ID: ALA75800

Max Phase: Preclinical

Molecular Formula: C28H29NO4

Molecular Weight: 443.54

Molecule Type: Small molecule

Representations

Synonyms (1): SNAP-5294
Synonyms from Alternative Forms(1):

Canonical SMILES:  COc1ccc(C2(OCCN3CCCC(C(=O)O)C3)c3ccccc3-c3ccccc32)cc1

Standard InChI:  InChI=1S/C28H29NO4/c1-32-22-14-12-21(13-15-22)28(33-18-17-29-16-6-7-20(19-29)27(30)31)25-10-4-2-8-23(25)24-9-3-5-11-26(24)28/h2-5,8-15,20H,6-7,16-19H2,1H3,(H,30,31)

Standard InChI Key:  PDWYUQWCERDHRZ-UHFFFAOYSA-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: 443.54

Molecular Weight (Monoisotopic): 443.2097

AlogP: 4.78

#Rotatable Bonds: 7

Polar Surface Area: 59.00

Molecular Species: ZWITTERION

HBA: 4

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 3.31

CX Basic pKa: 9.19

CX LogP: 2.31

CX LogD: 2.31

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.57

Np Likeness Score: -0.24

References

1. Dhar TG, Borden LA, Tyagarajan S, Smith KE, Branchek TA, Weinshank RL, Gluchowski C..  (1994)  Design, synthesis and evaluation of substituted triarylnipecotic acid derivatives as GABA uptake inhibitors: identification of a ligand with moderate affinity and selectivity for the cloned human GABA transporter GAT-3.,  37  (15): [PMID:8057281] [10.1021/jm00041a012]

2. Hack S, Wörlein B, Höfner G, Pabel J, Wanner KT..  (2011)  Development of imidazole alkanoic acids as mGAT3 selective GABA uptake inhibitors.,  46  (5): [PMID:21353350] [10.1016/j.ejmech.2011.01.042]

3. Kerscher-Hack S, Renukappa-Gutke T, Höfner G, Wanner KT..  (2016)  Synthesis and biological evaluation of a series of N-alkylated imidazole alkanoic acids as mGAT3 selective GABA uptake inhibitors.,  124  [PMID:27654218] [10.1016/j.ejmech.2016.09.012]

Source

Source(1):

• Scientific Literature