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

ID: ALA4225856

PubChem CID: 129900321

Max Phase: Preclinical

Molecular Formula: C24H32N4O5S

Molecular Weight: 488.61

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)CO)C(C)(C)C)cc1

Standard InChI:  InChI=1S/C24H32N4O5S/c1-14-20(34-13-26-14)16-7-5-15(6-8-16)10-25-22(32)18-9-17(30)11-28(18)23(33)21(24(2,3)4)27-19(31)12-29/h5-8,13,17-18,21,29-30H,9-12H2,1-4H3,(H,25,32)(H,27,31)/t17-,18+,21-/m1/s1

Standard InChI Key:  OFCMFZVSIVJIET-LVCYWYKZSA-N

Molfile:  

     RDKit          2D

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   30.9460   -2.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2341   -2.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9460   -4.5709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   31.9763   -5.8491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.3731   -5.5480    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   36.6868   -7.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9440   -8.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7690   -8.1394    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.0207   -7.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3513   -6.8716    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   36.4619   -8.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5171   -4.5709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8890   -2.4075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8026   -4.1584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8026   -3.3334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.5171   -2.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0881   -4.5709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3737   -4.1584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
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 24 25  2  0
 25 26  1  0
 26 22  1  0
 23 27  1  0
  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:

   

   ALA4225856

   ---

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: 488.61

Molecular Weight (Monoisotopic): 488.2093

AlogP: 1.22

#Rotatable Bonds: 7

Polar Surface Area: 131.86

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.14

CX Basic pKa: 2.65

CX LogP: -0.15

CX LogD: -0.15

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.46

Np Likeness Score: -0.42

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