(25S)-Spirostane-3b,5b,6a-triol 3-[4''-rhamnosylglucoside]

Details

• Internal ID: 5a6e308d-d234-4247-b79f-351d137274a1
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins
• IUPAC Name: 2-[6-(18,19-dihydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl)oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CC(C6(C5(CCC(C6)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)C)O)O)O)O)O)C)O)O)C)C)OC1
• SMILES (Isomeric): CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CC(C6(C5(CCC(C6)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)C)O)O)O)O)O)C)O)O)C)C)OC1
• InChI: InChI=1S/C39H64O14/c1-17-6-11-39(48-16-17)18(2)27-24(53-39)13-23-21-12-26(41)38(47)14-20(7-10-37(38,5)22(21)8-9-36(23,27)4)50-35-32(46)30(44)33(25(15-40)51-35)52-34-31(45)29(43)28(42)19(3)49-34/h17-35,40-47H,6-16H2,1-5H3
• InChI Key: GBRQGKIXYHHYOW-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₆₄O₁₄
• Molecular Weight: 756.90 g/mol
• Exact Mass: 756.42960671 g/mol
• Topological Polar Surface Area (TPSA): 217.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 0.56
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 5

Synonyms

• CHEBI:193251
• 2-[6-(18,19-dihydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl)oxy-4,5-dihydroxy-2-(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	-	0.5246	52.46%
Caco-2	-	0.8831	88.31%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6174	61.74%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8889	88.89%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.6250	62.50%
BSEP inhibitior	-	0.5487	54.87%
P-glycoprotein inhibitior	+	0.7200	72.00%
P-glycoprotein substrate	-	0.5763	57.63%
CYP3A4 substrate	+	0.7431	74.31%
CYP2C9 substrate	-	0.8018	80.18%
CYP2D6 substrate	-	0.8301	83.01%
CYP3A4 inhibition	-	0.9473	94.73%
CYP2C9 inhibition	-	0.9215	92.15%
CYP2C19 inhibition	-	0.8997	89.97%
CYP2D6 inhibition	-	0.9561	95.61%
CYP1A2 inhibition	-	0.9215	92.15%
CYP2C8 inhibition	+	0.7156	71.56%
CYP inhibitory promiscuity	-	0.9616	96.16%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6223	62.23%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.9156	91.56%
Skin irritation	-	0.6555	65.55%
Skin corrosion	-	0.9521	95.21%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7573	75.73%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.8410	84.10%
skin sensitisation	-	0.9420	94.20%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.8314	83.14%
Acute Oral Toxicity (c)	I	0.8185	81.85%
Estrogen receptor binding	+	0.7412	74.12%
Androgen receptor binding	+	0.7359	73.59%
Thyroid receptor binding	-	0.6270	62.70%
Glucocorticoid receptor binding	-	0.4718	47.18%
Aromatase binding	+	0.6613	66.13%
PPAR gamma	+	0.6942	69.42%
Honey bee toxicity	-	0.5340	53.40%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.7523	75.23%

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	98.17%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	97.65%	96.61%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.95%	91.11%
CHEMBL1914	P06276	Butyrylcholinesterase	96.06%	95.00%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	95.77%	97.31%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.56%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	95.02%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.61%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.82%	100.00%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	92.74%	92.86%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	92.41%	89.05%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	92.35%	95.50%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	88.48%	97.86%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.30%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.14%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.95%	89.00%
CHEMBL332	P03956	Matrix metalloproteinase-1	87.67%	94.50%
CHEMBL206	P03372	Estrogen receptor alpha	87.13%	97.64%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.47%	96.21%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.27%	92.94%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	85.52%	100.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	84.63%	91.71%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.50%	86.92%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.46%	95.89%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	84.35%	95.58%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	84.06%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	83.63%	92.50%
CHEMBL4302	P08183	P-glycoprotein 1	82.35%	92.98%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	82.16%	97.50%
CHEMBL5524	Q99873	Protein-arginine N-methyltransferase 1	81.99%	96.67%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.89%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.29%	92.62%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	81.22%	98.46%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	81.04%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.63%	86.33%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	80.23%	98.99%

Plants that contains it

• Allium tuberosum

Cross-Links

• PubChem: 85254531
• LOTUS: LTS0252854
• wikiData: Q105006046