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

Details

• Internal ID: c2f7ec3c-5aaa-48cb-99e1-c08b1a96f9ad
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: [(3S,8S,9R,10R,12R,13S,14R,17R)-17-acetyl-8,14-dihydroxy-3-[(2R,4S,5R,6R)-5-[(2S,4S,5S,6R)-4-hydroxy-5-[(2S,4S,5S,6R)-4-hydroxy-5-[(2S,4R,5R,6R)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-2,3,4,7,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-12-yl] acetate
• SMILES (Canonical): CC1C(C(CC(O1)OC2C(OC(CC2OC)OC3CCC4(C5CC(C6(C(CCC6(C5(CC=C4C3)O)O)C(=O)C)C)OC(=O)C)C)C)O)OC7CC(C(C(O7)C)OC8CC(C(C(O8)C)OC9C(C(C(C(O9)CO)O)O)O)OC)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@@H]2[C@H](O[C@H](C[C@@H]2OC)O[C@H]3CC[C@@]4([C@H]5C[C@H]([C@@]6([C@@H](CC[C@@]6([C@@]5(CC=C4C3)O)O)C(=O)C)C)OC(=O)C)C)C)O)O[C@H]7C[C@@H]([C@@H]([C@H](O7)C)O[C@H]8C[C@H]([C@@H]([C@H](O8)C)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)OC)O
• InChI: InChI=1S/C55H88O23/c1-24(57)32-13-16-55(65)53(32,8)39(72-29(6)58)22-38-52(7)14-12-31(17-30(52)11-15-54(38,55)64)73-42-20-35(66-9)49(27(4)70-42)77-41-19-34(60)47(25(2)69-41)75-40-18-33(59)48(26(3)68-40)76-43-21-36(67-10)50(28(5)71-43)78-51-46(63)45(62)44(61)37(23-56)74-51/h11,25-28,31-51,56,59-65H,12-23H2,1-10H3/t25-,26-,27-,28-,31+,32+,33+,34+,35+,36-,37-,38-,39-,40+,41+,42+,43+,44-,45+,46-,47-,48-,49-,50-,51+,52+,53+,54+,55-/m1/s1
• InChI Key: XJRYNFZORKISAV-MRHYGIKZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₅H₈₈O₂₃
• Molecular Weight: 1117.30 g/mol
• Exact Mass: 1116.57163905 g/mol
• Topological Polar Surface Area (TPSA): 316.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 0.94
• H-Bond Acceptor: 23
• H-Bond Donor: 8
• Rotatable Bonds: 15

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8203	82.03%
Caco-2	-	0.8686	86.86%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8142	81.42%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8329	83.29%
OATP1B3 inhibitior	+	0.8977	89.77%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6553	65.53%
BSEP inhibitior	+	0.9292	92.92%
P-glycoprotein inhibitior	+	0.7468	74.68%
P-glycoprotein substrate	+	0.6981	69.81%
CYP3A4 substrate	+	0.7364	73.64%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8921	89.21%
CYP3A4 inhibition	-	0.8616	86.16%
CYP2C9 inhibition	-	0.9127	91.27%
CYP2C19 inhibition	-	0.9401	94.01%
CYP2D6 inhibition	-	0.9540	95.40%
CYP1A2 inhibition	-	0.9162	91.62%
CYP2C8 inhibition	+	0.6472	64.72%
CYP inhibitory promiscuity	-	0.9614	96.14%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5884	58.84%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9010	90.10%
Skin irritation	+	0.5519	55.19%
Skin corrosion	-	0.9405	94.05%
Ames mutagenesis	-	0.6270	62.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7683	76.83%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.7473	74.73%
skin sensitisation	-	0.9309	93.09%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.7966	79.66%
Acute Oral Toxicity (c)	I	0.4167	41.67%
Estrogen receptor binding	+	0.8282	82.82%
Androgen receptor binding	+	0.7541	75.41%
Thyroid receptor binding	+	0.6275	62.75%
Glucocorticoid receptor binding	+	0.7981	79.81%
Aromatase binding	+	0.7207	72.07%
PPAR gamma	+	0.8460	84.60%
Honey bee toxicity	-	0.6302	63.02%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5655	56.55%
Fish aquatic toxicity	+	0.9263	92.63%

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	98.92%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.44%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.25%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	93.98%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.81%	89.00%
CHEMBL2581	P07339	Cathepsin D	91.69%	98.95%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.58%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.19%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.55%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.88%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.29%	95.89%
CHEMBL5028	O14672	ADAM10	85.80%	97.50%
CHEMBL5255	O00206	Toll-like receptor 4	84.68%	92.50%
CHEMBL226	P30542	Adenosine A1 receptor	83.95%	95.93%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.87%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.47%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.44%	94.45%
CHEMBL2996	Q05655	Protein kinase C delta	83.12%	97.79%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.11%	94.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.70%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.35%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.89%	92.62%

Plants that contains it

• Asclepias incarnata
• Phyllolobium chinense

Cross-Links

• PubChem: 101024591
• LOTUS: LTS0116490
• wikiData: Q105215072