(3S,5S,10S,13R,14S,17R)-3-[(2R,5R)-6-[[(3R,6S)-4,6-dihydroxy-2-methyloxan-3-yl]oxymethyl]-3,5-dihydroxy-4-methoxyoxan-2-yl]oxy-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde

Details

• Internal ID: 806a8924-973b-4590-9f50-38e292d65d13
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: (3S,5S,10S,13R,14S,17R)-3-[(2R,5R)-6-[[(3R,6S)-4,6-dihydroxy-2-methyloxan-3-yl]oxymethyl]-3,5-dihydroxy-4-methoxyoxan-2-yl]oxy-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
• SMILES (Canonical): CC1C(C(CC(O1)O)O)OCC2C(C(C(C(O2)OC3CCC4(C5CCC6(C(CCC6(C5CCC4(C3)O)O)C7=CC(=O)OC7)C)C=O)O)OC)O
• SMILES (Isomeric): CC1[C@@H](C(C[C@H](O1)O)O)OCC2[C@H](C(C([C@@H](O2)O[C@H]3CC[C@@]4(C5CC[C@@]6([C@H](CC[C@@]6(C5CC[C@@]4(C3)O)O)C7=CC(=O)OC7)C)C=O)O)OC)O
• InChI: InChI=1S/C36H54O14/c1-18-30(24(38)13-27(40)48-18)47-16-25-28(41)31(45-3)29(42)32(50-25)49-20-4-9-34(17-37)22-5-8-33(2)21(19-12-26(39)46-15-19)7-11-36(33,44)23(22)6-10-35(34,43)14-20/h12,17-18,20-25,27-32,38,40-44H,4-11,13-16H2,1-3H3/t18?,20-,21+,22?,23?,24?,25?,27-,28+,29?,30-,31?,32+,33+,34-,35-,36-/m0/s1
• InChI Key: WEDKAKRDVPRQSU-AWRXHTBRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₄O₁₄
• Molecular Weight: 710.80 g/mol
• Exact Mass: 710.35135639 g/mol
• Topological Polar Surface Area (TPSA): 211.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): 0.26
• H-Bond Acceptor: 14
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9131	91.31%
Caco-2	-	0.8820	88.20%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8032	80.32%
OATP2B1 inhibitior	-	0.8701	87.01%
OATP1B1 inhibitior	+	0.9032	90.32%
OATP1B3 inhibitior	+	0.9689	96.89%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9173	91.73%
P-glycoprotein inhibitior	+	0.7183	71.83%
P-glycoprotein substrate	+	0.7613	76.13%
CYP3A4 substrate	+	0.7295	72.95%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8909	89.09%
CYP3A4 inhibition	-	0.8985	89.85%
CYP2C9 inhibition	-	0.9074	90.74%
CYP2C19 inhibition	-	0.9304	93.04%
CYP2D6 inhibition	-	0.9504	95.04%
CYP1A2 inhibition	-	0.9408	94.08%
CYP2C8 inhibition	+	0.5797	57.97%
CYP inhibitory promiscuity	-	0.9113	91.13%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5321	53.21%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9242	92.42%
Skin irritation	-	0.5593	55.93%
Skin corrosion	-	0.9400	94.00%
Ames mutagenesis	-	0.5370	53.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7873	78.73%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.6552	65.52%
skin sensitisation	-	0.9224	92.24%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.8619	86.19%
Acute Oral Toxicity (c)	I	0.8655	86.55%
Estrogen receptor binding	+	0.8275	82.75%
Androgen receptor binding	+	0.8029	80.29%
Thyroid receptor binding	-	0.6262	62.62%
Glucocorticoid receptor binding	+	0.6830	68.30%
Aromatase binding	+	0.7034	70.34%
PPAR gamma	+	0.6817	68.17%
Honey bee toxicity	-	0.6670	66.70%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9563	95.63%

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	98.98%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.13%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.33%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.33%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.19%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	96.02%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.99%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.98%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.35%	86.33%
CHEMBL1871	P10275	Androgen Receptor	90.45%	96.43%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.45%	95.56%
CHEMBL5957	P21589	5'-nucleotidase	88.13%	97.78%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.75%	95.89%
CHEMBL4208	P20618	Proteasome component C5	86.06%	90.00%
CHEMBL5255	O00206	Toll-like receptor 4	85.05%	92.50%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.03%	82.69%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.33%	96.77%
CHEMBL2581	P07339	Cathepsin D	83.01%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.58%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.52%	97.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.42%	96.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.66%	91.71%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.15%	92.62%

Plants that contains it

• Adonis mongolica
• Adonis tianschanicus
• Maquira coriacea

Cross-Links

• PubChem: 11218
• LOTUS: LTS0230590
• wikiData: Q105302911