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

ID: ALA4225985

PubChem CID: 145970152

Max Phase: Preclinical

Molecular Formula: C28H37N5O5S

Molecular Weight: 555.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N1CC(C(=O)N[C@H](C(=O)N2C[C@H](O)C[C@H]2C(=O)NCc2ccc(-c3scnc3C)cc2)C(C)(C)C)C1

Standard InChI:  InChI=1S/C28H37N5O5S/c1-16-23(39-15-30-16)19-8-6-18(7-9-19)11-29-26(37)22-10-21(35)14-33(22)27(38)24(28(3,4)5)31-25(36)20-12-32(13-20)17(2)34/h6-9,15,20-22,24,35H,10-14H2,1-5H3,(H,29,37)(H,31,36)/t21-,22+,24-/m1/s1

Standard InChI Key:  ACOSWKMXFBUZPG-AOHZBQACSA-N

Molfile:  

     RDKit          2D

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  1 34  1  0
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 37 38  2  0
 37 39  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4225985

   ---

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: 555.70

Molecular Weight (Monoisotopic): 555.2515

AlogP: 1.71

#Rotatable Bonds: 7

Polar Surface Area: 131.94

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.43

CX Basic pKa: 2.65

CX LogP: -0.19

CX LogD: -0.19

Aromatic Rings: 2

Heavy Atoms: 39

QED Weighted: 0.48

Np Likeness Score: -0.68

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