(8R,9S,10R,13S,14S,16S,17Z)-17-ethylidene-16-[(2R,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one

Details

• Internal ID: 05e728ea-8aa9-41ae-993c-46db425f57e1
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: (8R,9S,10R,13S,14S,16S,17Z)-17-ethylidene-16-[(2R,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
• SMILES (Canonical): CC=C1C(CC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)OC5C(C(C(C(O5)CO)O)OC6C(C(C(C(O6)CO)O)O)O)OC7C(C(C(C(O7)C)O)O)O
• SMILES (Isomeric): C/C=C/1\[C@H](C[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O[C@@H]7[C@@H]([C@@H]([C@H]([C@@H](O7)C)O)O)O
• InChI: InChI=1S/C39H60O16/c1-5-20-23(13-22-19-7-6-17-12-18(42)8-10-38(17,3)21(19)9-11-39(20,22)4)51-37-34(55-35-31(48)29(46)26(43)16(2)50-35)33(28(45)25(15-41)53-37)54-36-32(49)30(47)27(44)24(14-40)52-36/h5,12,16,19,21-37,40-41,43-49H,6-11,13-15H2,1-4H3/b20-5+/t16-,19+,21-,22-,23-,24+,25+,26-,27+,28+,29+,30-,31+,32+,33-,34+,35+,36-,37+,38-,39+/m0/s1
• InChI Key: BGQDUIOTKONDFO-CHXHILGESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₆₀O₁₆
• Molecular Weight: 784.90 g/mol
• Exact Mass: 784.38813582 g/mol
• Topological Polar Surface Area (TPSA): 255.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -1.06
• H-Bond Acceptor: 16
• H-Bond Donor: 9
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7478	74.78%
Caco-2	-	0.8806	88.06%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.8320	83.20%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8271	82.71%
OATP1B3 inhibitior	-	0.2720	27.20%
MATE1 inhibitior	-	0.9812	98.12%
OCT2 inhibitior	-	0.6776	67.76%
BSEP inhibitior	+	0.7538	75.38%
P-glycoprotein inhibitior	+	0.6976	69.76%
P-glycoprotein substrate	-	0.5950	59.50%
CYP3A4 substrate	+	0.7336	73.36%
CYP2C9 substrate	-	0.7956	79.56%
CYP2D6 substrate	-	0.8844	88.44%
CYP3A4 inhibition	-	0.9665	96.65%
CYP2C9 inhibition	-	0.9294	92.94%
CYP2C19 inhibition	-	0.9317	93.17%
CYP2D6 inhibition	-	0.9478	94.78%
CYP1A2 inhibition	-	0.8984	89.84%
CYP2C8 inhibition	+	0.5291	52.91%
CYP inhibitory promiscuity	-	0.9271	92.71%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6219	62.19%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9260	92.60%
Skin irritation	-	0.5361	53.61%
Skin corrosion	-	0.9475	94.75%
Ames mutagenesis	-	0.9078	90.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.7919	79.19%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.7226	72.26%
skin sensitisation	-	0.9265	92.65%
Respiratory toxicity	+	0.9111	91.11%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.8782	87.82%
Acute Oral Toxicity (c)	III	0.5451	54.51%
Estrogen receptor binding	+	0.7815	78.15%
Androgen receptor binding	+	0.7797	77.97%
Thyroid receptor binding	-	0.5606	56.06%
Glucocorticoid receptor binding	+	0.6460	64.60%
Aromatase binding	+	0.6769	67.69%
PPAR gamma	+	0.6654	66.54%
Honey bee toxicity	-	0.6253	62.53%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9527	95.27%

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	98.49%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.94%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	96.79%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.53%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.78%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.62%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.45%	95.56%
CHEMBL1871	P10275	Androgen Receptor	89.88%	96.43%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.33%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.76%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.93%	94.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.56%	91.24%
CHEMBL2581	P07339	Cathepsin D	82.93%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.42%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	81.40%	92.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.70%	94.45%

Plants that contains it

• Tribulus cistoides

Cross-Links

• PubChem: 163187524
• LOTUS: LTS0187940
• wikiData: Q104935687