[(1S,3R,5S,7R,9S,10S,12R,14R,15S,18R,19R,22S,23R)-10,22-dihydroxy-14-(hydroxymethyl)-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosan-9-yl] acetate

Details

• Internal ID: 76fcacdc-b2cd-4bfe-b284-7396e577b65e
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: [(1S,3R,5S,7R,9S,10S,12R,14R,15S,18R,19R,22S,23R)-10,22-dihydroxy-14-(hydroxymethyl)-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosan-9-yl] acetate
• SMILES (Canonical): CC1CC(C2(C(O1)OC3CC4CCC5C(C4(CC3O2)CO)CCC6(C5(CCC6C7=CC(=O)OC7)O)C)O)OC(=O)C
• SMILES (Isomeric): C[C@@H]1C[C@@H]([C@]2([C@@H](O1)O[C@@H]3C[C@@H]4CC[C@@H]5[C@@H]([C@]4(C[C@H]3O2)CO)CC[C@]6([C@@]5(CC[C@@H]6C7=CC(=O)OC7)O)C)O)OC(=O)C
• InChI: InChI=1S/C31H44O10/c1-16-10-25(39-17(2)33)31(36)27(38-16)40-23-12-19-4-5-22-21(29(19,15-32)13-24(23)41-31)6-8-28(3)20(7-9-30(22,28)35)18-11-26(34)37-14-18/h11,16,19-25,27,32,35-36H,4-10,12-15H2,1-3H3/t16-,19+,20-,21+,22-,23-,24-,25+,27+,28-,29-,30+,31+/m1/s1
• InChI Key: GLXUNTFWMNVCKD-SVDYBJNLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₄O₁₀
• Molecular Weight: 576.70 g/mol
• Exact Mass: 576.29344760 g/mol
• Topological Polar Surface Area (TPSA): 141.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.36
• H-Bond Acceptor: 10
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9479	94.79%
Caco-2	-	0.8229	82.29%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8609	86.09%
OATP2B1 inhibitior	-	0.7145	71.45%
OATP1B1 inhibitior	+	0.8685	86.85%
OATP1B3 inhibitior	+	0.9421	94.21%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8416	84.16%
P-glycoprotein inhibitior	+	0.6600	66.00%
P-glycoprotein substrate	+	0.7107	71.07%
CYP3A4 substrate	+	0.7287	72.87%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9051	90.51%
CYP3A4 inhibition	-	0.6910	69.10%
CYP2C9 inhibition	-	0.9049	90.49%
CYP2C19 inhibition	-	0.9393	93.93%
CYP2D6 inhibition	-	0.9550	95.50%
CYP1A2 inhibition	-	0.9137	91.37%
CYP2C8 inhibition	+	0.5558	55.58%
CYP inhibitory promiscuity	-	0.9075	90.75%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4722	47.22%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9346	93.46%
Skin irritation	+	0.5387	53.87%
Skin corrosion	-	0.9427	94.27%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3627	36.27%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.5217	52.17%
skin sensitisation	-	0.9365	93.65%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.7255	72.55%
Acute Oral Toxicity (c)	I	0.8907	89.07%
Estrogen receptor binding	+	0.7465	74.65%
Androgen receptor binding	+	0.8015	80.15%
Thyroid receptor binding	-	0.6207	62.07%
Glucocorticoid receptor binding	+	0.6104	61.04%
Aromatase binding	+	0.7143	71.43%
PPAR gamma	+	0.5580	55.80%
Honey bee toxicity	-	0.6689	66.89%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9659	96.59%

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	99.18%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.95%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.66%	91.11%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	95.64%	82.69%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.52%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	94.00%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.98%	97.25%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.66%	96.77%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.26%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.90%	97.09%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	89.89%	93.04%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.51%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.21%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.00%	95.56%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	85.84%	81.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.64%	94.00%
CHEMBL4208	P20618	Proteasome component C5	85.59%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.42%	89.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.21%	97.28%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.04%	96.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.32%	95.89%

Plants that contains it

• Anemone narcissiflora
• Asclepias curassavica
• Hyperbaena columbica
• Viburnum lantanoides

Cross-Links

• PubChem: 10370921
• NPASS: NPC277058
• LOTUS: LTS0107908
• wikiData: Q105011421