[(2R,3R,4S,5R,6R)-2-[[(3S,5R,8S,9R,10S,13R,14S,17R)-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-3-yl]oxy]-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl] acetate

Details

• Internal ID: 808e8a4d-f78c-4d55-aaf8-94e90b18963d
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: [(2R,3R,4S,5R,6R)-2-[[(3S,5R,8S,9R,10S,13R,14S,17R)-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-3-yl]oxy]-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl] acetate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CCC5C6=CC(=O)OC6)O)C)C)OC(=O)C)OC)OC7C(C(C(C(O7)CO)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@H]2CC[C@]3([C@@H](C2)CC[C@H]4[C@H]3CC[C@]5([C@@]4(CC[C@@H]5C6=CC(=O)OC6)O)C)C)OC(=O)C)OC)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
• InChI: InChI=1S/C38H58O14/c1-18-31(52-34-30(44)29(43)28(42)26(16-39)51-34)32(46-5)33(49-19(2)40)35(48-18)50-22-8-11-36(3)21(15-22)6-7-25-24(36)9-12-37(4)23(10-13-38(25,37)45)20-14-27(41)47-17-20/h14,18,21-26,28-35,39,42-45H,6-13,15-17H2,1-5H3/t18-,21-,22+,23-,24-,25+,26-,28-,29+,30-,31-,32+,33-,34+,35+,36+,37-,38+/m1/s1
• InChI Key: BVEIWCWYYKAMOE-CREZJNJOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₅₈O₁₄
• Molecular Weight: 738.90 g/mol
• Exact Mass: 738.38265652 g/mol
• Topological Polar Surface Area (TPSA): 200.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.51
• H-Bond Acceptor: 14
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7964	79.64%
Caco-2	-	0.8836	88.36%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8047	80.47%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9048	90.48%
OATP1B3 inhibitior	+	0.9615	96.15%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7850	78.50%
P-glycoprotein inhibitior	+	0.7498	74.98%
P-glycoprotein substrate	+	0.7235	72.35%
CYP3A4 substrate	+	0.7327	73.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9026	90.26%
CYP3A4 inhibition	-	0.8841	88.41%
CYP2C9 inhibition	-	0.9054	90.54%
CYP2C19 inhibition	-	0.9238	92.38%
CYP2D6 inhibition	-	0.9467	94.67%
CYP1A2 inhibition	-	0.9221	92.21%
CYP2C8 inhibition	+	0.4886	48.86%
CYP inhibitory promiscuity	-	0.9513	95.13%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5527	55.27%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9226	92.26%
Skin irritation	-	0.5611	56.11%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	-	0.6670	66.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7366	73.66%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.9209	92.09%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.8141	81.41%
Acute Oral Toxicity (c)	I	0.8305	83.05%
Estrogen receptor binding	+	0.7749	77.49%
Androgen receptor binding	+	0.8140	81.40%
Thyroid receptor binding	-	0.6877	68.77%
Glucocorticoid receptor binding	+	0.6669	66.69%
Aromatase binding	+	0.6911	69.11%
PPAR gamma	+	0.7209	72.09%
Honey bee toxicity	-	0.6091	60.91%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9314	93.14%

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	99.22%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.42%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.50%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.84%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.41%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.38%	86.33%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	94.15%	81.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.34%	96.77%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.15%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.83%	94.00%
CHEMBL2581	P07339	Cathepsin D	89.07%	98.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.77%	95.89%
CHEMBL1937	Q92769	Histone deacetylase 2	87.90%	94.75%
CHEMBL5255	O00206	Toll-like receptor 4	87.64%	92.50%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.94%	97.36%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.08%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.99%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.87%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.05%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.90%	96.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.26%	94.33%
CHEMBL226	P30542	Adenosine A1 receptor	81.87%	95.93%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.13%	93.04%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.13%	82.69%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.64%	97.25%

Plants that contains it

• Adenium obesum

Cross-Links

• PubChem: 162864517
• LOTUS: LTS0044057
• wikiData: Q104946480