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

ID: ALA3237585

Chembl Id: CHEMBL3237585

PubChem CID: 90671412

Max Phase: Preclinical

Molecular Formula: C28H31N3O2S

Molecular Weight: 473.64

Molecule Type: Small molecule

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-HRRPPENISA-N

Alternative Forms

1. Parent:

   

   ALA3237585

   ethyl (1S,2R,3R,4S,5S)-2-amino-5-[3-(4-aminoanilino)phenyl]-3-phenylsulfanylbicyclo[2.2.1]heptane-2-carboxylate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 473.64

Molecular Weight (Monoisotopic): 473.2137

AlogP: 5.56

#Rotatable Bonds: 7

Polar Surface Area: 90.37

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 7.30

CX LogP: 5.00

CX LogD: 4.74

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.31

Np 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

Source(1):

• Scientific Literature