ID: ALA2325894

Max Phase: Preclinical

Molecular Formula: C17H18N6O2

Molecular Weight: 338.37

Molecule Type: Small molecule

Representations

Canonical SMILES:  C[C@@H](NC(=O)c1c[nH]c2ncc(C3CC3)nc12)C(=O)N1CC(C#N)C1

Standard InChI:  InChI=1S/C17H18N6O2/c1-9(17(25)23-7-10(4-18)8-23)21-16(24)12-5-19-15-14(12)22-13(6-20-15)11-2-3-11/h5-6,9-11H,2-3,7-8H2,1H3,(H,19,20)(H,21,24)/t9-/m1/s1

Standard InChI Key:  XUHZZDAPCLYTNF-SECBINFHSA-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: 338.37

Molecular Weight (Monoisotopic): 338.1491

AlogP: 0.94

#Rotatable Bonds: 4

Polar Surface Area: 114.77

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 11.66

CX Basic pKa: 0.73

CX LogP: -0.38

CX LogD: -0.38

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.86

Np Likeness Score: -1.17

References

1. Soth M, Hermann JC, Yee C, Alam M, Barnett JW, Berry P, Browner MF, Frank K, Frauchiger S, Harris S, He Y, Hekmat-Nejad M, Hendricks T, Henningsen R, Hilgenkamp R, Ho H, Hoffman A, Hsu PY, Hu DQ, Itano A, Jaime-Figueroa S, Jahangir A, Jin S, Kuglstatter A, Kutach AK, Liao C, Lynch S, Menke J, Niu L, Patel V, Railkar A, Roy D, Shao A, Shaw D, Steiner S, Sun Y, Tan SL, Wang S, Vu MD..  (2013)  3-Amido pyrrolopyrazine JAK kinase inhibitors: development of a JAK3 vs JAK1 selective inhibitor and evaluation in cellular and in vivo models.,  56  (1): [PMID:23214979] [10.1021/jm301646k]

2. Lynch SM, DeVicente J, Hermann JC, Jaime-Figueroa S, Jin S, Kuglstatter A, Li H, Lovey A, Menke J, Niu L, Patel V, Roy D, Soth M, Steiner S, Tivitmahaisoon P, Vu MD, Yee C..  (2013)  Strategic use of conformational bias and structure based design to identify potent JAK3 inhibitors with improved selectivity against the JAK family and the kinome.,  23  (9): [PMID:23540648] [10.1016/j.bmcl.2013.02.012]

Source

Source(1):

• Scientific Literature