RCG

(1R,2R,3S,3aR,8bS)-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-1,8b-bis(oxidanyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide

Created: 2017-08-24
Last modified:  2021-03-13

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Chemical Details

Formal Charge0
Atom Count68
Chiral Atom Count5
Bond Count72
Aromatic Bond Count18
2D diagram of RCG
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Chemical Component Summary

Name(1R,2R,3S,3aR,8bS)-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-1,8b-bis(oxidanyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide
SynonymsRocaglamide; Rocaglamide A
Systematic Name (OpenEye OEToolkits)(1~{R},2~{R},3~{S},3~{a}~{R},8~{b}~{S})-6,8-dimethoxy-3~{a}-(4-methoxyphenyl)-~{N},~{N}-dimethyl-1,8~{b}-bis(oxidanyl)-3-phenyl-2,3-dihydro-1~{H}-cyclopenta[b][1]benzofuran-2-carboxamide
FormulaC29 H31 N O7
Molecular Weight505.559
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESCACTVS3.385COc1ccc(cc1)[C]23Oc4cc(OC)cc(OC)c4[C]2(O)[CH](O)[CH]([CH]3c5ccccc5)C(=O)N(C)C
SMILESOpenEye OEToolkits2.0.6CN(C)C(=O)C1C(C2(C(C1O)(c3c(cc(cc3OC)OC)O2)O)c4ccc(cc4)OC)c5ccccc5
Canonical SMILESCACTVS3.385 COc1ccc(cc1)[C@@]23Oc4cc(OC)cc(OC)c4[C@]2(O)[C@H](O)[C@@H]([C@H]3c5ccccc5)C(=O)N(C)C
Canonical SMILESOpenEye OEToolkits2.0.6 CN(C)C(=O)[C@@H]1[C@H]([C@]2([C@@]([C@@H]1O)(c3c(cc(cc3OC)OC)O2)O)c4ccc(cc4)OC)c5ccccc5
InChIInChI1.03 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
InChIKeyInChI1.03 DAPAQENNNINUPW-IDAMAFBJSA-N

Drug Info: DrugBank

DrugBank IDDB15495 
NameRocaglamide
Groups experimental
DescriptionRocaglamide, also referred to as rocaglamide-A, is the eponymous member of a class of anti-cancer phytochemicals known as rocaglamides.[A186760] Rocaglamides are secondary metabolites of the plant genus _Aglaia_, and extracts of the plant have traditionally been used as a form of insect repellant due to its natural insecticidal properties.[A186796] Reports of _Aglaia_ anti-tumor activity date back as far as 1973, and rocaglamide-A was first isolated in 1982 from the species _A. elliptifolia_.[A186760] Rocaglamide and a number of its derivatives (e.g. [didesmethylrocaglamide]) are currently being studied for use as chemotherapeutic agents in the treatment of various leukemias, lymphomas, and carcinomas, as well as adjuvant therapy in the treatment of certain chemotherapy-resistant cancers.[A186781,A186784,A186799,A186766]
SynonymsRocaglamide
CategoriesHeterocyclic Compounds, Fused-Ring
CAS number84573-16-0

Drug Targets

NameTarget SequencePharmacological ActionActions
Prohibitin 1MAAKVFESIGKFGLALAVAGGVVNSALYNVDAGHRAVIFDRFRGVQDIVV...unknowninhibitor
Transcription factor RelBMLRSGPASGPSVPTGRAMPSRRVARPPAAPELGALGSPDLSSLSLAVSRS...unknowninhibitor
Nuclear factor NF-kappa-B p100 subunitMESCYNPGLDGIIEYDDFKLNSSIVEPKEPAPETADGPYLVIVEQPKQRG...unknowninhibitor
Transcription factor p65MDELFPLIFPAEPAQASGPYVEIIEQPKQRGMRFRYKCEGRSAGSIPGER...unknowninhibitor
Proto-oncogene c-RelMASGAYNPYIEIIEQPRQRGMRFRYKCEGRSAGSIPGEHSTDNNRTYPSI...unknowninhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL438139
PubChem 331783
ChEMBL CHEMBL438139
ChEBI CHEBI:66309
CCDC/CSD BIXKIC