(2S,3S,4S,5R,6S)-6-[(6-carboxy-8-hydroxy-9,10-dioxo-9,10-dihydroanthracen-1-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 177501
• Molecular Formular: C21H16O12
• Molecular Mass: 460.34454
• Monoisotopic Mass: 460.06417595
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1C(=O)O)Oc1cccc2c1C(=O)c1c(C2=O)cc(cc1O)C(=O)O)O)O)O
• Canonical SMILES: O[C@@H]1[C@H](O)[C@@H](O[C@H]([C@H]1O)C(=O)O)Oc1cccc2c1C(=O)c1c(C2=O)cc(cc1O)C(=O)O
• InChI: InChI=1S/C21H16O12/c22-9-5-6(19(28)29)4-8-11(9)14(24)12-7(13(8)23)2-1-3-10(12)32-21-17(27)15(25)16(26)18(33-21)20(30)31/h1-5,15-18,21-22,25-27H,(H,28,29)(H,30,31)/t15-,16-,17+,18-,21+/m0/s1
• InChIKey: PCIJYIRYSXMDQB-HUTLKBDOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[(6-carboxy-8-hydroxy-9,10-dioxo-9,10-dihydroanthracen-1-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-[(6-carboxy-8-hydroxy-9,10-dioxoanthracen-1-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 6-Carboxy-9,10-dihydro-8-hydroxy-9,10-dioxo-1-anthracenyl β-D-Glucopyranosiduronic Acid; Rhein 8-β-D-Glucuronide

Database IDs

• CAS Number: 70793-10-1
• PubChem SID: 164233411
• PubChem CID: 156112

CALCULATED PROPERTIES

• Acid pKa: 2.5142865
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -4.246653
• LogD (pH = 7.4): -6.244319
• Log P: 0.6713648
• Molar Refractivity: 104.3808 cm^3
• Polarizability: 40.69191 Å^3
• Polar Surface Area: 208.12 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - R318510

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)