16,23-Epoxy-5beta-cholestane triglycoside

Details

• Internal ID: 31839089-7cda-486b-b3db-234552180bc4
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: (2S,3R,4R,5R,6S)-2-[(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[[(1R,2S,4S,6S,7R,8S,9R,10S,13S,14S,17S,19R)-7-hydroxy-8,10,14-trimethyl-6-(2-methylprop-1-enyl)-5-oxapentacyclo[11.8.0.02,10.04,9.014,19]henicosan-17-yl]oxy]oxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1C2C(CC3C2(CCC4C3CCC5C4(CCC(C5)OC6C(C(C(C(O6)CO)O)O)OC7C(C(C(C(O7)CO)O)O)OC8C(C(C(C(O8)C)O)O)O)C)C)OC(C1O)C=C(C)C
• SMILES (Isomeric): C[C@H]1[C@H]2[C@H](C[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC[C@H]5[C@@]4(CC[C@@H](C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)O)O)O)C)C)O[C@H]([C@@H]1O)C=C(C)C
• InChI: InChI=1S/C45H74O17/c1-18(2)13-27-31(48)19(3)30-26(58-27)15-25-23-8-7-21-14-22(9-11-44(21,5)24(23)10-12-45(25,30)6)57-42-39(36(53)33(50)28(16-46)59-42)62-43-40(37(54)34(51)29(17-47)60-43)61-41-38(55)35(52)32(49)20(4)56-41/h13,19-43,46-55H,7-12,14-17H2,1-6H3/t19-,20-,21+,22-,23+,24-,25-,26-,27-,28+,29+,30-,31+,32-,33+,34+,35+,36-,37-,38+,39+,40+,41-,42+,43-,44-,45-/m0/s1
• InChI Key: AJNYRTVTKHEZMG-BYMWGYRGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₅H₇₄O₁₇
• Molecular Weight: 887.10 g/mol
• Exact Mass: 886.49260089 g/mol
• Topological Polar Surface Area (TPSA): 267.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): -0.15
• H-Bond Acceptor: 17
• H-Bond Donor: 10
• Rotatable Bonds: 9

Synonyms

• (3beta,5beta,16beta,22R,23S)-22-hydroxy-16,23-epoxycholest-24-en-3-yl 6-deoxy-alpha-L-mannopyranosyl-(1->2)-beta-D-glucopyranosyl-(1->2)-beta-D-glucopyranoside
• CHEBI:65855
• LMST05050027
• Q27134348
• (2S,3R,4R,5R,6S)-2-[(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[[(1R,2S,4S,6S,7R,8S,9R,10S,13S,14S,17S,19R)-7-hydroxy-8,10,14-trimethyl-6-(2-methylprop-1-enyl)-5-oxapentacyclo[11.8.0.02,10.04,9.014,19]henicosan-17-yl]oxy]oxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-methyloxane-3,4,5-triol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6382	63.82%
Caco-2	-	0.8835	88.35%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7733	77.33%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8699	86.99%
OATP1B3 inhibitior	-	0.2200	22.00%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.7699	76.99%
P-glycoprotein inhibitior	+	0.7282	72.82%
P-glycoprotein substrate	-	0.6162	61.62%
CYP3A4 substrate	+	0.7395	73.95%
CYP2C9 substrate	-	0.8037	80.37%
CYP2D6 substrate	-	0.8331	83.31%
CYP3A4 inhibition	-	0.9655	96.55%
CYP2C9 inhibition	-	0.8609	86.09%
CYP2C19 inhibition	-	0.8930	89.30%
CYP2D6 inhibition	-	0.9379	93.79%
CYP1A2 inhibition	-	0.8844	88.44%
CYP2C8 inhibition	+	0.5788	57.88%
CYP inhibitory promiscuity	-	0.8975	89.75%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6539	65.39%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9119	91.19%
Skin irritation	-	0.6432	64.32%
Skin corrosion	-	0.9504	95.04%
Ames mutagenesis	-	0.7332	73.32%
Human Ether-a-go-go-Related Gene inhibition	+	0.8594	85.94%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.7966	79.66%
skin sensitisation	-	0.9031	90.31%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	-	0.8957	89.57%
Acute Oral Toxicity (c)	III	0.4516	45.16%
Estrogen receptor binding	+	0.8277	82.77%
Androgen receptor binding	+	0.6982	69.82%
Thyroid receptor binding	-	0.5758	57.58%
Glucocorticoid receptor binding	+	0.5773	57.73%
Aromatase binding	+	0.6748	67.48%
PPAR gamma	+	0.7154	71.54%
Honey bee toxicity	-	0.5076	50.76%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9438	94.38%

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	97.90%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.35%	91.11%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	95.31%	95.58%
CHEMBL233	P35372	Mu opioid receptor	92.96%	97.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.34%	97.09%
CHEMBL237	P41145	Kappa opioid receptor	92.18%	98.10%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.00%	100.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.73%	96.61%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.46%	92.94%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.84%	94.45%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.55%	96.21%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.07%	95.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.37%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.00%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.25%	89.00%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	85.51%	92.86%
CHEMBL5524	Q99873	Protein-arginine N-methyltransferase 1	85.10%	96.67%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	84.21%	97.86%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	83.96%	97.50%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	83.68%	98.99%
CHEMBL226	P30542	Adenosine A1 receptor	83.25%	95.93%
CHEMBL1937	Q92769	Histone deacetylase 2	83.14%	94.75%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.22%	97.25%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	82.03%	89.05%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	82.03%	98.46%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.65%	97.36%
CHEMBL5255	O00206	Toll-like receptor 4	80.19%	92.50%

Plants that contains it

• Ornithogalum saundersiae

Cross-Links

• PubChem: 10102192
• LOTUS: LTS0060007
• wikiData: Q27134348