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

ID: ALA4229211

Chembl Id: CHEMBL4229211

PubChem CID: 129900326

Max Phase: Preclinical

Molecular Formula: C27H36N4O4S

Molecular Weight: 512.68

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)C2CCC2)C(C)(C)C)cc1

Standard InChI:  InChI=1S/C27H36N4O4S/c1-16-22(36-15-29-16)18-10-8-17(9-11-18)13-28-25(34)21-12-20(32)14-31(21)26(35)23(27(2,3)4)30-24(33)19-6-5-7-19/h8-11,15,19-21,23,32H,5-7,12-14H2,1-4H3,(H,28,34)(H,30,33)/t20-,21+,23-/m1/s1

Standard InChI Key:  DKNMIOWXDLCWDG-FUPPJEDESA-N

Alternative Forms

1. Parent:

   

   ALA4229211

   ---

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: 512.68

Molecular Weight (Monoisotopic): 512.2457

AlogP: 3.03

#Rotatable Bonds: 7

Polar Surface Area: 111.63

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.55

CX Basic pKa: 2.65

CX LogP: 1.89

CX LogD: 1.89

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.53

Np Likeness Score: -0.65

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