3-Amino-N'-[2-chloro-10-oxo-9,10-dihydroanthracene-9-ylidene]benzohydrazide

ID: ALA2283224

PubChem CID: 76316309

Max Phase: Preclinical

Molecular Formula: C21H16ClN3O2

Molecular Weight: 377.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1cccc(C(=O)N/N=C2\c3cc(Cl)ccc3C(=O)C3C=CC=CC23)c1

Standard InChI:  InChI=1S/C21H16ClN3O2/c22-13-8-9-17-18(11-13)19(15-6-1-2-7-16(15)20(17)26)24-25-21(27)12-4-3-5-14(23)10-12/h1-11,15-16H,23H2,(H,25,27)/b24-19-

Standard InChI Key:  JKQVGXSXQYCQTC-CLCOLTQESA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    2.2751   -2.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2740   -3.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9908   -3.4840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7052   -3.0677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7023   -2.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9890   -1.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4173   -1.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1353   -2.2301    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4142   -0.9949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5627   -1.8280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1384   -3.0568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8523   -3.4696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2819   -4.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5664   -3.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2802   -3.4719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9974   -3.0565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9978   -2.2276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2750   -1.8159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5650   -2.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5686   -4.7095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8592   -4.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1534   -4.7049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1517   -5.5205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8616   -5.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5686   -5.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2711   -0.9910    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.9974   -4.7056    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  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  1 10  1  0
  8 11  1  0
 11 12  2  0
 12 21  1  0
 12 14  1  0
 20 13  1  0
 13 15  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 18 26  1  0
 13 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2283224

   3-amino-N-[(Z)-(7-chloro-10-oxo-4a,9a-dihydroanthracen-9-ylidene)amino]benzamide

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: 377.83

Molecular Weight (Monoisotopic): 377.0931

AlogP: 3.61

#Rotatable Bonds: 2

Polar Surface Area: 84.55

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.74

CX Basic pKa: 2.97

CX LogP: 2.98

CX LogD: 2.98

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.62

Np Likeness Score: -0.51

References

1. Bansal SK, Sinha BN, Khosa RL.  (2013)  -Amino butyric acid analogs as novel potent GABA-AT inhibitors: molecular docking, synthesis, and biological evaluation,  22  (1): [10.1007/s00044-012-0023-0]

Source

Source(1):

• Scientific Literature