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

ID: ALA1962723

Chembl Id: CHEMBL1962723

Max Phase: Preclinical

Molecular Formula: C14H19FN4O2

Molecular Weight: 294.33

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C14H19FN4O2/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:  OLFDULIIJWCYCK-NSHDSACASA-N

Alternative Forms

1. Alternative Forms:

   

   ALA1962723

   F-Amidine (trifluoroacetate salt)

2. Parent:

   

   ALA1962723

   ---

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: 294.33

Molecular Weight (Monoisotopic): 294.1492

AlogP: 0.59

#Rotatable Bonds: 8

Polar Surface Area: 108.07

Molecular Species: NEUTRAL

HBA: 3

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.34

CX LogP: -0.27

CX LogD: -1.25

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.32

Np Likeness Score: -0.52

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. 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]

3. 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]

4. 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(1):

• Scientific Literature