3beta-[2-O-(alpha-L-Rhamnopyranosyl)-alpha-L-arabinopyranosyloxy]-20,23-dihydroxylupane-28-oic acid 6-O-[4-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl]-beta-D-glucopyranosyl ester

Details

• Internal ID: 94a5924e-f248-42f3-8236-fa6a55861436
• 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] (1R,3aS,5aR,5bR,7aR,8R,9S,11aR,11bR,13aR,13bS)-9-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-8-(hydroxymethyl)-1-(2-hydroxypropan-2-yl)-5a,5b,8,11a-tetramethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OCC3C(C(C(C(O3)OC(=O)C45CCC(C4C6CCC7C8(CCC(C(C8CCC7(C6(CC5)C)C)(C)CO)OC9C(C(C(CO9)O)O)OC1C(C(C(C(O1)C)O)O)O)C)C(C)(C)O)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@]45CC[C@H]([C@@H]4[C@H]6CC[C@@H]7[C@]8(CC[C@@H]([C@@]([C@@H]8CC[C@]7([C@@]6(CC5)C)C)(C)CO)O[C@H]9[C@@H]([C@H]([C@H](CO9)O)O)O[C@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)C)O)O)O)C)C(C)(C)O)O)O)O)CO)O)O)O
• InChI: InChI=1S/C59H98O27/c1-23-34(63)38(67)42(71)49(79-23)84-46-28(19-60)81-48(45(74)41(46)70)78-21-29-37(66)40(69)44(73)51(82-29)86-53(75)59-16-11-25(54(3,4)76)33(59)26-9-10-31-55(5)14-13-32(56(6,22-61)30(55)12-15-58(31,8)57(26,7)17-18-59)83-52-47(36(65)27(62)20-77-52)85-50-43(72)39(68)35(64)24(2)80-50/h23-52,60-74,76H,9-22H2,1-8H3/t23-,24-,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-,51-,52-,55-,56-,57+,58+,59-/m0/s1
• InChI Key: JJDRKUGCWIAGCT-NNXAVZJTSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₉H₉₈O₂₇
• Molecular Weight: 1239.40 g/mol
• Exact Mass: 1238.62954785 g/mol
• Topological Polar Surface Area (TPSA): 433.00 Ų
• XlogP: -2.70
• Atomic LogP (AlogP): -3.49
• H-Bond Acceptor: 27
• H-Bond Donor: 16
• Rotatable Bonds: 14

Synonyms

• 3beta-[2-O-(alpha-L-Rhamnopyranosyl)-alpha-L-arabinopyranosyloxy]-20,23-dihydroxylupane-28-oic acid 6-O-[4-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl]-beta-D-glucopyranosyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5878	58.78%
Caco-2	-	0.8784	87.84%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7552	75.52%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8807	88.07%
OATP1B3 inhibitior	+	0.8702	87.02%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.8289	82.89%
P-glycoprotein inhibitior	+	0.7447	74.47%
P-glycoprotein substrate	+	0.6106	61.06%
CYP3A4 substrate	+	0.7509	75.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8626	86.26%
CYP3A4 inhibition	-	0.9394	93.94%
CYP2C9 inhibition	-	0.8941	89.41%
CYP2C19 inhibition	-	0.9060	90.60%
CYP2D6 inhibition	-	0.9604	96.04%
CYP1A2 inhibition	-	0.9213	92.13%
CYP2C8 inhibition	+	0.7758	77.58%
CYP inhibitory promiscuity	-	0.9775	97.75%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6894	68.94%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.8993	89.93%
Skin irritation	-	0.6714	67.14%
Skin corrosion	-	0.9539	95.39%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7778	77.78%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.6688	66.88%
skin sensitisation	-	0.9351	93.51%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.9466	94.66%
Acute Oral Toxicity (c)	I	0.5589	55.89%
Estrogen receptor binding	+	0.7996	79.96%
Androgen receptor binding	+	0.7553	75.53%
Thyroid receptor binding	+	0.5843	58.43%
Glucocorticoid receptor binding	+	0.7645	76.45%
Aromatase binding	+	0.6577	65.77%
PPAR gamma	+	0.8275	82.75%
Honey bee toxicity	-	0.6002	60.02%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.8367	83.67%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.57%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.79%	91.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	95.43%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.73%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.29%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.92%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	91.62%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.86%	89.00%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	89.56%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.45%	92.94%
CHEMBL2581	P07339	Cathepsin D	89.31%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.74%	94.00%
CHEMBL2243	O00519	Anandamide amidohydrolase	87.72%	97.53%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.05%	96.61%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.92%	91.24%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.75%	86.92%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.84%	95.50%
CHEMBL1974	P36888	Tyrosine-protein kinase receptor FLT3	85.72%	91.83%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.61%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.54%	94.45%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	85.38%	95.71%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.01%	93.04%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	84.95%	96.90%
CHEMBL5028	O14672	ADAM10	84.84%	97.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.77%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.54%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.30%	96.77%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	82.89%	97.86%
CHEMBL3401	O75469	Pregnane X receptor	82.89%	94.73%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.12%	91.07%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.41%	97.33%
CHEMBL5255	O00206	Toll-like receptor 4	81.31%	92.50%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	81.28%	89.05%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.19%	95.89%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	80.94%	92.86%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.58%	94.33%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.23%	100.00%

Plants that contains it

• Pulsatilla chinensis

Cross-Links

• PubChem: 11829266
• NPASS: NPC215916
• LOTUS: LTS0067886
• wikiData: Q105129583