3-({(R)-1-[(S)-2-(3-Aminomethyl-phenyl)-1-(4-carbamimidoyl-benzylcarbamoyl)-ethylcarbamoyl]-4-phenyl-butylsulfamoyl}-methyl)-benzoic acid

ID: ALA4471466

Chembl Id: CHEMBL4471466

PubChem CID: 70306716

Max Phase: Preclinical

Molecular Formula: C37H42N6O6S

Molecular Weight: 698.85

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N=C(N)c1ccc(CNC(=O)[C@H](Cc2cccc(CN)c2)NC(=O)[C@@H](CCCc2ccccc2)NS(=O)(=O)Cc2cccc(C(=O)O)c2)cc1

Standard InChI:  InChI=1S/C37H42N6O6S/c38-22-28-11-4-10-27(19-28)21-33(35(44)41-23-26-15-17-30(18-16-26)34(39)40)42-36(45)32(14-6-9-25-7-2-1-3-8-25)43-50(48,49)24-29-12-5-13-31(20-29)37(46)47/h1-5,7-8,10-13,15-20,32-33,43H,6,9,14,21-24,38H2,(H3,39,40)(H,41,44)(H,42,45)(H,46,47)/t32-,33+/m1/s1

Standard InChI Key:  BHQDUYVBGREBCB-SAIUNTKASA-N

Alternative Forms

1. Parent:

   

   ALA4471466

   3-[[(2R)-1-[[(2S)-3-[3-(aminomethyl)phenyl]-1-[(4-carbamimidoylphenyl)methylamino]-1-oxopropan-2-yl]amino]-1-oxo-5-phenylpentan-2-yl]sulfamoylmethyl]benzoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 698.85

Molecular Weight (Monoisotopic): 698.2887

AlogP: 2.98

#Rotatable Bonds: 18

Polar Surface Area: 217.56

Molecular Species: ZWITTERION

HBA: 7

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 4.03

CX Basic pKa: 11.40

CX LogP: 0.88

CX LogD: -0.38

Aromatic Rings: 4

Heavy Atoms: 50

QED Weighted: 0.06

Np Likeness Score: -0.45

References

1. Steinmetzer T, Pilgram O, Wenzel BM, Wiedemeyer SJA..  (2020)  Fibrinolysis Inhibitors: Potential Drugs for the Treatment and Prevention of Bleeding.,  63  (4): [PMID:31658420] [10.1021/acs.jmedchem.9b01060]

2. Hinkes S, Wuttke A, Saupe SM, Ivanova T, Wagner S, Knörlein A, Heine A, Klebe G, Steinmetzer T..  (2016)  Optimization of Cyclic Plasmin Inhibitors: From Benzamidines to Benzylamines.,  59  (13): [PMID:27280436] [10.1021/acs.jmedchem.6b00606]

Source

Source(1):

• Scientific Literature