CHEBI:66309 - rocaglamide

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ChEBI Name rocaglamide
ChEBI ID CHEBI:66309
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C29H31NO7
Net Charge 0
Average Mass 505.55890
Monoisotopic Mass 505.21005
InChI InChI=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
InChIKey DAPAQENNNINUPW-IDAMAFBJSA-N
SMILES COc1ccc(cc1)[C@@]12Oc3cc(OC)cc(OC)c3[C@]1(O)[C@H](O)[C@@H]([C@H]2c1ccccc1)C(=O)N(C)C
Metabolite of Species Details
Aglaia duperreana (IPNI:577056-1) Found in root (BTO:0001188). See: DOI
Aglaia elliptifolia (IPNI:577069-1) Found in root (BTO:0001188). See: DOI
Aglaia elliptifolia (IPNI:577069-1) Found in stem (BTO:0001300). See: DOI
Aglaia odorata (NCBI:txidtxid210347) Found in leaf (BTO:0000713). See: DOI
Roles Classification
Biological Role(s): 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.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
antileishmanial agent
An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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-carboxamide ChemIDplus
Manual Xref Database
US2009082371 Patent
View more database links
Registry Numbers Types Sources
4219080 Reaxys Registry Number Reaxys
84573-16-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
20685036 PubMed citation Europe PMC
20706274 PubMed citation Europe PMC
21417924 PubMed citation Europe PMC
22283818 PubMed citation Europe PMC
Last Modified
06 March 2014