3-hydroxy-N'-(5-hydroxy-2-nitrobenzylidene)-2-naphthohydrazide

ID: ALA1208866

PubChem CID: 7258059

Max Phase: Preclinical

Molecular Formula: C18H13N3O5

Molecular Weight: 351.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N/N=C/c1cc(O)ccc1[N+](=O)[O-])c1cc2ccccc2cc1O

Standard InChI:  InChI=1S/C18H13N3O5/c22-14-5-6-16(21(25)26)13(7-14)10-19-20-18(24)15-8-11-3-1-2-4-12(11)9-17(15)23/h1-10,22-23H,(H,20,24)/b19-10+

Standard InChI Key:  CJBZZTGVNGNXRD-VXLYETTFSA-N

Molfile:  

     RDKit          2D

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   -5.3056  -11.4291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3068  -12.2565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5919  -12.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5937  -11.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8784  -11.4255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8776  -12.2523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1623  -12.6633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4473  -12.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4520  -11.4186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1679  -11.0113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7401  -11.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0231  -11.4099    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7451  -10.1767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3112  -10.9930    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4058  -11.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1177  -10.9843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8329  -11.3959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5443  -10.9797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5398  -10.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8178   -9.7459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1093  -10.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7312  -12.6583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8381  -12.2222    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5541  -12.6322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1251  -12.6372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8098   -8.9209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
 11 13  2  0
  3  6  2  0
 12 14  1  0
  6  7  1  0
 14 15  2  0
  1  2  2  0
 15 16  1  0
  7  8  2  0
 16 17  2  0
  5  4  2  0
 17 18  1  0
  8  9  1  0
 18 19  2  0
  4  1  1  0
 19 20  1  0
  9 10  2  0
 20 21  2  0
 21 16  1  0
 10  5  1  0
  8 22  1  0
  9 11  1  0
  2  3  1  0
 23 24  2  0
 23 25  1  0
 17 23  1  0
 11 12  1  0
 20 26  1  0
M  CHG  2  23   1  25  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1208866

   3-Hydroxy-N'-(5-hydroxy-2-nitrobenzylidene)-2-naphthohydrazide

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: 351.32

Molecular Weight (Monoisotopic): 351.0855

AlogP: 2.92

#Rotatable Bonds: 4

Polar Surface Area: 125.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.74

CX Basic pKa: ┄

CX LogP: 3.94

CX LogD: 2.96

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.38

Np Likeness Score: -1.08

References

1. Lee S, Jung KY, Park J, Cho JH, Kim YC, Chang S..  (2010)  Synthesis of potent chemical inhibitors of dynamin GTPase.,  20  (16): [PMID:20621477] [10.1016/j.bmcl.2010.06.092]

Source

Source(1):

• Scientific Literature