Uralsaponin X

Details

• Internal ID: 40e5ff6c-f395-496e-bd11-d35878c68c7d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aR,9R,11R,12aS,14aR,14bS)-9-acetyloxy-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]-5-[(2R,3R,4S,5S,6S)-6-carboxy-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxyoxane-2-carboxylic acid
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(C(OC3OC4CCC5(C(C4(C)C)CCC6(C5C(=O)C=C7C6(CCC8(C7CC(CC8OC(=O)C)(C)C(=O)O)C)C)C)C)C(=O)O)O)O)C(=O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2O[C@@H]3[C@H]([C@@H]([C@H](O[C@H]3O[C@H]4CC[C@]5([C@H](C4(C)C)CC[C@@]6([C@@H]5C(=O)C=C7[C@]6(CC[C@@]8([C@H]7C[C@@](C[C@H]8OC(=O)C)(C)C(=O)O)C)C)C)C)C(=O)O)O)O)C(=O)O)O)O)O)O)O
• InChI: InChI=1S/C50H74O22/c1-19-27(53)28(54)33(59)41(66-19)71-37-32(58)30(56)35(40(62)63)70-43(37)72-36-31(57)29(55)34(39(60)61)69-42(36)68-25-11-12-48(7)24(45(25,3)4)10-13-50(9)38(48)23(52)16-21-22-17-46(5,44(64)65)18-26(67-20(2)51)47(22,6)14-15-49(21,50)8/h16,19,22,24-38,41-43,53-59H,10-15,17-18H2,1-9H3,(H,60,61)(H,62,63)(H,64,65)/t19-,22-,24-,25-,26+,27-,28+,29-,30-,31-,32-,33+,34-,35-,36+,37+,38+,41-,42+,43-,46+,47+,48-,49+,50+/m0/s1
• InChI Key: CWRRYAWFDXCSDM-XTIAVVEZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₀H₇₄O₂₂
• Molecular Weight: 1027.10 g/mol
• Exact Mass: 1026.46717398 g/mol
• Topological Polar Surface Area (TPSA): 352.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 0.64
• H-Bond Acceptor: 19
• H-Bond Donor: 10
• Rotatable Bonds: 10

Synonyms

• PF9RBL8YHN
• UNII-PF9RBL8YHN
• 1616062-89-5
• 3beta-O-(alpha-L-Rhamnopyranosyl-(1->2)-beta-D-glucuronopyranosyl-(1->2)-beta-D-glucuronopyranosyl)-22beta-acetoxy-11-oxo-olean-12-en-30-oic acid
• beta-D-Glucopyranosiduronic acid, (3beta,20beta,22beta)-22-(acetyloxy)-20-carboxy-11-oxo-30-norolean-12-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1->2)-o-beta-D-glucopyranuronosyl-(1->2)-
• RefChem:51650
• Q27286524
• .BETA.-D-GLUCOPYRANOSIDURONIC ACID, (3.BETA.,20.BETA.,22.BETA.)-22-(ACETYLOXY)-20-CARBOXY-11-OXO-30-NOROLEAN-12-EN-3-YL O-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->2)-O-.BETA.-D-GLUCOPYRANURONOSYL-(1->2)-
• 3.BETA.-O-(.ALPHA.-L-RHAMNOPYRANOSYL-(1->2)-.BETA.-D-GLUCURONOPYRANOSYL-(1->2)-.BETA.-D-GLUCURONOPYRANOSYL)-22.BETA.-ACETOXY-11-OXO-OLEAN-12-EN-30-OIC ACID

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9175	91.75%
Caco-2	-	0.8747	87.47%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8274	82.74%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.3876	38.76%
OATP1B3 inhibitior	-	0.3487	34.87%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.6250	62.50%
BSEP inhibitior	+	0.8796	87.96%
P-glycoprotein inhibitior	+	0.7494	74.94%
P-glycoprotein substrate	-	0.5580	55.80%
CYP3A4 substrate	+	0.7348	73.48%
CYP2C9 substrate	-	0.7915	79.15%
CYP2D6 substrate	-	0.8989	89.89%
CYP3A4 inhibition	-	0.8221	82.21%
CYP2C9 inhibition	-	0.8659	86.59%
CYP2C19 inhibition	-	0.9292	92.92%
CYP2D6 inhibition	-	0.9493	94.93%
CYP1A2 inhibition	-	0.8720	87.20%
CYP2C8 inhibition	+	0.7182	71.82%
CYP inhibitory promiscuity	-	0.9677	96.77%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6115	61.15%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9008	90.08%
Skin irritation	-	0.5622	56.22%
Skin corrosion	-	0.9226	92.26%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6640	66.40%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	+	0.5783	57.83%
skin sensitisation	-	0.7947	79.47%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.7717	77.17%
Acute Oral Toxicity (c)	IV	0.6236	62.36%
Estrogen receptor binding	+	0.7679	76.79%
Androgen receptor binding	+	0.7424	74.24%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7678	76.78%
Aromatase binding	+	0.6068	60.68%
PPAR gamma	+	0.8202	82.02%
Honey bee toxicity	-	0.6666	66.66%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9872	98.72%

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	98.24%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.88%	91.49%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	97.13%	94.78%
CHEMBL3714130	P46095	G-protein coupled receptor 6	94.66%	97.36%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.67%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.23%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.21%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.59%	86.33%
CHEMBL2581	P07339	Cathepsin D	89.83%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.99%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	86.82%	91.19%
CHEMBL221	P23219	Cyclooxygenase-1	86.69%	90.17%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.52%	93.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.86%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.63%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.30%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.81%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.89%	92.94%

Plants that contains it

• Glycyrrhiza glabra
• Glycyrrhiza inflata
• Glycyrrhiza uralensis

Cross-Links

• PubChem: 91618087
• NPASS: NPC180559