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

ID: ALA2316248

Chembl Id: CHEMBL2316248

PubChem CID: 71562629

Max Phase: Preclinical

Molecular Formula: C28H37N3O6

Molecular Weight: 511.62

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)NCCCC(=O)O

Standard InChI:  InChI=1S/C28H37N3O6/c1-4-19(2)26(37-18-20-12-7-5-8-13-20)23-25(31(35)36)24(21-14-9-6-10-15-21)30-28(23,3)27(34)29-17-11-16-22(32)33/h5-10,12-15,19,23-26,30H,4,11,16-18H2,1-3H3,(H,29,34)(H,32,33)/t19-,23+,24-,25-,26-,28-/m0/s1

Standard InChI Key:  YKTQCNRQDSRVTE-PWSGGEEBSA-N

Alternative Forms

1. Parent:

   

   ALA2316248

   4-[[(2S,3S,4S,5S)-2-methyl-3-[(1S,2S)-2-methyl-1-phenylmethoxybutyl]-4-nitro-5-phenylpyrrolidine-2-carbonyl]amino]butanoic 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: 511.62

Molecular Weight (Monoisotopic): 511.2682

AlogP: 3.96

#Rotatable Bonds: 13

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: 3.73

CX Basic pKa: 7.06

CX LogP: 1.91

CX LogD: 1.43

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.21

Np Likeness Score: -0.08

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