((S)-1-Benzyl-3-chloro-2-oxo-propyl)-carbamic acid benzyl ester

ID: ALA303579

Chembl Id: CHEMBL303579

Cas Number: 26049-94-5

PubChem CID: 99625

Product Number: S129975

Max Phase: Preclinical

Molecular Formula: C18H18ClNO3

Molecular Weight: 331.80

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@@H](Cc1ccccc1)C(=O)CCl)OCc1ccccc1

Standard InChI:  InChI=1S/C18H18ClNO3/c19-12-17(21)16(11-14-7-3-1-4-8-14)20-18(22)23-13-15-9-5-2-6-10-15/h1-10,16H,11-13H2,(H,20,22)/t16-/m0/s1

Standard InChI Key:  OYHLRJGDELITAF-INIZCTEOSA-N

Alternative Forms

1. Parent:

   

   ALA303579

   Z-L-Phe chloromethyl ketone

Molecule Features

Natural Product: Yes

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: 331.80

Molecular Weight (Monoisotopic): 331.0975

AlogP: 3.33

#Rotatable Bonds: 7

Polar Surface Area: 55.40

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.48

CX Basic pKa: ┄

CX LogP: 4.11

CX LogD: 4.11

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.79

Np Likeness Score: -0.13

References

1. Hayashi Y, Iijima K, Katada J, Kiso Y..  (2000)  Structure-activity relationship studies of chloromethyl ketone derivatives for selective human chymase inhibitors.,  10  (3): [PMID:10698435] [10.1016/s0960-894x(99)00659-9]

2. Diamandis P, Wildenhain J, Clarke ID, Sacher AG, Graham J, Bellows DS, Ling EK, Ward RJ, Jamieson LG, Tyers M, Dirks PB..  (2007)  Chemical genetics reveals a complex functional ground state of neural stem cells.,  3  (5): [PMID:17417631] [10.1038/nchembio873]

3. Yuan J, Johnson RL, Huang R, Wichterman J, Jiang H, Hayton K, Fidock DA, Wellems TE, Inglese J, Austin CP, Su XZ..  (2009)  Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.,  5  (10): [PMID:19734910] [10.1038/nchembio.215]

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

6. PubChem BioAssay data set, 

7. PubChem BioAssay data set, 

8. PubChem BioAssay data set, 

9. PubChem BioAssay data set, 

10. Cleenewerck M, Grootaert MOJ, Gladysz R, Adriaenssens Y, Roelandt R, Joossens J, Lambeir AM, De Meyer GRY, Declercq W, Augustyns K, Martinet W, Van der Veken P..  (2016)  Inhibitor screening and enzymatic activity determination for autophagy target Atg4B using a gel electrophoresis-based assay.,  123  [PMID:27517808] [10.1016/j.ejmech.2016.07.073]

11. Stevens M, Abdeen S, Salim N, Ray AM, Washburn A, Chitre S, Sivinski J, Park Y, Hoang QQ, Chapman E, Johnson SM..  (2019)  HSP60/10 chaperonin systems are inhibited by a variety of approved drugs, natural products, and known bioactive molecules.,  29  (9): [PMID:30852084] [10.1016/j.bmcl.2019.02.028]

12. Quintana M, Bilbao A, Comas-Barceló J, Bujons J, Triola G..  (2019)  Identification of benzo[cd]indol-2(1H)-ones as novel Atg4B inhibitors via a structure-based virtual screening and a novel AlphaScreen assay.,  178  [PMID:31226656] [10.1016/j.ejmech.2019.05.086]

13. Yang G, Li Y, Zhao Y, Ouyang L, Chen Y, Liu B, Liu J..  (2021)  Targeting Atg4B for cancer therapy: Chemical mediators.,  209  [PMID:33077263] [10.1016/j.ejmech.2020.112917]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays