(2S,4R)-1-((2S,3S)-2-(1-fluorocyclopropanecarboxamido)-3-hydroxybutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide

ID: ALA4228692

PubChem CID: 145967743

Max Phase: Preclinical

Molecular Formula: C24H29FN4O5S

Molecular Weight: 504.58

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)C2(F)CC2)[C@@H](C)O)cc1

Standard InChI:  InChI=1S/C24H29FN4O5S/c1-13-20(35-12-27-13)16-5-3-15(4-6-16)10-26-21(32)18-9-17(31)11-29(18)22(33)19(14(2)30)28-23(34)24(25)7-8-24/h3-6,12,14,17-19,30-31H,7-11H2,1-2H3,(H,26,32)(H,28,34)/t14-,17-,18+,19+/m1/s1

Standard InChI Key:  KPVWXDKGVYUNBF-OAOYMFHYSA-N

Molfile:  

     RDKit          2D

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M  END

Alternative Forms

1. Parent:

   

   ALA4228692

   ---

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: 504.58

Molecular Weight (Monoisotopic): 504.1843

AlogP: 1.06

#Rotatable Bonds: 8

Polar Surface Area: 131.86

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.87

CX Basic pKa: 2.65

CX LogP: -0.46

CX LogD: -0.46

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.43

Np Likeness Score: -0.55

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