Glycyrrhizin

Details

• Internal ID: daf53057-4edb-48fe-8d11-6133d266a392
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5S,6S)-2-[[(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]-6-carboxy-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• SMILES (Canonical): CC1(C2CCC3(C(C2(CCC1OC4C(C(C(C(O4)C(=O)O)O)O)OC5C(C(C(C(O5)C(=O)O)O)O)O)C)C(=O)C=C6C3(CCC7(C6CC(CC7)(C)C(=O)O)C)C)C)C
• SMILES (Isomeric): C[C@]12CC[C@](C[C@H]1C3=CC(=O)[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)O[C@@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)C(=O)O)O)O)O)C)(C)C(=O)O
• InChI: InChI=1S/C42H62O16/c1-37(2)21-8-11-42(7)31(20(43)16-18-19-17-39(4,36(53)54)13-12-38(19,3)14-15-41(18,42)6)40(21,5)10-9-22(37)55-35-30(26(47)25(46)29(57-35)33(51)52)58-34-27(48)23(44)24(45)28(56-34)32(49)50/h16,19,21-31,34-35,44-48H,8-15,17H2,1-7H3,(H,49,50)(H,51,52)(H,53,54)/t19-,21-,22-,23-,24-,25-,26-,27+,28-,29-,30+,31+,34-,35-,38+,39-,40-,41+,42+/m0/s1
• InChI Key: LPLVUJXQOOQHMX-QWBHMCJMSA-N
• Popularity: 4,403 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₆₂O₁₆
• Molecular Weight: 822.90 g/mol
• Exact Mass: 822.40378589 g/mol
• Topological Polar Surface Area (TPSA): 267.00 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 2.25
• H-Bond Acceptor: 13
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

• glycyrrhizin
• 1405-86-3
• Glycyrrhizinic acid
• Glycyron
• Glycyrrhetinic acid glycoside
• potenlini
• Glizigen
• Glycyrrizin
• glycyrrhizate
• glyzyrrhizin
• Glycyrrhizin [JAN]
• 18-beta-Glycyrrhizic acid
• beta-Glycyrrhizin
• 18beta-Glycyrrhizic acid
• Rizinsan K2 A2 (free acid)
• HSDB 496
• CHEBI:15939
• Neo-Umor
• EINECS 215-785-7
• Liquorice
• .beta.-glycyrrhizin
• NSC 167409
• NSC 234419
• NSC-167409
• NSC-234419
• UNII-6FO62043WK
• BRN 0077922
• CCRIS 8444
• DTXSID8047006
• 6FO62043WK
• C42H62O16
• 18.beta.-glycyrrhizic acid
• Glycyrrhizinate
• CHEMBL441687
• NSC 2800
• DTXCID6027006
• 4-18-00-05156 (Beilstein Handbook Reference)
• (3beta,20beta)-20-carboxy-11-oxo-30-norolean-12-en-3-yl-2-O-beta-D-glucopyranuronosyl-alpha-D-glucopyranosiduronic acid
• 20beta-Carboxy-11-oxo-30-norolean-12-en-3beta-yl-2-O-beta-D-glucopyranuronosyl-alpha-D-glucopyranosiduronic acid
• 30-hydroxy-11,30-dioxoolean-12-en-3beta-yl (2-O-beta-D-glucopyranosyluronic acid)-alpha-D-glucopyranosiduronic acid
• alpha-D-Glucopyranosiduronic acid, (3beta,20beta)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-beta-D-glucopyranuronosyl-
• alpha-D-Glucopyranosiduronic acid, (3beta,20beta)-20-carboxy-11-oxo-30-norolean-12-en-3-yl-2-O-beta-D-glucopyranuron osyl-
• GLYCYRRHIZIN (II)
• GLYCYRRHIZIN [II]
• Glycyrrhitin
• Dermacrin
• (3beta,20beta)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-beta-D-glucopyranuronosyl-alpha-D-glucopyranosiduronic acid
• alpha-D-glucopyranosiduronic acid, (3 beta,20 beta)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-beta-D-glucopyranuronosyl-
• Dipotassium glycyrrhizinate
• GLYCYRRHIZIC ACID (MART.)
• GLYCYRRHIZIC ACID [MART.]
• GLYCYRRHIZIC ACID (USP-RS)
• GLYCYRRHIZIC ACID [USP-RS]
• NSC167409
• Glycyram
• Zinc Glycyrrhizate
• Acid, Glycyrrhizic
• (2S,3S,4S,5R,6S)-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}-5-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid
• (3beta,20beta)-20-Carboxy-11-oxo-30-norlean-12-en-3-yl-2-O-beta-1- 7-glucopyranuronosyl-alpha-D-glucopyranosiduronic acid
• alpha-D-Glucopyranosiduronic acid, (3beta,20beta)-20-carboxy-11-oxo-30-norlean-12-en-3-yl-2-O-beta-1- 7-glucopyranuronosyl-
• CAS-1405-86-3
• Acid, Glycyrrhizinic
• MFCD00065194
• NSC234419
• C42-H62-O16
• NCGC00183128-01
• (2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5S,6S)-2-[[(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]-6-carboxy-4,5-dihydroxy-tetrahydropyran-3-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid
• ammonium-glycyrrhizinate
• Glycyrrhizic acid, 2K
• beta-Glycyrrhizinic acid
• Licorice, Glycyrrhiza, and Ammoniated Glycyrrhizin
• D0T8QB
• GLYCYRRHIZIN [HSDB]
• Glycyrrhizia uralensis Fisch
• SCHEMBL17684
• BIDD:ER0363
• GLYCYRRHIZIC ACID [MI]
• GTPL4688
• GLYCYRRHIZIC ACID [INCI]
• Glycyrrhizin (Glycyrrhizic Acid)
• LPLVUJXQOOQHMX-QWBHMCJMSA-N
• GLYCYRRHIZIC ACID [WHO-DD]
• .alpha.-D-Glucopyranosiduronic acid, (3.beta.,20.beta.)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-.beta.-D-glucopyranuronosyl-
• HY-N0184
• Tox21_111520
• Tox21_113426
• Tox21_303493
• BDBM50185127
• HMDB:0029843
• s2302
• AKOS015893086
• AKOS015969345
• CCG-270511
• CS-7695
• DB13751
• GM-1292
• NCGC00257455-01
• NCGC00386162-01
• NCGC00386162-02
• AS-13001
• E958
• LS-72973
• G0150
• AB01566834_01
• EN300-25023649
• Q418705
• Q-201172
• BRD-K83486494-318-01-5
• GLYCYRRHIZIC ACID (GLYCYRRHIZIN) (CONSTITUENT OF LICORICE)
• GLYCYRRHIZIC ACID (GLYCYRRHIZIN) (CONSTITUENT OF LICORICE) [DSC]
• Glycyrrhizic acid, United States Pharmacopeia (USP) Reference Standard
• xy-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• Glycyrrhizic Acid, Pharmaceutical Secondary Standard; Certified Reference Material
• (2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5S,6S)-2-[[(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]-6-carbo
• (2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5S,6S)-2-[[(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]-6-carboxy-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylicacid
• (3.beta.,20.beta.)-20-Carboxy-11-oxo-30-norlean-12-en-3-yl-2-O-.beta.-1- 7-glucopyranuronosyl-.alpha.-D-glucopyranosiduronic acid
• (3.BETA.,20.BETA.)-20-CARBOXY-11-OXO-30-NOROLEAN-12-EN-3-YL 2-O-.BETA.-D-GLUCOPYRANURONOSYL-.ALPHA.-D-GLUCOPYRANOSIDURONIC ACID
• (3beta,20beta)-20-Carboxy-11-oxo-30-norlean-12-en-3-yl-2-O-beta-1-7-glucopyranuronosyl-alpha-D-glucopyranosiduronic acid
• 20BETA-CARBOXY-11-OXO-30-NOROLEAN-12-EN-3BETA-YL-2-O-BE TA-D-GLUCOPYRANURONOSYL-ALPHA-D-GLUCOPYRANOSIDURONIC ACID
• alpha-D-Glucopyranosiduronic acid, (3beta,20beta)-20-carboxy-11-oxo-30-norlean-12-en-3-yl-2-O-beta-1-7-glucopyranuronosyl-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8728	87.28%
Caco-2	-	0.8793	87.93%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8383	83.83%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.4761	47.61%
OATP1B3 inhibitior	-	0.3963	39.63%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.6929	69.29%
BSEP inhibitior	+	0.6059	60.59%
P-glycoprotein inhibitior	+	0.7608	76.08%
P-glycoprotein substrate	-	0.7951	79.51%
CYP3A4 substrate	+	0.7215	72.15%
CYP2C9 substrate	-	0.7908	79.08%
CYP2D6 substrate	-	0.8981	89.81%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.8692	86.92%
CYP2C19 inhibition	-	0.9112	91.12%
CYP2D6 inhibition	-	0.9423	94.23%
CYP1A2 inhibition	-	0.8358	83.58%
CYP2C8 inhibition	+	0.6827	68.27%
CYP inhibitory promiscuity	-	0.9568	95.68%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6106	61.06%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9082	90.82%
Skin irritation	-	0.5295	52.95%
Skin corrosion	-	0.9236	92.36%
Ames mutagenesis	-	0.9000	90.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4544	45.44%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	+	0.6908	69.08%
skin sensitisation	-	0.8115	81.15%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.4867	48.67%
Acute Oral Toxicity (c)	IV	0.6130	61.30%
Estrogen receptor binding	+	0.7736	77.36%
Androgen receptor binding	+	0.7324	73.24%
Thyroid receptor binding	-	0.8319	83.19%
Glucocorticoid receptor binding	+	0.7152	71.52%
Aromatase binding	+	0.6753	67.53%
PPAR gamma	+	0.7700	77.00%
Honey bee toxicity	-	0.7043	70.43%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9886	98.86%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4235	P28845	11-beta-hydroxysteroid dehydrogenase 1	10 nM; 18.6 nM; 6 nM; 6 nM	IC50; IC50; IC50; IC50	PMID: 19564108; PMID: 22148241; PMID: 22360639; via Super-PRED
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	1 nM; 0.7 nM; 0.4 nM; 0.4 nM	IC50; IC50; IC50; IC50	PMID: 19564108; PMID: 22148241; PMID: 22360639; via Super-PRED
CHEMBL1697668	Q9Y6L6	Solute carrier organic anion transporter family member 1B1	15900 nM	Ki	PMID: 12963436
CHEMBL1743121	Q9NPD5	Solute carrier organic anion transporter family member 1B3	12500 nM	Ki	PMID: 12963436

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.50%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.87%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.08%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	91.01%	90.17%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.76%	97.36%
CHEMBL1951	P21397	Monoamine oxidase A	90.37%	91.49%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.94%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.22%	96.09%
CHEMBL2581	P07339	Cathepsin D	87.28%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.35%	99.23%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.00%	93.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.34%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.48%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.60%	86.33%
CHEMBL5255	O00206	Toll-like receptor 4	81.43%	92.50%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.36%	92.94%

Plants that contains it

• Abrus precatorius
• Glycyrrhiza
• Glycyrrhiza aspera
• Glycyrrhiza glabra
• Glycyrrhiza inflata
• Glycyrrhiza uralensis
• Glycyrrhiza uralensis
• Mitracarpus hirtus
• Rheum officinale
• Rheum palmatum
• Rheum tanguticum
• Tetradium ruticarpum

Cross-Links

• PubChem: 14982
• NPASS: NPC202666
• ChEMBL: CHEMBL441687
• LOTUS: LTS0121878
• wikiData: Q418705