5-(2-(1,3-dioxo-1-phenylbutan-2-ylidene)hydrazineyl)-4-hydroxybenzene-1,3-disulfonic acid

ID: ALA4529607

PubChem CID: 155545554

Max Phase: Preclinical

Molecular Formula: C16H14N2O9S2

Molecular Weight: 442.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)/C(=N\Nc1cc(S(=O)(=O)O)cc(S(=O)(=O)O)c1O)C(=O)c1ccccc1

Standard InChI:  InChI=1S/C16H14N2O9S2/c1-9(19)14(15(20)10-5-3-2-4-6-10)18-17-12-7-11(28(22,23)24)8-13(16(12)21)29(25,26)27/h2-8,17,21H,1H3,(H,22,23,24)(H,25,26,27)/b18-14+

Standard InChI Key:  ZKZRXFBZWUCICQ-NBVRZTHBSA-N

Molfile:  

 
     RDKit          2D

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    6.9337   -9.6577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3465   -8.9520    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.5289   -8.9474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3494   -5.7822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7621   -6.4921    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.1705   -5.7798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6434   -6.9089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6423   -7.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3503   -8.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0600   -7.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0572   -6.9053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3485   -6.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3461   -5.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4726   -6.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0577   -9.3634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9356   -6.5005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9354   -5.6833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2276   -5.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2274   -4.4577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5200   -5.6837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9350   -4.0489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5196   -4.0493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8122   -5.2752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5202   -6.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6422   -4.4603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3494   -4.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3496   -3.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6368   -2.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9326   -3.2363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  5  4  2  0
  6  5  2  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
 12 13  1  0
 11  5  1  0
  5 14  1  0
  9  2  1  0
  2 15  1  0
  7 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 19 21  1  0
 19 22  2  0
 20 23  2  0
 20 24  1  0
 21 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4529607

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 442.43

Molecular Weight (Monoisotopic): 442.0141

AlogP: 1.13

#Rotatable Bonds: 7

Polar Surface Area: 187.50

Molecular Species: ACID

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: -3.19

CX Basic pKa: ┄

CX LogP: -1.33

CX LogD: -3.56

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.12

Np Likeness Score: -0.62

References

1. Viswanathan A, Kute D, Musa A, Konda Mani S, Sipilä V, Emmert-Streib F, Zubkov FI, Gurbanov AV, Yli-Harja O, Kandhavelu M..  (2019)  2-(2-(2,4-dioxopentan-3-ylidene)hydrazineyl)benzonitrile as novel inhibitor of receptor tyrosine kinase and PI3K/AKT/mTOR signaling pathway in glioblastoma.,  166  [PMID:30731398] [10.1016/j.ejmech.2019.01.021]

Source

Source(1):

• Scientific Literature