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

ID: ALA417327

PubChem CID: 14840974

Max Phase: Preclinical

Molecular Formula: C20H19NO4

Molecular Weight: 337.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C/C(=C\c1ccc(O)c(O)c1)C(=O)OCCCCc1ccccc1

Standard InChI:  InChI=1S/C20H19NO4/c21-14-17(12-16-9-10-18(22)19(23)13-16)20(24)25-11-5-4-8-15-6-2-1-3-7-15/h1-3,6-7,9-10,12-13,22-23H,4-5,8,11H2/b17-12+

Standard InChI Key:  DGNPQJDIHXBGJD-SFQUDFHCSA-N

Molfile:  

     RDKit          2D

 25 26  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
    3.1167   -8.4792    0.0000 C   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   -8.0667    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
    3.1250   -9.3042    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
    2.4167   -9.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6917   -8.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6917   -9.3042    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 18  1  0
 17 13  1  0
 18 21  1  0
 19 16  2  0
 20 16  1  0
 21 22  1  0
 22 17  1  0
 23 20  2  0
 24 19  1  0
 25 23  1  0
  8  6  1  0
 25 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA417327

   2-Cyano-3-(3,4-dihydroxy-phenyl)-acrylic acid 4-phenyl-butyl 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: 337.38

Molecular Weight (Monoisotopic): 337.1314

AlogP: 3.57

#Rotatable Bonds: 7

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: 4.62

CX LogD: 4.58

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.26

Np Likeness Score: 0.00

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]

Source

Source(1):

• Scientific Literature