ID: ALA191384

Max Phase: Preclinical

Molecular Formula: C20H16N6S

Molecular Weight: 372.46

Molecule Type: Small molecule

Representations

Synonyms (1): AS-601245
Synonyms from Alternative Forms(1):

Canonical SMILES:  N#C/C(=C1/Nc2ccccc2S1)c1ccnc(NCCc2cccnc2)n1

Standard InChI:  InChI=1S/C20H16N6S/c21-12-15(19-25-17-5-1-2-6-18(17)27-19)16-8-11-24-20(26-16)23-10-7-14-4-3-9-22-13-14/h1-6,8-9,11,13,25H,7,10H2,(H,23,24,26)/b19-15+

Standard InChI Key:  AVLYNJZZQYEFEA-XDJHFCHBSA-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: 372.46

Molecular Weight (Monoisotopic): 372.1157

AlogP: 3.94

#Rotatable Bonds: 5

Polar Surface Area: 86.52

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 11.25

CX Basic pKa: 5.50

CX LogP: 3.26

CX LogD: 3.26

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.66

Np Likeness Score: -1.33

References

1. Ijjaali I, Petitet F, Dubus E, Barberan O, Michel A..  (2007)  Assessing potency of c-Jun N-terminal kinase 3 (JNK3) inhibitors using 2D molecular descriptors and binary QSAR methodology.,  15  (12): [PMID:17451961] [10.1016/j.bmc.2007.03.062]

2. Asano Y, Kitamura S, Ohra T, Aso K, Igata H, Tamura T, Kawamoto T, Tanaka T, Sogabe S, Matsumoto S, Yamaguchi M, Kimura H, Itoh F..  (2008)  Discovery, synthesis and biological evaluation of isoquinolones as novel and highly selective JNK inhibitors (1).,  16  (8): [PMID:18313304] [10.1016/j.bmc.2008.02.027]

3. Fedorov O, Marsden B, Pogacic V, Rellos P, Müller S, Bullock AN, Schwaller J, Sundström M, Knapp S..  (2007)  A systematic interaction map of validated kinase inhibitors with Ser/Thr kinases.,  104  (51): [PMID:18077363] [10.1073/pnas.0708800104]

4. Bain J, Plater L, Elliott M, Shpiro N, Hastie CJ, McLauchlan H, Klevernic I, Arthur JS, Alessi DR, Cohen P..  (2007)  The selectivity of protein kinase inhibitors: a further update.,  408  (3): [PMID:17850214] [10.1042/bj20070797]

5. Kamenecka T, Jiang R, Song X, Duckett D, Chen W, Ling YY, Habel J, Laughlin JD, Chambers J, Figuera-Losada M, Cameron MD, Lin L, Ruiz CH, LoGrasso PV..  (2010)  Synthesis, biological evaluation, X-ray structure, and pharmacokinetics of aminopyrimidine c-jun-N-terminal kinase (JNK) inhibitors.,  53  (1): [PMID:19947601] [10.1021/jm901351f]

6. Siddiqui MA, Reddy PA..  (2010)  Small molecule JNK (c-Jun N-terminal kinase) inhibitors.,  53  (8): [PMID:20146479] [10.1021/jm9003279]

7. Bryk R, Wu K, Raimundo BC, Boardman PE, Chao P, Conn GL, Anderson E, Cole JL, Duffy NP, Nathan C, Griffin JH..  (2011)  Identification of new inhibitors of protein kinase R guided by statistical modeling.,  21  (13): [PMID:21632247] [10.1016/j.bmcl.2011.04.149]

8. Gao Y, Davies SP, Augustin M, Woodward A, Patel UA, Kovelman R, Harvey KJ..  (2013)  A broad activity screen in support of a chemogenomic map for kinase signalling research and drug discovery.,  451  (2): [PMID:23398362] [10.1042/bj20121418]

9. Genomics of Drug Sensitity in Cancer screening data, Wellcome Trust Sanger Institute,  [10.6019/CHEMBL1201861]

10. Peleli M, Aggeli IK, Matralis AN, Kourounakis AP, Beis I, Gaitanaki C..  (2015)  Evaluation of two novel antioxidants with differential effects on curcumin-induced apoptosis in C2 skeletal myoblasts; involvement of JNKs.,  23  (3): [PMID:25577709] [10.1016/j.bmc.2014.12.046]

11. Fedorov O, Marsden B, Pogacic V, Rellos P, Müller S, Bullock AN, Schwaller J, Sundström M, Knapp S..  (2007)  A systematic interaction map of validated kinase inhibitors with Ser/Thr kinases.,  104  (51): [PMID:18077363] [10.1073/pnas.0708800104]

Source

Source(2):

• Scientific Literature
• Sanger Institute Genomics of Drug Sensitivity in Cancer