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CHEBI:66516 - soulattrolide

ChEBI IDCHEBI:66516
ChEBI Namesoulattrolide
Stars
DefinitionA member of the class of coumarins that is 11,12-dihydro-2H,6H,10H-dipyrano[2,3-f:2',3'-h]chromen-2-one substituted by a phenyl group at position 4, methyl groups at positions 6, 6, 10 and 11 and a hydroxy group at position 12 (the 10S,11R,12S stereoisomer). Isolated from Calophyllum brasiliense and Calophyllum soulattri, it exhibits anti-HIV activity.
Last Modified8 July 2013
DownloadsMolfile
FormulaC25H24O5
Net Charge0
Average Mass404.462
Monoisotopic Mass404.16237
SMILESC[C@H]1[C@H](C)Oc2c3c(c4c(-c5ccccc5)cc(=O)oc4c2[C@H]1O)OC(C)(C)C=C3
InChIInChI=1S/C25H24O5/c1-13-14(2)28-22-16-10-11-25(3,4)30-23(16)19-17(15-8-6-5-7-9-15)12-18(26)29-24(19)20(22)21(13)27/h5-14,21,27H,1-4H3/t13-,14-,21-/m0/s1
InChIKeyBXENDTPSKAICGV-RXSFTSLZSA-N
Species of MetaboliteComponentSourceComments
Calophyllum brasiliense (IPNI:427115-1) leaf (BTO:0000713) PubMed (15340243)
Calophyllum teysmannii (ncbitaxon:667334) latex (BTO:0000710) PubMed (8864237)
Calophyllum soulattri (ncbitaxon:257776) bark (BTO:0001301) DOI (10.1039/P19770001505)
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.
HIV-1 reverse transcriptase inhibitor  An entity which inhibits the activity of HIV-1 reverse transcriptase.
ChEBI Ontology
Outgoing Relation(s)
soulattrolide (CHEBI:66516) has role HIV-1 reverse transcriptase inhibitor (CHEBI:53756)
soulattrolide (CHEBI:66516) has role metabolite (CHEBI:25212)
soulattrolide (CHEBI:66516) is a coumarins (CHEBI:23403)
soulattrolide (CHEBI:66516) is a secondary alcohol (CHEBI:35681)
IUPAC Name 
(10S,11R,12S)-12-hydroxy-6,6,10,11-tetramethyl-4-phenyl-11,12-dihydro-2H,6H,10H-dipyrano[2,3-f:2',3'-h]chromen-2-one
Synonym  Source
(10α,11β,12β)-(−)-11,12-dihydro-12-hydroxy-6,6,10,11-tetramethyl-4-phenyl-2H,6H,10H-benzo(1,2-b:3,4-b':5,6-b'')tripyran-2-oneChemIDplus
Manual XrefsDatabases
WO9932492Patent
Registry NumbersSources
Reaxys:1443041Reaxys
CAS:65025-62-9ChemIDplus
Citations