[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,4S,5R,9S,10R,13S)-13-[(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate

Details

• Internal ID: 1fe64ba7-7a52-4e94-b89e-426e4a6ceec2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides > Steviol glycosides
• IUPAC Name: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,4S,5R,9S,10R,13S)-13-[(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC34CCC5C6(CCCC(C6CCC5(C3)CC4=C)(C)C(=O)OC7C(C(C(C(O7)CO)O)O)O)C)CO)O)OC8C(C(C(C(O8)CO)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@@]34CC[C@H]5[C@@]6(CCC[C@@]([C@H]6CC[C@]5(C3)CC4=C)(C)C(=O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C)CO)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O)O
• InChI: InChI=1S/C44H70O22/c1-17-12-43-10-6-22-41(3,8-5-9-42(22,4)40(58)65-38-33(57)30(54)26(50)20(14-46)61-38)23(43)7-11-44(17,16-43)66-39-35(64-36-31(55)28(52)24(48)18(2)59-36)34(27(51)21(15-47)62-39)63-37-32(56)29(53)25(49)19(13-45)60-37/h18-39,45-57H,1,5-16H2,2-4H3/t18-,19-,20-,21-,22+,23+,24-,25-,26-,27-,28+,29+,30+,31+,32-,33-,34+,35-,36-,37+,38+,39+,41-,42-,43-,44+/m1/s1
• InChI Key: QSRAJVGDWKFOGU-NDJMUUGGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₇₀O₂₂
• Molecular Weight: 951.00 g/mol
• Exact Mass: 950.43587386 g/mol
• Topological Polar Surface Area (TPSA): 354.00 Ų
• XlogP: -2.30
• Atomic LogP (AlogP): -4.09
• H-Bond Acceptor: 22
• H-Bond Donor: 13
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6595	65.95%
Caco-2	-	0.8999	89.99%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.7345	73.45%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8236	82.36%
OATP1B3 inhibitior	+	0.8494	84.94%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7526	75.26%
BSEP inhibitior	+	0.6159	61.59%
P-glycoprotein inhibitior	+	0.7321	73.21%
P-glycoprotein substrate	-	0.5962	59.62%
CYP3A4 substrate	+	0.7039	70.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8539	85.39%
CYP3A4 inhibition	-	0.9564	95.64%
CYP2C9 inhibition	-	0.8609	86.09%
CYP2C19 inhibition	-	0.8613	86.13%
CYP2D6 inhibition	-	0.9466	94.66%
CYP1A2 inhibition	-	0.8591	85.91%
CYP2C8 inhibition	+	0.5373	53.73%
CYP inhibitory promiscuity	-	0.9338	93.38%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6988	69.88%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9064	90.64%
Skin irritation	-	0.5581	55.81%
Skin corrosion	-	0.9425	94.25%
Ames mutagenesis	-	0.8354	83.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7298	72.98%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.8852	88.52%
skin sensitisation	-	0.9051	90.51%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.7859	78.59%
Acute Oral Toxicity (c)	I	0.4473	44.73%
Estrogen receptor binding	+	0.7593	75.93%
Androgen receptor binding	+	0.7174	71.74%
Thyroid receptor binding	-	0.5836	58.36%
Glucocorticoid receptor binding	+	0.6037	60.37%
Aromatase binding	+	0.6326	63.26%
PPAR gamma	+	0.7151	71.51%
Honey bee toxicity	-	0.7085	70.85%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9758	97.58%

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	98.21%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.78%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.58%	97.25%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	93.66%	96.21%
CHEMBL3714130	P46095	G-protein coupled receptor 6	92.89%	97.36%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.18%	96.77%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	91.99%	91.24%
CHEMBL237	P41145	Kappa opioid receptor	89.60%	98.10%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.77%	94.45%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.77%	95.50%
CHEMBL2581	P07339	Cathepsin D	88.74%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.63%	97.09%
CHEMBL5255	O00206	Toll-like receptor 4	87.57%	92.50%
CHEMBL340	P08684	Cytochrome P450 3A4	86.54%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.99%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.17%	91.07%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.66%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.25%	93.04%
CHEMBL226	P30542	Adenosine A1 receptor	82.25%	95.93%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.68%	94.33%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.65%	100.00%

Plants that contains it

• Stevia rebaudiana

Cross-Links

• PubChem: 134762113
• LOTUS: LTS0148066
• wikiData: Q104251807