ID: ALA477147

Max Phase: Preclinical

Molecular Formula: C25H27N3O4

Molecular Weight: 433.51

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C[C@H](C[C@@H]1CCNC1=O)NC(=O)[C@H](Cc1ccccc1)NC(=O)/C=C/c1ccccc1

Standard InChI:  InChI=1S/C25H27N3O4/c29-17-21(16-20-13-14-26-24(20)31)27-25(32)22(15-19-9-5-2-6-10-19)28-23(30)12-11-18-7-3-1-4-8-18/h1-12,17,20-22H,13-16H2,(H,26,31)(H,27,32)(H,28,30)/b12-11+/t20-,21-,22-/m0/s1

Standard InChI Key:  GLPMVVAUDLVTNQ-QENTWVPSSA-N

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

Properties

Molecular Weight: 433.51

Molecular Weight (Monoisotopic): 433.2002

AlogP: 1.64

#Rotatable Bonds: 10

Polar Surface Area: 104.37

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.65

CX Basic pKa:

CX LogP: 1.69

CX LogD: 1.69

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.39

Np Likeness Score: 0.45

References

1. Kuo CJ, Shie JJ, Fang JM, Yen GR, Hsu JT, Liu HG, Tseng SN, Chang SC, Lee CY, Shih SR, Liang PH..  (2008)  Design, synthesis, and evaluation of 3C protease inhibitors as anti-enterovirus 71 agents.,  16  (15): [PMID:18583140] [10.1016/j.bmc.2008.06.015]

2. Zhai Y, Zhao X, Cui Z, Wang M, Wang Y, Li L, Sun Q, Yang X, Zeng D, Liu Y, Sun Y, Lou Z, Shang L, Yin Z..  (2015)  Cyanohydrin as an Anchoring Group for Potent and Selective Inhibitors of Enterovirus 71 3C Protease.,  58  (23): [PMID:26571192] [10.1021/acs.jmedchem.5b01013]

3. Dai W, Jochmans D, Xie H, Yang H, Li J, Su H, Chang D, Wang J, Peng J, Zhu L, Nian Y, Hilgenfeld R, Jiang H, Chen K, Zhang L, Xu Y, Neyts J, Liu H..  (2022)  Design, Synthesis, and Biological Evaluation of Peptidomimetic Aldehydes as Broad-Spectrum Inhibitors against Enterovirus and SARS-CoV-2.,  65  (4.0): [PMID:33872498] [10.1021/acs.jmedchem.0c02258]

Source

Source(1):

• Scientific Literature