(2S,3S,4S,5R,6R)-6-{[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 169700
• Molecular Formular: C36H54O10
• Molecular Mass: 646.80796
• Monoisotopic Mass: 646.37169793
• SMILES: C1[C@@H]2[C@](CC[C@]1(C)C(=O)O)(CC[C@@]1(C2=CC(=O)[C@H]2[C@]1(CC[C@@H]1[C@@]2(CC[C@@H](C1(C)C)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)C)C)C)C
• Canonical SMILES: O[C@@H]1[C@H](O)[C@@H](O[C@H]([C@H]1O)C(=O)O)O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2C(=O)C=C2[C@@]1(C)CC[C@@]1([C@H]2C[C@](C)(CC1)C(=O)O)C)C)C
• InChI: InChI=1S/C36H54O10/c1-31(2)21-8-11-36(7)27(34(21,5)10-9-22(31)45-29-25(40)23(38)24(39)26(46-29)28(41)42)20(37)16-18-19-17-33(4,30(43)44)13-12-32(19,3)14-15-35(18,36)6/h16,19,21-27,29,38-40H,8-15,17H2,1-7H3,(H,41,42)(H,43,44)/t19-,21-,22-,23-,24-,25+,26-,27+,29+,32+,33-,34-,35+,36+/m0/s1
• InChIKey: HLDYLAJAWSKPFZ-QDPIGISRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-{[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-{[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: (3β,20β)-20-Carboxy-11-oxo-30-norolean-12-en-3-yl β-D-Glucopyranosiduronic Acid; 3β-(β-D-Glucopyranuronosyloxy)-11-oxoolean-12-en-30-oic Acid; GM 3290; Glycyrrhetic Acid 3-O-Glucuronide; Starrhizin; Glycyrrhetic Acid 3-O-β-D-Glucuronide

Database IDs

• CAS Number: 34096-83-8
• PubChem SID: 162263832
• PubChem CID: 161800

CALCULATED PROPERTIES

• Acid pKa: 3.5367644
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): 1.5889075
• LogD (pH = 7.4): -1.6177611
• Log P: 4.580767
• Molar Refractivity: 166.5492 cm^3
• Polarizability: 66.86188 Å^3
• Polar Surface Area: 170.82 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - G735010

A metabolite of Glycyrrhetic acid, an anti-inflammatory (topical).

REFERENCES

• Lamkhioued, B., et al.: J. Immunol., 159, 4593 (1997)
• Sonoda, Y., et al.: J. Biol. Chem., 272, 15366 (1997)
• Utsunomiya, T., et al.: Antimicrob. Agents Chemother., 41, 551 (1997)