2-Cyano-3-(3,4-dihydroxy-phenyl)-acrylic acid 3-pyridin-3-yl-propyl ester

ID: ALA36649

PubChem CID: 14840981

Max Phase: Preclinical

Molecular Formula: C18H16N2O4

Molecular Weight: 324.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C/C(=C\c1ccc(O)c(O)c1)C(=O)OCCCc1cccnc1

Standard InChI:  InChI=1S/C18H16N2O4/c19-11-15(9-14-5-6-16(21)17(22)10-14)18(23)24-8-2-4-13-3-1-7-20-12-13/h1,3,5-7,9-10,12,21-22H,2,4,8H2/b15-9+

Standard InChI Key:  YXYJIJRAAWHSIH-OQLLNIDSSA-N

Molfile:  

     RDKit          2D

 24 25  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
    3.1167   -9.3042    0.0000 N   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
    3.8292   -8.0667    0.0000 C   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
    3.8375   -9.7167    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   -7.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5417   -8.4792    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
    4.5542   -9.3000    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 12  2  0
  9  7  1  0
 10  3  2  0
 11 18  1  0
 12 13  1  0
 13  7  2  0
 14  3  1  0
 15  6  1  0
 16  8  1  0
 17 21  1  0
 18 17  2  0
 19 24  1  0
 20 14  1  0
 21 23  1  0
 22 17  1  0
 23 20  1  0
 24 22  2  0
  8  6  1  0
 19 11  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA36649

   2-Cyano-3-(3,4-dihydroxy-phenyl)-acrylic acid 3-pyridin-3-yl-propyl 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: 324.34

Molecular Weight (Monoisotopic): 324.1110

AlogP: 2.58

#Rotatable Bonds: 6

Polar Surface Area: 103.44

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.41

CX Basic pKa: 4.93

CX LogP: 2.96

CX LogD: 2.92

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.28

Np Likeness Score: -0.27

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