CHEBI:66516 - soulattrolide

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ChEBI Name soulattrolide
ChEBI ID CHEBI:66516
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information No supplier information found for this compound.
Download Molfile XML SDF
Formula C25H24O5
Net Charge 0
Average Mass 404.45510
Monoisotopic Mass 404.16237
InChI InChI=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
InChIKey BXENDTPSKAICGV-RXSFTSLZSA-N
SMILES C[C@@H]1Oc2c3C=CC(C)(C)Oc3c3c(cc(=O)oc3c2[C@@H](O)[C@H]1C)-c1ccccc1
Metabolite of Species Details
Calophyllum brasiliense (IPNI:427115-1) Found in leaf (BTO:0000713). See: PubMed
Calophyllum soulattri (NCBI:txid257776) Found in bark (BTO:0001301). See: DOI
Calophyllum teysmannii (NCBI:txid667334) Found in latex (BTO:0000710). See: PubMed
Roles Classification
Biological Role(s): HIV-1 reverse transcriptase inhibitor
An entity which inhibits the activity of HIV-1 reverse transcriptase.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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ChEBI Ontology
Outgoing 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-one ChemIDplus
Manual Xref Database
WO9932492 Patent
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Registry Numbers Types Sources
1443041 Reaxys Registry Number Reaxys
65025-62-9 CAS Registry Number ChemIDplus
Citations Types Sources
15340243 PubMed citation Europe PMC
7506311 PubMed citation Europe PMC
8864237 PubMed citation Europe PMC
Last Modified
08 July 2013