2-(2-((9-methyl-9H-carbazol-3-yl)methylene)hydrazinyl)-4-(4-nitrophenyl)thiazole

ID: ALA4476549

PubChem CID: 155538288

Max Phase: Preclinical

Molecular Formula: C23H17N5O2S

Molecular Weight: 427.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1c2ccccc2c2cc(/C=N/Nc3nc(-c4ccc([N+](=O)[O-])cc4)cs3)ccc21

Standard InChI:  InChI=1S/C23H17N5O2S/c1-27-21-5-3-2-4-18(21)19-12-15(6-11-22(19)27)13-24-26-23-25-20(14-31-23)16-7-9-17(10-8-16)28(29)30/h2-14H,1H3,(H,25,26)/b24-13+

Standard InChI Key:  MFNMCNWOSBONTF-ZMOGYAJESA-N

Molfile:  

 
     RDKit          2D

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   11.0584  -17.5265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7665  -17.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7647  -16.2981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4733  -16.7034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4736  -17.5220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2522  -17.7748    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2518  -16.4502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7314  -17.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5410  -17.0243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8720  -16.2787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.5795  -15.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7159  -14.8701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5281  -14.7805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8567  -14.0323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5062  -18.5515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6689  -13.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2139  -14.5469    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.9587  -14.2107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8691  -13.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0689  -13.2327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4766  -12.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2558  -13.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8599  -12.5518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6860  -11.7524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9027  -11.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3020  -12.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2900  -11.2013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1149  -10.4030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0688  -11.4487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
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  5  6  1  0
  6  7  1  0
  7  9  1  0
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  8  9  2  0
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 10 11  2  0
 11 12  1  0
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 13  8  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
  7 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 18  2  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 21 23  1  0
 29 30  2  0
 29 31  1  0
 26 29  1  0
M  CHG  2  29   1  31  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4476549

   ---

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: 427.49

Molecular Weight (Monoisotopic): 427.1103

AlogP: 5.81

#Rotatable Bonds: 5

Polar Surface Area: 85.35

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.73

CX Basic pKa: 5.35

CX LogP: 6.46

CX LogD: 6.42

Aromatic Rings: 5

Heavy Atoms: 31

QED Weighted: 0.22

Np Likeness Score: -1.70

References

1. Shaikh MS, Kanhed AM, Chandrasekaran B, Palkar MB, Agrawal N, Lherbet C, Hampannavar GA, Karpoormath R..  (2019)  Discovery of novel N-methyl carbazole tethered rhodanine derivatives as direct inhibitors of Mycobacterium tuberculosis InhA.,  29  (16): [PMID:31227345] [10.1016/j.bmcl.2019.06.015]

Source

Source(1):

• Scientific Literature