(S)-2-{[5-((R)-2-Amino-3-mercapto-propylamino)-biphenyl-2-carbonyl]-amino}-4-methylsulfanyl-butyric acid methyl ester

ID: ALA135561

Chembl Id: CHEMBL135561

Cas Number: 170006-73-2

PubChem CID: 3005532

Max Phase: Preclinical

Molecular Formula: C22H29N3O3S2

Molecular Weight: 447.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@H](CCSC)NC(=O)c1ccc(NC[C@@H](N)CS)cc1-c1ccccc1

Standard InChI:  InChI=1S/C22H29N3O3S2/c1-28-22(27)20(10-11-30-2)25-21(26)18-9-8-17(24-13-16(23)14-29)12-19(18)15-6-4-3-5-7-15/h3-9,12,16,20,24,29H,10-11,13-14,23H2,1-2H3,(H,25,26)/t16-,20+/m1/s1

Standard InChI Key:  GKFPROVOIQKYTO-UZLBHIALSA-N

Alternative Forms

1. Parent:

   

   ALA135561

   methyl (2S)-2-[[4-[[(2R)-2-amino-3-sulfanylpropyl]amino]-2-phenylbenzoyl]amino]-4-methylsulfanylbutanoate

2. Alternative Forms:

   

   ALA135561

   ---

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: 447.63

Molecular Weight (Monoisotopic): 447.1650

AlogP: 3.05

#Rotatable Bonds: 11

Polar Surface Area: 93.45

Molecular Species: BASE

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.25

CX Basic pKa: 9.26

CX LogP: 2.47

CX LogD: 0.85

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.31

Np Likeness Score: -0.73

References

1. Augeri DJ, O'Connor SJ, Janowick D, Szczepankiewicz B, Sullivan G, Larsen J, Kalvin D, Cohen J, Devine E, Zhang H, Cherian S, Saeed B, Ng SC, Rosenberg S..  (1998)  Potent and selective non-cysteine-containing inhibitors of protein farnesyltransferase.,  41  (22): [PMID:9784104] [10.1021/jm980298s]

2. Ohkanda J, Buckner FS, Lockman JW, Yokoyama K, Carrico D, Eastman R, de Luca-Fradley K, Davies W, Croft SL, Van Voorhis WC, Gelb MH, Sebti SM, Hamilton AD..  (2004)  Design and synthesis of peptidomimetic protein farnesyltransferase inhibitors as anti-Trypanosoma brucei agents.,  47  (2): [PMID:14711313] [10.1021/jm030236o]

3. PubChem BioAssay data set, 

4. Genomics of Drug Sensitity in Cancer screening data, Wellcome Trust Sanger Institute,  [10.6019/CHEMBL1201861]

5. Mansha M, Kumari UU, Cournia Z, Ullah N..  (2016)  Pyrazole-based potent inhibitors of GGT1: Synthesis, biological evaluation, and molecular docking studies.,  124  [PMID:27620969] [10.1016/j.ejmech.2016.09.002]

6. Buuh ZY, Lyu Z, Wang RE..  (2018)  Interrogating the Roles of Post-Translational Modifications of Non-Histone Proteins.,  61  (8): [PMID:28505447] [10.1021/acs.jmedchem.6b01817]

7. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

8. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]

Source

Source(4):

• Scientific Literature
• Sanger Institute Genomics of Drug Sensitivity in Cancer
• PubChem BioAssays
• SARS-CoV-2 Screening Data 2020-21