Anti-Bacterial Agents Anti-Infective Agents Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) Cytochrome P-450 Enzyme Inhibitors Enzyme Inhibitors Lactones Macrolides P-glycoprotein inhibitors Polyketides Protein Synthesis Inhibitors
CAS number	20350-15-6

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Cytohesin-2	MEDGVYEPPDLTPEERMELENIRRRKQELLVEIQRLREELSEAMSEVEGL...	unknown
ADP-ribosylation factor 1	MGNIFANLFKGLFGKKEMRILMVGLDAAGKTTILYKLKLGEIVTTIPTIG...	unknown
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	inhibitor

Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682