(2S,4R)-1-((S)-2-acetamidopropanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide

ID: ALA4227864

Chembl Id: CHEMBL4227864

PubChem CID: 72734456

Max Phase: Preclinical

Molecular Formula: C21H26N4O4S

Molecular Weight: 430.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@@H](C)C(=O)N1C[C@H](O)C[C@H]1C(=O)NCc1ccc(-c2scnc2C)cc1

Standard InChI:  InChI=1S/C21H26N4O4S/c1-12-19(30-11-23-12)16-6-4-15(5-7-16)9-22-20(28)18-8-17(27)10-25(18)21(29)13(2)24-14(3)26/h4-7,11,13,17-18,27H,8-10H2,1-3H3,(H,22,28)(H,24,26)/t13-,17+,18-/m0/s1

Standard InChI Key:  JKHAXURJIZDRKK-VHSSKADRSA-N

Alternative Forms

1. Parent:

   

   ALA4227864

   (2~{s},4~{r})-1-[(2~{s})-2-Acetamidopropanoyl]-~{n}-[[4-(4-Methyl-1,3-Thiazol-5-Yl)phenyl]methyl]-4-Oxidanyl-Pyrrolidine-2-Carboxamide

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: 430.53

Molecular Weight (Monoisotopic): 430.1675

AlogP: 1.22

#Rotatable Bonds: 6

Polar Surface Area: 111.63

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.61

CX Basic pKa: 2.65

CX LogP: -0.60

CX LogD: -0.60

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.64

Np Likeness Score: -0.92

References

1. Soares P, Gadd MS, Frost J, Galdeano C, Ellis L, Epemolu O, Rocha S, Read KD, Ciulli A..  (2018)  Group-Based Optimization of Potent and Cell-Active Inhibitors of the von Hippel-Lindau (VHL) E3 Ubiquitin Ligase: Structure-Activity Relationships Leading to the Chemical Probe (2S,4R)-1-((S)-2-(1-Cyanocyclopropanecarboxamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide (VH298).,  61  (2): [PMID:28853884] [10.1021/acs.jmedchem.7b00675]

2. Soares P, Lucas X, Ciulli A..  (2018)  Thioamide substitution to probe the hydroxyproline recognition of VHL ligands.,  26  (11): [PMID:29650462] [10.1016/j.bmc.2018.03.034]

Source

Source(1):

• Scientific Literature