1-(4,4-diphenylbut-3-en-1-yl)piperidine-3-carboxylic acid hydrochloride

• ChemBase ID: 72758
• Molecular Formular: C22H26ClNO2
• Molecular Mass: 371.90034
• Monoisotopic Mass: 371.16520676
• SMILES: c1cccc(c1)/C(=C/CCN1CC(CCC1)C(=O)O)/c1ccccc1.Cl
• Canonical SMILES: OC(=O)C1CCCN(C1)CC/C=C(/c1ccccc1)\c1ccccc1.Cl
• InChI: InChI=1S/C22H25NO2.ClH/c24-22(25)20-13-7-15-23(17-20)16-8-14-21(18-9-3-1-4-10-18)19-11-5-2-6-12-19;/h1-6,9-12,14,20H,7-8,13,15-17H2,(H,24,25);1H
• InChIKey: SNGGBKYQZVAQKA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(4,4-diphenylbut-3-en-1-yl)piperidine-3-carboxylic acid hydrochloride
• IUPAC Traditional name: 1-(4,4-diphenylbut-3-en-1-yl)piperidine-3-carboxylic acid hydrochloride
• Synonyms: SKF 89976A hydrochloride; 1-(4,4-Diphenyl-3-butenyl)-3-piperidinecarboxylic acid hydrochloride; SKF-89976A

Database IDs

• CAS Number: 85375-15-1
• MDL Number: MFCD01321071
• PubChem SID: 24278796; 162037679
• PubChem CID: 6917797

CALCULATED PROPERTIES

• Acid pKa: 3.423893
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.7419478
• LogD (pH = 7.4): 1.7434552
• Log P: 1.744291
• Molar Refractivity: 111.4549 cm^3
• Polarizability: 39.503056 Å^3
• Polar Surface Area: 40.54 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble20 mg/mL; H2O: insoluble
• Apperance: white solid

Safety Information

• Storage Condition: -20°C
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: Angiotensin receptor
• Gene Information: human ... SLC6A1(6529), SLC6A11(6538), SLC6A12(6539)rat ... Slc6a1(79212), Slc6a12(50676)

Product Information

• Purity: >98% (HPLC)
• Salt Data: hydrochloride
• Empirical Formula (Hill Notation): C22H25NO2 · HCl

DETAILS

Selleck Chemicals - S1589

Research Area: Neurological Disease
Biological Activity:
SKF 89976A is a GABA transporter type 1 inhibitor with IC50 of 0.13, 550, 944 and 7210 μM for hGAT-1, rGAT-2, hGAT-3 and hBGT-1 respectively. It is selective for GAT-1. It inhibits transport current competitively (Ki = 7 μM) and transmitter-gated current non-competitively (Ki = 0.03 nM). Able to pass the blood-brain barrier after systemic administration and is active in vivo. [1]References on SKF 89976A HCl[1] Acta Physiol Scand. , 152(2):173-9, 1994 Oct.

Sigma Aldrich - S9066

Biochem/physiol Actions
GABA transporter type 1 (GAT-1) inhibitor that crosses the blood brain barrier.

REFERENCES

• Lewin L et al. Acta Physiol Scand. 1994 Oct;152(2)