[(3S,8S,9R,10R,12R,13S,14R,17S)-17-acetyl-8,14,17-trihydroxy-3-[(2R,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,4R,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-1,2,3,4,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-12-yl] pyridine-3-carboxylate

Details

• Internal ID: 67e993f0-a0ae-442e-bd2e-e923007f82eb
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: [(3S,8S,9R,10R,12R,13S,14R,17S)-17-acetyl-8,14,17-trihydroxy-3-[(2R,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,4R,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-1,2,3,4,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-12-yl] pyridine-3-carboxylate
• SMILES (Canonical): CC1C(C(CC(O1)OC2C(OC(CC2OC)OC3C(OC(CC3OC)OC4CCC5(C6CC(C7(C(CCC7(C6(CC=C5C4)O)O)(C(=O)C)O)C)OC(=O)C8=CN=CC=C8)C)C)C)OC)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@@H](C[C@@H](O1)O[C@@H]2[C@H](O[C@H](C[C@@H]2OC)O[C@@H]3[C@H](O[C@H](C[C@@H]3OC)O[C@H]4CC[C@@]5([C@H]6C[C@H]([C@@]7([C@@](CC[C@@]7([C@@]6(CC=C5C4)O)O)(C(=O)C)O)C)OC(=O)C8=CN=CC=C8)C)C)C)OC)O
• InChI: InChI=1S/C48H71NO16/c1-25-40(51)32(56-7)20-38(59-25)64-42-27(3)61-39(22-34(42)58-9)65-41-26(2)60-37(21-33(41)57-8)62-31-13-14-44(5)30(19-31)12-15-47(54)35(44)23-36(63-43(52)29-11-10-18-49-24-29)45(6)46(53,28(4)50)16-17-48(45,47)55/h10-12,18,24-27,31-42,51,53-55H,13-17,19-23H2,1-9H3/t25-,26+,27+,31-,32+,33-,34-,35+,36+,37-,38-,39-,40-,41+,42+,44-,45+,46+,47-,48+/m0/s1
• InChI Key: KGBKRGOQFYYJML-KTOCMDRPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₇₁NO₁₆
• Molecular Weight: 918.10 g/mol
• Exact Mass: 917.47728518 g/mol
• Topological Polar Surface Area (TPSA): 220.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 3.70
• H-Bond Acceptor: 17
• H-Bond Donor: 4
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9040	90.40%
Caco-2	-	0.8666	86.66%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.5831	58.31%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8577	85.77%
OATP1B3 inhibitior	+	0.9262	92.62%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8592	85.92%
BSEP inhibitior	+	0.9775	97.75%
P-glycoprotein inhibitior	+	0.7514	75.14%
P-glycoprotein substrate	+	0.7474	74.74%
CYP3A4 substrate	+	0.7334	73.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8841	88.41%
CYP3A4 inhibition	-	0.7933	79.33%
CYP2C9 inhibition	-	0.8783	87.83%
CYP2C19 inhibition	-	0.8750	87.50%
CYP2D6 inhibition	-	0.9278	92.78%
CYP1A2 inhibition	-	0.6563	65.63%
CYP2C8 inhibition	+	0.7981	79.81%
CYP inhibitory promiscuity	-	0.8955	89.55%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4890	48.90%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9040	90.40%
Skin irritation	-	0.6381	63.81%
Skin corrosion	-	0.9252	92.52%
Ames mutagenesis	-	0.6070	60.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7137	71.37%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	-	0.5051	50.51%
skin sensitisation	-	0.8547	85.47%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.8994	89.94%
Acute Oral Toxicity (c)	II	0.3399	33.99%
Estrogen receptor binding	+	0.8006	80.06%
Androgen receptor binding	+	0.7558	75.58%
Thyroid receptor binding	+	0.6049	60.49%
Glucocorticoid receptor binding	+	0.7613	76.13%
Aromatase binding	+	0.6183	61.83%
PPAR gamma	+	0.7899	78.99%
Honey bee toxicity	-	0.6494	64.94%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9303	93.03%

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	97.97%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.08%	86.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	94.52%	91.07%
CHEMBL2581	P07339	Cathepsin D	92.59%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.11%	99.23%
CHEMBL2243	O00519	Anandamide amidohydrolase	92.01%	97.53%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.89%	100.00%
CHEMBL255	P29275	Adenosine A2b receptor	91.28%	98.59%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.13%	85.14%
CHEMBL4040	P28482	MAP kinase ERK2	90.63%	83.82%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.47%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.80%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.58%	95.89%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	89.21%	97.33%
CHEMBL226	P30542	Adenosine A1 receptor	88.23%	95.93%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	87.42%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.16%	91.11%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	84.86%	96.39%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.53%	92.94%
CHEMBL2996	Q05655	Protein kinase C delta	84.47%	97.79%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	84.40%	83.00%
CHEMBL5028	O14672	ADAM10	83.42%	97.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.80%	97.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.37%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.68%	92.62%

Plants that contains it

• Orthosia guilleminiana

Cross-Links

• PubChem: 162995667
• LOTUS: LTS0148794
• wikiData: Q105140671