[(2R,3S,4R,5S)-3-[(2S,3R,4S,5S,6S)-4-acetyloxy-3-hydroxy-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,10R,11S,12aS,14bS)-5,11-dihydroxy-9,9-bis(hydroxymethyl)-2,2,6a,6b,12a-pentamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate

Details

• Internal ID: 645fa96d-ca57-4a80-b694-4fc19dc297c5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [(2R,3S,4R,5S)-3-[(2S,3R,4S,5S,6S)-4-acetyloxy-3-hydroxy-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,10R,11S,12aS,14bS)-5,11-dihydroxy-9,9-bis(hydroxymethyl)-2,2,6a,6b,12a-pentamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)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=CCC6C(C5(CC4O)C)(CCC7C6(CC(C(C7(CO)CO)OC8C(C(C(C(O8)CO)O)O)O)O)C)C)(C)C)O)O)O)OC(=O)C)OC9C(C(C(CO9)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@]([C@@]5(C[C@H]4O)C)(CC[C@@H]7[C@]6(C[C@@H]([C@@H](C7(CO)CO)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)C)C)(C)C)O)O)O)OC(=O)C)O[C@H]9[C@@H]([C@H]([C@@H](CO9)O)O)O
• InChI: InChI=1S/C54H86O25/c1-22-40(76-44-37(67)33(63)27(60)18-71-44)41(74-23(2)58)39(69)46(73-22)77-42-34(64)28(61)19-72-47(42)79-48(70)54-13-12-49(3,4)14-25(54)24-8-9-30-50(5)15-26(59)43(78-45-38(68)36(66)35(65)29(17-55)75-45)53(20-56,21-57)31(50)10-11-51(30,6)52(24,7)16-32(54)62/h8,22,25-47,55-57,59-69H,9-21H2,1-7H3/t22-,25-,26-,27+,28-,29+,30+,31+,32+,33-,34+,35+,36-,37+,38+,39+,40-,41-,42-,43-,44-,45-,46-,47+,50-,51+,52+,54+/m0/s1
• InChI Key: PEFMJTAKJMUYNX-JRIBXKEZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₈₆O₂₅
• Molecular Weight: 1135.20 g/mol
• Exact Mass: 1134.54581822 g/mol
• Topological Polar Surface Area (TPSA): 400.00 Ų
• XlogP: -1.90
• Atomic LogP (AlogP): -3.27
• H-Bond Acceptor: 25
• H-Bond Donor: 14
• 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	-	0.8765	87.65%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8703	87.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.3418	34.18%
OATP1B3 inhibitior	-	0.4610	46.10%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5026	50.26%
BSEP inhibitior	+	0.9533	95.33%
P-glycoprotein inhibitior	+	0.7460	74.60%
P-glycoprotein substrate	+	0.5882	58.82%
CYP3A4 substrate	+	0.7364	73.64%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8774	87.74%
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	+	0.7413	74.13%
CYP inhibitory promiscuity	-	0.9733	97.33%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6024	60.24%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.8998	89.98%
Skin irritation	-	0.5876	58.76%
Skin corrosion	-	0.9441	94.41%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7459	74.59%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.9013	90.13%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.7268	72.68%
Acute Oral Toxicity (c)	III	0.8023	80.23%
Estrogen receptor binding	+	0.7954	79.54%
Androgen receptor binding	+	0.7504	75.04%
Thyroid receptor binding	+	0.6225	62.25%
Glucocorticoid receptor binding	+	0.7756	77.56%
Aromatase binding	+	0.6464	64.64%
PPAR gamma	+	0.8278	82.78%
Honey bee toxicity	-	0.6631	66.31%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
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	99.12%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.86%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	93.73%	96.77%
CHEMBL3714130	P46095	G-protein coupled receptor 6	93.57%	97.36%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.63%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.85%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.34%	86.33%
CHEMBL1937	Q92769	Histone deacetylase 2	89.84%	94.75%
CHEMBL218	P21554	Cannabinoid CB1 receptor	89.73%	96.61%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.65%	100.00%
CHEMBL2581	P07339	Cathepsin D	87.92%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.05%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.03%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.54%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.45%	86.92%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.24%	95.50%
CHEMBL340	P08684	Cytochrome P450 3A4	84.98%	91.19%
CHEMBL5028	O14672	ADAM10	84.42%	97.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.65%	89.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.00%	96.21%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	81.88%	95.17%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	81.35%	89.44%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.14%	93.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.08%	94.33%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	80.71%	91.65%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	80.71%	87.67%
CHEMBL226	P30542	Adenosine A1 receptor	80.62%	95.93%

Plants that contains it

• Platycodon grandiflorus

Cross-Links

• PubChem: 154497232
• LOTUS: LTS0010453
• wikiData: Q105206978