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CHEBI:65593 - caseargrewiin B

Default Structure
ChEBI IDCHEBI:65593
ChEBI Namecaseargrewiin B
Stars
DefinitionA diterpenoid of the clerodane group isolated from the bark of Casearia grewiifolia and has been shown to exhibit antimalarial and antimycobacterial activity.
Last Modified26 August 2015
DownloadsMolfile
FormulaC37H46O11
Net Charge0
Average Mass666.764
Monoisotopic Mass666.30401
SMILES[H][C@@]12C[C@@H](OC(=O)CCC)C=C3[C@@H](OC(C)=O)O[C@@H](OC(C)=O)[C@]31[C@@H](O)[C@H](OC(=O)/C=C/c1ccc(O)cc1)[C@@H](C)[C@@]2(C)C/C=C(/C)C=C
InChIInChI=1S/C37H46O11/c1-8-10-30(41)46-27-19-28-34(44-23(5)38)48-35(45-24(6)39)37(28)29(20-27)36(7,18-17-21(3)9-2)22(4)32(33(37)43)47-31(42)16-13-25-11-14-26(40)15-12-25/h9,11-17,19,22,27,29,32-35,40,43H,2,8,10,18,20H2,1,3-7H3/b16-13+,21-17-/t22-,27+,29+,32-,33+,34+,35-,36-,37-/m1/s1
InChIKeyYJKQLKAAMAXUDU-LRBOKHHASA-N
Species of MetaboliteComponentSourceComments
Casearia grewiifolia (IPNI:779573-1) bark (BTO:0001301) PubMed (15730240)
Roles Classification
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antimycobacterial drug  A drug used to treat or prevent infections caused by Mycobacteria, a genus of actinobacteria. Aerobic and nonmotile, members of the genus include the pathogens responsible for causing tuberculosis and leprosy.
antimalarial  A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
Applications:
antimycobacterial drug  A drug used to treat or prevent infections caused by Mycobacteria, a genus of actinobacteria. Aerobic and nonmotile, members of the genus include the pathogens responsible for causing tuberculosis and leprosy.
antimalarial  A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
ChEBI Ontology
Outgoing Relation(s)
caseargrewiin B (CHEBI:65593) has role antimalarial (CHEBI:38068)
caseargrewiin B (CHEBI:65593) has role antimycobacterial drug (CHEBI:64912)
caseargrewiin B (CHEBI:65593) has role metabolite (CHEBI:25212)
caseargrewiin B (CHEBI:65593) is a acetate ester (CHEBI:47622)
caseargrewiin B (CHEBI:65593) is a butyrate ester (CHEBI:50477)
caseargrewiin B (CHEBI:65593) is a cinnamate ester (CHEBI:36087)
caseargrewiin B (CHEBI:65593) is a cyclic ether (CHEBI:37407)
caseargrewiin B (CHEBI:65593) is a diterpenoid (CHEBI:23849)
caseargrewiin B (CHEBI:65593) is a organic heterotricyclic compound (CHEBI:26979)
IUPAC Name 
(1S*,3R*,5R*,6aS*,7S*,8S*,9R*,10R*,10aS*)-1,3-bis(acetyloxy)-10-hydroxy-9-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-7,8-dimethyl-7-[(2Z)-3-methylpenta-2,4-dien-1-yl]-3,5,6,6a,7,8,9,10-octahydronaphtho[1,8a-c]furan-5-yl butanoate
Synonym  Source
rel-(2R,5S,6R,7R,8S,9S,10S,18R,19S)-18,19-diacetoxy-18,19-epoxy-2-butanoyloxy-6-hydroxy-7-(p-hydroxycinnamoyloxy)cleroda-3,12(Z),14-trieneChEBI
Registry NumbersSources
Reaxys:15803802Reaxys
Citations