(2R,3R)-2,3-dihydroxybutanedioic acid; 3-(1-methyl-1H-pyrrol-2-yl)pyridine

• ChemBase ID: 175144
• Molecular Formular: C14H16N2O6
• Molecular Mass: 308.28664
• Monoisotopic Mass: 308.10083624
• SMILES: c1cncc(c1)c1cccn1C.[C@H]([C@@H](O)C(=O)O)(O)C(=O)O
• Canonical SMILES: OC(=O)[C@@H]([C@H](C(=O)O)O)O.Cn1cccc1c1cccnc1
• InChI: InChI=1S/C10H10N2.C4H6O6/c1-12-7-3-5-10(12)9-4-2-6-11-8-9;5-1(3(7)8)2(6)4(9)10/h2-8H,1H3;1-2,5-6H,(H,7,8)(H,9,10)/t;1-,2-/m.1/s1
• InChIKey: PTXGRAGZPFUOEG-LREBCSMRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-2,3-dihydroxybutanedioic acid; 3-(1-methyl-1H-pyrrol-2-yl)pyridine
• IUPAC Traditional name: L(+)-tartaric acid; α-nicotyrine
• Synonyms: 3-(1-Methyl-1H-pyrrol-2-yl)pyridine (2R,3R)-2,3-Dihydroxybutanedioate; β-Nicotyrine Tartrate; β-Nicotyrine Monotartrate; β-Nicotyrine L-Tartrate

Database IDs

• CAS Number: 4315-37-1
• PubChem SID: 164231054
• PubChem CID: 71751031

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.5864077
• LogD (pH = 7.4): 1.6258277
• Log P: 1.62636
• Molar Refractivity: 48.5703 cm^3
• Polarizability: 19.921307 Å^3
• Polar Surface Area: 17.82 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N445005

Nicotryrine is an alkaloid derived from the dehydrogenation of nicotine and its analog, nornicotine. An alkaloid occurring in cigaret smoke.

REFERENCES

• Swain, M.L., et al.: J. Am. Chem. Soc., 71, 1341 (1949)