ID: ALA466465

Max Phase: Preclinical

Molecular Formula: C14H21ClN2O3S

Molecular Weight: 332.85

Molecule Type: Small molecule

Representations

Synonyms (1): Tosyl-L-Lysine Chloromethyl Ketone
Synonyms from Alternative Forms(1):

Canonical SMILES:  Cc1ccc(S(=O)(=O)N[C@@H](CCCCN)C(=O)CCl)cc1

Standard InChI:  InChI=1S/C14H21ClN2O3S/c1-11-5-7-12(8-6-11)21(19,20)17-13(14(18)10-15)4-2-3-9-16/h5-8,13,17H,2-4,9-10,16H2,1H3/t13-/m0/s1

Standard InChI Key:  RDFCSSHDJSZMTQ-ZDUSSCGKSA-N

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

Properties

Molecular Weight: 332.85

Molecular Weight (Monoisotopic): 332.0961

AlogP: 1.58

#Rotatable Bonds: 9

Polar Surface Area: 89.26

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.40

CX Basic pKa: 9.78

CX LogP: 1.64

CX LogD: -0.34

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.53

Np Likeness Score: -0.52

References

1. Berggren K, Johansson B, Fex T, Kihlberg J, Björck L, Luthman K..  (2009)  Synthesis and biological evaluation of reversible inhibitors of IdeS, a bacterial cysteine protease and virulence determinant.,  17  (9): [PMID:19362485] [10.1016/j.bmc.2009.03.026]

2. PubChem BioAssay data set, 

3. PubChem BioAssay data set, 

4. Qi J, Zhu J, Liu X, Ding L, Zheng C, Han G, Lv J, Zhou Y..  (2011)  Synthesis and acrosin inhibitory activities of substituted ethyl 5-(4-aminophenyl)-1H-pyrazole-3-carboxylate derivatives.,  21  (19): [PMID:21880490] [10.1016/j.bmcl.2011.07.110]

5. PubChem BioAssay data set, 

6. Ding L, Zhu J, Zheng C, Sheng C, Qi J, Liu X, Han G, Zhao J, Lv J, Zhou Y..  (2011)  Synthesis and acrosin inhibitory activity of substituted 4-amino-N-(diaminomethylene) benzenesulfonamide derivatives.,  21  (22): [PMID:21983437] [10.1016/j.bmcl.2011.09.060]

7. Liu X, Chen Q, Zhu J, Fan Y, Ding L, Zhao J, Han G, Tian W, Qi J, Zhou Y, Lv J..  (2012)  Synthesis and acrosin inhibitory activity of methyl 5-substituted-1H-benzo[d]imidazol-2-yl carbamate derivatives.,  22  (10): [PMID:22507960] [10.1016/j.bmcl.2012.03.042]

8. Franco FM, Jones DE, Harris PK, Han Z, Wildman SA, Jarvis CM, Janetka JW..  (2015)  Structure-based discovery of small molecule hepsin and HGFA protease inhibitors: Evaluation of potency and selectivity derived from distinct binding pockets.,  23  (10): [PMID:25882520] [10.1016/j.bmc.2015.03.072]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays