3-((2S,3R,4S,5S)-3-((1S,2S)-1-(2-fluorobenzyloxy)-2-methylbutyl)-4-nitro-5-(thiophen-3-yl)pyrrolidine-2-carboxamido)propanoic acid

ID: ALA2316000

Chembl Id: CHEMBL2316000

PubChem CID: 71562627

Max Phase: Preclinical

Molecular Formula: C24H30FN3O6S

Molecular Weight: 507.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H](C)[C@H](OCc1ccccc1F)[C@H]1[C@H]([N+](=O)[O-])[C@H](c2ccsc2)N[C@@H]1C(=O)NCCC(=O)O

Standard InChI:  InChI=1S/C24H30FN3O6S/c1-3-14(2)23(34-12-15-6-4-5-7-17(15)25)19-21(24(31)26-10-8-18(29)30)27-20(22(19)28(32)33)16-9-11-35-13-16/h4-7,9,11,13-14,19-23,27H,3,8,10,12H2,1-2H3,(H,26,31)(H,29,30)/t14-,19+,20-,21-,22-,23-/m0/s1

Standard InChI Key:  LTOBCHWWQGTKCV-WLKHMSELSA-N

Alternative Forms

1. Parent:

   

   ALA2316000

   3-[[(2S,3R,4S,5S)-3-[(1S,2S)-1-[(2-fluorophenyl)methoxy]-2-methylbutyl]-4-nitro-5-thiophen-3-ylpyrrolidine-2-carbonyl]amino]propanoic 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: 507.58

Molecular Weight (Monoisotopic): 507.1839

AlogP: 3.38

#Rotatable Bonds: 12

Polar Surface Area: 130.80

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.64

CX Basic pKa: 6.80

CX LogP: 1.14

CX LogD: 0.49

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.30

Np Likeness Score: -0.93

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