2-(4-chloro-2-methyl-anilino)-N-[(2-hydroxy-1-naphthyl)methyleneamino]butanamide

ID: ALA4470562

PubChem CID: 135533790

Max Phase: Preclinical

Molecular Formula: C22H22ClN3O2

Molecular Weight: 395.89

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCC(Nc1ccc(Cl)cc1C)C(=O)N/N=C/c1c(O)ccc2ccccc12

Standard InChI:  InChI=1S/C22H22ClN3O2/c1-3-19(25-20-10-9-16(23)12-14(20)2)22(28)26-24-13-18-17-7-5-4-6-15(17)8-11-21(18)27/h4-13,19,25,27H,3H2,1-2H3,(H,26,28)/b24-13+

Standard InChI Key:  PXDXAUOKFYVERK-ZMOGYAJESA-N

Molfile:  

 
     RDKit          2D

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   29.6884  -27.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9867  -28.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2657  -27.9262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4078  -28.2941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.2447  -27.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9481  -26.6828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9294  -25.8622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2080  -25.4673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5040  -25.8989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5262  -26.7181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3721  -26.6504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0890  -27.0427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.7872  -26.6180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.4895  -26.9879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1809  -26.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9039  -26.9331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1492  -25.7356    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.8405  -25.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9356  -27.7496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5212  -27.8045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.5626  -25.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2534  -25.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2222  -24.4324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4942  -24.0519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8063  -24.4892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9129  -23.9958    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   34.5920  -26.5016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
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  1  7  1  0
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  1 12  1  0
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 17 20  1  0
 15 21  2  0
 19 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 19  1  0
 24 27  1  0
 22 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4470562

   ---

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: 395.89

Molecular Weight (Monoisotopic): 395.1401

AlogP: 4.85

#Rotatable Bonds: 6

Polar Surface Area: 73.72

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.57

CX Basic pKa: 1.70

CX LogP: 5.15

CX LogD: 5.12

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.41

Np Likeness Score: -1.31

References

1. Zou Y, Hu Y, Ge S, Zheng Y, Li Y, Liu W, Guo W, Zhang Y, Xu Q, Lai Y..  (2019)  Effective Virtual Screening Strategy toward heme-containing proteins: Identification of novel IDO1 inhibitors.,  184  [PMID:31610376] [10.1016/j.ejmech.2019.111750]

Source

Source(1):

• Scientific Literature