1-{2-[2-(5-Nitro-pyridin-2-ylamino)-ethylamino]-acetyl}-pyrrolidine-2-carbonitrile

ID: ALA77539

Chembl Id: CHEMBL77539

PubChem CID: 10969177

Max Phase: Preclinical

Molecular Formula: C14H18N6O3

Molecular Weight: 318.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C[C@@H]1CCCN1C(=O)CNCCNc1ccc([N+](=O)[O-])cn1

Standard InChI:  InChI=1S/C14H18N6O3/c15-8-11-2-1-7-19(11)14(21)10-16-5-6-17-13-4-3-12(9-18-13)20(22)23/h3-4,9,11,16H,1-2,5-7,10H2,(H,17,18)/t11-/m0/s1

Standard InChI Key:  VEHQFHWMDLMEIN-NSHDSACASA-N

Alternative Forms

1. Parent:

   

   ALA77539

   1-{2-[2-(5-Nitro-pyridin-2-ylamino)-ethylamino]-acetyl}-pyrrolidine-2-carbonitrile

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: 318.34

Molecular Weight (Monoisotopic): 318.1440

AlogP: 0.51

#Rotatable Bonds: 7

Polar Surface Area: 124.19

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.05

CX LogP: -0.33

CX LogD: -1.07

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.43

Np Likeness Score: -1.68

References

1. Villhauer EB, Brinkman JA, Naderi GB, Dunning BE, Mangold BL, Mone MD, Russell ME, Weldon SC, Hughes TE..  (2002)  1-[2-[(5-Cyanopyridin-2-yl)amino]ethylamino]acetyl-2-(S)-pyrrolidinecarbonitrile: a potent, selective, and orally bioavailable dipeptidyl peptidase IV inhibitor with antihyperglycemic properties.,  45  (12): [PMID:12036346] [10.1021/jm025522z]

2. Villhauer EB, Brinkman JA, Naderi GB, Burkey BF, Dunning BE, Prasad K, Mangold BL, Russell ME, Hughes TE..  (2003)  1-[[(3-hydroxy-1-adamantyl)amino]acetyl]-2-cyano-(S)-pyrrolidine: a potent, selective, and orally bioavailable dipeptidyl peptidase IV inhibitor with antihyperglycemic properties.,  46  (13): [PMID:12801240] [10.1021/jm030091l]

Source

Source(1):

• Scientific Literature