(2R,3R,5R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 2-(1H-indol-3-yl)acetate

• ChemBase ID: 171620
• Molecular Formular: C16H19NO7
• Molecular Mass: 337.32456
• Monoisotopic Mass: 337.11615195
• SMILES: c1ccc2c(c1)c(c[nH]2)CC(=O)O[C@H]1OC([C@@H](C([C@@H]1O)O)O)CO
• Canonical SMILES: OCC1O[C@H](OC(=O)Cc2c[nH]c3c2cccc3)[C@H](C([C@H]1O)O)O
• InChI: InChI=1S/C16H19NO7/c18-7-11-13(20)14(21)15(22)16(23-11)24-12(19)5-8-6-17-10-4-2-1-3-9(8)10/h1-4,6,11,13-18,20-22H,5,7H2/t11?,13-,14?,15+,16+/m0/s1
• InChIKey: HHDMMUWDSFASNB-UEMFJGIRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,5R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 2-(1H-indol-3-yl)acetate
• IUPAC Traditional name: (2R,3R,5R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 2-(1H-indol-3-yl)acetate
• Synonyms: 1-(1H-Indole-3-acetate) β-D-Glucopyranose; 1-O-(Indol-3'-ylacetyl)-β-D-glucopyranose; Indole-3-acetic Acid β-D-Glucopyranosyl Ester; Indole-3-acetic Acid β-Glucoside; Indole-3-acetyl β-D-Glucopyranose

Database IDs

• CAS Number: 19817-95-9
• PubChem SID: 164227530
• PubChem CID: 71749489

CALCULATED PROPERTIES

• Acid pKa: 12.195537
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -0.55831206
• LogD (pH = 7.4): -0.5583189
• Log P: -0.558312
• Molar Refractivity: 80.8833 cm^3
• Polarizability: 33.538174 Å^3
• Polar Surface Area: 132.24 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - I627020

A metabolite of Indole-3-acetic acid in plants.

REFERENCES

• Barratt, N., et al.: Physiol. Plant, 105, 207 (1999)
• Jackson, R., et al.: J. Biol. Chem., 276, 4350 (1999)
• Staswick, P., et al.: Plant Cell, 17, 616 (1999)