2,3-dihydroxybutanedioic acid; 3-(1,2,3,6-tetrahydropyridin-2-yl)pyridine

• ChemBase ID: 160623
• Molecular Formular: C14H18N2O6
• Molecular Mass: 310.30252
• Monoisotopic Mass: 310.11648631
• SMILES: c1ccncc1C1NCC=CC1.C(C(O)C(=O)O)(O)C(=O)O
• Canonical SMILES: C1=CCC(NC1)c1cccnc1.OC(=O)C(C(C(=O)O)O)O
• InChI: InChI=1S/C10H12N2.C4H6O6/c1-2-7-12-10(5-1)9-4-3-6-11-8-9;5-1(3(7)8)2(6)4(9)10/h1-4,6,8,10,12H,5,7H2;1-2,5-6H,(H,7,8)(H,9,10)
• InChIKey: YNIQLVONLDUCKG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,3-dihydroxybutanedioic acid; 3-(1,2,3,6-tetrahydropyridin-2-yl)pyridine
• IUPAC Traditional name: (.+-.)-tartaric acid; anatabine
• Synonyms: 1,2,3,6-Tetrahydro-2,3'-bipyridine Tartrate; 1,2,3,6-Tetrahydro-2,3'-dipyridine Tartrate; (+/-)-Anatabine Tartrate; (R,S)-Anatabine Tartrate (2:3)

Database IDs

• PubChem SID: 162254758
• PubChem CID: 45790729

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -1.956176
• LogD (pH = 7.4): -0.40024453
• Log P: 1.0180413
• Molar Refractivity: 49.9239 cm^3
• Polarizability: 19.214947 Å^3
• Polar Surface Area: 24.92 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: Yellow Solid
• Melting Point: 98-100°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A637510

A nicotine metabolite.

REFERENCES

• Kool, J., et al.: J. Med. Chem., 49, 3287 (2006)
• Newman, D., et al.: J. Nat. Prod., 70, 461 (2006)
• Kool, J., et al.: Drug Metab. Dispos., 35, 640 (2006)