1-[(2R,3R,4S,5S,6S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-3-{1-hydroxy-4-[methyl(nitroso)amino]butyl}-1λ5-pyridin-1-ylium

• ChemBase ID: 174133
• Molecular Formular: C16H23N3O8
• Molecular Mass: 385.36912
• Monoisotopic Mass: 385.14851471
• SMILES: [n+]1(cccc(c1)C(CCCN(C)N=O)O)[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)[O-])O)O)O
• Canonical SMILES: O=NN(CCCC(c1ccc[n+](c1)[C@@H]1O[C@@H](C(=O)[O-])[C@H]([C@@H]([C@@H]1O)O)O)O)C
• InChI: InChI=1S/C16H23N3O8/c1-18(17-26)6-3-5-10(20)9-4-2-7-19(8-9)15-13(23)11(21)12(22)14(27-15)16(24)25/h2,4,7-8,10-15,20-23H,3,5-6H2,1H3/t10?,11-,12-,13+,14-,15+/m0/s1
• InChIKey: VSVYJUYJFLYYSI-UKOUFMKDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,3R,4S,5S,6S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-3-{1-hydroxy-4-[methyl(nitroso)amino]butyl}-1λ^5-pyridin-1-ylium
• IUPAC Traditional name: 1-[(2R,3R,4S,5S,6S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-3-{1-hydroxy-4-[methyl(nitroso)amino]butyl}-1λ^5-pyridin-1-ylium
• Synonyms: 1-β-D-Glucopyranuronosyl-3-[1-hydroxy-4-(methylnitrosoamino)butyl]pyridinium Inner Salt; NNAL-N-β-D-Glucuronide; 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol N-β-D-Glucuronide

Database IDs

• CAS Number: 350508-29-1
• PubChem SID: 164230043
• PubChem CID: 53297450

CALCULATED PROPERTIES

• Acid pKa: 2.7073894
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -5.774142
• LogD (pH = 7.4): -5.774143
• Log P: -5.7297688
• Molar Refractivity: 102.5007 cm^3
• Polarizability: 35.50654 Å^3
• Polar Surface Area: 166.83 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 127-130°C

Safety Information

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

DETAILS

Toronto Research Chemicals - M325745

A metabolite of NNAL.

REFERENCES

• Hecht, S.S., et al.: Chem. Res. Toxicol., 14, 555 (2001)