Compound: Rocaglamide
SMILES: O=C(N(C)C)[C@H]1[C@@H](O)[C@@]2(O)c3c(OC)cc(OC)cc3O[C@]2([C@@H]1c4ccccc4)c5ccc(OC)cc5
InChIKey: DAPAQENNNINUPW-IDAMAFBJSA-N
Synonyms: Rocaglamide, 84573-16-0, DTXSID101004852, NSC-326408, Rocaglamide A, FRG4N852F7, CHEBI:66309, 1H-Cyclopenta(b)benzofuran-2-carboxamide, 2,3,3a,8b-tetrahydro-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-, (1R,2R,3S,3aR,8bS)-, (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, (1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide, (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, (1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3-dihydro-1H-cyclopenta(b)(1)benzofuran-2-carboxamide, 1H-Cyclopenta[b]benzofuran-2-carboxamide, 2,3,3a,8b-tetrahydro-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-, (1R,2R,3S,3aR,8bS)-, RefChem:883680, DTXCID901431744, (1R,2R,3S,3aR,8bS)-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, C29H31NO7, Roc-A, MLS002701812, CHEMBL438139, NSC326408, (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-cyclopenta[b]benzofuran-2-carboxamide, (-)-(1alpha,2alpha,3beta,3abeta,8bbeta)-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, (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, (-)-ROCAGLAMIDE, MFCD08702699, Rocaglamide; Rocaglamide A, SCHEMBL752144, orb1296181, SCHEMBL29407815, EX-A3220, BDBM50196926, s7428, AT25539, CS-5246, DB15495, AC-36727, AS-79589, DA-67269, HY-19356, NCI60_002832, SMR001565405, B603847K064, Q3437403, BRD-K97248244-001-01-8, BRD-K97248244-001-02-6, (1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3-dihydro-1H-cyclopenta[b]benzofuran-2-carboxamide, 117894-34-5, 1H-Cyclopenta[b]benzofuran-2-carboxamide,3,3a,8b-tetrahydro-1,8b-dihydroxy-6,8-dimethoxy- 3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-, [1R-(1.alpha.,2.alpha.,3.beta.,3a.beta.,8b.beta.)]-, 1H-Cyclopenta[b]benzofuran-2-carboxamide,3,3a,8b-tetrahydro-1,8b-dihydroxy-6,8-dimethoxy- 3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-,(1R,2R,3S,3aR,8bS)-, RCG
Theoretical properties:
molecular_formula: C29H31NO7
molecular_weight: 505.6 g/mol
exact_mass: 505.21005233 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 7
rotatable_bond_count: 6
heavy_atom_count: 37
topological_polar_surface_area: 97.7 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "Rocaglamide is 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. It has a role as a metabolite, an antineoplastic agent and an antileishmanial agent. It is a monomethoxybenzene, an organic heterotricyclic compound and a monocarboxylic acid amide.", "chebi": "An organic heterotricyclic compound that is 2,3,3a,8b-tetrahydro-1<em>H</em>-benzo[<em>b</em>]cyclopenta[<em>d</em>]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 <em>N</em>,<em>N</em>-dimethylcarbamoyl group at position 1. Isolated from <em>Aglaia odorata</em> and <em>Aglaia duperreana</em>, it exhibits antineoplastic activity.", "chembl": "ROCAGLAMIDE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "Rocaglamide is a natural product which belongs to a class of molecules called flavaglines. This compound was isolated in 1982 by Ming-Lu King (\u91d1\u660e\u5112) and colleagues based on its antileukemic activity. The name of Rocaglamide is named from two parts: Roc- and aglamide. Roc- means Republic of China (\u4e2d\u83ef\u6c11\u570b), where this product was first isolated; aglamide indicates this product is isolated from Large-leaved Aglaia (Scientific name: Aglaia rimosa).  Like other flavaglines, rocaglamide displays potent insecticidal, antifungal, anti-inflammatory and anticancer activities. Rocaglamide A (RocA) inhibits eukaryotic translation initiation by binding to the translation initiation factor eIF4A and converting it into a translational repressor.\nRocaglamide was first synthesized by Barry Trost in 1990. Although other syntheses have been described since, Trost\u2019s remains the only one to afford rocaglamide in an enantio-specific manner."}