(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[[10-(hydroxymethyl)-17-(1-hydroxy-5-methylhex-4-enyl)-8,14-dimethyl-1,2,3,4,5,6,7,9,11,12,13,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 4e916697-54bb-4d31-8550-441aa40d20fb
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[[10-(hydroxymethyl)-17-(1-hydroxy-5-methylhex-4-enyl)-8,14-dimethyl-1,2,3,4,5,6,7,9,11,12,13,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC(=CCCC(C1CCC2(C1CCC3C2(CCC4C3(CCC(C4)OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)CO)O)O)O)CO)C)C)O)C
• SMILES (Isomeric): CC(=CCCC(C1CCC2(C1CCC3C2(CCC4C3(CCC(C4)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)CO)C)C)O)C
• InChI: InChI=1S/C39H66O13/c1-20(2)6-5-7-25(43)23-12-14-37(3)24(23)8-9-28-38(37,4)13-10-21-16-22(11-15-39(21,28)19-42)49-36-34(32(47)30(45)27(18-41)51-36)52-35-33(48)31(46)29(44)26(17-40)50-35/h6,21-36,40-48H,5,7-19H2,1-4H3/t21?,22?,23?,24?,25?,26-,27-,28?,29-,30-,31+,32+,33-,34-,35+,36-,37?,38?,39?/m1/s1
• InChI Key: VNXIXXWLGRKKST-QLRGAEDESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₆₆O₁₃
• Molecular Weight: 742.90 g/mol
• Exact Mass: 742.45034216 g/mol
• Topological Polar Surface Area (TPSA): 219.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 1.12
• H-Bond Acceptor: 13
• H-Bond Donor: 9
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6877	68.77%
Caco-2	-	0.8816	88.16%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7251	72.51%
OATP2B1 inhibitior	-	0.8643	86.43%
OATP1B1 inhibitior	+	0.8690	86.90%
OATP1B3 inhibitior	+	0.8189	81.89%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.6054	60.54%
P-glycoprotein inhibitior	+	0.7231	72.31%
P-glycoprotein substrate	-	0.5896	58.96%
CYP3A4 substrate	+	0.7221	72.21%
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	+	0.5584	55.84%
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	-	0.9158	91.58%
Skin irritation	-	0.5956	59.56%
Skin corrosion	-	0.9488	94.88%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8633	86.33%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.6789	67.89%
skin sensitisation	-	0.8991	89.91%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.5642	56.42%
Acute Oral Toxicity (c)	I	0.5677	56.77%
Estrogen receptor binding	+	0.7830	78.30%
Androgen receptor binding	+	0.7698	76.98%
Thyroid receptor binding	-	0.5864	58.64%
Glucocorticoid receptor binding	+	0.5407	54.07%
Aromatase binding	+	0.6634	66.34%
PPAR gamma	+	0.6719	67.19%
Honey bee toxicity	-	0.5653	56.53%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
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	97.97%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.67%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.57%	96.09%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	94.48%	95.58%
CHEMBL233	P35372	Mu opioid receptor	94.22%	97.93%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.67%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.38%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.36%	97.25%
CHEMBL1937	Q92769	Histone deacetylase 2	93.19%	94.75%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	93.12%	96.38%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	91.74%	94.62%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	90.81%	92.86%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.49%	95.89%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	89.22%	94.23%
CHEMBL2094135	Q96BI3	Gamma-secretase	89.07%	98.05%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.35%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.84%	95.50%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	87.56%	97.50%
CHEMBL279	P35968	Vascular endothelial growth factor receptor 2	87.11%	95.52%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	85.32%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.04%	96.95%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	84.42%	82.50%
CHEMBL237	P41145	Kappa opioid receptor	84.27%	98.10%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.58%	95.89%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.53%	100.00%
CHEMBL2581	P07339	Cathepsin D	83.41%	98.95%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.79%	95.71%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.91%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.89%	92.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.75%	99.17%
CHEMBL226	P30542	Adenosine A1 receptor	80.52%	95.93%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.32%	91.24%

Plants that contains it

• Gynostemma pentaphyllum

Cross-Links

• PubChem: 11968574
• NPASS: NPC16625
• LOTUS: LTS0150875
• wikiData: Q105290013