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

Details

• Internal ID: fee613d2-5ed8-4e6f-9cd8-476d1219619f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4aR,5R,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-5-hydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-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(OC(C(C2O)O)OCC3C(C(C(C(O3)OC(=O)C45CCC(CC4C6=CCC7C8(CCC(C(C8CCC7(C6(CC5O)C)C)(C)CO)OC9C(C(C(CO9)O)O)O)C)(C)C)O)O)O)CO)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)O)OC[C@@H]3[C@H]([C@@H]([C@H]([C@@H](O3)OC(=O)[C@]45CCC(C[C@H]4C6=CC[C@@H]7[C@]8(CC[C@@H]([C@@]([C@@H]8CC[C@]7([C@@]6(C[C@H]5O)C)C)(C)CO)O[C@H]9[C@@H]([C@H]([C@H](CO9)O)O)O)C)(C)C)O)O)O)CO)O)O)O
• InChI: InChI=1S/C53H86O23/c1-22-32(58)35(61)39(65)45(71-22)75-42-26(18-54)72-43(41(67)37(42)63)70-20-27-34(60)36(62)40(66)46(73-27)76-47(68)53-15-14-48(2,3)16-24(53)23-8-9-29-49(4)12-11-31(74-44-38(64)33(59)25(56)19-69-44)50(5,21-55)28(49)10-13-51(29,6)52(23,7)17-30(53)57/h8,22,24-46,54-67H,9-21H2,1-7H3/t22-,24-,25-,26+,27+,28+,29+,30+,31-,32-,33-,34+,35+,36-,37+,38+,39+,40+,41+,42+,43+,44-,45-,46-,49-,50-,51+,52+,53+/m0/s1
• InChI Key: RCCIGUCOKOWWHR-LEBXCWCVSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₈₆O₂₃
• Molecular Weight: 1091.20 g/mol
• Exact Mass: 1090.55598899 g/mol
• Topological Polar Surface Area (TPSA): 374.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -2.43
• H-Bond Acceptor: 23
• 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	+	0.7891	78.91%
Caco-2	-	0.8844	88.44%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8567	85.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8072	80.72%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.8695	86.95%
P-glycoprotein inhibitior	+	0.7448	74.48%
P-glycoprotein substrate	+	0.5656	56.56%
CYP3A4 substrate	+	0.7403	74.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8587	85.87%
CYP3A4 inhibition	-	0.9300	93.00%
CYP2C9 inhibition	-	0.8838	88.38%
CYP2C19 inhibition	-	0.9101	91.01%
CYP2D6 inhibition	-	0.9422	94.22%
CYP1A2 inhibition	-	0.8933	89.33%
CYP2C8 inhibition	+	0.7388	73.88%
CYP inhibitory promiscuity	-	0.9668	96.68%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6254	62.54%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9015	90.15%
Skin irritation	-	0.6103	61.03%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7657	76.57%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.8583	85.83%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.9097	90.97%
Acute Oral Toxicity (c)	III	0.7945	79.45%
Estrogen receptor binding	+	0.8147	81.47%
Androgen receptor binding	+	0.7401	74.01%
Thyroid receptor binding	+	0.5638	56.38%
Glucocorticoid receptor binding	+	0.7511	75.11%
Aromatase binding	+	0.6602	66.02%
PPAR gamma	+	0.8303	83.03%
Honey bee toxicity	-	0.6618	66.18%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5350	53.50%
Fish aquatic toxicity	+	0.9411	94.11%

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	98.27%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.18%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	92.90%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.80%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.74%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.67%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.56%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.46%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.03%	94.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.34%	96.61%
CHEMBL226	P30542	Adenosine A1 receptor	86.66%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.19%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.92%	95.50%
CHEMBL1937	Q92769	Histone deacetylase 2	85.67%	94.75%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.61%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.97%	95.56%
CHEMBL5028	O14672	ADAM10	83.13%	97.50%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.84%	96.77%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.91%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.75%	91.07%
CHEMBL5255	O00206	Toll-like receptor 4	80.61%	92.50%

Plants that contains it

• Caulophyllum thalictroides

Cross-Links

• PubChem: 45270954
• LOTUS: LTS0182634
• wikiData: Q104393399