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

Details

• Internal ID: 97771625-4169-4fb6-bc38-30d2391ccd6c
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: (2S,3S,4R,5R,6S)-2-[[(1R,3R,5S,8S,9S,10S,13S,14S,16S,17R)-3-hydroxy-17-[(2S,3S)-3-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC(C)CCC(C(C)C1C(CC2C1(CCC3C2CCC4C3(C(CC(C4)O)OC5C(C(C(C(O5)CO)O)O)O)C)C)OC6C(C(C(C(O6)CO)O)O)O)O
• SMILES (Isomeric): C[C@@H]([C@H]1[C@H](C[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3([C@@H](C[C@@H](C4)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C)C)O[C@@H]6[C@H]([C@@H]([C@H]([C@@H](O6)CO)O)O)O)[C@H](CCC(C)C)O
• InChI: InChI=1S/C39H68O14/c1-17(2)6-9-24(43)18(3)29-25(50-36-34(48)32(46)30(44)26(15-40)51-36)14-23-21-8-7-19-12-20(42)13-28(39(19,5)22(21)10-11-38(23,29)4)53-37-35(49)33(47)31(45)27(16-41)52-37/h17-37,40-49H,6-16H2,1-5H3/t18-,19+,20-,21-,22+,23+,24+,25+,26+,27-,28-,29+,30+,31-,32-,33+,34+,35-,36+,37+,38+,39+/m1/s1
• InChI Key: HLBSFOSIJVBLBR-SDRYYQTDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₆₈O₁₄
• Molecular Weight: 760.90 g/mol
• Exact Mass: 760.46090684 g/mol
• Topological Polar Surface Area (TPSA): 239.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 0.03
• H-Bond Acceptor: 14
• H-Bond Donor: 10
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5073	50.73%
Caco-2	-	0.8685	86.85%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6483	64.83%
OATP2B1 inhibitior	-	0.7251	72.51%
OATP1B1 inhibitior	+	0.8886	88.86%
OATP1B3 inhibitior	+	0.8916	89.16%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	-	0.8410	84.10%
P-glycoprotein inhibitior	+	0.6780	67.80%
P-glycoprotein substrate	-	0.5582	55.82%
CYP3A4 substrate	+	0.7264	72.64%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8203	82.03%
CYP3A4 inhibition	-	0.9558	95.58%
CYP2C9 inhibition	-	0.8950	89.50%
CYP2C19 inhibition	-	0.8957	89.57%
CYP2D6 inhibition	-	0.9593	95.93%
CYP1A2 inhibition	-	0.9207	92.07%
CYP2C8 inhibition	+	0.5952	59.52%
CYP inhibitory promiscuity	-	0.9729	97.29%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6776	67.76%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9075	90.75%
Skin irritation	-	0.7045	70.45%
Skin corrosion	-	0.9555	95.55%
Ames mutagenesis	-	0.7644	76.44%
Human Ether-a-go-go-Related Gene inhibition	+	0.7258	72.58%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.7175	71.75%
skin sensitisation	-	0.9339	93.39%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.9277	92.77%
Acute Oral Toxicity (c)	I	0.6587	65.87%
Estrogen receptor binding	+	0.6583	65.83%
Androgen receptor binding	+	0.6848	68.48%
Thyroid receptor binding	-	0.5764	57.64%
Glucocorticoid receptor binding	-	0.5349	53.49%
Aromatase binding	+	0.6421	64.21%
PPAR gamma	+	0.6429	64.29%
Honey bee toxicity	-	0.6578	65.78%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.7773	77.73%

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	98.59%	96.09%
CHEMBL237	P41145	Kappa opioid receptor	95.89%	98.10%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.40%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.24%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.79%	91.11%
CHEMBL2094135	Q96BI3	Gamma-secretase	94.69%	98.05%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	92.10%	95.58%
CHEMBL226	P30542	Adenosine A1 receptor	91.07%	95.93%
CHEMBL2007625	O75874	Isocitrate dehydrogenase [NADP] cytoplasmic	90.55%	99.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.80%	95.89%
CHEMBL2996	Q05655	Protein kinase C delta	88.11%	97.79%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.75%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.06%	100.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	86.68%	96.38%
CHEMBL2581	P07339	Cathepsin D	86.22%	98.95%
CHEMBL4581	P52732	Kinesin-like protein 1	85.96%	93.18%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.79%	94.45%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	85.78%	95.36%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.44%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.30%	97.14%
CHEMBL259	P32245	Melanocortin receptor 4	84.06%	95.38%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.58%	91.03%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.35%	97.36%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.09%	91.24%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	82.69%	82.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.57%	92.62%
CHEMBL4073	P09237	Matrix metalloproteinase 7	82.56%	97.56%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	81.78%	92.86%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	81.74%	97.29%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	81.67%	89.05%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	80.75%	97.86%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.50%	89.00%

Plants that contains it

• Ornithogalum thyrsoides

Cross-Links

• PubChem: 163041399
• LOTUS: LTS0262255
• wikiData: Q105030072