(2S,4R)-1-((S)-3,3-dimethyl-2-(2,2,2-trifluoroacetamido)butanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide

ID: ALA4228963

PubChem CID: 145986800

Max Phase: Preclinical

Molecular Formula: C24H29F3N4O4S

Molecular Weight: 526.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ncsc1-c1ccc(CNC(=O)[C@@H]2C[C@@H](O)CN2C(=O)[C@@H](NC(=O)C(F)(F)F)C(C)(C)C)cc1

Standard InChI:  InChI=1S/C24H29F3N4O4S/c1-13-18(36-12-29-13)15-7-5-14(6-8-15)10-28-20(33)17-9-16(32)11-31(17)21(34)19(23(2,3)4)30-22(35)24(25,26)27/h5-8,12,16-17,19,32H,9-11H2,1-4H3,(H,28,33)(H,30,35)/t16-,17+,19-/m1/s1

Standard InChI Key:  LDFHQQVQPPLUDX-ZIFCJYIRSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA4228963

   ---

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: 526.58

Molecular Weight (Monoisotopic): 526.1862

AlogP: 2.79

#Rotatable Bonds: 6

Polar Surface Area: 111.63

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.12

CX Basic pKa: 2.65

CX LogP: 1.80

CX LogD: 1.42

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.54

Np Likeness Score: -0.58

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]

Source

Source(1):

• Scientific Literature