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

ID: ALA282103

Chembl Id: CHEMBL282103

PubChem CID: 9866559

Max Phase: Preclinical

Molecular Formula: C22H29N3O3S

Molecular Weight: 415.56

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H29N3O3S/c1-14(2)10-20(22(27)28)25-21(26)18-9-8-17(24-12-16(23)13-29)11-19(18)15-6-4-3-5-7-15/h3-9,11,14,16,20,24,29H,10,12-13,23H2,1-2H3,(H,25,26)(H,27,28)/t16-,20+/m1/s1

Standard InChI Key:  IIPCWBJMJZVLOK-UZLBHIALSA-N

Alternative Forms

1. Parent:

   

   ALA282103

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

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: 415.56

Molecular Weight (Monoisotopic): 415.1930

AlogP: 3.25

#Rotatable Bonds: 10

Polar Surface Area: 104.45

Molecular Species: ZWITTERION

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.76

CX Basic pKa: 9.26

CX LogP: 0.87

CX LogD: 0.87

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.38

Np Likeness Score: -0.38

References

1. Vasudevan A, Qian Y, Vogt A, Blaskovich MA, Ohkanda J, Sebti SM, Hamilton AD..  (1999)  Potent, highly selective, and non-thiol inhibitors of protein geranylgeranyltransferase-I.,  42  (8): [PMID:10212118] [10.1021/jm9900873]

2. Ochocki JD, Distefano MD..  (2013)  Prenyltransferase Inhibitors: Treating Human Ailments from Cancer to Parasitic Infections.,  4  (3): [PMID:25530833] [10.1039/c2md20299a]

3. 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]

Source

Source(1):

• Scientific Literature