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

ID: ALA37180

PubChem CID: 14840975

Max Phase: Preclinical

Molecular Formula: C19H17NO5

Molecular Weight: 339.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1CCOC(=O)/C(C#N)=C/c1ccc(O)c(O)c1

Standard InChI:  InChI=1S/C19H17NO5/c1-24-18-5-3-2-4-14(18)8-9-25-19(23)15(12-20)10-13-6-7-16(21)17(22)11-13/h2-7,10-11,21-22H,8-9H2,1H3/b15-10+

Standard InChI Key:  WTQFKFWJPRXJSN-XNTDXEJSSA-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
    3.8375   -8.0625    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
    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
    4.5542   -8.4667    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
    3.1292   -8.4792    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
    4.5542   -9.2917    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 13  2  0
  9  7  1  0
 10  3  2  0
 11 12  1  0
 12 20  1  0
 13 15  1  0
 14  3  1  0
 15  7  2  0
 16  6  1  0
 17  8  1  0
 18 11  1  0
 19 14  1  0
 20 19  1  0
 21 11  2  0
 22 12  2  0
 23 18  1  0
 24 22  1  0
 25 24  2  0
  8  6  1  0
 25 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA37180

   2-Cyano-3-(3,4-dihydroxy-phenyl)-acrylic acid 2-(2-methoxy-phenyl)-ethyl 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: 339.35

Molecular Weight (Monoisotopic): 339.1107

AlogP: 2.80

#Rotatable Bonds: 6

Polar Surface Area: 99.78

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: ┄

CX LogP: 3.58

CX LogD: 3.54

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.36

Np Likeness Score: -0.07

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