2-amino-4-(2-amino-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4-oxobutanoic acid

• ChemBase ID: 170685
• Molecular Formular: C16H22N2O9
• Molecular Mass: 386.35388
• Monoisotopic Mass: 386.13253029
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1CO)Oc1c(c(ccc1)C(=O)CC(N)C(=O)O)N)O)O)O
• Canonical SMILES: OC[C@@H]1O[C@@H](Oc2cccc(c2N)C(=O)CC(C(=O)O)N)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C16H22N2O9/c17-7(15(24)25)4-8(20)6-2-1-3-9(11(6)18)26-16-14(23)13(22)12(21)10(5-19)27-16/h1-3,7,10,12-14,16,19,21-23H,4-5,17-18H2,(H,24,25)/t7?,10-,12-,13+,14-,16-/m1/s1
• InChIKey: SYBDIVKHFDAAJV-IIGCVACPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-4-(2-amino-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4-oxobutanoic acid
• IUPAC Traditional name: 2-amino-4-(2-amino-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4-oxobutanoic acid
• Synonyms: rac-3OHKG; α,2-Diamino-3-(β-D-glucopyranosyloxy)-γ-oxo-benzenebutanoic Acid; 3-[3-(β-D-Glucosyloxy)anthraniloyl]alanine; 3-Hydroxykynurenine-O-β-glucoside (Mixture of Diastereomers)

Database IDs

• CAS Number: 23224-46-6
• PubChem SID: 164226595
• PubChem CID: 10960012

CALCULATED PROPERTIES

• Acid pKa: 0.91227376
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): -4.4805164
• LogD (pH = 7.4): -4.4902287
• Log P: -4.479995
• Molar Refractivity: 89.1755 cm^3
• Polarizability: 35.38676 Å^3
• Polar Surface Area: 205.79 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol (Sparingly); Water
• Apperance: Yellow Solid
• Melting Point: 203-209°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H943660

The most abundant of the UV filters in human lens.

REFERENCES

• Bova, L.M., et al.: Inv. Iphthalmology & Visual Science, 40, 13, 3237 (1999)