ID: ALA559437

Max Phase: Preclinical

Molecular Formula: C19H24ClN3O3

Molecular Weight: 377.87

Molecule Type: Small molecule

Representations

Canonical SMILES:  COC[C@@H](C1CC1)n1cc(Cl)nc(Nc2cc(C)c(OC)cc2C)c1=O

Standard InChI:  InChI=1S/C19H24ClN3O3/c1-11-8-16(26-4)12(2)7-14(11)21-18-19(24)23(9-17(20)22-18)15(10-25-3)13-5-6-13/h7-9,13,15H,5-6,10H2,1-4H3,(H,21,22)/t15-/m0/s1

Standard InChI Key:  DLFAZPBXJQLULP-HNNXBMFYSA-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: 377.87

Molecular Weight (Monoisotopic): 377.1506

AlogP: 3.86

#Rotatable Bonds: 7

Polar Surface Area: 65.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 1.13

CX LogP: 3.57

CX LogD: 3.57

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.79

Np Likeness Score: -0.67

References

1. Hartz RA, Ahuja VT, Rafalski M, Schmitz WD, Brenner AB, Denhart DJ, Ditta JL, Deskus JA, Yue EW, Arvanitis AG, Lelas S, Li YW, Molski TF, Wong H, Grace JE, Lentz KA, Li J, Lodge NJ, Zaczek R, Combs AP, Olson RE, Mattson RJ, Bronson JJ, Macor JE..  (2009)  In vitro intrinsic clearance-based optimization of N3-phenylpyrazinones as corticotropin-releasing factor-1 (CRF1) receptor antagonists.,  52  (14): [PMID:19552436] [10.1021/jm900302q]

2. Hartz RA, Ahuja VT, Arvanitis AG, Rafalski M, Yue EW, Denhart DJ, Schmitz WD, Ditta JL, Deskus JA, Brenner AB, Hobbs FW, Payne J, Lelas S, Li YW, Molski TF, Mattson GK, Peng Y, Wong H, Grace JE, Lentz KA, Qian-Cutrone J, Zhuo X, Shu YZ, Lodge NJ, Zaczek R, Combs AP, Olson RE, Bronson JJ, Mattson RJ, Macor JE..  (2009)  Synthesis, structure-activity relationships, and in vivo evaluation of N3-phenylpyrazinones as novel corticotropin-releasing factor-1 (CRF1) receptor antagonists.,  52  (14): [PMID:19552437] [10.1021/jm900301y]

3. Deskus JA, Dischino DD, Mattson RJ, Ditta JL, Parker MF, Denhart DJ, Zuev D, Huang H, Hartz RA, Ahuja VT, Wong H, Mattson GK, Molski TF, Grace JE, Zueva L, Nielsen JM, Dulac H, Li YW, Guaraldi M, Azure M, Onthank D, Hayes M, Wexler E, McDonald J, Lodge NJ, Bronson JJ, Macor JE..  (2012)  [18F](R)-5-chloro-1-(1-cyclopropyl-2-methoxyethyl)-3-(4-(2-fluoroethoxy)-2,5-dimethyl phenylamino)pyrazin-2(1H)-one: introduction of N3-phenylpyrazinones as potential CRF-R1 PET imaging agents.,  22  (21): [PMID:23010264] [10.1016/j.bmcl.2012.08.112]

4. St Jean DJ, Fotsch C..  (2012)  Mitigating heterocycle metabolism in drug discovery.,  55  (13): [PMID:22533875] [10.1021/jm300343m]

Source

Source(1):

• Scientific Literature