(+/-)-1,8b-dihydroxy-N-(2-hydroxyethoxy)-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxamide

ID: ALA2059882

Chembl Id: CHEMBL2059882

PubChem CID: 70682197

Max Phase: Preclinical

Molecular Formula: C29H31NO9

Molecular Weight: 537.57

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  COc1ccc(C23Oc4cc(OC)cc(OC)c4C2(O)C(O)C(C(=O)NOCCO)C3c2ccccc2)cc1

Standard InChI:  InChI=1S/C29H31NO9/c1-35-19-11-9-18(10-12-19)29-24(17-7-5-4-6-8-17)23(27(33)30-38-14-13-31)26(32)28(29,34)25-21(37-3)15-20(36-2)16-22(25)39-29/h4-12,15-16,23-24,26,31-32,34H,13-14H2,1-3H3,(H,30,33)

Standard InChI Key:  MSKWOUVZXRMKBX-UHFFFAOYSA-N

Associated Targets(Human)

EIF4A1 Tchem Eukaryotic initiation factor 4A-I (286 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

EIF4A1 Eukaryotic initiation factor 4A-I (8 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 537.57Molecular Weight (Monoisotopic): 537.1999AlogP: 2.00#Rotatable Bonds: 9
Polar Surface Area: 135.94Molecular Species: NEUTRALHBA: 9HBD: 4
#RO5 Violations: 1HBA (Lipinski): 10HBD (Lipinski): 4#RO5 Violations (Lipinski): 1
CX Acidic pKa: 6.64CX Basic pKa: CX LogP: 1.63CX LogD: 1.01
Aromatic Rings: 3Heavy Atoms: 39QED Weighted: 0.24Np Likeness Score: 1.17

References

1. Rodrigo CM, Cencic R, Roche SP, Pelletier J, Porco JA..  (2012)  Synthesis of rocaglamide hydroxamates and related compounds as eukaryotic translation inhibitors: synthetic and biological studies.,  55  (1): [PMID:22128783] [10.1021/jm201263k]

Source