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

• ChemBase ID: 177739
• Molecular Formular: C16H20N2O7
• Molecular Mass: 352.3392
• Monoisotopic Mass: 352.12705099
• SMILES: c1(ccc2c(c1)c(c[nH]2)CCN)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: NCCc1c[nH]c2c1cc(cc2)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C16H20N2O7/c17-4-3-7-6-18-10-2-1-8(5-9(7)10)24-16-13(21)11(19)12(20)14(25-16)15(22)23/h1-2,5-6,11-14,16,18-21H,3-4,17H2,(H,22,23)/t11-,12-,13+,14-,16+/m0/s1
• InChIKey: QALKNDMLQRCLGT-JHZZJYKESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[3-(2-aminoethyl)-1H-indol-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[3-(2-aminoethyl)-1H-indol-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 3-(2-Aminoethyl)-1H-indol-5-yl β-D-Glucopyranosiduronic acid; 5-Hydroxytryptamine O-Glucuronide; 5-Hydroxytryptamine Glucuronide; Serotonin β-D-Glucuronide

Database IDs

• CAS Number: 18186-43-1
• PubChem SID: 164233649
• PubChem CID: 71752181

CALCULATED PROPERTIES

• Acid pKa: 3.0418255
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -3.0287669
• LogD (pH = 7.4): -3.0293224
• Log P: -3.02796
• Molar Refractivity: 84.3656 cm^3
• Polarizability: 34.80395 Å^3
• Polar Surface Area: 158.26 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - S274990

A metabolite of 5-Hydroxytryptamine, also known as Serotonin (S274990).

REFERENCES

• Uutela, P. et al.: Anal. Chem., 81, 8417 (2009)
• Koehle, C. et al.: Biochem. Pharmacol., 69, 1397 (2009)
• Krishnaswamy, S. et al.: Xenobiotica, 33, 169 (2009)