(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,6S)-6-[(1S)-1-[(3S,5R,8R,9S,10S,13S,14S,17R)-3-[(2R,3R,4S,5S,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-17-hydroxy-10,13-dimethyl-1,2,3,4,5,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl]ethoxy]-4-hydroxy-2-methyloxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 34e4f698-5bf7-41b3-996f-535d3a0f9a05
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[(2R,3S,4R,6S)-6-[(1S)-1-[(3S,5R,8R,9S,10S,13S,14S,17R)-3-[(2R,3R,4S,5S,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-17-hydroxy-10,13-dimethyl-1,2,3,4,5,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl]ethoxy]-4-hydroxy-2-methyloxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CCC3(C4CCC5(C(C4C=CC3C2)CCC5(C(C)OC6CC(C(C(O6)C)OC7C(C(C(C(O7)CO)O)O)O)O)O)C)C)O)OC)O
• SMILES (Isomeric): C[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@H]2CC[C@@]3([C@H]4CC[C@]5([C@H]([C@@H]4C=C[C@H]3C2)CC[C@@]5([C@H](C)O[C@H]6C[C@H]([C@@H]([C@H](O6)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)O)C)C)O)OC)O
• InChI: InChI=1S/C40H66O15/c1-18-29(43)35(49-6)33(47)37(51-18)53-22-9-12-38(4)21(15-22)7-8-23-24(38)10-13-39(5)25(23)11-14-40(39,48)20(3)52-28-16-26(42)34(19(2)50-28)55-36-32(46)31(45)30(44)27(17-41)54-36/h7-8,18-37,41-48H,9-17H2,1-6H3/t18-,19-,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: UUONYWJVZTYDMU-GXZDAPJUSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₆₆O₁₅
• Molecular Weight: 786.90 g/mol
• Exact Mass: 786.44017139 g/mol
• Topological Polar Surface Area (TPSA): 226.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.49
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5820	58.20%
Caco-2	-	0.8789	87.89%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6171	61.71%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8324	83.24%
OATP1B3 inhibitior	+	0.8872	88.72%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.5656	56.56%
P-glycoprotein inhibitior	+	0.7326	73.26%
P-glycoprotein substrate	+	0.6265	62.65%
CYP3A4 substrate	+	0.7301	73.01%
CYP2C9 substrate	-	0.8020	80.20%
CYP2D6 substrate	-	0.8461	84.61%
CYP3A4 inhibition	-	0.9442	94.42%
CYP2C9 inhibition	-	0.9202	92.02%
CYP2C19 inhibition	-	0.9212	92.12%
CYP2D6 inhibition	-	0.9571	95.71%
CYP1A2 inhibition	-	0.9073	90.73%
CYP2C8 inhibition	+	0.5687	56.87%
CYP inhibitory promiscuity	-	0.9550	95.50%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6778	67.78%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.9159	91.59%
Skin irritation	-	0.6136	61.36%
Skin corrosion	-	0.9515	95.15%
Ames mutagenesis	-	0.6054	60.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7822	78.22%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.6636	66.36%
skin sensitisation	-	0.9307	93.07%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.9682	96.82%
Acute Oral Toxicity (c)	I	0.5826	58.26%
Estrogen receptor binding	+	0.7468	74.68%
Androgen receptor binding	+	0.7266	72.66%
Thyroid receptor binding	-	0.5559	55.59%
Glucocorticoid receptor binding	+	0.6008	60.08%
Aromatase binding	+	0.6434	64.34%
PPAR gamma	+	0.7271	72.71%
Honey bee toxicity	-	0.6500	65.00%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.7856	78.56%

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	99.19%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.29%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.16%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.84%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.66%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.95%	85.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.59%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.66%	100.00%
CHEMBL1914	P06276	Butyrylcholinesterase	87.56%	95.00%
CHEMBL226	P30542	Adenosine A1 receptor	87.28%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.06%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.00%	96.21%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.94%	92.62%
CHEMBL2581	P07339	Cathepsin D	83.91%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.90%	86.33%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	83.47%	97.31%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.98%	96.61%
CHEMBL1871	P10275	Androgen Receptor	82.20%	96.43%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.99%	89.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.60%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.00%	97.14%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	80.86%	95.58%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.57%	92.94%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.19%	96.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.16%	95.50%

Plants that contains it

• Trachelospermum asiaticum

Cross-Links

• PubChem: 21626494
• LOTUS: LTS0051004
• wikiData: Q105279498