3-[(E)-2-(4-Chlorophenyl)vinyl]-N-[(2R)-2,3-dihydroxypropyl]-4-methoxybenzamide

ID: ALA1949788

Chembl Id: CHEMBL1949788

PubChem CID: 57325478

Max Phase: Preclinical

Molecular Formula: C19H20ClNO4

Molecular Weight: 361.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C(=O)NC[C@@H](O)CO)cc1/C=C/c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C19H20ClNO4/c1-25-18-9-6-15(19(24)21-11-17(23)12-22)10-14(18)5-2-13-3-7-16(20)8-4-13/h2-10,17,22-23H,11-12H2,1H3,(H,21,24)/b5-2+/t17-/m1/s1

Standard InChI Key:  FRFTWFWYLIBTEB-WAUBUAMCSA-N

Alternative Forms

1. Parent:

   

   ALA1949788

   3-[(E)-2-(4-chlorophenyl)ethenyl]-N-[(2R)-2,3-dihydroxypropyl]-4-methoxybenzamide

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: 361.83

Molecular Weight (Monoisotopic): 361.1081

AlogP: 2.60

#Rotatable Bonds: 7

Polar Surface Area: 78.79

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.95

CX Basic pKa: ┄

CX LogP: 2.51

CX LogD: 2.51

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.66

Np Likeness Score: -0.38

References

1. Hada K, Suda A, Asoh K, Tsukuda T, Hasegawa M, Sato Y, Ogawa K, Kuramoto S, Aoki Y, Shimma N, Ishikawa T, Koyano H..  (2012)  Angiogenesis inhibitors identified by cell-based high-throughput screening: synthesis, structure-activity relationships and biological evaluation of 3-[(E)-styryl]benzamides that specifically inhibit endothelial cell proliferation.,  20  (4): [PMID:22269278] [10.1016/j.bmc.2011.12.058]

Source

Source(1):

• Scientific Literature