(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{2-methoxy-4-[2-(methylamino)propyl]phenoxy}oxane-2-carboxylic acid

• ChemBase ID: 170221
• Molecular Formular: C17H25NO8
• Molecular Mass: 371.3823
• Monoisotopic Mass: 371.15801677
• SMILES: c1c(c(cc(c1)CC(NC)C)OC)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: CNC(Cc1ccc(c(c1)OC)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)C
• InChI: InChI=1S/C17H25NO8/c1-8(18-2)6-9-4-5-10(11(7-9)24-3)25-17-14(21)12(19)13(20)15(26-17)16(22)23/h4-5,7-8,12-15,17-21H,6H2,1-3H3,(H,22,23)/t8?,12-,13-,14+,15-,17+/m0/s1
• InChIKey: HCHNINKPRWVEFF-AHLSELSJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{2-methoxy-4-[2-(methylamino)propyl]phenoxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{2-methoxy-4-[2-(methylamino)propyl]phenoxy}oxane-2-carboxylic acid
• Synonyms: 2-Methoxy-4-[2-(methylamino)propyl]phenyl β-D-Glucopyranosiduronic Acid; HMMA glucuronide; 4-Hydroxy-3-methoxy Methamphetamine 4-β-D-Glucuronide(Mixture of Diastereomers)

Database IDs

• CAS Number: 146367-87-5
• PubChem SID: 164226131
• PubChem CID: 42642712

CALCULATED PROPERTIES

• Acid pKa: 2.8697362
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -2.6445343
• LogD (pH = 7.4): -2.644408
• Log P: -2.6439934
• Molar Refractivity: 88.9357 cm^3
• Polarizability: 35.882088 Å^3
• Polar Surface Area: 137.71 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H825470

The main metabolite of 3,4-methylenedioxymethamphetamine (MDMA) (M303985).

REFERENCES

• Lin, L., et al.: Drug Metab. Dispos., 25, 1059 (1997)
• Kreth, K., et al.: Biochem. Pharmacol., 59, 1563 (1997)
• Shima, N., et al.: Xenobiotica, 36, 259 ( 2006),