CAS 471-53-4|Enoxolone|jintan|(2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-hydroxy-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-carbox...

General Information

Structure

Molecular Formula

C₃₀H₄₆O₄

Molecular Mass

470.68384

Exact Mass

470.33960995

Charge

InChI

InChI=1S/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)/t19-,21-,22-,23+,26+,27-,28-,29+,30+/m0/s1

InChIKey

MPDGHEJMBKOTSU-YKLVYJNSSA-N

Canonic Smiles

O=C1C=C2[C@@H]3C[C@](C)(CC[C@]3(C)CC[C@]2([C@]2([C@H]1[C@@]1(C)CC[C@@H](C([C@@H]1CC2)(C)C)O)C)C)C(=O)O

Isomeric Smiles

C1[C@@H](C([C@H]2[C@](C1)([C@@H]1[C@@](CC2)([C@]2(C(=CC1=O)[C@H]1[C@@](CC2)(CC[C@](C1)(C)C(=O)O)C)C)C)C)(C)C)O

Calculated Properties

JChem

Acid pKa

4.4443316

H Acceptors

H Donor

LogD (pH = 5.5)

4.940498

LogD (pH = 7.4)

3.1778886

Log P

6.031328

Molar Refractivity

134.2685

Polarizability

53.29785

Polar Surface Area

74.6

Rotatable Bonds

Lipinski's Rule of Five

false

Data Source

Names and Identifiers

Synonyms

Enoxolone(2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-hydroxy-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 acid18β-Glycyrrhetinic acidGlycyrrhetin3β-Hydroxy-11-oxo-18β,20β-olean-12-en-29-oic acidGlycyrrhetinic acid3β-Hydroxy-11-oxoolean-12-en-30-olic acid甘草次酸18β-甘草次酸EnoxoloneArthrodontUralenic acidGlycyrrhetinateSTX 352α-Glycyrrhetinic Acid3β-Hydroxy-11-oxo-olean-12-en-30-oic Acid18β-Glycyrrhetinic AcidGlycyrrhetic Acid(3β,20β)-3-Hydroxy-11-oxoolean-12-en-29-oic AcidNSC 35347PO 12Subglycyrrhelinic Acid18β-Glycyrrhetic AcidGM 1658EnoxoloneGlycyrrhetinic acidGlycyrrhetic acidBiosoneRhetinic acidBiogastrone acid

IUPAC Traditional name

jintan (2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-hydroxy-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 name

(2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-hydroxy-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

Names and Identifiers

Registration numbers

CAS Number

Chemspider ID

ATC CODE

Wikipedia Title

PubChem CID

CHEMBL

CHEBI ID

EC Number

Beilstein Number

PubChem SID

2487337024895033162037861

MDL Number

MFCD00003706

Registration numbers

Properties

Pharmacology Properties

Gene Information

human ... HSD11B1(3290), HSD11B2(3291)rat ... Hsd11b1(25116), Hsd11b2(25117)

Mechanism of Action

Reported to inhibit reactive oxygen species generation by human neutrophils in-vitro

Reported to trap hydroxyl radicals to suppress rat liver injury caused by ischemia-perfusion

Calcium-mobilizer in P815 cells in-vitro

Physical Property

Melting Point

292-295 °C(lit.)

Optical Rotation

[α]22/D +170.0°, c = 1 in chloroform

[α]20/D +165±3°, c = 1% in chloroform

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Selleck Chemicals

S2296

Research Area: Inflammation
Biological Activity:
Enoxolone is a pentacyclic triterpenoid derivative of the beta-amyrin type obtained from the hydrolysis of glycyrrhizic acid, which was obtained from the herb liquorice.It inhibits the enzymes (15-hydroxyprostaglandin dehydrogenase and delta-13-prostaglandin) that metabolize the prostaglandins PGE-2 and PGF-2α to their respective 15-keto-13,14-dihydro metabolites which are inactive. This causes an increased level of prostaglandins in the digestive system. Prostaglandins inhibit gastric secretion but stimulate pancreatic secretion and mucous secretion in the intestines and markedly increase intestinal motility. [1]

Wikipedia

Glycyrrhetinic_acid

Sigma Aldrich

G10105

Packaging
10, 25 g in poly bottle

TRC

G735000

An anti-inflammatory (topical).

Molecule Details

References

PubChem Literature

From Data Sources

• http://en.wikipedia.org/wiki/Glycyrrhetinic_acid

• Carmichael, J., et al.: Cancer Res., 47, 943 (1987)

• Deschesnes, R., et al.: J. Pharmacol. Exp. Ther., 320, 853 (1987)

• Yamaguchi, H., et al.: Biol. Pharm. Bull., 31, 1008 (1987)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 596A, (nmr)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, GIE000; BGD000; GIEO5O; CBO500

• Beaton, J.M. et al., J.C.S., 1955, 3126, (synth)

• Robson, J.M. et al., Carbenoxolone Sodium, Orig. Pap. Discuss. Group Meet., Butterworth, London, 1969, (rev)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 1057D, (ir)

• U.K. Pat., 1960, 843 133; CA, 55, 2027i, (Carbenoxolone)

• Witz, P. et al., Bull. Soc. Chim. Fr., 1963, 1101, (cd)

• Sakano, K. et al., Agric. Biol. Chem., 1986, 50, 763, (deriv)

• Canonica, L. et al., Gazz. Chim. Ital., 1967, 97, 1347; 1968, 98, 602, (Glycyrrhetol)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 7889; 8042, (synonyms)

• Saito, S. et al., Chem. Pharm. Bull., 1994, 42, 1016, (synth)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 758; 873

• Wahlberg, I. et al., Acta Chem. Scand., 1971, 25, 3192, (ms)

• Sandiya, R. et al., J. Het. Chem., 1984, 21, 845, (isol)

• Mer, J., Am. Perfum. Aromat., 1959, 74, 39, (isol)

• Budzikiewicz, H. et al., J.A.C.S., 1963, 85, 3688, (ms)

• Murav'ev, I.A. et al., CA, 1966, 69, 44029v, (rev)

• Tolstikov, G.A. et al., Khim. Prir. Soedin., 1985, 21, 645; Chem. Nat. Compd. (Engl. Transl.), 1985, 21, 605, (cmr)

• Kanaoka, M. et al., Chem. Pharm. Bull., 1988, 36, 3264, (synth)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC Traditional name

jintan (2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-hydroxy-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 name

(2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-hydroxy-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

Registration numbers

CAS Number

Chemspider ID

ATC CODE

Wikipedia Title

PubChem CID

CHEMBL

CHEBI ID

EC Number

Beilstein Number

PubChem SID

2487337024895033162037861

MDL Number

Molecule Details

S2296

G10105

Packaging
10, 25 g in poly bottle

TRC

G735000

An anti-inflammatory (topical).

References

PubChem Literature

From Data Sources

• http://en.wikipedia.org/wiki/Glycyrrhetinic_acid

• Carmichael, J., et al.: Cancer Res., 47, 943 (1987)

• Deschesnes, R., et al.: J. Pharmacol. Exp. Ther., 320, 853 (1987)

• Yamaguchi, H., et al.: Biol. Pharm. Bull., 31, 1008 (1987)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 596A, (nmr)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, GIE000; BGD000; GIEO5O; CBO500

• Beaton, J.M. et al., J.C.S., 1955, 3126, (synth)

• Robson, J.M. et al., Carbenoxolone Sodium, Orig. Pap. Discuss. Group Meet., Butterworth, London, 1969, (rev)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 1057D, (ir)

• U.K. Pat., 1960, 843 133; CA, 55, 2027i, (Carbenoxolone)

• Witz, P. et al., Bull. Soc. Chim. Fr., 1963, 1101, (cd)

• Sakano, K. et al., Agric. Biol. Chem., 1986, 50, 763, (deriv)

• Canonica, L. et al., Gazz. Chim. Ital., 1967, 97, 1347; 1968, 98, 602, (Glycyrrhetol)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 7889; 8042, (synonyms)

• Saito, S. et al., Chem. Pharm. Bull., 1994, 42, 1016, (synth)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 758; 873

• Wahlberg, I. et al., Acta Chem. Scand., 1971, 25, 3192, (ms)

• Sandiya, R. et al., J. Het. Chem., 1984, 21, 845, (isol)

• Mer, J., Am. Perfum. Aromat., 1959, 74, 39, (isol)

• Budzikiewicz, H. et al., J.A.C.S., 1963, 85, 3688, (ms)

• Murav'ev, I.A. et al., CA, 1966, 69, 44029v, (rev)

• Tolstikov, G.A. et al., Khim. Prir. Soedin., 1985, 21, 645; Chem. Nat. Compd. (Engl. Transl.), 1985, 21, 605, (cmr)

• Kanaoka, M. et al., Chem. Pharm. Bull., 1988, 36, 3264, (synth)

Bioactivity

PubChem BioAssay

Properties

Pharmacology Properties

Gene Information

human ... HSD11B1(3290), HSD11B2(3291)rat ... Hsd11b1(25116), Hsd11b2(25117)

Mechanism of Action

Reported to inhibit reactive oxygen species generation by human neutrophils in-vitro

Reported to trap hydroxyl radicals to suppress rat liver injury caused by ischemia-perfusion

Calcium-mobilizer in P815 cells in-vitro

Physical Property

Melting Point

292-295 °C(lit.)

Optical Rotation

[α]22/D +170.0°, c = 1 in chloroform

[α]20/D +165±3°, c = 1% in chloroform

Molecule

ID:72941