(2S,4R)-1-((S)-2-(2-fluoro-2-methylpropanamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide

ID: ALA4229225

PubChem CID: 145986595

Max Phase: Preclinical

Molecular Formula: C26H35FN4O4S

Molecular Weight: 518.66

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(C)(C)F)C(C)(C)C)cc1

Standard InChI:  InChI=1S/C26H35FN4O4S/c1-15-20(36-14-29-15)17-9-7-16(8-10-17)12-28-22(33)19-11-18(32)13-31(19)23(34)21(25(2,3)4)30-24(35)26(5,6)27/h7-10,14,18-19,21,32H,11-13H2,1-6H3,(H,28,33)(H,30,35)/t18-,19+,21-/m1/s1

Standard InChI Key:  QZNQKYSTRCIAKT-SVFBPWRDSA-N

Molfile:  

     RDKit          2D

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   27.8867  -25.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  9  4  1  1
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  1 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4229225

   ---

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: 518.66

Molecular Weight (Monoisotopic): 518.2363

AlogP: 2.98

#Rotatable Bonds: 7

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: 11.33

CX Basic pKa: 2.65

CX LogP: 1.74

CX LogD: 1.74

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.52

Np Likeness Score: -0.51

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