(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2R,3R,4S,5S,6R)-5-hydroxy-2-[1-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethoxy]-4-methoxy-6-methyloxan-3-yl]oxyoxan-2-yl]methoxy]oxane-3,4,5-triol

Details

• Internal ID: 3806a506-c909-4ee2-8c34-0c4fb8281df4
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2R,3R,4S,5S,6R)-5-hydroxy-2-[1-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethoxy]-4-methoxy-6-methyloxan-3-yl]oxyoxan-2-yl]methoxy]oxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OC(C)C2CCC3C2(CCC4C3CC=C5C4(CCC(C5)O)C)C)OC6C(C(C(C(O6)COC7C(C(C(C(O7)CO)O)O)O)O)O)O)OC)O
• SMILES (Isomeric): C[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)OC(C)[C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4(CC[C@@H](C5)O)C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)O)O)OC)O
• InChI: InChI=1S/C40H66O16/c1-17(22-8-9-23-21-7-6-19-14-20(42)10-12-39(19,3)24(21)11-13-40(22,23)4)52-38-35(34(50-5)27(43)18(2)53-38)56-37-33(49)31(47)29(45)26(55-37)16-51-36-32(48)30(46)28(44)25(15-41)54-36/h6,17-18,20-38,41-49H,7-16H2,1-5H3/t17?,18-,20+,21+,22-,23+,24+,25-,26-,27+,28-,29-,30+,31+,32-,33-,34+,35-,36-,37+,38-,39+,40-/m1/s1
• InChI Key: CSBVMGGUINEYEA-SWFHLPEHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₆₆O₁₆
• Molecular Weight: 802.90 g/mol
• Exact Mass: 802.43508601 g/mol
• Topological Polar Surface Area (TPSA): 247.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): -0.54
• H-Bond Acceptor: 16
• H-Bond Donor: 9
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6883	68.83%
Caco-2	-	0.8854	88.54%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6871	68.71%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8882	88.82%
OATP1B3 inhibitior	+	0.8726	87.26%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.5442	54.42%
P-glycoprotein inhibitior	+	0.7121	71.21%
P-glycoprotein substrate	+	0.6981	69.81%
CYP3A4 substrate	+	0.7406	74.06%
CYP2C9 substrate	-	0.8037	80.37%
CYP2D6 substrate	-	0.8331	83.31%
CYP3A4 inhibition	-	0.9630	96.30%
CYP2C9 inhibition	-	0.9225	92.25%
CYP2C19 inhibition	-	0.9112	91.12%
CYP2D6 inhibition	-	0.9427	94.27%
CYP1A2 inhibition	-	0.9167	91.67%
CYP2C8 inhibition	+	0.6902	69.02%
CYP inhibitory promiscuity	-	0.9551	95.51%
UGT catelyzed	+	0.7362	73.62%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6001	60.01%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9185	91.85%
Skin irritation	-	0.5781	57.81%
Skin corrosion	-	0.9454	94.54%
Ames mutagenesis	-	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7585	75.85%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.6820	68.20%
skin sensitisation	-	0.9142	91.42%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.8607	86.07%
Acute Oral Toxicity (c)	I	0.4817	48.17%
Estrogen receptor binding	+	0.7915	79.15%
Androgen receptor binding	+	0.7267	72.67%
Thyroid receptor binding	-	0.6146	61.46%
Glucocorticoid receptor binding	+	0.5634	56.34%
Aromatase binding	+	0.6701	67.01%
PPAR gamma	+	0.7180	71.80%
Honey bee toxicity	-	0.6385	63.85%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.8242	82.42%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.95%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.64%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	96.87%	95.93%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	93.63%	95.89%
CHEMBL2581	P07339	Cathepsin D	92.94%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.44%	97.09%
CHEMBL1871	P10275	Androgen Receptor	91.28%	96.43%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.43%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.82%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.91%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.57%	97.25%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	87.15%	89.05%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	86.57%	93.04%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.56%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.27%	94.00%
CHEMBL1937	Q92769	Histone deacetylase 2	85.14%	94.75%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.66%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.57%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	83.51%	90.17%
CHEMBL2996	Q05655	Protein kinase C delta	83.03%	97.79%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.08%	95.83%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.01%	97.36%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.15%	93.56%
CHEMBL5028	O14672	ADAM10	80.49%	97.50%
CHEMBL5255	O00206	Toll-like receptor 4	80.08%	92.50%

Plants that contains it

• Periploca sepium

Cross-Links

• PubChem: 101682679
• LOTUS: LTS0059473
• wikiData: Q104969066