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CHEBI:65552 - (+)-calanolide A

ChEBI IDCHEBI:65552
ChEBI Name(+)-calanolide A
Stars
DefinitionAn organic heterotetracyclic compound that is 11,12-dihydro-2H,6H,10H-dipyrano[2,3-f:2',3'-h]chromen-2-one substituted by a hydroxy group at position 12, methyl groups at positions 6, 6, 10 and 11 and a propyl group at position 4 (the 10R,11S,12S stereoisomer). Isolated from Calophyllum lanigerum var austrocoriaceum and Calophyllum brasiliense, it exhibits potent activity against HIV-1 reverse transcriptase.
Last Modified25 March 2015
DownloadsMolfile
FormulaC22H26O5
Net Charge0
Average Mass370.445
Monoisotopic Mass370.17802
SMILESCCCc1cc(=O)oc2c3c(c4c(c12)OC(C)(C)C=C4)O[C@H](C)[C@@H](C)[C@@H]3O
InChIInChI=1S/C22H26O5/c1-6-7-13-10-15(23)26-21-16(13)20-14(8-9-22(4,5)27-20)19-17(21)18(24)11(2)12(3)25-19/h8-12,18,24H,6-7H2,1-5H3/t11-,12-,18+/m1/s1
InChIKeyNIDRYBLTWYFCFV-FMTVUPSXSA-N
Species of MetaboliteComponentSourceComments
Calophyllum brasiliense (IPNI:427115-1) leaf (BTO:0000713) PubMed (15340243)
Calophyllum lanigerum var. austrocoriaceum (IPNI:876292-1)
twig (BTO:0001411) PubMed (9784162)
fruit (BTO:0000486) PubMed (9784162)
Roles Classification
Biological Roles:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
HIV-1 reverse transcriptase inhibitor  An entity which inhibits the activity of HIV-1 reverse transcriptase.
ChEBI Ontology
Outgoing Relation(s)
(+)-calanolide A (CHEBI:65552) has role HIV-1 reverse transcriptase inhibitor (CHEBI:53756)
(+)-calanolide A (CHEBI:65552) has role plant metabolite (CHEBI:76924)
(+)-calanolide A (CHEBI:65552) is a cyclic ether (CHEBI:37407)
(+)-calanolide A (CHEBI:65552) is a organic heterotetracyclic compound (CHEBI:38163)
(+)-calanolide A (CHEBI:65552) is a secondary alcohol (CHEBI:35681)
(+)-calanolide A (CHEBI:65552) is a δ-lactone (CHEBI:18946)
IUPAC Name 
(10R,11S,12S)-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-11,12-dihydro-2H,6H,10H-dipyrano[2,3-f:2',3'-h]chromen-2-one
Synonyms  Source
(+)-(10R,11S,12S)-10,11-trans-dihydro-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-2H,6H-benzo[1,2-b:3,4-b':5,6-b'']tripyran-2-oneChEBI
(10R,11S,12S)-11,12-dihydro-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-2H,6H,10H-benzo(1,2-b:3,4-b':5,6-b'')tripyran-2-oneChEBI
calanolide AChEBI
Manual XrefsDatabases
C00002454KNApSAcK
C09147KEGG COMPOUND
Registry NumbersSources
Reaxys:5856917Reaxys
CAS:142632-32-4ChemIDplus
CAS:142632-32-4KEGG COMPOUND
Citations