N'-(3-(benzyloxy)benzylidene)-3,4,5-trihydroxybenzohydrazide

ID: ALA3735192

PubChem CID: 9564003

Max Phase: Preclinical

Molecular Formula: C21H18N2O5

Molecular Weight: 378.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N/N=C/c1cccc(OCc2ccccc2)c1)c1cc(O)c(O)c(O)c1

Standard InChI:  InChI=1S/C21H18N2O5/c24-18-10-16(11-19(25)20(18)26)21(27)23-22-12-15-7-4-8-17(9-15)28-13-14-5-2-1-3-6-14/h1-12,24-26H,13H2,(H,23,27)/b22-12+

Standard InChI Key:  FDXVECHDYOYVRS-WSDLNYQXSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5972    1.5031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951    3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933    3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933    5.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1924    6.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4914    5.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4915    3.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1925    3.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003    1.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003    1.4932    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4990    0.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8003    1.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4969   -0.4591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0994    0.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3984    1.4886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3985    2.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0995    3.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8004    2.9887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0995    4.9387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4377    3.5886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4377    0.8886    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
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  4 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 19  1  0
 24 26  1  0
 23 27  1  0
 22 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3735192

   N'~1~-{(E)-1-[3-(Benzyloxy)phenyl]methylidene}-3,4,5-trihydroxybenzohydrazide

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: 378.38

Molecular Weight (Monoisotopic): 378.1216

AlogP: 3.15

#Rotatable Bonds: 6

Polar Surface Area: 111.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.90

CX Basic pKa: 1.19

CX LogP: 3.62

CX LogD: 3.50

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.30

Np Likeness Score: -0.86

References

1. Wang X, Sun C, Fang L, Yin D.  (2015)  Discovery of novel sphingosine kinase 1 inhibitors via structure-based hierarchical virtual screening,  6  (3): [10.1039/C4MD00312H]

2. Xi M, Ge J, Wang X, Sun C, Liu T, Fang L, Xiao Q, Yin D..  (2016)  Development of hydroxy-based sphingosine kinase inhibitors and anti-inflammation in dextran sodium sulfate induced colitis in mice.,  24  (14): [PMID:27255176] [10.1016/j.bmc.2016.05.047]

Source

Source(1):

• Scientific Literature