(S)-5-Cyclopropyl-N-(1-(4-(hydroxycarbamoyl)phenyl)ethyl)[2,2'-bithiazole]-4-carboxamide

ID: ALA4476497

PubChem CID: 139302991

Max Phase: Preclinical

Molecular Formula: C19H18N4O3S2

Molecular Weight: 414.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@H](NC(=O)c1nc(-c2nccs2)sc1C1CC1)c1ccc(C(=O)NO)cc1

Standard InChI:  InChI=1S/C19H18N4O3S2/c1-10(11-2-6-13(7-3-11)16(24)23-26)21-17(25)14-15(12-4-5-12)28-19(22-14)18-20-8-9-27-18/h2-3,6-10,12,26H,4-5H2,1H3,(H,21,25)(H,23,24)/t10-/m0/s1

Standard InChI Key:  GVBDKSWKGOTDLU-JTQLQIEISA-N

Molfile:  

 
     RDKit          2D

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    9.2748   -4.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5316   -4.1784    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.8582   -3.6874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1890   -4.1784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7563   -5.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5005   -6.4213    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1715   -6.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8436   -6.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5854   -5.6338    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.8615   -2.8636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4036   -3.9255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2300   -3.1190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7921   -4.4791    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2736   -2.1544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4497   -2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0067   -4.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3952   -4.7799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6102   -4.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9989   -5.0776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1723   -5.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9624   -6.1367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5703   -5.5821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8331   -3.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5613   -6.4395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7757   -6.1877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7361   -7.2458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1649   -6.7421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
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  5  1  1  0
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  9 10  1  0
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  5 12  1  0
 12 13  2  0
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 18 19  2  0
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 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 17 24  1  6
 21 25  1  0
 25 26  1  0
 25 27  2  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4476497

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 414.51

Molecular Weight (Monoisotopic): 414.0820

AlogP: 3.75

#Rotatable Bonds: 6

Polar Surface Area: 104.21

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.05

CX Basic pKa: 1.14

CX LogP: 3.06

CX LogD: 3.05

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.42

Np Likeness Score: -1.33

References

1. Zhang SW, Gong CJ, Su MB, Chen F, He T, Zhang YM, Shen QQ, Su Y, Ding J, Li J, Chen Y, Nan FJ..  (2020)  Synthesis and in Vitro and in Vivo Biological Evaluation of Tissue-Specific Bisthiazole Histone Deacetylase (HDAC) Inhibitors.,  63  (2): [PMID:31855601] [10.1021/acs.jmedchem.9b01792]

Source

Source(1):

• Scientific Literature