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

ID: ALA2316252

Chembl Id: CHEMBL2316252

PubChem CID: 71562757

Max Phase: Preclinical

Molecular Formula: C30H41N3O6

Molecular Weight: 539.67

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)NCCCCCC(=O)O

Standard InChI:  InChI=1S/C30H41N3O6/c1-4-21(2)28(39-20-22-14-8-5-9-15-22)25-27(33(37)38)26(23-16-10-6-11-17-23)32-30(25,3)29(36)31-19-13-7-12-18-24(34)35/h5-6,8-11,14-17,21,25-28,32H,4,7,12-13,18-20H2,1-3H3,(H,31,36)(H,34,35)/t21-,25+,26-,27-,28-,30-/m0/s1

Standard InChI Key:  ALGIMSOSPFMUHU-TXDVSOHRSA-N

Alternative Forms

1. Parent:

   

   ALA2316252

   6-[[(2S,3S,4S,5S)-2-methyl-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: 539.67

Molecular Weight (Monoisotopic): 539.2995

AlogP: 4.74

#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: 3.86

CX Basic pKa: 7.06

CX LogP: 2.81

CX LogD: 2.33

Aromatic Rings: 2

Heavy Atoms: 39

QED Weighted: 0.17

Np Likeness Score: -0.01

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