(E)-2-Cyano-3-(3,4-dihydroxy-5-nitrophenyl)acrylic Acid

ID: ALA4521833

Cas Number: 160391-70-8

PubChem CID: 23189849

Product Number: T394673, Order Now?

Max Phase: Preclinical

Molecular Formula: C10H6N2O6

Molecular Weight: 250.17

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#C/C(=C\c1cc(O)c(O)c([N+](=O)[O-])c1)C(=O)O

Standard InChI:  InChI=1S/C10H6N2O6/c11-4-6(10(15)16)1-5-2-7(12(17)18)9(14)8(13)3-5/h1-3,13-14H,(H,15,16)/b6-1+

Standard InChI Key:  XDDDOLQEZBJWFZ-LZCJLJQNSA-N

Molfile:  

 
     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
   12.1804   -6.9995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4697   -7.4052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4664   -8.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8878   -7.4109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1796   -6.1823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7597   -8.6322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0523   -8.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3457   -8.6264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3424   -9.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0498   -9.8551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7564   -9.4494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0465  -10.6723    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7539  -11.0838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3398  -11.0780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6316   -9.8493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6383   -8.2150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7623   -6.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0548   -6.5864    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  1  4  2  0
  1  5  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  6 11  2  0
 12 13  2  0
 12 14  1  0
 10 12  1  0
  9 15  1  0
  8 16  1  0
  3  6  1  0
 17 18  3  0
  2 17  1  0
M  CHG  2  12   1  14  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4521833

   Tyrphostin AG 1290

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: 250.17

Molecular Weight (Monoisotopic): 250.0226

AlogP: 1.00

#Rotatable Bonds: 3

Polar Surface Area: 144.69

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.21

CX Basic pKa: ┄

CX LogP: 1.28

CX LogD: -3.43

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.24

Np Likeness Score: -0.32

References

1. Silva T, Mohamed T, Shakeri A, Rao PP, Martínez-González L, Pérez DI, Martínez A, Valente MJ, Garrido J, Uriarte E, Serrão P, Soares-da-Silva P, Remião F, Borges F..  (2016)  Development of Blood-Brain Barrier Permeable Nitrocatechol-Based Catechol O-Methyltransferase Inhibitors with Reduced Potential for Hepatotoxicity.,  59  (16): [PMID:27463695] [10.1021/acs.jmedchem.6b00666]

Source

Source(1):

• Scientific Literature