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

ID: ALA4228328

PubChem CID: 122528991

Max Phase: Preclinical

Molecular Formula: C25H34N4O4S

Molecular Weight: 486.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)NCc1ccc(-c2scnc2C)cc1)C(C)(C)C

Standard InChI:  InChI=1S/C25H34N4O4S/c1-6-20(31)28-22(25(3,4)5)24(33)29-13-18(30)11-19(29)23(32)26-12-16-7-9-17(10-8-16)21-15(2)27-14-34-21/h7-10,14,18-19,22,30H,6,11-13H2,1-5H3,(H,26,32)(H,28,31)/t18-,19+,22-/m1/s1

Standard InChI Key:  DAQZMDAVCMVVFQ-XQBPLPMBSA-N

Molfile:  

     RDKit          2D

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    6.0376  -13.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.8605  -18.3186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1123  -17.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4427  -17.0508    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.5534  -18.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6085  -14.7501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1796  -14.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4651  -14.3376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  6  1  1  1
  6 28  1  0
 10 29  1  6
 28 30  1  0
 30 31  2  0
  1 32  1  0
 30 33  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4228328

   ---

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: 486.64

Molecular Weight (Monoisotopic): 486.2301

AlogP: 2.64

#Rotatable Bonds: 7

Polar Surface Area: 111.63

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.60

CX Basic pKa: 2.65

CX LogP: 1.37

CX LogD: 1.37

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.56

Np Likeness Score: -0.63

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