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

Details

• Internal ID: 5b9a2747-41c8-47aa-8d81-35dc9b681b34
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [(2S,3R,4S,5S)-3-[(2S,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl] (4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(COC2OC(=O)C34CCC(CC3C5=CCC6C7(CCC(C(C7CCC6(C5(CC4O)C)C)(C)C)OC8C(C(C(C(O8)COC9C(C(C(CO9)O)O)O)O)O)O)C)(C)C)O)O)O)O)OC1C(C(C(CO1)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](CO[C@H]2OC(=O)[C@]34CCC(C[C@H]3C5=CC[C@@H]6[C@]7(CC[C@@H](C([C@@H]7CC[C@]6([C@@]5(C[C@H]4O)C)C)(C)C)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO[C@H]9[C@@H]([C@H]([C@H](CO9)O)O)O)O)O)O)C)(C)C)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O
• InChI: InChI=1S/C57H92O25/c1-23-44(80-47-41(69)35(63)27(59)20-74-47)39(67)43(71)48(77-23)81-45-36(64)28(60)21-75-50(45)82-51(72)57-16-15-52(2,3)17-25(57)24-9-10-31-54(6)13-12-33(53(4,5)30(54)11-14-55(31,7)56(24,8)18-32(57)61)79-49-42(70)38(66)37(65)29(78-49)22-76-46-40(68)34(62)26(58)19-73-46/h9,23,25-50,58-71H,10-22H2,1-8H3/t23-,25-,26-,27+,28-,29+,30-,31+,32+,33-,34-,35-,36-,37+,38-,39-,40+,41+,42+,43+,44-,45+,46-,47-,48-,49-,50-,54-,55+,56+,57+/m0/s1
• InChI Key: KGIMWFCFOCEQAH-BDWAAXLMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₇H₉₂O₂₅
• Molecular Weight: 1177.30 g/mol
• Exact Mass: 1176.59276842 g/mol
• Topological Polar Surface Area (TPSA): 393.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -2.30
• H-Bond Acceptor: 25
• H-Bond Donor: 14
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8271	82.71%
Caco-2	-	0.8818	88.18%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8653	86.53%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.4617	46.17%
OATP1B3 inhibitior	-	0.4215	42.15%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6776	67.76%
BSEP inhibitior	+	0.9358	93.58%
P-glycoprotein inhibitior	+	0.7467	74.67%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.7426	74.26%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8572	85.72%
CYP3A4 inhibition	-	0.9495	94.95%
CYP2C9 inhibition	-	0.8812	88.12%
CYP2C19 inhibition	-	0.8995	89.95%
CYP2D6 inhibition	-	0.9413	94.13%
CYP1A2 inhibition	-	0.8966	89.66%
CYP2C8 inhibition	+	0.7278	72.78%
CYP inhibitory promiscuity	-	0.9650	96.50%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6211	62.11%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9000	90.00%
Skin irritation	-	0.5934	59.34%
Skin corrosion	-	0.9470	94.70%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7923	79.23%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.8767	87.67%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7000	70.00%
Nephrotoxicity	-	0.9371	93.71%
Acute Oral Toxicity (c)	III	0.7349	73.49%
Estrogen receptor binding	+	0.7905	79.05%
Androgen receptor binding	+	0.7392	73.92%
Thyroid receptor binding	+	0.5744	57.44%
Glucocorticoid receptor binding	+	0.7750	77.50%
Aromatase binding	+	0.6813	68.13%
PPAR gamma	+	0.8231	82.31%
Honey bee toxicity	-	0.6715	67.15%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5295	52.95%
Fish aquatic toxicity	+	0.9671	96.71%

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	95.93%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.19%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.21%	86.33%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.27%	97.36%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.33%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.00%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	86.88%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.80%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.17%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.76%	89.00%
CHEMBL5028	O14672	ADAM10	85.60%	97.50%
CHEMBL1937	Q92769	Histone deacetylase 2	85.53%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.33%	95.56%
CHEMBL2581	P07339	Cathepsin D	83.68%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.42%	94.00%
CHEMBL5255	O00206	Toll-like receptor 4	82.36%	92.50%
CHEMBL1871	P10275	Androgen Receptor	81.54%	96.43%

Plants that contains it

• Stachys riederi

Cross-Links

• PubChem: 10102806
• LOTUS: LTS0069828
• wikiData: Q105140791