((((S)-2-(1H-Imidazol-4-yl)-1-methylcarbamoylethylcarbamoyl)-methyl)-(3-phenyl-propyl)-amino)-acetic acid

ID: ALA3235416

Chembl Id: CHEMBL3235416

Cas Number: 1333227-66-9

PubChem CID: 54589400

Max Phase: Preclinical

Molecular Formula: C20H27N5O4

Molecular Weight: 401.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)[C@H](Cc1c[nH]cn1)NC(=O)CN(CCCc1ccccc1)CC(=O)O

Standard InChI:  InChI=1S/C20H27N5O4/c1-21-20(29)17(10-16-11-22-14-23-16)24-18(26)12-25(13-19(27)28)9-5-8-15-6-3-2-4-7-15/h2-4,6-7,11,14,17H,5,8-10,12-13H2,1H3,(H,21,29)(H,22,23)(H,24,26)(H,27,28)/t17-/m0/s1

Standard InChI Key:  QEPAXTJXHXPFJN-KRWDZBQOSA-N

Alternative Forms

1. Parent:

   

   ALA3235416

   N-(Carboxymethyl)-N-(3-Phenylpropyl)glycyl-N-Methyl-L-Histidinamide

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: 401.47

Molecular Weight (Monoisotopic): 401.2063

AlogP: 0.20

#Rotatable Bonds: 12

Polar Surface Area: 127.42

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.32

CX Basic pKa: 8.30

CX LogP: -1.91

CX LogD: -2.15

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.40

Np Likeness Score: -0.70

References

1. Charton J, Gauriot M, Guo Q, Hennuyer N, Marechal X, Dumont J, Hamdane M, Pottiez V, Landry V, Sperandio O, Flipo M, Buee L, Staels B, Leroux F, Tang WJ, Deprez B, Deprez-Poulain R..  (2014)  Imidazole-derived 2-[N-carbamoylmethyl-alkylamino]acetic acids, substrate-dependent modulators of insulin-degrading enzyme in amyloid-β hydrolysis.,  79  [PMID:24735644] [10.1016/j.ejmech.2014.04.009]

2. Leroux F, Bosc D, Beghyn T, Hermant P, Warenghem S, Landry V, Pottiez V, Guillaume V, Charton J, Herledan A, Urata S, Liang W, Sheng L, Tang WJ, Deprez B, Deprez-Poulain R..  (2019)  Identification of ebselen as a potent inhibitor of insulin degrading enzyme by a drug repurposing screening.,  179  [PMID:31276900] [10.1016/j.ejmech.2019.06.057]

Source

Source(1):

• Scientific Literature