(+)-calanolide A (CHEBI:65552)

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ChEBI Name	(+)-calanolide A

ChEBI ID	CHEBI:65552

Definition	An 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.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

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Formula

C22H26O5

Net Charge

Average Mass

370.43880

Monoisotopic Mass

370.17802

InChI

InChI=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

InChIKey

NIDRYBLTWYFCFV-FMTVUPSXSA-N

SMILES

CCCc1cc(=O)oc2c3[C@@H](O)[C@H](C)[C@@H](C)Oc3c3C=CC(C)(C)Oc3c12

Metabolite of Species	Details
Calophyllum brasiliense (IPNI:427115-1)	Found in leaf (BTO:0000713). See: PubMed
Calophyllum lanigerum var. austrocoriaceum (IPNI:876292-1)	Found in twig (BTO:0001411). See: PubMed
Calophyllum lanigerum var. austrocoriaceum (IPNI:876292-1)	Found in fruit (BTO:0000486). See: PubMed

Roles Classification
Biological Role(s):	HIV-1 reverse transcriptase inhibitor An entity which inhibits the activity of HIV-1 reverse transcriptase. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.

ChEBI Ontology
Outgoing	(+)-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 δ-lactone (CHEBI:18946) (+)-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)

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	Sources
(+)-(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-one	ChEBI
(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-one	ChEBI
calanolide A	ChEBI

Last Modified

25 March 2015