ID: ALA1195284

Max Phase: Preclinical

Molecular Formula: C20H25NO3S2

Molecular Weight: 391.56

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cc1ccsc1C(=COCCN1CCC[C@@H](C(=O)O)C1)c1sccc1C

Standard InChI:  InChI=1S/C20H25NO3S2/c1-14-5-10-25-18(14)17(19-15(2)6-11-26-19)13-24-9-8-21-7-3-4-16(12-21)20(22)23/h5-6,10-11,13,16H,3-4,7-9,12H2,1-2H3,(H,22,23)/t16-/m1/s1

Standard InChI Key:  LDRYKGXVXNQQTQ-MRXNPFEDSA-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: 391.56

Molecular Weight (Monoisotopic): 391.1276

AlogP: 4.63

#Rotatable Bonds: 7

Polar Surface Area: 49.77

Molecular Species: ZWITTERION

HBA: 5

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 3.27

CX Basic pKa: 9.12

CX LogP: 2.04

CX LogD: 2.03

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.55

Np Likeness Score: -0.79

References

1. Quandt G, Höfner G, Wanner KT..  (2013)  Synthesis and evaluation of N-substituted nipecotic acid derivatives with an unsymmetrical bis-aromatic residue attached to a vinyl ether spacer as potential GABA uptake inhibitors.,  21  (11): [PMID:23598250] [10.1016/j.bmc.2013.02.056]

2. Jurik A, Zdrazil B, Holy M, Stockner T, Sitte HH, Ecker GF..  (2015)  A binding mode hypothesis of tiagabine confirms liothyronine effect on γ-aminobutyric acid transporter 1 (GAT1).,  58  (5): [PMID:25679268] [10.1021/jm5015428]

Source

Source(1):

• Scientific Literature