5-({(S)-[(2S,3S,4S)-3-((1S,2S)-1-Benzyloxy-2-methyl-butyl)-2-methyl-4-nitro-5-phenyl-pyrrolidin-2-yl]-oxo-methyl}-amino)-pentanoic acid

ID: ALA2316250

Chembl Id: CHEMBL2316250

PubChem CID: 71562755

Max Phase: Preclinical

Molecular Formula: C29H39N3O6

Molecular Weight: 525.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H](C)[C@H](OCc1ccccc1)[C@H]1[C@H]([N+](=O)[O-])[C@H](c2ccccc2)N[C@]1(C)C(=O)NCCCCC(=O)O

Standard InChI:  InChI=1S/C29H39N3O6/c1-4-20(2)27(38-19-21-13-7-5-8-14-21)24-26(32(36)37)25(22-15-9-6-10-16-22)31-29(24,3)28(35)30-18-12-11-17-23(33)34/h5-10,13-16,20,24-27,31H,4,11-12,17-19H2,1-3H3,(H,30,35)(H,33,34)/t20-,24+,25-,26-,27-,29-/m0/s1

Standard InChI Key:  NNZKSFDPIUDSQY-XJIXUFHVSA-N

Alternative Forms

1. Parent:

   

   ALA2316250

   5-[[(2S,3S,4S,5S)-2-methyl-3-[(1S,2S)-2-methyl-1-phenylmethoxybutyl]-4-nitro-5-phenylpyrrolidine-2-carbonyl]amino]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: 525.65

Molecular Weight (Monoisotopic): 525.2839

AlogP: 4.35

#Rotatable Bonds: 14

Polar Surface Area: 130.80

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.96

CX Basic pKa: 7.06

CX LogP: 2.37

CX LogD: 1.90

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.19

Np Likeness Score: -0.04

References

1. San Sebastián E, Zimmerman T, Zubia A, Vara Y, Martin E, Sirockin F, Dejaegere A, Stote RH, Lopez X, Pantoja-Uceda D, Valcárcel M, Mendoza L, Vidal-Vanaclocha F, Cossío FP, Blanco FJ..  (2013)  Design, synthesis, and functional evaluation of leukocyte function associated antigen-1 antagonists in early and late stages of cancer development.,  56  (3): [PMID:23339734] [10.1021/jm3016848]

Source

Source(1):

• Scientific Literature