sodium (2R,3R,4R,5S,6R)-6-{2-chloro-4-[4-(3-{3-oxo-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-2-yl}propyl)piperazin-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylate

• ChemBase ID: 171392
• Molecular Formular: C25H29ClN5NaO8
• Molecular Mass: 585.96923
• Monoisotopic Mass: 585.16023487
• SMILES: C1N(CCN(C1)c1ccc(c(c1)Cl)O[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)[O-])CCCn1nc2n(c1=O)cccc2.[Na+]
• Canonical SMILES: O[C@H]1[C@@H](O)[C@H](O[C@@H]([C@@H]1O)C(=O)[O-])Oc1ccc(cc1Cl)N1CCN(CC1)CCCn1nc2n(c1=O)cccc2.[Na+]
• InChI: InChI=1S/C25H30ClN5O8.Na/c26-16-14-15(5-6-17(16)38-24-21(34)19(32)20(33)22(39-24)23(35)36)29-12-10-28(11-13-29)7-3-9-31-25(37)30-8-2-1-4-18(30)27-31;/h1-2,4-6,8,14,19-22,24,32-34H,3,7,9-13H2,(H,35,36);/q;+1/p-1/t19-,20-,21+,22-,24+;/m1./s1
• InChIKey: BKZGRCKUFZLVMW-IHLVZGQESA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2R,3R,4R,5S,6R)-6-{2-chloro-4-[4-(3-{3-oxo-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-2-yl}propyl)piperazin-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylate
• IUPAC Traditional name: sodium (2R,3R,4R,5S,6R)-6-{2-chloro-4-[4-(3-{3-oxo-[1,2,4]triazolo[4,3-a]pyridin-2-yl}propyl)piperazin-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylate
• Synonyms: 2-Chloro-4-[4-[3-(3-oxo-1,2,4-triazolo[4,3-a]pyridin-2(3H)-yl)propyl]-1-piperazinyl]phenyl β-D-Glucopyranosiduronic Acid Sodium; 2-[3-[4-(m-Chloro-p-hydroxyphenyl)-1-piperazinyl]propyl]-s-triazolo[4,3-a]pyridin-3(2H)-one Glucuronide Sodium; 4-Hydroxytrazodone Glucuronide Sodium; 4'-Hydroxy Trazodone β-D-Glucuronide Sodium Salt

Database IDs

• PubChem SID: 164227302
• PubChem CID: 71749386

CALCULATED PROPERTIES

• Acid pKa: 2.901843
• H Acceptors: 11
• H Donor: 3
• LogD (pH = 5.5): -1.8447093
• LogD (pH = 7.4): -2.229062
• Log P: -1.8392359
• Molar Refractivity: 150.7094 cm^3
• Polarizability: 53.418736 Å^3
• Polar Surface Area: 161.67 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Off-White Solid
• Melting Point: 163-168°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - H970025

A major glucuronide metabolite of Trazodone-HCl (T718500).

REFERENCES

• Yamato, C., et al.: Xenobiotica, 4, 765 (1974)