(S)-1-(5-amino-4-benzamido-5-oxopentylamino)-2-chloroethaniminium

ID: ALA1962361

Chembl Id: CHEMBL1962361

Max Phase: Preclinical

Molecular Formula: C14H19ClN4O2

Molecular Weight: 310.79

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(CCl)NCCC[C@H](NC(=O)c1ccccc1)C(N)=O

Standard InChI:  InChI=1S/C14H19ClN4O2/c15-9-12(16)18-8-4-7-11(13(17)20)19-14(21)10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2,(H2,16,18)(H2,17,20)(H,19,21)/t11-/m0/s1

Standard InChI Key:  BPWATVWOHQZVRP-NSHDSACASA-N

Alternative Forms

1. Alternative Forms:

   

   ALA1962361

   Cl-amidine TFA

2. Parent:

   

   ALA1962361

   ---

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: 310.79

Molecular Weight (Monoisotopic): 310.1197

AlogP: 0.86

#Rotatable Bonds: 8

Polar Surface Area: 108.07

Molecular Species: BASE

HBA: 3

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.96

CX LogP: 0.19

CX LogD: -1.99

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.25

Np Likeness Score: -0.46

References

1. Bicker KL, Anguish L, Chumanevich AA, Cameron MD, Cui X, Witalison E, Subramanian V, Zhang X, Chumanevich AP, Hofseth LJ, Coonrod SA, Thompson PR..  (2012)  D-amino acid based protein arginine deiminase inhibitors: Synthesis, pharmacokinetics, and in cellulo efficacy.,  3  (12): [PMID:23420624] [10.1021/ml300288d]

2. Bello AM, Wasilewski E, Wei L, Moscarello MA, Kotra LP..  (2013)  Interrogation of the Active Sites of Protein Arginine Deiminases (PAD1, -2, and -4) Using Designer Probes.,  4  (2): [PMID:24900657] [10.1021/ml300377d]

3. Ferretti P, U KP, Vagaska B, Merchant R, Matthews CJ, Marson CM.  (2013)  Discovery of a structurally novel, drug-like and potent inhibitor of peptidylarginine deiminase,  4  (7): [10.1039/C3MD00091E]

4. Subramanian V, Knight JS, Parelkar S, Anguish L, Coonrod SA, Kaplan MJ, Thompson PR..  (2015)  Design, synthesis, and biological evaluation of tetrazole analogs of Cl-amidine as protein arginine deiminase inhibitors.,  58  (3): [PMID:25559347] [10.1021/jm501636x]

5.  (2015)  Therapeutic compositions and methods, 

6. Muth A, Subramanian V, Beaumont E, Nagar M, Kerry P, McEwan P, Srinath H, Clancy K, Parelkar S, Thompson PR..  (2017)  Development of a Selective Inhibitor of Protein Arginine Deiminase 2.,  60  (7): [PMID:28328217] [10.1021/acs.jmedchem.7b00274]

7. Tjin CC, Wissner RF, Jamali H, Schepartz A, Ellman JA..  (2018)  Synthesis and Biological Evaluation of an Indazole-Based Selective Protein Arginine Deiminase 4 (PAD4) Inhibitor.,  9  (10): [PMID:30344909] [10.1021/acsmedchemlett.8b00283]

8. Jamali H, Khan HA, Tjin CC, Ellman JA..  (2016)  Cellular Activity of New Small Molecule Protein Arginine Deiminase 3 (PAD3) Inhibitors.,  7  (9): [PMID:27660689] [10.1021/acsmedchemlett.6b00215]

9. Dhiman N, Kaur K, Jaitak V..  (2020)  Tetrazoles as anticancer agents: A review on synthetic strategies, mechanism of action and SAR studies.,  28  (15): [PMID:32631569] [10.1016/j.bmc.2020.115599]

10. Yang C, Dong ZZ, Zhang J, Teng D, Luo X, Li D, Zhou Y..  (2021)  Peptidylarginine deiminases 4 as a promising target in drug discovery.,  226  [PMID:34520958] [10.1016/j.ejmech.2021.113840]

Source

Source(2):

• Scientific Literature
• BindingDB Database