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

Details

• Internal ID: e802dd23-f1e8-4956-b4d0-f24087f1ef16
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-2-[[(2R,3R,5R,8R,9S,10R,12R,13R,14S,17S)-2,12-dihydroxy-4,4,10,13,14-pentamethyl-17-[(2S)-6-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyhept-5-en-2-yl]-2,3,5,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-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(CO8)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](CO8)O)O)O)O)O)O)C
• InChI: InChI=1S/C53H90O23/c1-22(2)10-9-14-52(7,76-47-42(68)38(64)36(62)29(73-47)21-70-45-40(66)33(59)26(57)20-69-45)31-13-15-51(6)23-11-12-30-49(3,4)44(25(56)17-50(30,5)24(23)16-32(58)53(31,51)8)75-48-43(39(65)35(61)28(19-55)72-48)74-46-41(67)37(63)34(60)27(18-54)71-46/h10,23-48,54-68H,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+,50-,51+,52+,53+/m1/s1
• InChI Key: NZXNJMVGDPUWMR-XRCXIAAFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₉₀O₂₃
• Molecular Weight: 1095.30 g/mol
• Exact Mass: 1094.58728911 g/mol
• Topological Polar Surface Area (TPSA): 377.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -2.59
• H-Bond Acceptor: 23
• H-Bond Donor: 15
• Rotatable Bonds: 15

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	-	0.9152	91.52%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7251	72.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8375	83.75%
OATP1B3 inhibitior	+	0.8189	81.89%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.8878	88.78%
P-glycoprotein inhibitior	+	0.7509	75.09%
P-glycoprotein substrate	+	0.5991	59.91%
CYP3A4 substrate	+	0.7421	74.21%
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	+	0.7411	74.11%
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	-	0.9015	90.15%
Skin irritation	-	0.5956	59.56%
Skin corrosion	-	0.9488	94.88%
Ames mutagenesis	-	0.5754	57.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.8432	84.32%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.5634	56.34%
skin sensitisation	-	0.8991	89.91%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.8906	89.06%
Acute Oral Toxicity (c)	I	0.5677	56.77%
Estrogen receptor binding	+	0.7884	78.84%
Androgen receptor binding	+	0.7557	75.57%
Thyroid receptor binding	+	0.5541	55.41%
Glucocorticoid receptor binding	+	0.7429	74.29%
Aromatase binding	+	0.6354	63.54%
PPAR gamma	+	0.7991	79.91%
Honey bee toxicity	-	0.5711	57.11%
Biodegradation	-	0.7500	75.00%
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
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.22%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.13%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	95.63%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.05%	97.09%
CHEMBL206	P03372	Estrogen receptor alpha	95.01%	97.64%
CHEMBL218	P21554	Cannabinoid CB1 receptor	94.71%	96.61%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	94.06%	95.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.10%	94.45%
CHEMBL3714130	P46095	G-protein coupled receptor 6	92.89%	97.36%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	91.52%	91.24%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.01%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.75%	96.21%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.54%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.41%	96.09%
CHEMBL1937	Q92769	Histone deacetylase 2	90.26%	94.75%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	89.62%	97.86%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.52%	96.77%
CHEMBL1914	P06276	Butyrylcholinesterase	89.46%	95.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	88.38%	95.71%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	87.90%	96.38%
CHEMBL233	P35372	Mu opioid receptor	87.81%	97.93%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.26%	97.14%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	86.78%	96.90%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.31%	86.33%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	86.10%	91.03%
CHEMBL2243	O00519	Anandamide amidohydrolase	85.75%	97.53%
CHEMBL1951	P21397	Monoamine oxidase A	85.49%	91.49%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	85.34%	95.58%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	84.72%	100.00%
CHEMBL2996	Q05655	Protein kinase C delta	84.50%	97.79%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.39%	85.14%
CHEMBL228	P31645	Serotonin transporter	83.93%	95.51%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	83.60%	92.86%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.31%	92.94%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.67%	93.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.36%	92.62%
CHEMBL5555	O00767	Acyl-CoA desaturase	82.22%	97.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.78%	94.33%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	81.62%	97.50%
CHEMBL259	P32245	Melanocortin receptor 4	81.56%	95.38%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	81.26%	100.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.81%	95.83%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	80.37%	82.50%
CHEMBL5957	P21589	5'-nucleotidase	80.04%	97.78%

Plants that contains it

• Gynostemma pentaphyllum

Cross-Links

• PubChem: 163084562
• LOTUS: LTS0005062
• wikiData: Q105188508