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CHEBI:66309 - rocaglamide

ChEBI IDCHEBI:66309
ChEBI Namerocaglamide
Stars
DefinitionAn organic heterotricyclic compound that is 2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan substituted by hydroxy groups at positions 1 and 8b, methoxy groups at positions 6 and 8, a 4-methoxyphenyl group at position 3a, a phenyl group at position 3 and a N,N-dimethylcarbamoyl group at position 1. Isolated from Aglaia odorata and Aglaia duperreana, it exhibits antineoplastic activity.
Last Modified6 March 2014
DownloadsMolfile
FormulaC29H31NO7
Net Charge0
Average Mass505.567
Monoisotopic Mass505.21005
SMILESCOc1ccc([C@@]23Oc4cc(OC)cc(OC)c4[C@]2(O)[C@H](O)[C@H](C(=O)N(C)C)[C@H]3c2ccccc2)cc1
InChIInChI=1S/C29H31NO7/c1-30(2)27(32)23-24(17-9-7-6-8-10-17)29(18-11-13-19(34-3)14-12-18)28(33,26(23)31)25-21(36-5)15-20(35-4)16-22(25)37-29/h6-16,23-24,26,31,33H,1-5H3/t23-,24-,26-,28+,29+/m1/s1
InChIKeyDAPAQENNNINUPW-IDAMAFBJSA-N
Species of MetaboliteComponentSourceComments
Aglaia duperreana (IPNI:577056-1) root (BTO:0001188) DOI (10.1021/np990242g)
Aglaia elliptifolia (IPNI:577069-1)
root (BTO:0001188) DOI (10.1039/C39820001150)
stem (BTO:0001300) DOI (10.1039/C39820001150)
Aglaia odorata (ncbitaxon:210347) leaf (BTO:0000713) DOI (10.1016/S0031-9422(00)94986-0)
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.
antileishmanial agent  An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
Applications:
antileishmanial agent  An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
rocaglamide (CHEBI:66309) has role antileishmanial agent (CHEBI:70868)
rocaglamide (CHEBI:66309) has role antineoplastic agent (CHEBI:35610)
rocaglamide (CHEBI:66309) has role metabolite (CHEBI:25212)
rocaglamide (CHEBI:66309) is a monocarboxylic acid amide (CHEBI:29347)
rocaglamide (CHEBI:66309) is a monomethoxybenzene (CHEBI:25235)
rocaglamide (CHEBI:66309) is a organic heterotricyclic compound (CHEBI:26979)
IUPAC Name 
(1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxamide
Synonym  Source
(−)-(1α,2α,3β,3aβ,8bβ)-2,3,3a,8b-tetrahydro-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-1H-cyclopenta(b)benzofuran-2-carboxamideChemIDplus
Manual XrefsDatabases
US2009082371Patent
Registry NumbersSources
Reaxys:4219080Reaxys
CAS:84573-16-0ChemIDplus
Citations