(2S,3S,4S,5R,6R)-6-[(2-chloro-4-{[2-(diethylamino)ethyl]carbamoyl}-5-methoxyphenyl)amino]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 174577
• Molecular Formular: C20H30ClN3O8
• Molecular Mass: 475.9205
• Monoisotopic Mass: 475.17214262
• SMILES: c1c(c(cc(c1C(=O)NCCN(CC)CC)OC)N[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)Cl
• Canonical SMILES: CCN(CCNC(=O)c1cc(Cl)c(cc1OC)N[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)CC
• InChI: InChI=1S/C20H30ClN3O8/c1-4-24(5-2)7-6-22-18(28)10-8-11(21)12(9-13(10)31-3)23-19-16(27)14(25)15(26)17(32-19)20(29)30/h8-9,14-17,19,23,25-27H,4-7H2,1-3H3,(H,22,28)(H,29,30)/t14-,15-,16+,17-,19+/m0/s1
• InChIKey: SOHPSIDRULBFFB-YUAHOQAQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-[(2-chloro-4-{[2-(diethylamino)ethyl]carbamoyl}-5-methoxyphenyl)amino]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-[(2-chloro-4-{[2-(diethylamino)ethyl]carbamoyl}-5-methoxyphenyl)amino]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[[2-Chloro-4-[[[2-(diethylamino)ethyl]amino]carbonyl]-5-methoxyphenyl]amino]-1-deoxy-β-D-Glucopyranuronic Acid; Metoclopramide N4-Glucuronide; Metoclopramide N4-β-D-Glucuronide

Database IDs

• CAS Number: 27313-54-8
• PubChem SID: 164230487
• PubChem CID: 71750715

CALCULATED PROPERTIES

• Acid pKa: 2.7966003
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -3.1262689
• LogD (pH = 7.4): -3.134359
• Log P: -3.1260266
• Molar Refractivity: 116.5407 cm^3
• Polarizability: 44.905033 Å^3
• Polar Surface Area: 160.82 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - M338690

A major glucuronide metabolite of Metoclopramide (M338685).

REFERENCES

• Arita, T., et al.: Chem. Pharm. Bull., 18, 1675 ( (1970)
• Maurich, V, et al.: Eur. J. Med. Chem., 30, 757 (1970)