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

ID: ALA37154

PubChem CID: 14840972

Max Phase: Preclinical

Molecular Formula: C18H15NO4

Molecular Weight: 309.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C/C(=C\c1ccc(O)c(O)c1)C(=O)OCCc1ccccc1

Standard InChI:  InChI=1S/C18H15NO4/c19-12-15(10-14-6-7-16(20)17(21)11-14)18(22)23-9-8-13-4-2-1-3-5-13/h1-7,10-11,20-21H,8-9H2/b15-10+

Standard InChI Key:  VSHGPCHQEFUWCE-XNTDXEJSSA-N

Molfile:  

     RDKit          2D

 23 24  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
    5.2542   -5.5917    0.0000 O   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
    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
    3.8292   -7.2417    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
    3.1167   -6.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8375   -8.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1292   -8.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4042   -7.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4042   -8.0667    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 13  1  0
 12  3  1  0
 13  7  2  0
 14  6  1  0
 15  8  1  0
 16 12  1  0
 17 18  1  0
 18 16  1  0
 19 17  2  0
 20 17  1  0
 21 20  2  0
 22 19  1  0
 23 21  1  0
  8  6  1  0
 23 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA37154

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

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: 309.32

Molecular Weight (Monoisotopic): 309.1001

AlogP: 2.79

#Rotatable Bonds: 5

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: 3.73

CX LogD: 3.69

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.38

Np Likeness Score: -0.04

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]

Source

Source(1):

• Scientific Literature