EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:65922 - fukanefuromarin B

ChEBI IDCHEBI:65922
ChEBI Namefukanefuromarin B
Stars
DefinitionA 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 trans configuration) and a 4,8-dimethyl-4(E),7-nonadien-6-onyl moiety at position 2. Isolated from the roots of Ferula fukanensis, it inhibits production of nitric oxide (NO).
Last Modified28 January 2013
DownloadsMolfile
FormulaC24H28O5
Net Charge0
Average Mass396.483
Monoisotopic Mass396.19367
SMILESCC(C)=CC(=O)/C=C(\C)CCC[C@@]1(C)Oc2c(c(=O)oc3cc(O)ccc23)[C@H]1C
InChIInChI=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-/m1/s1
InChIKeyNWTCYOAKBSTWBB-NDIQIQBTSA-N
Species of MetaboliteComponentSourceComments
Ferula fukanensis (IPNI:842281-1) root (BTO:0001188) PubMed (15043424)
Roles Classification
Biological Roles:
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).
ChEBI Ontology
Outgoing Relation(s)
fukanefuromarin B (CHEBI:65922) has role EC 1.14.13.39 (nitric oxide synthase) inhibitor (CHEBI:61908)
fukanefuromarin B (CHEBI:65922) has role metabolite (CHEBI:25212)
fukanefuromarin B (CHEBI:65922) is a furanocoumarin (CHEBI:24128)
fukanefuromarin B (CHEBI:65922) is a ketone (CHEBI:17087)
fukanefuromarin B (CHEBI:65922) is a phenols (CHEBI:33853)
fukanefuromarin B (CHEBI:65922) is a sesquiterpenoid (CHEBI:26658)
IUPAC Name 
(2R*,3R*)-2-[(4E)-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-2R*,3R*-dimethyl-2-[4,8-dimethyl-4-(E)-7-nonadien-6-onyl]-furo[3,2-c]coumarinChEBI
Registry NumbersSources
Reaxys:10216263Reaxys
Citations