CHEBI:65923 - fukanefuromarin C

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ChEBI Name fukanefuromarin C
ChEBI ID CHEBI:65923
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-4(Z),7-nonadien-6-onyl moiety at position 2. Isolated from the roots of Ferula fukanensis, it inhibits 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/h8-9,11-13,16,25H,6-7,10H2,1-5H3/b15-12-/t16-,24+/m0/s1
InChIKey NWTCYOAKBSTWBB-NWMOAKGTSA-N
SMILES C[C@H]1c2c(O[C@]1(C)CCC\C(C)=C/C(=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
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing fukanefuromarin C (CHEBI:65923) has role EC 1.14.13.39 (nitric oxide synthase) inhibitor (CHEBI:61908)
fukanefuromarin C (CHEBI:65923) has role metabolite (CHEBI:25212)
fukanefuromarin C (CHEBI:65923) is a furanocoumarin (CHEBI:24128)
fukanefuromarin C (CHEBI:65923) is a ketone (CHEBI:17087)
fukanefuromarin C (CHEBI:65923) is a phenols (CHEBI:33853)
fukanefuromarin C (CHEBI:65923) is a sesquiterpenoid (CHEBI:26658)
IUPAC Name
(2R*,3S*)-2-[(4Z)-4,8-dimethyl-6-oxonona-4,7-dien-1-yl]-7-hydroxy-2,3-dimethyl-2,3-dihydro-4H-furo[3,2-c]chromen-4-one
Synonym Source
2,3-dihydro-7-hydroxy-2S*,3R*-dimethyl-2-[4,8-dimethyl-4(Z),7-nonadien-6-only]furo[3,2-c]coumarin ChEBI
Registry Number Type Source
10216261 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
15043424 PubMed citation Europe PMC
Last Modified
28 January 2013