[(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)-5a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylate

Details

• Internal ID: f3bb1315-3fc9-4fa9-a1db-4b1914ba2964
• 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)-5a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-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)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)CO)O)O)O
• InChI: InChI=1S/C59H96O26/c1-23(2)26-11-16-59(54(75)85-52-45(73)41(69)38(66)30(81-52)21-77-49-46(74)42(70)47(29(19-60)80-49)83-50-43(71)39(67)35(63)24(3)78-50)18-17-57(7)27(34(26)59)9-10-32-55(5)14-13-33(56(6,22-61)31(55)12-15-58(32,57)8)82-53-48(37(65)28(62)20-76-53)84-51-44(72)40(68)36(64)25(4)79-51/h24-53,60-74H,1,9-22H2,2-8H3/t24-,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-,53-,55-,56-,57+,58+,59-/m0/s1
• InChI Key: OUHBKBTZUPLIIA-QEEGUAPESA-N
• Popularity: 25 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₉H₉₆O₂₆
• Molecular Weight: 1221.40 g/mol
• Exact Mass: 1220.61898316 g/mol
• Topological Polar Surface Area (TPSA): 413.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -2.69
• H-Bond Acceptor: 26
• H-Bond Donor: 15
• Rotatable Bonds: 14

Synonyms

• 129741-57-7
• Chinensioside A
• MFCD11215450
• s9081
• CCG-270659
• AC-34007

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6980	69.80%
Caco-2	-	0.8767	87.67%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7315	73.15%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8828	88.28%
OATP1B3 inhibitior	+	0.8452	84.52%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7276	72.76%
BSEP inhibitior	+	0.9171	91.71%
P-glycoprotein inhibitior	+	0.7441	74.41%
P-glycoprotein substrate	+	0.6420	64.20%
CYP3A4 substrate	+	0.7487	74.87%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8587	85.87%
CYP3A4 inhibition	-	0.9279	92.79%
CYP2C9 inhibition	-	0.9079	90.79%
CYP2C19 inhibition	-	0.9070	90.70%
CYP2D6 inhibition	-	0.9472	94.72%
CYP1A2 inhibition	-	0.9055	90.55%
CYP2C8 inhibition	+	0.7681	76.81%
CYP inhibitory promiscuity	-	0.9594	95.94%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6772	67.72%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.8995	89.95%
Skin irritation	+	0.5344	53.44%
Skin corrosion	-	0.9440	94.40%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7945	79.45%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.9117	91.17%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.9159	91.59%
Acute Oral Toxicity (c)	I	0.5670	56.70%
Estrogen receptor binding	+	0.7980	79.80%
Androgen receptor binding	+	0.7555	75.55%
Thyroid receptor binding	+	0.5880	58.80%
Glucocorticoid receptor binding	+	0.7621	76.21%
Aromatase binding	+	0.6610	66.10%
PPAR gamma	+	0.8257	82.57%
Honey bee toxicity	-	0.5863	58.63%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9592	95.92%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL233	P35372	Mu opioid receptor	96.93%	97.93%
CHEMBL3714130	P46095	G-protein coupled receptor 6	95.75%	97.36%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.24%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.95%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.82%	96.09%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	92.17%	91.24%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.91%	86.33%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.67%	96.61%
CHEMBL226	P30542	Adenosine A1 receptor	91.29%	95.93%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	91.07%	92.86%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.98%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.74%	92.94%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	89.24%	95.50%
CHEMBL2581	P07339	Cathepsin D	89.18%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.89%	89.00%
CHEMBL325	Q13547	Histone deacetylase 1	87.07%	95.92%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	86.39%	96.38%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.17%	94.45%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.67%	96.77%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	85.48%	97.86%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	85.39%	97.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.11%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	85.03%	91.19%
CHEMBL1974	P36888	Tyrosine-protein kinase receptor FLT3	84.93%	91.83%
CHEMBL5255	O00206	Toll-like receptor 4	84.68%	92.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.67%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.54%	94.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.36%	94.00%
CHEMBL5028	O14672	ADAM10	83.81%	97.50%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	83.78%	85.83%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	83.56%	100.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.84%	96.90%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.57%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.20%	95.89%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.11%	93.04%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	81.64%	89.05%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	81.36%	92.32%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	81.31%	96.09%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.15%	95.83%
CHEMBL2243	O00519	Anandamide amidohydrolase	80.17%	97.53%

Plants that contains it

• Pulsatilla cernua
• Pulsatilla chinensis

Cross-Links

• PubChem: 71307558
• NPASS: NPC219542
• LOTUS: LTS0003824
• wikiData: Q105200129