3-(4-{5-[4-(2-Hexadecylcarbamoyl-vinyl)-phenyl]-1H-imidazol-4-yl}-phenyl)-acrylic acid

ID: ALA293171

Chembl Id: CHEMBL293171

PubChem CID: 10886395

Max Phase: Preclinical

Molecular Formula: C37H49N3O3

Molecular Weight: 583.82

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCCNC(=O)/C=C/c1ccc(-c2[nH]cnc2-c2ccc(/C=C/C(=O)O)cc2)cc1

Standard InChI:  InChI=1S/C37H49N3O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-28-38-34(41)26-20-30-16-22-32(23-17-30)36-37(40-29-39-36)33-24-18-31(19-25-33)21-27-35(42)43/h16-27,29H,2-15,28H2,1H3,(H,38,41)(H,39,40)(H,42,43)/b26-20+,27-21+

Standard InChI Key:  SIRGTBAIRYUVNA-CRYYDKFDSA-N

Alternative Forms

1. Parent:

   

   ALA293171

   3-(4-{5-[4-(2-Hexadecylcarbamoyl-vinyl)-phenyl]-1H-imidazol-4-yl}-phenyl)-acrylic acid

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: 583.82

Molecular Weight (Monoisotopic): 583.3774

AlogP: 9.45

#Rotatable Bonds: 21

Polar Surface Area: 95.08

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.19

CX Basic pKa: 5.64

CX LogP: 8.72

CX LogD: 7.10

Aromatic Rings: 3

Heavy Atoms: 43

QED Weighted: 0.09

Np Likeness Score: -0.09

References

1. Slee DH, Romano SJ, Yu J, Nguyen TN, John JK, Raheja NK, Axe FU, Jones TK, Ripka WC..  (2001)  Development of potent non-carbohydrate imidazole-based small molecule selectin inhibitors with antiinflammatory activity.,  44  (13): [PMID:11405647] [10.1021/jm000508c]

2. Gaikwad N, Nanduri S, Madhavi YV..  (2019)  Cinnamamide: An insight into the pharmacological advances and structure-activity relationships.,  181  [PMID:31376564] [10.1016/j.ejmech.2019.07.064]

3. Sethi A, Sanam S, Alvala M..  (2021)  Non-carbohydrate strategies to inhibit lectin proteins with special emphasis on galectins.,  222  [PMID:34146913] [10.1016/j.ejmech.2021.113561]

Source

Source(1):

• Scientific Literature