(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[3-(2-hydroxyethyl)-1H-indol-5-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 171421
• Molecular Formular: C16H19NO8
• Molecular Mass: 353.32396
• Monoisotopic Mass: 353.11106657
• SMILES: c1c(cc2c(c1)[nH]cc2CCO)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: OCCc1c[nH]c2c1cc(cc2)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C16H19NO8/c18-4-3-7-6-17-10-2-1-8(5-9(7)10)24-16-13(21)11(19)12(20)14(25-16)15(22)23/h1-2,5-6,11-14,16-21H,3-4H2,(H,22,23)/t11-,12-,13+,14-,16+/m0/s1
• InChIKey: NFLHLWRXDOXSCF-JHZZJYKESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[3-(2-hydroxyethyl)-1H-indol-5-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[3-(2-hydroxyethyl)-1H-indol-5-yl]oxy}oxane-2-carboxylic acid
• Synonyms: 3-(2-Hydroxyethyl)-1H-indol-5-yl β-D-Glucopyranosiduronic Acid; 3-(2-Hydroxyethyl)indol-5-yl β-D-Glucosiduronic Acid; 5-Hydroxy Tryptophol β-D-Glucuronide

Database IDs

• CAS Number: 27939-38-4
• PubChem SID: 164227331
• PubChem CID: 71749400

CALCULATED PROPERTIES

• Acid pKa: 3.338151
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -2.8046308
• LogD (pH = 7.4): -4.075783
• Log P: -0.6580396
• Molar Refractivity: 82.7081 cm^3
• Polarizability: 33.94545 Å^3
• Polar Surface Area: 152.47 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H976010

A metabolite of 5-Hydroxytryptamine (H974990).

REFERENCES

• Kveder, S., et al.: Biochem. J., 85, 447 (1962)
• Iskric, S., et al.: Anal. Biochem., 7, 297 (1962)