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CHEBI:43129 - (+)-6a-hydroxymaackiain

ChEBI IDCHEBI:43129
ChEBI Name(+)-6a-hydroxymaackiain
Stars
DefinitionA member of the class of pterocarpans that is (6aS,11aS)-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromene which is substituted by a hydroxy group at position 3, a second hydroxy group at position 6a (resulting in the CIP stereochemical designation changing to R,R), and a methylenedioxy group at positions 8-9. It is a metabolite of the pea phytoalexin (+)-pisatin, produced by the pea-pathogenic Fusarium oxysporum forma specialis pisi, and a number of other fungi, including Fusarium anruioides, Fusarium avenaceum, Mycosphaerella pinodes, and Stemphylium botryosum.
Last Modified28 July 2014
DownloadsMolfile
FormulaC16H12O6
Net Charge0
Average Mass300.266
Monoisotopic Mass300.06339
SMILES[H][C@]12Oc3cc4c(cc3[C@@]1(O)COc1cc(O)ccc12)OCO4
InChIInChI=1S/C16H12O6/c17-8-1-2-9-11(3-8)19-6-16(18)10-4-13-14(21-7-20-13)5-12(10)22-15(9)16/h1-5,15,17-18H,6-7H2/t15-,16+/m1/s1
InChIKeyGLMPLZUBQDAZEN-CVEARBPZSA-N
ChEBI Ontology
Outgoing Relation(s)
(+)-6a-hydroxymaackiain (CHEBI:43129) has functional parent (+)-maackiain (CHEBI:73030)
(+)-6a-hydroxymaackiain (CHEBI:43129) is a pterocarpans (CHEBI:26377)
(+)-6a-hydroxymaackiain (CHEBI:43129) is a tertiary alcohol (CHEBI:26878)
Incoming Relation(s)
(+)-pisatin (CHEBI:67347) has functional parent (+)-6a-hydroxymaackiain (CHEBI:43129)
IUPAC Name 
(6aR,12aR)-6H-[1,3]dioxolo[5,6][1]benzofuro[3,2-c]chromene-3,6a(12aH)-diol
Synonyms  Source
(+)-O-demethylpisatinChEBI
O-demethylpisatinChEBI
UniProt Name  Source
(+)-6a-hydroxymaackiainUniProt
Manual XrefsDatabases
HMKPDBeChem
CPD-3942MetaCyc
C16230KEGG COMPOUND
LMPK12070133LIPID MAPS
C00009677KNApSAcK
Registry NumbersSources
Reaxys:6982403Reaxys
Citations