3-Amino-N'-[1,2-dihydroxy-10-oxo-9,10-dihydroanthracene-9-ylidene]benzohydrazide

ID: ALA2283221

PubChem CID: 136240204

Max Phase: Preclinical

Molecular Formula: C21H15N3O4

Molecular Weight: 373.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1cccc(C(=O)N/N=C2/c3ccccc3C(=O)c3ccc(O)c(O)c32)c1

Standard InChI:  InChI=1S/C21H15N3O4/c22-12-5-3-4-11(10-12)21(28)24-23-18-13-6-1-2-7-14(13)19(26)15-8-9-16(25)20(27)17(15)18/h1-10,25,27H,22H2,(H,24,28)/b23-18-

Standard InChI Key:  WPPLYYOOMJYZTO-NKFKGCMQSA-N

Molfile:  

     RDKit          2D

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    3.8623  -29.3111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1464  -29.7236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4306  -29.3111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4306  -28.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1464  -28.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8623  -28.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2899  -29.3111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5740  -30.5486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8623  -30.9611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2899  -31.7861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0058  -32.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0058  -33.0236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2899  -33.4361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5740  -33.0236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8623  -33.4361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1464  -33.0236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4306  -33.4361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7190  -33.0236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7190  -32.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4306  -31.7861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1464  -32.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8623  -31.7861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5740  -32.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8623  -34.2611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7174  -31.7861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2899  -30.9611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7190  -29.7236    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
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  6  7  1  0
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  9 10  1  0
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 22 23  1  0
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 15 24  1  0
 11 24  2  0
 16 25  2  0
 12 26  1  0
 11 27  1  0
 10 23  2  0
  4 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2283221

   ---

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: 373.37

Molecular Weight (Monoisotopic): 373.1063

AlogP: 2.41

#Rotatable Bonds: 2

Polar Surface Area: 125.01

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.63

CX Basic pKa: 2.82

CX LogP: 2.76

CX LogD: 2.56

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.24

Np Likeness Score: -0.32

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