3-hydroxy-N'-(3-hydroxy-4-methoxybenzylidene)-2-naphthohydrazide

ID: ALA1208927

PubChem CID: 6870911

Max Phase: Preclinical

Molecular Formula: C19H16N2O4

Molecular Weight: 336.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=N/NC(=O)c2cc3ccccc3cc2O)cc1O

Standard InChI:  InChI=1S/C19H16N2O4/c1-25-18-7-6-12(8-17(18)23)11-20-21-19(24)15-9-13-4-2-3-5-14(13)10-16(15)22/h2-11,22-23H,1H3,(H,21,24)/b20-11+

Standard InChI Key:  WOIMNRLXNFHPCG-RGVLZGJSSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    5.7694  -11.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7682  -11.9440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4831  -12.3569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4813  -10.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1966  -11.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1974  -11.9398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9127  -12.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6277  -11.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6230  -11.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9071  -10.6988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3349  -10.6892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0519  -11.0974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3299   -9.8642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7638  -10.6805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4808  -11.0887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1927  -10.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9079  -11.0834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6193  -10.6672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6148   -9.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8928   -9.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1843   -9.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3438  -12.3458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8848   -8.6084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3262   -9.4236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0437   -9.8307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  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
 20 23  1  0
  9 11  1  0
 19 24  1  0
  2  3  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1208927

   3-hydroxy-N'-(3-hydroxy-4-methoxybenzylidene)-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: 336.35

Molecular Weight (Monoisotopic): 336.1110

AlogP: 3.02

#Rotatable Bonds: 4

Polar Surface Area: 91.15

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.80

CX Basic pKa: 1.53

CX LogP: 3.84

CX LogD: 3.69

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.50

Np Likeness Score: -0.72

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