3-[5-[4-[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3,5-dihydroxyoxan-2-yl]oxy-3,4-dihydroxy-6-methyloxan-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: 35f2ef48-37f8-4f14-8929-3f4997e3b171
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 3-[5-[4-[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3,5-dihydroxyoxan-2-yl]oxy-3,4-dihydroxy-6-methyloxan-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(C(C(O1)OC2CCC3(C4CCC5(C(CCC5(C4CCC3(C2)O)O)C6=CC(=O)OC6)C)C=O)O)O)OC7C(C(C(CO7)O)OC8C(C(CO8)(CO)O)O)O
• SMILES (Isomeric): CC1C(C(C(C(O1)OC2CCC3(C4CCC5(C(CCC5(C4CCC3(C2)O)O)C6=CC(=O)OC6)C)C=O)O)O)OC7C(C(C(CO7)O)OC8C(C(CO8)(CO)O)O)O
• InChI: InChI=1S/C39H58O18/c1-18-29(56-32-28(46)30(24(42)14-52-32)57-34-31(47)37(48,16-41)17-53-34)26(44)27(45)33(54-18)55-20-3-8-36(15-40)22-4-7-35(2)21(19-11-25(43)51-13-19)6-10-39(35,50)23(22)5-9-38(36,49)12-20/h11,15,18,20-24,26-34,41-42,44-50H,3-10,12-14,16-17H2,1-2H3
• InChI Key: ZRLWFBSPJOLFST-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₅₈O₁₈
• Molecular Weight: 814.90 g/mol
• Exact Mass: 814.36231500 g/mol
• Topological Polar Surface Area (TPSA): 281.00 Ų
• XlogP: -3.40
• Atomic LogP (AlogP): -2.32
• H-Bond Acceptor: 18
• H-Bond Donor: 9
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7963	79.63%
Caco-2	-	0.8817	88.17%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8579	85.79%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8936	89.36%
OATP1B3 inhibitior	+	0.9593	95.93%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8018	80.18%
P-glycoprotein inhibitior	+	0.7171	71.71%
P-glycoprotein substrate	+	0.7335	73.35%
CYP3A4 substrate	+	0.7335	73.35%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8962	89.62%
CYP3A4 inhibition	-	0.8731	87.31%
CYP2C9 inhibition	-	0.9132	91.32%
CYP2C19 inhibition	-	0.9341	93.41%
CYP2D6 inhibition	-	0.9343	93.43%
CYP1A2 inhibition	-	0.9128	91.28%
CYP2C8 inhibition	+	0.6576	65.76%
CYP inhibitory promiscuity	-	0.9382	93.82%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5864	58.64%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9154	91.54%
Skin irritation	-	0.5515	55.15%
Skin corrosion	-	0.9392	93.92%
Ames mutagenesis	+	0.5330	53.30%
Human Ether-a-go-go-Related Gene inhibition	+	0.8400	84.00%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6227	62.27%
skin sensitisation	-	0.9252	92.52%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.7331	73.31%
Acute Oral Toxicity (c)	I	0.8538	85.38%
Estrogen receptor binding	+	0.8301	83.01%
Androgen receptor binding	+	0.7889	78.89%
Thyroid receptor binding	-	0.5871	58.71%
Glucocorticoid receptor binding	+	0.6575	65.75%
Aromatase binding	+	0.6696	66.96%
PPAR gamma	+	0.7288	72.88%
Honey bee toxicity	-	0.6779	67.79%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9644	96.44%

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	98.58%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	98.22%	95.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.25%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.23%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.14%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.51%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.45%	94.45%
CHEMBL3714130	P46095	G-protein coupled receptor 6	93.15%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.41%	97.09%
CHEMBL2581	P07339	Cathepsin D	91.00%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.64%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.78%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.65%	97.25%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.12%	82.69%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.90%	96.77%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	87.49%	91.71%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.04%	86.92%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.66%	92.94%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.62%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.11%	99.23%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	84.54%	83.57%
CHEMBL4208	P20618	Proteasome component C5	84.31%	90.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.22%	91.24%
CHEMBL1937	Q92769	Histone deacetylase 2	82.87%	94.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.62%	94.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.41%	97.14%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.25%	94.33%
CHEMBL4530	P00488	Coagulation factor XIII	80.13%	96.00%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	80.01%	92.88%

Plants that contains it

• Ornithogalum nutans

Cross-Links

• PubChem: 162868431
• LOTUS: LTS0229260
• wikiData: Q105382078