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

ID: ALA4228950

Chembl Id: CHEMBL4228950

PubChem CID: 129900324

Max Phase: Preclinical

Molecular Formula: C28H36N4O5S

Molecular Weight: 540.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)C1(C(=O)N[C@H](C(=O)N2C[C@H](O)C[C@H]2C(=O)NCc2ccc(-c3scnc3C)cc2)C(C)(C)C)CC1

Standard InChI:  InChI=1S/C28H36N4O5S/c1-16-22(38-15-30-16)19-8-6-18(7-9-19)13-29-24(35)21-12-20(34)14-32(21)25(36)23(27(3,4)5)31-26(37)28(10-11-28)17(2)33/h6-9,15,20-21,23,34H,10-14H2,1-5H3,(H,29,35)(H,31,37)/t20-,21+,23-/m1/s1

Standard InChI Key:  JNBFSDQPUBSKFV-FUPPJEDESA-N

Alternative Forms

1. Parent:

   

   ALA4228950

   ---

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: 540.69

Molecular Weight (Monoisotopic): 540.2406

AlogP: 2.60

#Rotatable Bonds: 8

Polar Surface Area: 128.70

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.32

CX Basic pKa: 2.65

CX LogP: 1.53

CX LogD: 1.53

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.44

Np Likeness Score: -0.35

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