(2R,3R,4R,5S,6R)-6-(4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbonyloxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 177500
• Molecular Formular: C21H16O12
• Molecular Mass: 460.34454
• Monoisotopic Mass: 460.06417595
• SMILES: c1ccc2c(c1O)C(=O)c1c(C2=O)cc(cc1O)C(=O)O[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)O
• Canonical SMILES: O[C@H]1[C@@H](O)[C@H](O[C@@H]([C@@H]1O)C(=O)O)OC(=O)c1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)ccc1
• InChI: InChI=1S/C21H16O12/c22-9-3-1-2-7-11(9)14(25)12-8(13(7)24)4-6(5-10(12)23)20(31)33-21-17(28)15(26)16(27)18(32-21)19(29)30/h1-5,15-18,21-23,26-28H,(H,29,30)/t15-,16-,17+,18-,21-/m1/s1
• InChIKey: IKYQBZPCZQHNKI-ZIKOTGLESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6R)-6-(4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbonyloxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6R)-6-(4,5-dihydroxy-9,10-dioxoanthracene-2-carbonyloxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-(9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylate) β-D-Glucopyranuronic Acid; Rhein Acyl-β-D-glucuronide

Database IDs

• CAS Number: 190605-03-9
• PubChem SID: 164233410
• PubChem CID: 71752059

CALCULATED PROPERTIES

• Acid pKa: 2.5793352
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -1.3044281
• LogD (pH = 7.4): -2.0003536
• Log P: 1.5213648
• Molar Refractivity: 104.6676 cm^3
• Polarizability: 40.85933 Å^3
• Polar Surface Area: 208.12 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - R318505

A metabolite of Rhein (R318500).

REFERENCES

• Oesterle, O.A., et al.: Chem. Pharm., 46, 701 (1996)
• Dahms, M., et al.: Drug Metab. Dispos, 25, 442 (1996)