N-(2-chloro-4-{[2-(diethylamino)ethyl]carbamoyl}-5-methoxyphenyl)sulfamic acid

• ChemBase ID: 174575
• Molecular Formular: C14H22ClN3O5S
• Molecular Mass: 379.85958
• Monoisotopic Mass: 379.0968695
• SMILES: c1c(c(cc(c1C(=O)NCCN(CC)CC)OC)NS(=O)(=O)O)Cl
• Canonical SMILES: CCN(CCNC(=O)c1cc(Cl)c(cc1OC)NS(=O)(=O)O)CC
• InChI: InChI=1S/C14H22ClN3O5S/c1-4-18(5-2)7-6-16-14(19)10-8-11(15)12(9-13(10)23-3)17-24(20,21)22/h8-9,17H,4-7H2,1-3H3,(H,16,19)(H,20,21,22)
• InChIKey: ZHMTXLHHLGRAPZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(2-chloro-4-{[2-(diethylamino)ethyl]carbamoyl}-5-methoxyphenyl)sulfamic acid
• IUPAC Traditional name: N-(2-chloro-4-{[2-(diethylamino)ethyl]carbamoyl}-5-methoxyphenyl)sulfamic acid
• Synonyms: N-[2-Chloro-4-[[[2-(diethylamino)ethyl]amino]carbonyl]-5-methoxyphenyl]sulfamic Acid; Metoclopramide N4-Sulfonate

Database IDs

• CAS Number: 27260-42-0
• PubChem SID: 164230485
• PubChem CID: 14621640

CALCULATED PROPERTIES

• Acid pKa: -2.0961864
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -0.7597438
• LogD (pH = 7.4): -0.7681332
• Log P: -0.7596413
• Molar Refractivity: 92.7399 cm^3
• Polarizability: 36.212605 Å^3
• Polar Surface Area: 107.97 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M338680

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)