Licoricesaponin A3

Details

• Internal ID: cc2535f6-8ab5-483a-ab14-a403b3af70c1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[(2R,3R,4S,5S,6S)-2-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-11-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-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)OC8C(C(C(C(O8)CO)O)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[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O
• InChI: InChI=1S/C48H72O21/c1-43(2)23-8-11-48(7)36(21(50)16-19-20-17-45(4,13-12-44(20,3)14-15-47(19,48)6)42(63)69-39-31(57)26(52)25(51)22(18-49)64-39)46(23,5)10-9-24(43)65-41-35(30(56)29(55)34(67-41)38(61)62)68-40-32(58)27(53)28(54)33(66-40)37(59)60/h16,20,22-36,39-41,49,51-58H,8-15,17-18H2,1-7H3,(H,59,60)(H,61,62)/t20-,22+,23-,24-,25+,26-,27-,28-,29-,30-,31+,32+,33-,34-,35+,36+,39-,40-,41+,44+,45-,46-,47+,48+/m0/s1
• InChI Key: HJFOOTRGDAPZMV-SMVKYPPISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₇₂O₂₁
• Molecular Weight: 985.10 g/mol
• Exact Mass: 984.45660930 g/mol
• Topological Polar Surface Area (TPSA): 346.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): -0.50
• H-Bond Acceptor: 19
• H-Bond Donor: 11
• Rotatable Bonds: 9

Synonyms

• 118325-22-7
• Licorice-saponin A3
• UNII-88G00OJY89
• 88G00OJY89
• beta-D-Glucopyranosiduronic acid, (3beta,20beta)-29-(beta-D-glucopyranosyloxy)-11,29-dioxoolean-12-en-3-yl 2-o-beta-D-glucopyranuronosyl-
• RefChem:42051
• (2S,3S,4S,5R,6R)-6-[(2R,3R,4S,5S,6S)-2-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-11-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-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
• Licorice saponin A3
• CHEMBL594996
• orb1684461
• SCHEMBL29889372
• DTXSID001316022
• HY-N6982
• C48H72O21
• AKOS040760517
• DA-54918
• MS-31837
• CS-0101425
• G16944
• Q27269927
• .BETA.-D-GLUCOPYRANOSIDURONIC ACID, (3.BETA.,20.BETA.)-29-(.BETA.-D-GLUCOPYRANOSYLOXY)-11,29-DIOXOOLEAN-12-EN-3-YL 2-O-.BETA.-D-GLUCOPYRANURONOSYL-
• |A-D-Glucopyranosiduronic acid, (3|A,20|A)-29-(|A-D-glucopyranosyloxy)-11,29-dioxoolean-12-en-3-yl 2-O-|A-D-glucopyranuronosyl-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7941	79.41%
Caco-2	-	0.8743	87.43%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8948	89.48%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.4052	40.52%
OATP1B3 inhibitior	-	0.5056	50.56%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.6474	64.74%
BSEP inhibitior	+	0.7693	76.93%
P-glycoprotein inhibitior	+	0.7498	74.98%
P-glycoprotein substrate	-	0.7276	72.76%
CYP3A4 substrate	+	0.7351	73.51%
CYP2C9 substrate	-	0.7966	79.66%
CYP2D6 substrate	-	0.8894	88.94%
CYP3A4 inhibition	-	0.8459	84.59%
CYP2C9 inhibition	-	0.8380	83.80%
CYP2C19 inhibition	-	0.9220	92.20%
CYP2D6 inhibition	-	0.9493	94.93%
CYP1A2 inhibition	-	0.8499	84.99%
CYP2C8 inhibition	+	0.7372	73.72%
CYP inhibitory promiscuity	-	0.9381	93.81%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6298	62.98%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9019	90.19%
Skin irritation	-	0.5723	57.23%
Skin corrosion	-	0.9450	94.50%
Ames mutagenesis	-	0.8900	89.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6469	64.69%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.5538	55.38%
skin sensitisation	-	0.9064	90.64%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.7855	78.55%
Acute Oral Toxicity (c)	III	0.7628	76.28%
Estrogen receptor binding	+	0.7684	76.84%
Androgen receptor binding	+	0.7447	74.47%
Thyroid receptor binding	-	0.5797	57.97%
Glucocorticoid receptor binding	+	0.7468	74.68%
Aromatase binding	+	0.6328	63.28%
PPAR gamma	+	0.8002	80.02%
Honey bee toxicity	-	0.6713	67.13%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9778	97.78%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.88%	91.11%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	97.65%	94.78%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.71%	94.45%
CHEMBL2581	P07339	Cathepsin D	93.38%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.98%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.50%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	92.13%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.50%	97.09%
CHEMBL1951	P21397	Monoamine oxidase A	87.98%	91.49%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.74%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	85.49%	92.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.71%	86.33%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.94%	93.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.37%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.31%	89.00%

Plants that contains it

• Glycyrrhiza glabra
• Glycyrrhiza inflata
• Glycyrrhiza uralensis
• Glycyrrhiza uralensis
• Mitracarpus hirtus

Cross-Links

• PubChem: 14187172
• NPASS: NPC247315
• LOTUS: LTS0020656
• wikiData: Q27269927