methyl (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aR,12aS,14aR,14bR)-8a-[(2S,3R,4S,5R)-4,5-dihydroxy-3-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyoxan-2-yl]oxycarbonyl-8-hydroxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylate

Details

• Internal ID: 50dffa2a-8438-4e01-a603-6fbad842d983
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: methyl (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aR,12aS,14aR,14bR)-8a-[(2S,3R,4S,5R)-4,5-dihydroxy-3-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyoxan-2-yl]oxycarbonyl-8-hydroxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylate
• SMILES (Canonical): CC1(CCC2(C(C1)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)C)OC6C(C(C(C(O6)C(=O)OC)O)O)O)C)C(=O)OC7C(C(C(CO7)O)O)OC(=O)C=CC8=CC=C(C=C8)O)C
• SMILES (Isomeric): C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(C[C@H]([C@@]5([C@H]4CC(CC5)(C)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H](CO6)O)O)OC(=O)/C=C/C7=CC=C(C=C7)O)O)C)C)(C)C)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)C(=O)OC)O)O)O
• InChI: InChI=1S/C51H72O16/c1-46(2)21-22-51(45(61)67-44-41(36(56)30(53)25-63-44)65-35(55)16-11-26-9-12-27(52)13-10-26)29(23-46)28-14-15-32-48(5)19-18-34(64-43-39(59)37(57)38(58)40(66-43)42(60)62-8)47(3,4)31(48)17-20-49(32,6)50(28,7)24-33(51)54/h9-14,16,29-34,36-41,43-44,52-54,56-59H,15,17-25H2,1-8H3/b16-11+/t29-,30+,31-,32+,33+,34-,36-,37-,38-,39+,40-,41+,43+,44-,48-,49+,50+,51+/m0/s1
• InChI Key: RKIQDHTZALPOIX-WTCXUWSSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₁H₇₂O₁₆
• Molecular Weight: 941.10 g/mol
• Exact Mass: 940.48203620 g/mol
• Topological Polar Surface Area (TPSA): 248.00 Ų
• XlogP: 6.40
• Atomic LogP (AlogP): 4.08
• H-Bond Acceptor: 16
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9201	92.01%
Caco-2	-	0.8668	86.68%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7894	78.94%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7246	72.46%
OATP1B3 inhibitior	+	0.8637	86.37%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.9435	94.35%
P-glycoprotein inhibitior	+	0.7539	75.39%
P-glycoprotein substrate	+	0.6304	63.04%
CYP3A4 substrate	+	0.7538	75.38%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8719	87.19%
CYP3A4 inhibition	-	0.7229	72.29%
CYP2C9 inhibition	-	0.8020	80.20%
CYP2C19 inhibition	-	0.8176	81.76%
CYP2D6 inhibition	-	0.9085	90.85%
CYP1A2 inhibition	-	0.7157	71.57%
CYP2C8 inhibition	+	0.8552	85.52%
CYP inhibitory promiscuity	-	0.9596	95.96%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5836	58.36%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9019	90.19%
Skin irritation	-	0.6617	66.17%
Skin corrosion	-	0.9384	93.84%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7427	74.27%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.7842	78.42%
skin sensitisation	-	0.8621	86.21%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.8670	86.70%
Acute Oral Toxicity (c)	III	0.3773	37.73%
Estrogen receptor binding	+	0.7917	79.17%
Androgen receptor binding	+	0.7555	75.55%
Thyroid receptor binding	+	0.6037	60.37%
Glucocorticoid receptor binding	+	0.7951	79.51%
Aromatase binding	+	0.5682	56.82%
PPAR gamma	+	0.8135	81.35%
Honey bee toxicity	-	0.6385	63.85%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9893	98.93%

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	98.91%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.21%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.68%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.82%	95.56%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	93.66%	89.67%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.97%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.61%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.80%	89.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	88.61%	93.99%
CHEMBL2179	P04062	Beta-glucocerebrosidase	88.43%	85.31%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	88.42%	89.44%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.02%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	85.41%	94.75%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.71%	91.07%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	83.24%	91.65%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.10%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.13%	89.62%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.28%	94.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.42%	99.17%
CHEMBL5028	O14672	ADAM10	80.32%	97.50%

Plants that contains it

• Tragopogon porrifolius

Cross-Links

• PubChem: 21626560
• LOTUS: LTS0065295
• wikiData: Q105238445