(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4,4,6a,6b,11,11,14b-heptamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-hydroxy-4-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methoxy]-5-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid

Details

• Internal ID: ac652ca0-63da-43ed-bb57-a049c829e5a4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4,4,6a,6b,11,11,14b-heptamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-hydroxy-4-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methoxy]-5-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid
• SMILES (Canonical): CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)OC6C(C(C(C(O6)C(=O)O)O)OCC7C(C(C(C(O7)CO)O)O)O)OC8C(C(C(CO8)O)O)O)C)C)C2C1)C)C(=O)OC9C(C(C(C(O9)CO)O)O)O)C
• SMILES (Isomeric): C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)C)(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)C(=O)O)O)OC[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O[C@H]9[C@@H]([C@H]([C@H](CO9)O)O)O
• InChI: InChI=1S/C54H86O23/c1-49(2)14-16-54(48(69)77-46-39(65)37(63)34(60)27(20-56)73-46)17-15-52(6)23(24(54)18-49)8-9-30-51(5)12-11-31(50(3,4)29(51)10-13-53(30,52)7)74-47-43(76-45-38(64)32(58)25(57)21-71-45)41(40(66)42(75-47)44(67)68)70-22-28-35(61)36(62)33(59)26(19-55)72-28/h8,24-43,45-47,55-66H,9-22H2,1-7H3,(H,67,68)/t24-,25-,26+,27+,28-,29-,30+,31-,32-,33+,34+,35-,36-,37-,38+,39+,40-,41-,42-,43+,45-,46-,47+,51-,52+,53+,54-/m0/s1
• InChI Key: ULRUWGOFNGDEMF-OQSIGQLTSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₈₆O₂₃
• Molecular Weight: 1103.20 g/mol
• Exact Mass: 1102.55598899 g/mol
• Topological Polar Surface Area (TPSA): 371.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): -1.26
• H-Bond Acceptor: 22
• H-Bond Donor: 13
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7601	76.01%
Caco-2	-	0.8807	88.07%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8703	87.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7557	75.57%
OATP1B3 inhibitior	-	0.4610	46.10%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5026	50.26%
BSEP inhibitior	+	0.8849	88.49%
P-glycoprotein inhibitior	+	0.7489	74.89%
P-glycoprotein substrate	-	0.6640	66.40%
CYP3A4 substrate	+	0.7305	73.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8785	87.85%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.8704	87.04%
CYP2C19 inhibition	-	0.9216	92.16%
CYP2D6 inhibition	-	0.9491	94.91%
CYP1A2 inhibition	-	0.9009	90.09%
CYP2C8 inhibition	+	0.7664	76.64%
CYP inhibitory promiscuity	-	0.9733	97.33%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6024	60.24%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9008	90.08%
Skin irritation	-	0.5876	58.76%
Skin corrosion	-	0.9441	94.41%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7185	71.85%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.9375	93.75%
skin sensitisation	-	0.9013	90.13%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.9237	92.37%
Acute Oral Toxicity (c)	III	0.8023	80.23%
Estrogen receptor binding	+	0.7701	77.01%
Androgen receptor binding	+	0.7469	74.69%
Thyroid receptor binding	+	0.5130	51.30%
Glucocorticoid receptor binding	+	0.7637	76.37%
Aromatase binding	+	0.6528	65.28%
PPAR gamma	+	0.8087	80.87%
Honey bee toxicity	-	0.6674	66.74%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5455	54.55%
Fish aquatic toxicity	+	0.9585	95.85%

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	97.77%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.84%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.10%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.81%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	92.72%	95.93%
CHEMBL2581	P07339	Cathepsin D	90.95%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.43%	86.33%
CHEMBL5255	O00206	Toll-like receptor 4	87.97%	92.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.86%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	87.23%	90.17%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.65%	93.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	85.40%	95.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.98%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.87%	100.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.30%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.01%	99.17%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.01%	95.50%
CHEMBL5028	O14672	ADAM10	81.63%	97.50%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.16%	96.77%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.89%	97.36%

Plants that contains it

• Caragana sinica

Cross-Links

• PubChem: 101629715
• LOTUS: LTS0062502
• wikiData: Q104400021