US9102637, 254

ID: ALA3684066

PubChem CID: 118061212

Max Phase: Preclinical

Molecular Formula: C24H19N7O2S

Molecular Weight: 469.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1nc(Nc2cccc3ncccc23)sc1NC(=O)c1ccc(Cn2ccnc2)cc1

Standard InChI:  InChI=1S/C24H19N7O2S/c25-21(32)20-23(30-22(33)16-8-6-15(7-9-16)13-31-12-11-26-14-31)34-24(29-20)28-19-5-1-4-18-17(19)3-2-10-27-18/h1-12,14H,13H2,(H2,25,32)(H,28,29)(H,30,33)

Standard InChI Key:  JGPTUBGWBPWAKX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
    8.4463    0.5739    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7426   -0.3981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2330   -1.4934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2524   -0.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2526   -1.3618    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990   -0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003   -1.4977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981   -1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981   -3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -3.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0317    0.7359    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.4979    1.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0996    2.4249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2115    3.6348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0188    3.5031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8143    5.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9284    6.2197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5337    7.5922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0249    7.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6334    9.1262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1257    9.2862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8539   10.5829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3211   10.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4780    8.7794    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1077    8.1692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9109    6.5438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3056    5.1713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17  8  1  0
 17 12  1  0
  6 18  1  0
 18 19  1  0
 19  4  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 28  1  0
 26 33  1  0
 33 34  2  0
 34 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3684066

   5-[[4-(Imidazol-1-ylmethyl)benzoyl]amino]-2-(quinolin-5-ylamino)-1,3-thiazole-4-carboxamide

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: 469.53

Molecular Weight (Monoisotopic): 469.1321

AlogP: 4.03

#Rotatable Bonds: 7

Polar Surface Area: 127.82

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.96

CX Basic pKa: 6.47

CX LogP: 3.89

CX LogD: 3.85

Aromatic Rings: 5

Heavy Atoms: 34

QED Weighted: 0.33

Np Likeness Score: -1.83

References

1.  (2015)  Bicyclic thiazole compounds, 

2. McDermott, Ultan U and 24 more authors.  2007-12-11  Identification of genotype-correlated sensitivity to selective kinase inhibitors by using high-throughput tumor cell line profiling.  [PMID:18077425]

3. Zarrinkar, Patrick P PP and 15 more authors.  2009-10-01  AC220 is a uniquely potent and selective inhibitor of FLT3 for the treatment of acute myeloid leukemia (AML).  [PMID:19654408]

4. Klaeger, Susan S and 47 more authors.  2017-12-01  The target landscape of clinical kinase drugs.  [PMID:29191878]

5. Narayan, Satya S and 7 more authors.  2019-01-01  ASR352, A potent anticancer agent: Synthesis, preliminary SAR, and biological activities against colorectal cancer bulk, 5-fluorouracil/oxaliplatin resistant and stem cells.  [PMID:30384048]

6. Read, Jon J and 19 more authors.  2019-08-01  Tool inhibitors and assays to interrogate the biology of the TRAF2 and NCK interacting kinase.  [PMID:31153805]

7. Nair, Satheesh and 39 more authors.  2020-07-09  Optimization of Nicotinamides as Potent and Selective IRAK4 Inhibitors with Efficacy in a Murine Model of Psoriasis.  [PMID:32676146]

Source

Source(1):

• BindingDB Database