6-((2S,3R,4S,5S)-3-((1S,2S)-1-(benzyloxy)-2-methylbutyl)-4-nitro-5-phenylpyrrolidine-2-carboxamido)hexanoic acid

ID: ALA2316251

Chembl Id: CHEMBL2316251

PubChem CID: 71562756

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@@H]1C(=O)NCCCCCC(=O)O

Standard InChI:  InChI=1S/C29H39N3O6/c1-3-20(2)28(38-19-21-13-7-4-8-14-21)24-26(29(35)30-18-12-6-11-17-23(33)34)31-25(27(24)32(36)37)22-15-9-5-10-16-22/h4-5,7-10,13-16,20,24-28,31H,3,6,11-12,17-19H2,1-2H3,(H,30,35)(H,33,34)/t20-,24+,25-,26-,27-,28-/m0/s1

Standard InChI Key:  ZGGRBJZCUULLTI-UZXVECFESA-N

Alternative Forms

1. Parent:

   

   ALA2316251

   6-[[(2S,3R,4S,5S)-3-[(1S,2S)-2-methyl-1-phenylmethoxybutyl]-4-nitro-5-phenylpyrrolidine-2-carbonyl]amino]hexanoic 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: 15

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: 3.52

CX Basic pKa: 7.33

CX LogP: 2.36

CX LogD: 2.04

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.18

Np Likeness Score: -0.07

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