methyl (2S,3R,4S)-4-[2-[[(2R,3R,4S,4aR,6aR,6bS,8aS,11R,12R,12aS,14aR,14bR)-2,3,12-trihydroxy-4,6a,6b,11,12,14b-hexamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,11,12a,14,14a-tetradecahydropicen-4-yl]methoxy]-2-oxoethyl]-3-ethenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate

Details

• Internal ID: 4d6e1e7e-41be-4bb9-a7ea-6387f678fd0e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: methyl (2S,3R,4S)-4-[2-[[(2R,3R,4S,4aR,6aR,6bS,8aS,11R,12R,12aS,14aR,14bR)-2,3,12-trihydroxy-4,6a,6b,11,12,14b-hexamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,11,12a,14,14a-tetradecahydropicen-4-yl]methoxy]-2-oxoethyl]-3-ethenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
• InChI: InChI=1S/C53H80O21/c1-9-25-26(27(43(65)68-8)22-69-44(25)73-45-39(62)37(60)35(58)30(20-54)71-45)18-34(57)70-23-49(4)32-13-14-51(6)33(48(32,3)19-29(56)42(49)64)11-10-28-41-52(7,67)24(2)12-15-53(41,17-16-50(28,51)5)47(66)74-46-40(63)38(61)36(59)31(21-55)72-46/h9-10,22,24-26,29-33,35-42,44-46,54-56,58-64,67H,1,11-21,23H2,2-8H3/t24-,25-,26+,29-,30-,31-,32-,33-,35-,36-,37+,38+,39-,40-,41-,42+,44+,45+,46+,48+,49-,50-,51-,52-,53+/m1/s1
• InChI Key: DZNGHAQRGZEQAX-XWNBIBGFSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₈₀O₂₁
• Molecular Weight: 1053.20 g/mol
• Exact Mass: 1052.51920956 g/mol
• Topological Polar Surface Area (TPSA): 338.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): -0.00
• H-Bond Acceptor: 21
• H-Bond Donor: 11
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6678	66.78%
Caco-2	-	0.8662	86.62%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7904	79.04%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7870	78.70%
OATP1B3 inhibitior	-	0.2184	21.84%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6021	60.21%
BSEP inhibitior	+	0.9470	94.70%
P-glycoprotein inhibitior	+	0.7474	74.74%
P-glycoprotein substrate	+	0.6724	67.24%
CYP3A4 substrate	+	0.7502	75.02%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8818	88.18%
CYP3A4 inhibition	-	0.8101	81.01%
CYP2C9 inhibition	-	0.9065	90.65%
CYP2C19 inhibition	-	0.8924	89.24%
CYP2D6 inhibition	-	0.9513	95.13%
CYP1A2 inhibition	-	0.8951	89.51%
CYP2C8 inhibition	+	0.8099	80.99%
CYP inhibitory promiscuity	-	0.9807	98.07%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6213	62.13%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.8992	89.92%
Skin irritation	-	0.5659	56.59%
Skin corrosion	-	0.9399	93.99%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7692	76.92%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.9052	90.52%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.5106	51.06%
Acute Oral Toxicity (c)	III	0.6632	66.32%
Estrogen receptor binding	+	0.7444	74.44%
Androgen receptor binding	+	0.7652	76.52%
Thyroid receptor binding	+	0.6430	64.30%
Glucocorticoid receptor binding	+	0.7898	78.98%
Aromatase binding	+	0.6147	61.47%
PPAR gamma	+	0.8252	82.52%
Honey bee toxicity	-	0.6658	66.58%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9459	94.59%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.94%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.61%	91.11%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	92.49%	91.07%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	92.28%	95.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.54%	95.56%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	90.69%	91.24%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.07%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.72%	96.77%
CHEMBL5028	O14672	ADAM10	87.70%	97.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.66%	94.45%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.53%	95.50%
CHEMBL5255	O00206	Toll-like receptor 4	87.52%	92.50%
CHEMBL340	P08684	Cytochrome P450 3A4	86.73%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.68%	97.09%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	86.03%	96.90%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.94%	95.83%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.96%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.47%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.09%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.87%	100.00%
CHEMBL2243	O00519	Anandamide amidohydrolase	83.76%	97.53%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.96%	92.94%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.79%	93.00%
CHEMBL1859	O95180	Voltage-gated T-type calcium channel alpha-1H subunit	82.00%	98.57%
CHEMBL2996	Q05655	Protein kinase C delta	81.57%	97.79%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.88%	94.33%
CHEMBL2581	P07339	Cathepsin D	80.54%	98.95%
CHEMBL4072	P07858	Cathepsin B	80.15%	93.67%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.01%	97.14%

Plants that contains it

• Desfontainia spinosa

Cross-Links

• PubChem: 101318311
• LOTUS: LTS0003459
• wikiData: Q104991900