EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:65553 - (−)-calanolide B

ChEBI IDCHEBI:65553
ChEBI Name(−)-calanolide B
Stars
ASCII Name(-)-calanolide B
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 10S,11R,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-/m0/s1
InChIKeyNIDRYBLTWYFCFV-PZROIBLQSA-N
Species of MetaboliteComponentSourceComments
Calophyllum teysmannii var. inophylloide (IPNI:876299-1) latex (BTO:0000710) PubMed (9784162)
Calophyllum brasiliense (IPNI:427115-1) leaf (BTO:0000713) PubMed (15340243)
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 B (CHEBI:65553) has role HIV-1 reverse transcriptase inhibitor (CHEBI:53756)
(−)-calanolide B (CHEBI:65553) has role plant metabolite (CHEBI:76924)
(−)-calanolide B (CHEBI:65553) is a cyclic ether (CHEBI:37407)
(−)-calanolide B (CHEBI:65553) is a organic heterotetracyclic compound (CHEBI:38163)
(−)-calanolide B (CHEBI:65553) is a secondary alcohol (CHEBI:35681)
(−)-calanolide B (CHEBI:65553) is a δ-lactone (CHEBI:18946)
IUPAC Name 
(10S,11R,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
(+)-(10S,11R,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
costatolideChEBI
(10S,11R,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
Manual XrefsDatabases
WO9932492Patent
Registry NumbersSources
Reaxys:7257193Reaxys
CAS:909-14-8ChemIDplus
Citations