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CHEBI:65592 - caseargrewiin A

Default Structure
ChEBI IDCHEBI:65592
ChEBI Namecaseargrewiin A
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 Modified29 July 2013
DownloadsMolfile
FormulaC30H44O8
Net Charge0
Average Mass532.674
Monoisotopic Mass532.30362
SMILES[H][C@]12C[C@H](OC(=O)CC(C)C)C=C3[C@H](OC(C)=O)O[C@H](OC(C)=O)[C@@]31[C@H](OC)C[C@H](C)[C@]2(C)CCC(=C)C=C
InChIInChI=1S/C30H44O8/c1-10-18(4)11-12-29(8)19(5)14-25(34-9)30-23(27(35-20(6)31)38-28(30)36-21(7)32)15-22(16-24(29)30)37-26(33)13-17(2)3/h10,15,17,19,22,24-25,27-28H,1,4,11-14,16H2,2-3,5-9H3/t19-,22+,24+,25+,27+,28-,29-,30-/m0/s1
InChIKeyOSFRHUJJEKKRCH-GTMUTZHESA-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 A (CHEBI:65592) has role antimalarial (CHEBI:38068)
caseargrewiin A (CHEBI:65592) has role antimycobacterial drug (CHEBI:64912)
caseargrewiin A (CHEBI:65592) has role metabolite (CHEBI:25212)
caseargrewiin A (CHEBI:65592) is a acetate ester (CHEBI:47622)
caseargrewiin A (CHEBI:65592) is a cyclic ether (CHEBI:37407)
caseargrewiin A (CHEBI:65592) is a diterpenoid (CHEBI:23849)
caseargrewiin A (CHEBI:65592) is a organic heterotricyclic compound (CHEBI:26979)
IUPAC Name 
(1R*,3S*,5S*,6aR*,7S*,8S*,10R*,10aR*)-1,3-bis(acetyloxy)-10-methoxy-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-3,5,6,6a,7,8,9,10-octahydronaphtho[1,8a-c]furan-5-yl 3-methylbutanoate
Synonym  Source
rel-(2S,5R,6R,8S,9S,10R,18S,19R)-18,19-diacetoxy-18,19-epoxy-6-methoxy-2-(3-methylbutanoyloxy)-cleroda-3,13(16),14-trieneChEBI
Registry NumbersSources
Reaxys:15803799Reaxys
Citations