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

ID: ALA4229276

PubChem CID: 145988632

Max Phase: Preclinical

Molecular Formula: C26H34N4O4S

Molecular Weight: 498.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ncsc1-c1ccc(CNC(=O)[C@@H]2C[C@@H](O)CN2C(=O)[C@@H](N2CCCC2=O)C(C)(C)C)cc1

Standard InChI:  InChI=1S/C26H34N4O4S/c1-16-22(35-15-28-16)18-9-7-17(8-10-18)13-27-24(33)20-12-19(31)14-30(20)25(34)23(26(2,3)4)29-11-5-6-21(29)32/h7-10,15,19-20,23,31H,5-6,11-14H2,1-4H3,(H,27,33)/t19-,20+,23-/m1/s1

Standard InChI Key:  UTQIQISFAOFPCJ-ZRCGQRJVSA-N

Molfile:  

     RDKit          2D

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  6  1  1  1
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 31 35  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4229276

   ---

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: 498.65

Molecular Weight (Monoisotopic): 498.2301

AlogP: 2.73

#Rotatable Bonds: 6

Polar Surface Area: 102.84

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.65

CX LogP: 1.12

CX LogD: 1.12

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.64

Np Likeness Score: -0.75

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