ID: ALA2441830

Max Phase: Preclinical

Molecular Formula: C22H19Cl2N3O2

Molecular Weight: 428.32

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1ccccc1N1Cc2nc(C)c(CN)c(-c3ccc(Cl)cc3Cl)c2C1=O

Standard InChI:  InChI=1S/C22H19Cl2N3O2/c1-12-15(10-25)20(14-8-7-13(23)9-16(14)24)21-17(26-12)11-27(22(21)28)18-5-3-4-6-19(18)29-2/h3-9H,10-11,25H2,1-2H3

Standard InChI Key:  CKZFVWOHYQPQSY-UHFFFAOYSA-N

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

Properties

Molecular Weight: 428.32

Molecular Weight (Monoisotopic): 427.0854

AlogP: 4.99

#Rotatable Bonds: 4

Polar Surface Area: 68.45

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 11.57

CX Basic pKa: 8.77

CX LogP: 3.50

CX LogD: 2.12

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.64

Np Likeness Score: -0.97

References

1. Devasthale P, Wang Y, Wang W, Fevig J, Feng J, Wang A, Harrity T, Egan D, Morgan N, Cap M, Fura A, Klei HE, Kish K, Weigelt C, Sun L, Levesque P, Moulin F, Li YX, Zahler R, Kirby MS, Hamann LG..  (2013)  Optimization of activity, selectivity, and liability profiles in 5-oxopyrrolopyridine DPP4 inhibitors leading to clinical candidate (Sa)-2-(3-(aminomethyl)-4-(2,4-dichlorophenyl)-2-methyl-5-oxo-5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)-N,N-dimethylacetamide (BMS-767778).,  56  (18): [PMID:23964740] [10.1021/jm4008906]

2. Devasthale P, Wang Y, Wang W, Fevig J, Feng J, Wang A, Harrity T, Egan D, Morgan N, Cap M, Fura A, Klei HE, Kish K, Weigelt C, Sun L, Levesque P, Moulin F, Li YX, Zahler R, Kirby MS, Hamann LG..  (2013)  Optimization of activity, selectivity, and liability profiles in 5-oxopyrrolopyridine DPP4 inhibitors leading to clinical candidate (Sa)-2-(3-(aminomethyl)-4-(2,4-dichlorophenyl)-2-methyl-5-oxo-5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)-N,N-dimethylacetamide (BMS-767778).,  56  (18): [PMID:23964740] [10.1021/jm4008906]

3. Devasthale P, Wang Y, Wang W, Fevig J, Feng J, Wang A, Harrity T, Egan D, Morgan N, Cap M, Fura A, Klei HE, Kish K, Weigelt C, Sun L, Levesque P, Moulin F, Li YX, Zahler R, Kirby MS, Hamann LG..  (2013)  Optimization of activity, selectivity, and liability profiles in 5-oxopyrrolopyridine DPP4 inhibitors leading to clinical candidate (Sa)-2-(3-(aminomethyl)-4-(2,4-dichlorophenyl)-2-methyl-5-oxo-5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)-N,N-dimethylacetamide (BMS-767778).,  56  (18): [PMID:23964740] [10.1021/jm4008906]

Source

Source(1):

• Scientific Literature