(2R,3R,4S,5S,6R)-2-[[(2R,3S,4S,5R,6S)-6-[(2S)-2-[(2R,3R,5R,8R,9S,10R,12R,13R,14S,17S)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,12-dihydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylhept-5-en-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 420fc955-35e8-4222-96a2-953d311c0691
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[[(2R,3S,4S,5R,6S)-6-[(2S)-2-[(2R,3R,5R,8R,9S,10R,12R,13R,14S,17S)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,12-dihydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylhept-5-en-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC(=CCCC(C)(C1CCC2(C1(C(CC3C2CCC4C3(CC(C(C4(C)C)OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)CO)O)O)O)O)C)O)C)C)OC7C(C(C(C(O7)COC8C(C(C(C(O8)CO)O)O)O)O)O)O)C
• SMILES (Isomeric): CC(=CCC[C@@](C)([C@H]1CC[C@@]2([C@@]1([C@@H](C[C@H]3[C@H]2CC[C@@H]4[C@@]3(C[C@H]([C@@H](C4(C)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)C)O)C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O)O)C
• InChI: InChI=1S/C54H92O24/c1-22(2)10-9-14-53(7,78-48-43(70)39(66)36(63)29(75-48)21-71-46-41(68)37(64)33(60)26(18-55)72-46)31-13-15-52(6)23-11-12-30-50(3,4)45(25(58)17-51(30,5)24(23)16-32(59)54(31,52)8)77-49-44(40(67)35(62)28(20-57)74-49)76-47-42(69)38(65)34(61)27(19-56)73-47/h10,23-49,55-70H,9,11-21H2,1-8H3/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+,51-,52+,53+,54+/m1/s1
• InChI Key: ICJSAPIMMCHSRJ-IZUZYRRNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₉₂O₂₄
• Molecular Weight: 1125.30 g/mol
• Exact Mass: 1124.59785380 g/mol
• Topological Polar Surface Area (TPSA): 398.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -3.23
• H-Bond Acceptor: 24
• H-Bond Donor: 16
• Rotatable Bonds: 16

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6877	68.77%
Caco-2	-	0.9194	91.94%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7251	72.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8432	84.32%
OATP1B3 inhibitior	+	0.8189	81.89%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.8863	88.63%
P-glycoprotein inhibitior	+	0.7497	74.97%
P-glycoprotein substrate	+	0.5308	53.08%
CYP3A4 substrate	+	0.7361	73.61%
CYP2C9 substrate	-	0.8025	80.25%
CYP2D6 substrate	-	0.8264	82.64%
CYP3A4 inhibition	-	0.9502	95.02%
CYP2C9 inhibition	-	0.8671	86.71%
CYP2C19 inhibition	-	0.9036	90.36%
CYP2D6 inhibition	-	0.9380	93.80%
CYP1A2 inhibition	-	0.9057	90.57%
CYP2C8 inhibition	+	0.7127	71.27%
CYP inhibitory promiscuity	-	0.9413	94.13%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6474	64.74%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9011	90.11%
Skin irritation	-	0.5956	59.56%
Skin corrosion	-	0.9488	94.88%
Ames mutagenesis	-	0.6824	68.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.8499	84.99%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.5384	53.84%
skin sensitisation	-	0.8991	89.91%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.7705	77.05%
Acute Oral Toxicity (c)	I	0.5677	56.77%
Estrogen receptor binding	+	0.7887	78.87%
Androgen receptor binding	+	0.7601	76.01%
Thyroid receptor binding	+	0.5671	56.71%
Glucocorticoid receptor binding	+	0.7511	75.11%
Aromatase binding	+	0.6413	64.13%
PPAR gamma	+	0.8035	80.35%
Honey bee toxicity	-	0.5742	57.42%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9172	91.72%

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	98.94%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.85%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.83%	97.09%
CHEMBL206	P03372	Estrogen receptor alpha	94.65%	97.64%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	93.98%	95.50%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.96%	96.61%
CHEMBL3714130	P46095	G-protein coupled receptor 6	93.62%	97.36%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.81%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	92.69%	95.93%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	92.55%	96.21%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.51%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.94%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.48%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	89.94%	91.24%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	89.44%	96.38%
CHEMBL233	P35372	Mu opioid receptor	88.47%	97.93%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	87.83%	97.86%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.21%	85.14%
CHEMBL1937	Q92769	Histone deacetylase 2	87.19%	94.75%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.66%	97.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.50%	86.33%
CHEMBL2996	Q05655	Protein kinase C delta	86.25%	97.79%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	85.79%	91.03%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	85.78%	96.90%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	85.43%	95.71%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	84.59%	100.00%
CHEMBL1914	P06276	Butyrylcholinesterase	84.14%	95.00%
CHEMBL259	P32245	Melanocortin receptor 4	84.10%	95.38%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	83.75%	95.58%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.32%	93.04%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.56%	94.33%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.85%	93.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.52%	95.89%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	81.41%	97.47%
CHEMBL5555	O00767	Acyl-CoA desaturase	81.31%	97.50%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	81.21%	97.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.12%	92.62%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.11%	96.77%
CHEMBL3401	O75469	Pregnane X receptor	80.87%	94.73%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.83%	96.95%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.70%	89.50%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.50%	92.94%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	80.48%	100.00%
CHEMBL2243	O00519	Anandamide amidohydrolase	80.38%	97.53%
CHEMBL228	P31645	Serotonin transporter	80.06%	95.51%

Plants that contains it

• Gynostemma pentaphyllum

Cross-Links

• PubChem: 162891449
• LOTUS: LTS0128890
• wikiData: Q105111030