(+)-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	ZINC000001645454

Download	Molfile XML SDF

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

Citations

Last Modified

25 March 2015