CHEBI:65929 - (2S*,3R*)-2,3-dihydro-7-hydroxy-2,3-dimethyl-2-[4,8-dimethyl-3(E),7-nonadien-6-onyl]-furo[3,2-c]coumarin

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ChEBI Name (2S*,3R*)-2,3-dihydro-7-hydroxy-2,3-dimethyl-2-[4,8-dimethyl-3(E),7-nonadien-6-onyl]-furo[3,2-c]coumarin
ChEBI ID CHEBI:65929
ChEBI ASCII Name (2S*,3R*)-2,3-dihydro-7-hydroxy-2,3-dimethyl-2-[4,8-dimethyl-3(E),7-nonadien-6-onyl]-furo[3,2-c]coumarin
Definition A furanocoumarin that is 2,3-dihydrofuro[3,2-c]coumarin substituted by a hydroxy group at position 7, methyl groups at positions 2 and 3 (relatively cis configuration) and a 4,8-dimethyl-3(E),7-nonadien-6-onyl moiety at position 2. Isolated from the roots of Ferula fukanensis and Ferula ferulioides, it exhibits inhibitory activity against production of nitric oxide (NO).
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C24H28O5
Net Charge 0
Average Mass 396.47610
Monoisotopic Mass 396.19367
InChI InChI=1S/C24H28O5/c1-14(2)11-18(26)12-15(3)7-6-10-24(5)16(4)21-22(29-24)19-9-8-17(25)13-20(19)28-23(21)27/h7-9,11,13,16,25H,6,10,12H2,1-5H3/b15-7+/t16-,24+/m0/s1
InChIKey VFFCJVAKVAWFMA-TVBPSSQPSA-N
SMILES C[C@H]1c2c(O[C@]1(C)CC\C=C(/C)CC(=O)C=C(C)C)c1ccc(O)cc1oc2=O
Metabolite of Species Details
Ferula fukanensis (IPNI:842281-1) Found in root (BTO:0001188). See: PubMed
Ferula ferulioides (NCBI:txid200487) Found in root (BTO:0001188). See: PubMed
Roles Classification
Biological Role(s): EC 1.14.13.39 (nitric oxide synthase) inhibitor
An EC 1.14.13.* (oxidoreductase acting on paired donors, incorporating 1 atom of oxygen, with NADH or NADPH as one donor) inhibitor that interferes with the action of nitric oxide synthase (EC 1.14.13.39).
(via (2S*,3R*)-2,3-dihydro-7-hydroxy-2,3-dimethyl-2-[4,8-dimethyl-3(E),7-nonadien-6-onyl]-furo[3,2-c]coumarin )
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via (2S*,3R*)-2,3-dihydro-7-hydroxy-2,3-dimethyl-2-[4,8-dimethyl-3(E),7-nonadien-6-onyl]-furo[3,2-c]coumarin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (2S*,3R*)-2,3-dihydro-7-hydroxy-2,3-dimethyl-2-[4,8-dimethyl-3(E),7-nonadien-6-onyl]-furo[3,2-c]coumarin (CHEBI:65929) has role EC 1.14.13.39 (nitric oxide synthase) inhibitor (CHEBI:61908)
(2S*,3R*)-2,3-dihydro-7-hydroxy-2,3-dimethyl-2-[4,8-dimethyl-3(E),7-nonadien-6-onyl]-furo[3,2-c]coumarin (CHEBI:65929) has role metabolite (CHEBI:25212)
(2S*,3R*)-2,3-dihydro-7-hydroxy-2,3-dimethyl-2-[4,8-dimethyl-3(E),7-nonadien-6-onyl]-furo[3,2-c]coumarin (CHEBI:65929) is a furanocoumarin (CHEBI:24128)
(2S*,3R*)-2,3-dihydro-7-hydroxy-2,3-dimethyl-2-[4,8-dimethyl-3(E),7-nonadien-6-onyl]-furo[3,2-c]coumarin (CHEBI:65929) is a ketone (CHEBI:17087)
(2S*,3R*)-2,3-dihydro-7-hydroxy-2,3-dimethyl-2-[4,8-dimethyl-3(E),7-nonadien-6-onyl]-furo[3,2-c]coumarin (CHEBI:65929) is a phenols (CHEBI:33853)
(2S*,3R*)-2,3-dihydro-7-hydroxy-2,3-dimethyl-2-[4,8-dimethyl-3(E),7-nonadien-6-onyl]-furo[3,2-c]coumarin (CHEBI:65929) is a sesquiterpenoid (CHEBI:26658)
IUPAC Name
(2R*,3S*)-2-[(3E)-4,8-dimethyl-6-oxonona-3,7-dien-1-yl]-7-hydroxy-2,3-dimethyl-2,3-dihydro-4H-furo[3,2-c]chromen-4-one
Citations Waiting for Citations Types Sources
11558588 PubMed citation Europe PMC
15043424 PubMed citation Europe PMC
Last Modified
28 January 2013