N-[4-(3-Phenyl-acryloyl)-phenyl]-acetamide

ID: ALA187926

Chembl Id: CHEMBL187926

Cas Number: 19337-19-0

PubChem CID: 5355577

Max Phase: Preclinical

Molecular Formula: C17H15NO2

Molecular Weight: 265.31

Molecule Type: Small molecule

Names and Identifiers

Synonyms: WR-080539 | 4'-Acetamidochalcone|19337-19-0|WR-080539|N-[4-[(E)-3-phenylprop-2-enoyl]phenyl]acetamide|CHEMBL187926|N-(4-cinnamoylphenyl)acetamide|CCRIS 2216|NSC 40307|SCHEMBL23086308|DTXSID001031246|NSC40307|BDBM50154614|NSC-40307|AKOS003620252|N-[4-(3-Phenyl-acryloyl)-phenyl]-acetamide

Canonical SMILES:  CC(=O)Nc1ccc(C(=O)/C=C/c2ccccc2)cc1

Standard InChI:  InChI=1S/C17H15NO2/c1-13(19)18-16-10-8-15(9-11-16)17(20)12-7-14-5-3-2-4-6-14/h2-12H,1H3,(H,18,19)/b12-7+

Standard InChI Key:  CUYJTAUCYGHYLW-KPKJPENVSA-N

Alternative Forms

1. Parent:

   

   ALA187926

   4'-Acetamidochalcone

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: 265.31

Molecular Weight (Monoisotopic): 265.1103

AlogP: 3.54

#Rotatable Bonds: 4

Polar Surface Area: 46.17

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.80

CX Basic pKa: ┄

CX LogP: 3.13

CX LogD: 3.13

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.68

Np Likeness Score: -0.62

References

1. Bhattacharjee AK, Geyer JA, Woodard CL, Kathcart AK, Nichols DA, Prigge ST, Li Z, Mott BT, Waters NC..  (2004)  A three-dimensional in silico pharmacophore model for inhibition of Plasmodium falciparum cyclin-dependent kinases and discovery of different classes of novel Pfmrk specific inhibitors.,  47  (22): [PMID:15481979] [10.1021/jm040108f]

2. Geyer JA, Keenan SM, Woodard CL, Thompson PA, Gerena L, Nichols DA, Gutteridge CE, Waters NC..  (2009)  Selective inhibition of Pfmrk, a Plasmodium falciparum CDK, by antimalarial 1,3-diaryl-2-propenones.,  19  (7): [PMID:19250824] [10.1016/j.bmcl.2009.02.042]

3. Chitre S, Ray AM, Stevens M, Doud EH, Liechty H, Washburn A, Tepper K, Sivinski J, O'Hagan HM, Georgiadis MM, Chapman E, Johnson SM..  (2022)  Bis-aryl-α,β-unsaturated ketone (ABK) chaperonin inhibitors exhibit selective cytotoxicity to colorectal cancer cells that correlates with levels of aberrant HSP60 in the cytosol.,  75  [PMID:36356534] [10.1016/j.bmc.2022.117072]

Source

Source(1):

• Scientific Literature