2-Cyano-3-(3,4-dihydroxy-phenyl)-acrylic acid 8-(3H-imidazol-1-yl)-octyl ester

ID: ALA36376

Cas Number: 132465-12-4

PubChem CID: 14840980

Max Phase: Preclinical

Molecular Formula: C21H25N3O4

Molecular Weight: 383.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C/C(=C\c1ccc(O)c(O)c1)C(=O)OCCCCCCCCn1ccnc1

Standard InChI:  InChI=1S/C21H25N3O4/c22-15-18(13-17-7-8-19(25)20(26)14-17)21(27)28-12-6-4-2-1-3-5-10-24-11-9-23-16-24/h7-9,11,13-14,16,25-26H,1-6,10,12H2/b18-13+

Standard InChI Key:  KDUSGJPGTVISRL-QGOAFFKASA-N

Molfile:  

     RDKit          2D

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    3.7875  -10.8500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6333   -5.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8625   -5.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2500   -4.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2500   -3.7292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7208  -11.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0250  -11.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3917   -4.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417  -10.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0167   -5.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7792   -4.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0167   -4.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6667  -11.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4792   -5.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7792   -5.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3917   -5.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8625   -6.2208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3917   -3.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042  -10.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1625   -4.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2500   -6.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042   -9.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2500   -7.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0208   -9.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6333   -7.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6333   -8.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0208   -8.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 20  1  0
  3  1  2  0
  4  1  1  0
  5  1  1  0
  6  5  3  0
  7  2  1  0
  8  7  2  0
  9 13  2  0
 10  2  1  0
 11  3  1  0
 12 16  2  0
 13 11  1  0
 14 10  2  0
 15  4  2  0
 16 17  1  0
 17 11  2  0
 18  4  1  0
 19  9  1  0
 20 23  1  0
 21 12  1  0
 22 18  1  0
 23 25  1  0
 24 22  1  0
 25 28  1  0
 26 24  1  0
 27 26  1  0
 28 27  1  0
  9 12  1  0
 14  8  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA36376

   2-Cyano-3-(3,4-dihydroxy-phenyl)-acrylic acid 8-(3H-imidazol-1-yl)-octyl 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: 383.45

Molecular Weight (Monoisotopic): 383.1845

AlogP: 3.79

#Rotatable Bonds: 11

Polar Surface Area: 108.37

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.42

CX Basic pKa: 6.53

CX LogP: 3.87

CX LogD: 3.90

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.20

Np Likeness Score: -0.54

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