Saniculoside R-1

Details

• Internal ID: f5275f8f-72a5-42d7-94c2-cc9b3b15abf0
• 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,7R,8S,8aR,9R,10R,12aS,14aR,14bR)-7,8,9-trihydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-10-(2-methylbutanoyloxy)-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2R,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid
• SMILES (Canonical): CCC(C)C(=O)OC1C(C2(C(CC1(C)C)C3=CCC4C5(CCC(C(C5CCC4(C3(C(C2O)O)C)C)(C)C)OC6C(C(C(C(O6)C(=O)O)O)OC7C(C(C(CO7)O)O)O)OC8C(C(C(C(O8)CO)O)O)O)C)CO)O
• SMILES (Isomeric): CCC(C)C(=O)O[C@H]1[C@@H]([C@]2([C@@H](CC1(C)C)C3=CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3([C@H]([C@H]2O)O)C)C)(C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O[C@@H]7[C@H]([C@@H]([C@@H](CO7)O)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)C)CO)O
• InChI: InChI=1S/C52H84O22/c1-10-21(2)43(67)74-41-40(64)52(20-54)23(17-47(41,3)4)22-11-12-27-49(7)15-14-28(48(5,6)26(49)13-16-50(27,8)51(22,9)38(62)39(52)63)70-46-37(73-45-33(60)31(58)30(57)25(18-53)69-45)35(34(61)36(72-46)42(65)66)71-44-32(59)29(56)24(55)19-68-44/h11,21,23-41,44-46,53-64H,10,12-20H2,1-9H3,(H,65,66)/t21?,23-,24+,25+,26-,27+,28-,29+,30+,31-,32-,33+,34-,35-,36-,37+,38-,39+,40-,41-,44+,45-,46+,49-,50+,51-,52-/m0/s1
• InChI Key: ARQLEOCMMPMRQH-ULDGSTSNSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₂H₈₄O₂₂
• Molecular Weight: 1061.20 g/mol
• Exact Mass: 1060.54542430 g/mol
• Topological Polar Surface Area (TPSA): 362.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): -1.17
• H-Bond Acceptor: 21
• H-Bond Donor: 13
• Rotatable Bonds: 12

Synonyms

• Saniculoside R 1
• 204331-80-6
• beta-D-Glucopyranosiduronic acid, (3beta,15alpha,16alpha,21beta,22alpha)-15,16,22,28-tetrahydroxy-21-(2-methyl-1-oxobutoxy)olean-12-en-3-yl O-alpha-L-arabinopyranosyl-(1-3)-O-(beta-D-glucopyranosyl-(1-2))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8539	85.39%
Caco-2	-	0.8829	88.29%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.8575	85.75%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7663	76.63%
OATP1B3 inhibitior	-	0.3799	37.99%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6026	60.26%
BSEP inhibitior	+	0.9009	90.09%
P-glycoprotein inhibitior	+	0.7485	74.85%
P-glycoprotein substrate	+	0.5686	56.86%
CYP3A4 substrate	+	0.7363	73.63%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8862	88.62%
CYP3A4 inhibition	-	0.6349	63.49%
CYP2C9 inhibition	-	0.8494	84.94%
CYP2C19 inhibition	-	0.8968	89.68%
CYP2D6 inhibition	-	0.9384	93.84%
CYP1A2 inhibition	-	0.9102	91.02%
CYP2C8 inhibition	+	0.7813	78.13%
CYP inhibitory promiscuity	-	0.9556	95.56%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5892	58.92%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9012	90.12%
Skin irritation	-	0.5592	55.92%
Skin corrosion	-	0.9422	94.22%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7684	76.84%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.8368	83.68%
skin sensitisation	-	0.9039	90.39%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.9406	94.06%
Acute Oral Toxicity (c)	III	0.7630	76.30%
Estrogen receptor binding	+	0.7946	79.46%
Androgen receptor binding	+	0.7548	75.48%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7836	78.36%
Aromatase binding	+	0.6460	64.60%
PPAR gamma	+	0.8181	81.81%
Honey bee toxicity	-	0.6660	66.60%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9719	97.19%

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	97.12%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.85%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.49%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.59%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	93.04%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.09%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	92.00%	95.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.95%	97.25%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	90.62%	96.77%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.27%	96.21%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.11%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.71%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.28%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.90%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.55%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	83.37%	92.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.09%	92.62%
CHEMBL5028	O14672	ADAM10	82.96%	97.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.36%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.06%	94.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.97%	100.00%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	81.61%	97.29%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.46%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.44%	93.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.18%	97.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.98%	99.17%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.07%	91.07%

Plants that contains it

• Sanicula europaea

Cross-Links

• PubChem: 101935953
• LOTUS: LTS0256894
• wikiData: Q104917511