(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1R,4S,5R,8S,9R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 167516
• Molecular Formular: C21H32O11
• Molecular Mass: 460.47218
• Monoisotopic Mass: 460.19446184
• SMILES: [C@@H]1([C@H]2[C@@]34[C@@H](CC1)[C@H](C(O[C@@H]3O[C@](CC2)(C)OO4)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)C)C
• Canonical SMILES: C[C@H]1C(O[C@@H]2O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]2O)O)O)O[C@H]2[C@@]34[C@H]1CC[C@H]([C@@H]4CC[C@](O2)(OO3)C)C
• InChI: InChI=1S/C21H32O11/c1-8-4-5-11-9(2)17(28-18-14(24)12(22)13(23)15(27-18)16(25)26)29-19-21(11)10(8)6-7-20(3,30-19)31-32-21/h8-15,17-19,22-24H,4-7H2,1-3H3,(H,25,26)/t8-,9-,10+,11+,12+,13+,14-,15+,17?,18+,19-,20-,21-/m1/s1
• InChIKey: ZPXMEOGHWWIMAF-PYDHBSTJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1R,4S,5R,8S,9R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^4,^1^3.0^8,^1^3]hexadecan-10-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1R,4S,5R,8S,9R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^4,^1^3.0^8,^1^3]hexadecan-10-yl]oxy}oxane-2-carboxylic acid
• Synonyms: (3R,5aS,6R,8aS,9S,12R,12aS)-Decahydro-3,6,9-trimethyl- 3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-yl β-D-Glucopyranosiduronic Acid; Dihydroartemisinin Glucuronide; Dihydro Artemisinin β-D-Glucuronide (Mixture of Isomers)

Database IDs

• CAS Number: 198976-06-6
• PubChem SID: 162261649
• PubChem CID: 71316128

CALCULATED PROPERTIES

• Acid pKa: 3.217841
• H Acceptors: 11
• H Donor: 4
• LogD (pH = 5.5): -0.87281287
• LogD (pH = 7.4): -2.0545533
• Log P: 1.3877044
• Molar Refractivity: 102.19 cm^3
• Polarizability: 42.645023 Å^3
• Polar Surface Area: 153.37 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 103-109°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D448370

A metabolite of Dihydro Artemisinin. Antimalarial.

REFERENCES

• Madden, S., et al.: Drug Metab. Dispos., 24, 469 (1996)
• de Vries, P., et al.: Drugs, 52, 818 (1996)
• Smith, S., et al.: Biochem. Pharmacol., 53, 5 (1996)