(2R,4aR,6aS,6bR,8aS,10R,12aR,12bS,14bR)-10-[(3-carboxypropanoyl)oxy]-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic acid

• ChemBase ID: 2073
• Molecular Formular: C34H50O7
• Molecular Mass: 570.7566
• Monoisotopic Mass: 570.35565394
• SMILES: CC1(C)[C@@H](CC[C@]2(C)[C@@H]1CC[C@]1(C)[C@H]2C(=O)C=C2[C@@H]3C[C@@](C)(CC[C@@]3(C)CC[C@@]12C)C(=O)O)OC(=O)CCC(=O)O
• Canonical SMILES: O=C(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)CCC(=O)O
• InChI: InChI=1S/C34H50O7/c1-29(2)23-10-13-34(7)27(32(23,5)12-11-24(29)41-26(38)9-8-25(36)37)22(35)18-20-21-19-31(4,28(39)40)15-14-30(21,3)16-17-33(20,34)6/h18,21,23-24,27H,8-17,19H2,1-7H3,(H,36,37)(H,39,40)/t21-,23+,24+,27-,30-,31+,32+,33+,34+/m0/s1
• InChIKey: OBZHEBDUNPOCJG-SZTGPWMUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4aR,6aS,6bR,8aS,10R,12aR,12bS,14bR)-10-[(3-carboxypropanoyl)oxy]-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic acid
• IUPAC Traditional name: @carbenoxolone
• Synonyms: Carbenoxolone

Database IDs

• CAS Number: 5697-56-3
• PubChem SID: 46508820; 160965527
• PubChem CID: 46936354

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.040276
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 3.942621
• LogD (pH = 7.4): 0.45077795
• Log P: 6.297316
• Molar Refractivity: 154.3133 cm^3
• Polarizability: 61.350376 Å^3
• Polar Surface Area: 117.97 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 5.46
• LOG S: -5.89
• Solubility (Water): 7.38e-04 g/l

DETAILS

DrugBank - DB02329

• Drug Groups: experimental
• Description: An agent derived from licorice root. It is used for the treatment of digestive tract ulcers, especially in the stomach. Antidiuretic side effects are frequent, but otherwise the drug is low in toxicity. [PubChem]
• References: Sandeep TC, Yau JL, MacLullich AM, Noble J, Deary IJ, Walker BR, Seckl JR: 11Beta-hydroxysteroid dehydrogenase inhibition improves cognitive function in healthy elderly men and type 2 diabetics. Proc Natl Acad Sci U S A. 2004 Apr 27;101(17):6734-9. Epub 2004 Apr 7. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Sandeep TC, Yau JL, MacLullich AM, Noble J, Deary IJ, Walker BR, Seckl JR: 11Beta-hydroxysteroid dehydrogenase inhibition improves cognitive function in healthy elderly men and type 2 diabetics. Proc Natl Acad Sci U S A. 2004 Apr 27;101(17):6734-9. Epub 2004 Apr 7. Pubmed