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

ID: ALA4225470

Chembl Id: CHEMBL4225470

PubChem CID: 129900323

Max Phase: Preclinical

Molecular Formula: C26H33FN4O4S

Molecular Weight: 516.64

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  Cc1ncsc1-c1ccc(CNC(=O)[C@@H]2C[C@@H](O)CN2C(=O)[C@@H](NC(=O)C2(F)CC2)C(C)(C)C)cc1

Standard InChI:  InChI=1S/C26H33FN4O4S/c1-15-20(36-14-29-15)17-7-5-16(6-8-17)12-28-22(33)19-11-18(32)13-31(19)23(34)21(25(2,3)4)30-24(35)26(27)9-10-26/h5-8,14,18-19,21,32H,9-13H2,1-4H3,(H,28,33)(H,30,35)/t18-,19+,21-/m1/s1

Standard InChI Key:  GFNCBUDQFXZVNN-SVFBPWRDSA-N

Alternative Forms

  1. Parent:

    ALA4225470

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Associated Targets(Human)

VHL Tchem Von Hippel-Lindau disease tumor suppressor/Elongin B/Elongin C (158 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HeLa (62764 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 516.64Molecular Weight (Monoisotopic): 516.2207AlogP: 2.73#Rotatable Bonds: 7
Polar Surface Area: 111.63Molecular Species: NEUTRALHBA: 6HBD: 3
#RO5 Violations: 1HBA (Lipinski): 8HBD (Lipinski): 3#RO5 Violations (Lipinski): 1
CX Acidic pKa: 11.24CX Basic pKa: 2.65CX LogP: 1.44CX LogD: 1.44
Aromatic Rings: 2Heavy Atoms: 36QED Weighted: 0.52Np Likeness Score: -0.48

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