(3S,5S,6S,8S,9R,10S,13R,14S,15S,17R)-17-[(2R,5S)-5-[(2R,3R,4R,5S)-3-hydroxy-5-(hydroxymethyl)-4-methoxyoxolan-2-yl]oxy-6-methylheptan-2-yl]-10,13-dimethyl-1,2,3,4,5,6,7,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,6,8,15-tetrol

Details

• Internal ID: 5bfc1890-b289-49d3-bd61-34fdddfd1b5f
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: (3S,5S,6S,8S,9R,10S,13R,14S,15S,17R)-17-[(2R,5S)-5-[(2R,3R,4R,5S)-3-hydroxy-5-(hydroxymethyl)-4-methoxyoxolan-2-yl]oxy-6-methylheptan-2-yl]-10,13-dimethyl-1,2,3,4,5,6,7,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,6,8,15-tetrol
• SMILES (Canonical): CC(C)C(CCC(C)C1CC(C2C1(CCC3C2(CC(C4C3(CCC(C4)O)C)O)O)C)O)OC5C(C(C(O5)CO)OC)O
• SMILES (Isomeric): C[C@H](CC[C@@H](C(C)C)O[C@H]1[C@@H]([C@H]([C@@H](O1)CO)OC)O)[C@H]2C[C@@H]([C@@H]3[C@@]2(CC[C@H]4[C@]3(C[C@@H]([C@@H]5[C@@]4(CC[C@@H](C5)O)C)O)O)C)O
• InChI: InChI=1S/C33H58O9/c1-17(2)24(41-30-27(38)28(40-6)25(16-34)42-30)8-7-18(3)20-14-22(36)29-32(20,5)12-10-26-31(4)11-9-19(35)13-21(31)23(37)15-33(26,29)39/h17-30,34-39H,7-16H2,1-6H3/t18-,19+,20-,21-,22+,23+,24+,25+,26-,27-,28+,29-,30-,31+,32-,33+/m1/s1
• InChI Key: XONIZWOKMLXCPO-MOCANMLZSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₅₈O₉
• Molecular Weight: 598.80 g/mol
• Exact Mass: 598.40808342 g/mol
• Topological Polar Surface Area (TPSA): 149.00 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.61
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9010	90.10%
Caco-2	-	0.8408	84.08%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6350	63.50%
OATP2B1 inhibitior	-	0.5795	57.95%
OATP1B1 inhibitior	+	0.8192	81.92%
OATP1B3 inhibitior	+	0.9107	91.07%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7292	72.92%
BSEP inhibitior	-	0.8322	83.22%
P-glycoprotein inhibitior	+	0.6404	64.04%
P-glycoprotein substrate	+	0.5618	56.18%
CYP3A4 substrate	+	0.7332	73.32%
CYP2C9 substrate	-	0.7983	79.83%
CYP2D6 substrate	-	0.8326	83.26%
CYP3A4 inhibition	-	0.6878	68.78%
CYP2C9 inhibition	-	0.7044	70.44%
CYP2C19 inhibition	-	0.8244	82.44%
CYP2D6 inhibition	-	0.9509	95.09%
CYP1A2 inhibition	-	0.8575	85.75%
CYP2C8 inhibition	-	0.5661	56.61%
CYP inhibitory promiscuity	-	0.8497	84.97%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6531	65.31%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9193	91.93%
Skin irritation	-	0.6783	67.83%
Skin corrosion	-	0.9517	95.17%
Ames mutagenesis	-	0.6615	66.15%
Human Ether-a-go-go-Related Gene inhibition	+	0.6498	64.98%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.7545	75.45%
skin sensitisation	-	0.9160	91.60%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.7763	77.63%
Acute Oral Toxicity (c)	I	0.4380	43.80%
Estrogen receptor binding	+	0.6035	60.35%
Androgen receptor binding	+	0.6755	67.55%
Thyroid receptor binding	-	0.6040	60.40%
Glucocorticoid receptor binding	+	0.5664	56.64%
Aromatase binding	+	0.5669	56.69%
PPAR gamma	+	0.5657	56.57%
Honey bee toxicity	-	0.6461	64.61%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.8355	83.55%

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	98.17%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.94%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	97.61%	95.93%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.01%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.46%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.04%	94.45%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	93.55%	95.58%
CHEMBL233	P35372	Mu opioid receptor	92.98%	97.93%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	92.42%	95.89%
CHEMBL237	P41145	Kappa opioid receptor	90.96%	98.10%
CHEMBL218	P21554	Cannabinoid CB1 receptor	89.98%	96.61%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.61%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.18%	100.00%
CHEMBL204	P00734	Thrombin	88.03%	96.01%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	87.44%	89.05%
CHEMBL2996	Q05655	Protein kinase C delta	86.85%	97.79%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.77%	97.14%
CHEMBL4581	P52732	Kinesin-like protein 1	86.28%	93.18%
CHEMBL268	P43235	Cathepsin K	86.22%	96.85%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	86.14%	95.36%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	84.86%	92.86%
CHEMBL4040	P28482	MAP kinase ERK2	84.49%	83.82%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.58%	100.00%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	82.84%	100.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.73%	96.21%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.58%	100.00%
CHEMBL2581	P07339	Cathepsin D	82.31%	98.95%
CHEMBL4588	P22894	Matrix metalloproteinase 8	82.19%	94.66%
CHEMBL2959	Q08881	Tyrosine-protein kinase ITK/TSK	82.04%	95.00%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	82.03%	92.78%
CHEMBL344	Q99705	Melanin-concentrating hormone receptor 1	82.01%	92.50%
CHEMBL1871	P10275	Androgen Receptor	81.43%	96.43%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.22%	95.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.70%	92.62%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.18%	91.03%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 23247568
• LOTUS: LTS0037336
• wikiData: Q105337825