2-Cyano-3-(3,4-dihydroxy-phenyl)-acrylic acid ethyl ester

ID: ALA38168

Cas Number: 132464-92-7

PubChem CID: 14840960

Product Number: E334439, Order Now?

Max Phase: Preclinical

Molecular Formula: C12H11NO4

Molecular Weight: 233.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)/C(C#N)=C/c1ccc(O)c(O)c1

Standard InChI:  InChI=1S/C12H11NO4/c1-2-17-12(16)9(7-13)5-8-3-4-10(14)11(15)6-8/h3-6,14-15H,2H2,1H3/b9-5+

Standard InChI Key:  RAHIHNWEZPLHGV-WEVVVXLNSA-N

Molfile:  

     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
    4.5417   -4.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8292   -4.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2542   -4.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5417   -3.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5417   -2.7042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3917   -3.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1125   -4.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6792   -3.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1125   -3.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9667   -4.3542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6792   -4.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3917   -4.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2542   -5.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3917   -2.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9667   -3.1167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5417   -6.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5417   -6.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  1  1  0
  5  4  3  0
  6  9  2  0
  7  2  1  0
  8 11  2  0
  9  7  1  0
 10  3  2  0
 11 12  1  0
 12  7  2  0
 13  3  1  0
 14  6  1  0
 15  8  1  0
 16 13  1  0
 17 16  1  0
  8  6  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA38168

   Ethyl 3,4-dihydroxybenzylidenecyanoacetate

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: 233.22

Molecular Weight (Monoisotopic): 233.0688

AlogP: 1.57

#Rotatable Bonds: 3

Polar Surface Area: 90.55

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.41

CX Basic pKa: ┄

CX LogP: 2.08

CX LogD: 2.04

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.36

Np Likeness Score: -0.08

References

1. Cho H, Ueda M, Tamaoka M, Hamaguchi M, Aisaka K, Kiso Y, Inoue T, Ogino R, Tatsuoka T, Ishihara T..  (1991)  Novel caffeic acid derivatives: extremely potent inhibitors of 12-lipoxygenase.,  34  (4): [PMID:2016727] [10.1021/jm00108a039]

2. Rodrigues N, Bennis K, Vivier D, Pereira V, C Chatelain F, Chapuy E, Deokar H, Busserolles J, Lesage F, Eschalier A, Ducki S..  (2014)  Synthesis and structure-activity relationship study of substituted caffeate esters as antinociceptive agents modulating the TREK-1 channel.,  75  [PMID:24561669] [10.1016/j.ejmech.2014.01.049]

3. Vivier D, Bennis K, Lesage F, Ducki S..  (2016)  Perspectives on the Two-Pore Domain Potassium Channel TREK-1 (TWIK-Related K(+) Channel 1). A Novel Therapeutic Target?,  59  (11): [PMID:26588045] [10.1021/acs.jmedchem.5b00671]

4. Vivier D, Soussia IB, Rodrigues N, Lolignier S, Devilliers M, Chatelain FC, Prival L, Chapuy E, Bourdier G, Bennis K, Lesage F, Eschalier A, Busserolles J, Ducki S..  (2017)  Development of the First Two-Pore Domain Potassium Channel TWIK-Related K+ Channel 1-Selective Agonist Possessing in Vivo Antinociceptive Activity.,  60  (3): [PMID:28051863] [10.1021/acs.jmedchem.6b01285]

Source

Source(1):

• Scientific Literature