[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4S,5S,6R)-6-(acetyloxymethyl)-4,5-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate

Details

• Internal ID: aea7df3b-a45f-412e-8e0d-5a79119e8e85
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4S,5S,6R)-6-(acetyloxymethyl)-4,5-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• SMILES (Canonical): CC(=O)OCC1C(C(C(C(O1)OC2CCC3(C(C2(C)C)CCC4(C3CC=C5C4(CCC6(C5CC(CC6)(C)C)C(=O)OC7C(C(C(C(O7)CO)O)O)O)C)C)C)OC8C(C(C(C(O8)CO)O)O)O)O)O
• SMILES (Isomeric): CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]4([C@@H]3CC=C5[C@]4(CC[C@@]6([C@H]5CC(CC6)(C)C)C(=O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C)C)C)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O
• InChI: InChI=1S/C50H80O19/c1-23(53)63-22-28-34(56)37(59)40(68-41-38(60)35(57)32(54)26(20-51)64-41)43(66-28)67-31-12-13-47(6)29(46(31,4)5)11-14-49(8)30(47)10-9-24-25-19-45(2,3)15-17-50(25,18-16-48(24,49)7)44(62)69-42-39(61)36(58)33(55)27(21-52)65-42/h9,25-43,51-52,54-61H,10-22H2,1-8H3/t25-,26+,27+,28+,29-,30+,31-,32+,33+,34+,35-,36-,37-,38+,39+,40+,41-,42-,43-,47-,48+,49+,50-/m0/s1
• InChI Key: RESKEUYNGYCRHA-LEQTZOMHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₀H₈₀O₁₉
• Molecular Weight: 985.20 g/mol
• Exact Mass: 984.52938032 g/mol
• Topological Polar Surface Area (TPSA): 301.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 0.71
• H-Bond Acceptor: 19
• H-Bond Donor: 10
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7181	71.81%
Caco-2	-	0.8838	88.38%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8914	89.14%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7253	72.53%
OATP1B3 inhibitior	-	0.5187	51.87%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5974	59.74%
BSEP inhibitior	+	0.8037	80.37%
P-glycoprotein inhibitior	+	0.7509	75.09%
P-glycoprotein substrate	-	0.8455	84.55%
CYP3A4 substrate	+	0.7260	72.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8774	87.74%
CYP3A4 inhibition	-	0.9061	90.61%
CYP2C9 inhibition	-	0.8653	86.53%
CYP2C19 inhibition	-	0.9130	91.30%
CYP2D6 inhibition	-	0.9498	94.98%
CYP1A2 inhibition	-	0.8749	87.49%
CYP2C8 inhibition	+	0.6847	68.47%
CYP inhibitory promiscuity	-	0.9549	95.49%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6115	61.15%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9029	90.29%
Skin irritation	-	0.6295	62.95%
Skin corrosion	-	0.9453	94.53%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6944	69.44%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.9572	95.72%
skin sensitisation	-	0.9028	90.28%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.7952	79.52%
Acute Oral Toxicity (c)	III	0.7689	76.89%
Estrogen receptor binding	+	0.7783	77.83%
Androgen receptor binding	+	0.7410	74.10%
Thyroid receptor binding	-	0.5261	52.61%
Glucocorticoid receptor binding	+	0.7668	76.68%
Aromatase binding	+	0.6422	64.22%
PPAR gamma	+	0.8044	80.44%
Honey bee toxicity	-	0.6675	66.75%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5605	56.05%
Fish aquatic toxicity	+	0.9722	97.22%

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	98.15%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.51%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.34%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.94%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.74%	96.77%
CHEMBL5255	O00206	Toll-like receptor 4	88.30%	92.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.54%	100.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	87.52%	95.17%
CHEMBL2581	P07339	Cathepsin D	87.02%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.47%	97.25%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.09%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.98%	89.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.86%	97.36%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.45%	94.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.42%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.74%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.66%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.38%	86.33%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.03%	96.61%

Plants that contains it

• Silphium perfoliatum

Cross-Links

• PubChem: 21607684
• LOTUS: LTS0012152
• wikiData: Q105235063