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

Details

• Internal ID: e6a275c7-5ee1-4972-b45a-3af6384485f7
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-(3,4,5-trihydroxyoxan-2-yl)oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
• SMILES (Canonical): CC12CCC3C(C1(CCC2C4=CC(=O)OC4)O)CCC5(C3(CCC(C5)OC6C(C(C(CO6)O)O)O)C=O)O
• SMILES (Isomeric): CC12CCC3C(C1(CCC2C4=CC(=O)OC4)O)CCC5(C3(CCC(C5)OC6C(C(C(CO6)O)O)O)C=O)O
• InChI: InChI=1S/C28H40O10/c1-25-6-3-18-19(28(25,35)9-5-17(25)15-10-21(31)36-12-15)4-8-27(34)11-16(2-7-26(18,27)14-29)38-24-23(33)22(32)20(30)13-37-24/h10,14,16-20,22-24,30,32-35H,2-9,11-13H2,1H3
• InChI Key: XMNREHIXCIWCGI-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₀O₁₀
• Molecular Weight: 536.60 g/mol
• Exact Mass: 536.26214747 g/mol
• Topological Polar Surface Area (TPSA): 163.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): 0.36
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8651	86.51%
Caco-2	-	0.8687	86.87%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8634	86.34%
OATP2B1 inhibitior	-	0.7284	72.84%
OATP1B1 inhibitior	+	0.9330	93.30%
OATP1B3 inhibitior	+	0.9689	96.89%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.4818	48.18%
P-glycoprotein inhibitior	-	0.5492	54.92%
P-glycoprotein substrate	+	0.6327	63.27%
CYP3A4 substrate	+	0.7069	70.69%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8978	89.78%
CYP3A4 inhibition	-	0.9595	95.95%
CYP2C9 inhibition	-	0.9124	91.24%
CYP2C19 inhibition	-	0.9090	90.90%
CYP2D6 inhibition	-	0.9294	92.94%
CYP1A2 inhibition	-	0.9078	90.78%
CYP2C8 inhibition	+	0.4446	44.46%
CYP inhibitory promiscuity	-	0.9619	96.19%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5249	52.49%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9440	94.40%
Skin irritation	-	0.5954	59.54%
Skin corrosion	-	0.9296	92.96%
Ames mutagenesis	+	0.5130	51.30%
Human Ether-a-go-go-Related Gene inhibition	+	0.8136	81.36%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.7214	72.14%
skin sensitisation	-	0.9049	90.49%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.8126	81.26%
Acute Oral Toxicity (c)	I	0.7349	73.49%
Estrogen receptor binding	+	0.8381	83.81%
Androgen receptor binding	+	0.8040	80.40%
Thyroid receptor binding	-	0.5933	59.33%
Glucocorticoid receptor binding	+	0.6197	61.97%
Aromatase binding	+	0.7049	70.49%
PPAR gamma	+	0.5270	52.70%
Honey bee toxicity	-	0.7448	74.48%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9745	97.45%

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	98.12%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.55%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.96%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.33%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.15%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.96%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	90.69%	82.69%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.20%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.12%	97.09%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	89.35%	83.57%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.28%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.21%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.06%	95.89%
CHEMBL2581	P07339	Cathepsin D	86.93%	98.95%
CHEMBL4208	P20618	Proteasome component C5	84.92%	90.00%
CHEMBL226	P30542	Adenosine A1 receptor	84.61%	95.93%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.62%	97.14%
CHEMBL1871	P10275	Androgen Receptor	82.12%	96.43%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.62%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.26%	89.00%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	80.72%	92.88%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	80.61%	94.78%

Plants that contains it

• Saussurea stella

Cross-Links

• PubChem: 3727251
• LOTUS: LTS0176419
• wikiData: Q105331245