(1S*,2R*,3S*,4S*,5S*)-Ethyl 2-Amino-5-(3-((4-aminophenyl)-amino)phenyl)-3-(phenylsulfanyl)bicyclo[2.2.1]heptane-2-carboxylate

ID: ALA3237583

Chembl Id: CHEMBL3237583

PubChem CID: 90671410

Max Phase: Preclinical

Molecular Formula: C28H31N3O2S

Molecular Weight: 473.64

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  CCOC(=O)[C@]1(N)[C@@H]2C[C@@H]([C@@H](c3cccc(Nc4ccc(N)cc4)c3)C2)[C@@H]1Sc1ccccc1

Standard InChI:  InChI=1S/C28H31N3O2S/c1-2-33-27(32)28(30)19-16-24(25(17-19)26(28)34-23-9-4-3-5-10-23)18-7-6-8-22(15-18)31-21-13-11-20(29)12-14-21/h3-15,19,24-26,31H,2,16-17,29-30H2,1H3/t19-,24+,25-,26-,28-/m0/s1

Standard InChI Key:  ABIZFOLNWICUKV-ZVIGXPOOSA-N

Associated Targets(Human)

RAC1 Tbio Ras-related C3 botulinum toxin substrate 1/T-lymphoma invasion and metastasis-inducing protein 1 (10 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RHOA Tbio Transforming protein RhoA (190 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: 473.64Molecular Weight (Monoisotopic): 473.2137AlogP: 5.56#Rotatable Bonds: 7
Polar Surface Area: 90.37Molecular Species: NEUTRALHBA: 6HBD: 3
#RO5 Violations: 1HBA (Lipinski): 5HBD (Lipinski): 5#RO5 Violations (Lipinski): 1
CX Acidic pKa: CX Basic pKa: 7.30CX LogP: 5.00CX LogD: 4.74
Aromatic Rings: 3Heavy Atoms: 34QED Weighted: 0.31Np Likeness Score: -0.08

References

1. Ruffoni A, Ferri N, Bernini SK, Ricci C, Corsini A, Maffucci I, Clerici F, Contini A..  (2014)  2-Amino-3-(phenylsulfanyl)norbornane-2-carboxylate: an appealing scaffold for the design of Rac1-Tiam1 protein-protein interaction inhibitors.,  57  (7): [PMID:24520998] [10.1021/jm401924s]

Source