3-(4-{4-[4-(2-Carboxy-vinyl)-phenyl]-5-[4-(2-hexadecylcarbamoyl-vinyl)-phenyl]-1H-imidazol-2-yl}-phenyl)-4,5-dihydro-isoxazole-5-carboxylic acid

ID: ALA302139

Chembl Id: CHEMBL302139

PubChem CID: 10101726

Max Phase: Preclinical

Molecular Formula: C47H56N4O6

Molecular Weight: 772.99

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCCNC(=O)/C=C/c1ccc(-c2[nH]c(-c3ccc(C4=NOC(C(=O)O)C4)cc3)nc2-c2ccc(/C=C/C(=O)O)cc2)cc1

Standard InChI:  InChI=1S/C47H56N4O6/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-32-48-42(52)30-20-34-16-22-37(23-17-34)44-45(38-24-18-35(19-25-38)21-31-43(53)54)50-46(49-44)39-28-26-36(27-29-39)40-33-41(47(55)56)57-51-40/h16-31,41H,2-15,32-33H2,1H3,(H,48,52)(H,49,50)(H,53,54)(H,55,56)/b30-20+,31-21+

Standard InChI Key:  XWAWRLLRDPZTQI-OQIGUVFWSA-N

Alternative Forms

1. Parent:

   

   ALA302139

   3-(4-{4-[4-(2-Carboxy-vinyl)-phenyl]-5-[4-(2-hexadecylcarbamoyl-vinyl)-phenyl]-1H-imidazol-2-yl}-phenyl)-4,5-dihydro-isoxazole-5-carboxylic 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: 772.99

Molecular Weight (Monoisotopic): 772.4200

AlogP: 10.70

#Rotatable Bonds: 24

Polar Surface Area: 153.97

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.35

CX Basic pKa: 5.01

CX LogP: 9.92

CX LogD: 5.19

Aromatic Rings: 4

Heavy Atoms: 57

QED Weighted: 0.04

Np Likeness Score: -0.33

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]

Source

Source(1):

• Scientific Literature