ID: ALA3108881

Max Phase: Preclinical

Molecular Formula: C21H22N4O5

Molecular Weight: 410.43

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cc1cc(CC(=O)N2C[C@H](O)C[C@H]2C(=O)NCc2ccc(-c3cnco3)cc2)on1

Standard InChI:  InChI=1S/C21H22N4O5/c1-13-6-17(30-24-13)8-20(27)25-11-16(26)7-18(25)21(28)23-9-14-2-4-15(5-3-14)19-10-22-12-29-19/h2-6,10,12,16,18,26H,7-9,11H2,1H3,(H,23,28)/t16-,18+/m1/s1

Standard InChI Key:  HFCLIEBJTGJKSV-AEFFLSMTSA-N

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

Properties

Molecular Weight: 410.43

Molecular Weight (Monoisotopic): 410.1590

AlogP: 1.46

#Rotatable Bonds: 6

Polar Surface Area: 121.70

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.55

CX Basic pKa: 0.98

CX LogP: -0.73

CX LogD: -0.73

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.63

Np Likeness Score: -1.20

References

1. Dias DM, Van Molle I, Baud MG, Galdeano C, Geraldes CF, Ciulli A..  (2014)  Is NMR Fragment Screening Fine-Tuned to Assess Druggability of Protein-Protein Interactions?,  5  (1): [PMID:24436777] [10.1021/ml400296c]

2. Rabinowitz MH..  (2013)  Inhibition of hypoxia-inducible factor prolyl hydroxylase domain oxygen sensors: tricking the body into mounting orchestrated survival and repair responses.,  56  (23): [PMID:23977883] [10.1021/jm400386j]

3. Guo W, Wisniewski JA, Ji H..  (2014)  Hot spot-based design of small-molecule inhibitors for protein-protein interactions.,  24  (11): [PMID:24751445] [10.1016/j.bmcl.2014.03.095]

4. Galdeano C, Gadd MS, Soares P, Scaffidi S, Van Molle I, Birced I, Hewitt S, Dias DM, Ciulli A..  (2014)  Structure-guided design and optimization of small molecules targeting the protein-protein interaction between the von Hippel-Lindau (VHL) E3 ubiquitin ligase and the hypoxia inducible factor (HIF) alpha subunit with in vitro nanomolar affinities.,  57  (20): [PMID:25166285] [10.1021/jm5011258]

5. Levine PM, Garabedian MJ, Kirshenbaum K..  (2014)  Targeting the androgen receptor with steroid conjugates.,  57  (20): [PMID:24936953] [10.1021/jm500101h]

6. Blaquiere N, Villemure E, Staben ST..  (2020)  Medicinal Chemistry of Inhibiting RING-Type E3 Ubiquitin Ligases.,  63  (15): [PMID:32142281] [10.1021/acs.jmedchem.9b01451]

7. Palacios DS..  (2022)  Drug Hunting at the Nexus of Medicinal Chemistry and Chemical Biology and the Discovery of Novel Therapeutic Modalities.,  65  (20.0): [PMID:36206538] [10.1021/acs.jmedchem.2c01491]

Source

Source(1):

• Scientific Literature