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

Details

• Internal ID: bd266819-af7a-42c3-a8ae-9236893bb965
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: 1-[(3S,8R,9S,10R,13S,14S)-3-[(2R,3R,4S,5R,6R)-4-[(2S,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3CCC4(C5CCC6(C(C5CC=C4C3)CC=C6C(=O)C)C)C)CO)O)OC7C(C(C(C(O7)C)OC8C(C(C(C(O8)CO)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2O[C@H]3CC[C@@]4([C@H]5CC[C@]6([C@H]([C@@H]5CC=C4C3)CC=C6C(=O)C)C)C)CO)O)O[C@H]7[C@@H]([C@@H]([C@H]([C@@H](O7)C)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C45H70O20/c1-17(48)23-8-9-24-22-7-6-20-14-21(10-12-44(20,4)25(22)11-13-45(23,24)5)60-43-39(65-40-34(55)31(52)28(49)18(2)58-40)38(30(51)27(16-47)62-43)64-41-36(57)33(54)37(19(3)59-41)63-42-35(56)32(53)29(50)26(15-46)61-42/h6,8,18-19,21-22,24-43,46-47,49-57H,7,9-16H2,1-5H3/t18-,19-,21-,22-,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: RHIHSDUDMFNGPU-LHIOEKOVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₅H₇₀O₂₀
• Molecular Weight: 931.00 g/mol
• Exact Mass: 930.44604462 g/mol
• Topological Polar Surface Area (TPSA): 313.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -2.21
• H-Bond Acceptor: 20
• H-Bond Donor: 11
• Rotatable Bonds: 11

Synonyms

• 20-Oxopregna-5,16-diene-3beta-yl 2-O-alpha-L-rhamnopyranosyl-3-O-(4-O-beta-D-glucopyranosyl-alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7478	74.78%
Caco-2	-	0.8829	88.29%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8320	83.20%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8742	87.42%
OATP1B3 inhibitior	-	0.2720	27.20%
MATE1 inhibitior	-	0.9812	98.12%
OCT2 inhibitior	-	0.6776	67.76%
BSEP inhibitior	+	0.8499	84.99%
P-glycoprotein inhibitior	+	0.7270	72.70%
P-glycoprotein substrate	-	0.5375	53.75%
CYP3A4 substrate	+	0.7212	72.12%
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	+	0.6732	67.32%
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	-	0.9114	91.14%
Skin irritation	-	0.5361	53.61%
Skin corrosion	-	0.9475	94.75%
Ames mutagenesis	-	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7935	79.35%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.8569	85.69%
skin sensitisation	-	0.9265	92.65%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.8326	83.26%
Acute Oral Toxicity (c)	III	0.5451	54.51%
Estrogen receptor binding	+	0.8481	84.81%
Androgen receptor binding	+	0.7436	74.36%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6463	64.63%
Aromatase binding	+	0.6313	63.13%
PPAR gamma	+	0.7596	75.96%
Honey bee toxicity	-	0.6402	64.02%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5755	57.55%
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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.64%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.60%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.50%	100.00%
CHEMBL2581	P07339	Cathepsin D	92.42%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.39%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.27%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	88.00%	95.93%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.56%	91.24%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.54%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.69%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	86.24%	92.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.78%	86.33%
CHEMBL1937	Q92769	Histone deacetylase 2	85.39%	94.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.88%	97.09%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	83.52%	89.05%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.07%	94.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.00%	95.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.87%	93.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.34%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.24%	96.00%

Plants that contains it

• Anthriscus sylvestris
• Tacca chantrieri

Cross-Links

• PubChem: 11115684
• NPASS: NPC250415
• LOTUS: LTS0169967
• wikiData: Q105236396