vinigrol (CHEBI:222218)

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CHEBI:222218 - vinigrol

ChEBI ID	CHEBI:222218
ChEBI Name	vinigrol
Stars
Definition	A diterpenoid with formula C₂₀H₃₄O₃. It is isolated from the fungal strain Virgaria nigra F-5408 and exhibits antihypertensive and antiplatelet aggregation activities.
Last Modified	2 July 2025
Submitter	MetaboLights
Downloads	Molfile

Formula	C20H34O3
Net Charge	0
Average Mass	322.489
Monoisotopic Mass	322.25079
SMILES	[H][C@@]12[C@H](O)C(CO)=C[C@@]3([H])[C@@H](C(C)C)CC[C@@H](C)[C@]1([H])CC[C@@H](C)[C@@]23O
InChI	InChI=1S/C20H34O3/c1-11(2)15-7-5-12(3)16-8-6-13(4)20(23)17(15)9-14(10-21)19(22)18(16)20/h9,11-13,15-19,21-23H,5-8,10H2,1-4H3/t12-,13-,15-,16+,17+,18+,19-,20+/m1/s1
InChIKey	WVVCBUGDSFLEHX-SBNBNJMHSA-N

Species of Metabolite	Component	Source	Comments
Virgaria nigra (ncbitaxon:1085564)	mycelium (BTO:0001436)	PubMed (3346190)	Strain: F-5408

Roles Classification

Biological Role:

fungal metabolite Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.

Applications:

platelet aggregation inhibitor A drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.

antihypertensive agent Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.

ChEBI Ontology

Outgoing Relation(s)
	vinigrol (CHEBI:222218) has role antihypertensive agent (CHEBI:35674)
	vinigrol (CHEBI:222218) has role fungal metabolite (CHEBI:76946)
	vinigrol (CHEBI:222218) has role platelet aggregation inhibitor (CHEBI:50427)
	vinigrol (CHEBI:222218) is a carbotricyclic compound (CHEBI:38032)
	vinigrol (CHEBI:222218) is a diterpenoid (CHEBI:23849)
	vinigrol (CHEBI:222218) is a primary alcohol (CHEBI:15734)
	vinigrol (CHEBI:222218) is a secondary alcohol (CHEBI:35681)
	vinigrol (CHEBI:222218) is a tertiary alcohol (CHEBI:26878)
	vinigrol (CHEBI:222218) is a triol (CHEBI:27136)
Incoming Relation(s)
	16-dehydroxyvinigrol (CHEBI:234555) has functional parent vinigrol (CHEBI:222218)
	4,16-didehydroxyvinigrol (CHEBI:234556) has functional parent vinigrol (CHEBI:222218)

IUPAC Name
(1R,4S,4aS,5S,8R,8aS,9R,12R)-3-(hydroxymethyl)-8,9-dimethyl-12-(propan-2-yl)-4,4a,5,6,7,8-hexahydro-1,5-butanonaphthalene-4,8a(1H)-diol

Synonyms	Source
(−)-vinigrol	ChEBI
antibiotic FR 900478	KNApSAcK
(1R,4S,4aS,5S,8R,8aS,9R,12R)-4,4a,5,6,7,8-hexahydro-3-(hydroxymethyl)-8,9-dimethyl-12-(1-methylethyl)-1,5-butanonaphthalene-4,8a(1H)-diol	ChEBI

UniProt Name	Source
vinigrol	UniProt

Manual Xrefs	Databases
C00017879	KNApSAcK

Registry Numbers	Sources
CAS:111025-83-3	ChEBI

Citations