(S)-2-[4-((R)-2-Amino-3-mercapto-propylamino)-2-naphthalen-1-yl-benzoylamino]-4-methyl-pentanoic acid

ID: ALA27449

Chembl Id: CHEMBL27449

Cas Number: 181045-83-0

PubChem CID: 9956145

Max Phase: Preclinical

Molecular Formula: C26H31N3O3S

Molecular Weight: 465.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(=O)c1ccc(NC[C@@H](N)CS)cc1-c1cccc2ccccc12)C(=O)O

Standard InChI:  InChI=1S/C26H31N3O3S/c1-16(2)12-24(26(31)32)29-25(30)22-11-10-19(28-14-18(27)15-33)13-23(22)21-9-5-7-17-6-3-4-8-20(17)21/h3-11,13,16,18,24,28,33H,12,14-15,27H2,1-2H3,(H,29,30)(H,31,32)/t18-,24+/m1/s1

Standard InChI Key:  PKMVDYSKPDHRLR-KOSHJBKYSA-N

Alternative Forms

1. Parent:

   

   ALA27449

   (2S)-2-[[[4-[[(2R)-2-amino-3-mercaptopropyl]amino]-2-(1-naphthalenyl)phenyl]-oxomethyl]amino]-4-methylpentanoic 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: 465.62

Molecular Weight (Monoisotopic): 465.2086

AlogP: 4.40

#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: 3.78

CX Basic pKa: 9.26

CX LogP: 1.86

CX LogD: 1.86

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.29

Np Likeness Score: -0.35

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. Bell IM..  (2004)  Inhibitors of farnesyltransferase: a rational approach to cancer chemotherapy?,  47  (8): [PMID:15055985] [10.1021/jm0305467]

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]

4.  (2013)  Inhibitors of protein prenyltransferases, 

5. Korzeniecki C, Priefer R..  (2021)  Targeting KRAS mutant cancers by preventing signaling transduction in the MAPK pathway.,  211  [PMID:33228976] [10.1016/j.ejmech.2020.113006]

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data