[(1R,3R,5R,8R,9S,10S,13R,14S,17R)-3-[(2R,3R,4R,5R,6S)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-1-yl] acetate

Details

• Internal ID: ae0a9665-12d3-4707-8315-46e6ec37d69c
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: [(1R,3R,5R,8R,9S,10S,13R,14S,17R)-3-[(2R,3R,4R,5R,6S)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-1-yl] acetate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CC3CCC4C(C3(C(C2)OC(=O)C)C)CCC5(C4(CCC5C6=CC(=O)OC6)O)C)O)OC)O
• SMILES (Isomeric): C[C@H]1[C@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2C[C@H]3CC[C@@H]4[C@@H]([C@]3([C@@H](C2)OC(=O)C)C)CC[C@]5([C@@]4(CC[C@@H]5C6=CC(=O)OC6)O)C)O)OC)O
• InChI: InChI=1S/C32H48O10/c1-16-26(35)28(38-5)27(36)29(40-16)42-20-13-19-6-7-23-22(31(19,4)24(14-20)41-17(2)33)8-10-30(3)21(9-11-32(23,30)37)18-12-25(34)39-15-18/h12,16,19-24,26-29,35-37H,6-11,13-15H2,1-5H3/t16-,19+,20+,21+,22-,23+,24+,26+,27+,28+,29-,30+,31-,32-/m0/s1
• InChI Key: NTCQLIABTKPIND-ALQIMMJZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₈O₁₀
• Molecular Weight: 592.70 g/mol
• Exact Mass: 592.32474772 g/mol
• Topological Polar Surface Area (TPSA): 141.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.65
• H-Bond Acceptor: 10
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9507	95.07%
Caco-2	-	0.8475	84.75%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7993	79.93%
OATP2B1 inhibitior	-	0.5856	58.56%
OATP1B1 inhibitior	+	0.9240	92.40%
OATP1B3 inhibitior	+	0.9765	97.65%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8614	86.14%
BSEP inhibitior	+	0.6012	60.12%
P-glycoprotein inhibitior	+	0.6828	68.28%
P-glycoprotein substrate	+	0.7062	70.62%
CYP3A4 substrate	+	0.7250	72.50%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9071	90.71%
CYP3A4 inhibition	-	0.8667	86.67%
CYP2C9 inhibition	-	0.9068	90.68%
CYP2C19 inhibition	-	0.9471	94.71%
CYP2D6 inhibition	-	0.9473	94.73%
CYP1A2 inhibition	-	0.9330	93.30%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.9265	92.65%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5140	51.40%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9333	93.33%
Skin irritation	-	0.5328	53.28%
Skin corrosion	-	0.9349	93.49%
Ames mutagenesis	-	0.6834	68.34%
Human Ether-a-go-go-Related Gene inhibition	+	0.6467	64.67%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.9124	91.24%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.7618	76.18%
Acute Oral Toxicity (c)	I	0.8350	83.50%
Estrogen receptor binding	+	0.7748	77.48%
Androgen receptor binding	+	0.8053	80.53%
Thyroid receptor binding	-	0.6367	63.67%
Glucocorticoid receptor binding	+	0.7596	75.96%
Aromatase binding	+	0.6779	67.79%
PPAR gamma	+	0.6233	62.33%
Honey bee toxicity	-	0.6445	64.45%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9625	96.25%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.80%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.50%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.46%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.70%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	94.36%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.14%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.89%	85.14%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	93.52%	81.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.69%	96.77%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.75%	97.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.56%	97.36%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.98%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.22%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.05%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.77%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.94%	82.69%
CHEMBL5255	O00206	Toll-like receptor 4	85.71%	92.50%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.59%	93.04%
CHEMBL2581	P07339	Cathepsin D	83.53%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	83.46%	91.19%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.35%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.61%	97.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.16%	92.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.41%	99.23%
CHEMBL4208	P20618	Proteasome component C5	80.35%	90.00%

Plants that contains it

• Acokanthera oblongifolia

Cross-Links

• PubChem: 20055382
• LOTUS: LTS0001845
• wikiData: Q104667988