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

ID: ALA4225714

PubChem CID: 117719894

Max Phase: Preclinical

Molecular Formula: C26H34N4O5S

Molecular Weight: 514.65

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)C2COC2)C(C)(C)C)cc1

Standard InChI:  InChI=1S/C26H34N4O5S/c1-15-21(36-14-28-15)17-7-5-16(6-8-17)10-27-24(33)20-9-19(31)11-30(20)25(34)22(26(2,3)4)29-23(32)18-12-35-13-18/h5-8,14,18-20,22,31H,9-13H2,1-4H3,(H,27,33)(H,29,32)/t19-,20+,22-/m1/s1

Standard InChI Key:  NKBZEWGYKXYCGU-RZUBCFFCSA-N

Molfile:  

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   13.1428   -6.3674    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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  7  2  1  1
  7 29  1  0
 11 30  1  6
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  1 34  1  0
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 35 36  1  0
 36  1  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4225714

   (2~{s},4~{r})-1-[(2~{s})-3,3-Dimethyl-2-(Oxetan-3-Ylcarbonylamino)butanoyl]-~{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: 514.65

Molecular Weight (Monoisotopic): 514.2250

AlogP: 1.87

#Rotatable Bonds: 7

Polar Surface Area: 120.86

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.38

CX Basic pKa: 2.65

CX LogP: 0.51

CX LogD: 0.51

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.52

Np Likeness Score: -0.53

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