(3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2R,3R,4R,5R,6R)-3,4,5-trihydroxy-6-methyloxan-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: eeac3c77-a170-402a-84f2-7ba56d938542
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: (3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2R,3R,4R,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-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)O
• SMILES (Isomeric): C[C@@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2CC[C@@]3([C@H]4CC[C@@]5([C@H](CC[C@@]5([C@@H]4CC[C@@]3(C2)O)O)C6=CC(=O)OC6)C)C=O)O)O)O
• InChI: InChI=1S/C29H42O10/c1-15-22(32)23(33)24(34)25(38-15)39-17-3-8-27(14-30)19-4-7-26(2)18(16-11-21(31)37-13-16)6-10-29(26,36)20(19)5-9-28(27,35)12-17/h11,14-15,17-20,22-25,32-36H,3-10,12-13H2,1-2H3/t15-,17+,18-,19+,20-,22+,23-,24-,25+,26-,27+,28+,29+/m1/s1
• InChI Key: HULMNSIAKWANQO-PZXOABCJSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₂O₁₀
• Molecular Weight: 550.60 g/mol
• Exact Mass: 550.27779753 g/mol
• Topological Polar Surface Area (TPSA): 163.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): 0.75
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• (3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2R,3R,4R,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
• 5822-57-1
• CHEMBL1169675
• DTXSID901315590
• AKOS030503046

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9049	90.49%
Caco-2	-	0.8540	85.40%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8685	86.85%
OATP2B1 inhibitior	-	0.7407	74.07%
OATP1B1 inhibitior	+	0.9424	94.24%
OATP1B3 inhibitior	+	0.9699	96.99%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6185	61.85%
P-glycoprotein inhibitior	-	0.4916	49.16%
P-glycoprotein substrate	+	0.5552	55.52%
CYP3A4 substrate	+	0.6952	69.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8978	89.78%
CYP3A4 inhibition	-	0.9010	90.10%
CYP2C9 inhibition	-	0.9147	91.47%
CYP2C19 inhibition	-	0.9441	94.41%
CYP2D6 inhibition	-	0.9327	93.27%
CYP1A2 inhibition	-	0.9305	93.05%
CYP2C8 inhibition	-	0.5828	58.28%
CYP inhibitory promiscuity	-	0.9472	94.72%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5635	56.35%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9448	94.48%
Skin irritation	-	0.5151	51.51%
Skin corrosion	-	0.9270	92.70%
Ames mutagenesis	-	0.6070	60.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.8583	85.83%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.7518	75.18%
skin sensitisation	-	0.9064	90.64%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.7721	77.21%
Acute Oral Toxicity (c)	I	0.8450	84.50%
Estrogen receptor binding	+	0.8368	83.68%
Androgen receptor binding	+	0.8045	80.45%
Thyroid receptor binding	-	0.5805	58.05%
Glucocorticoid receptor binding	+	0.6327	63.27%
Aromatase binding	+	0.6994	69.94%
PPAR gamma	-	0.4868	48.68%
Honey bee toxicity	-	0.7437	74.37%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9827	98.27%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4096	P04637	Cellular tumor antigen p53	39.8 nM	Potency	via Super-PRED
CHEMBL1293232	Q16637	Survival motor neuron protein	223.9 nM; 281.8 nM	Potency; Potency	via Super-PRED; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.26%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.21%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.54%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.71%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.08%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.68%	97.36%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.84%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.43%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.12%	97.09%
CHEMBL4208	P20618	Proteasome component C5	87.97%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.26%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.16%	95.89%
CHEMBL3492	P49721	Proteasome Macropain subunit	86.24%	90.24%
CHEMBL2581	P07339	Cathepsin D	86.05%	98.95%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.99%	92.94%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.78%	91.71%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.42%	96.77%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.94%	93.40%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.61%	85.14%
CHEMBL226	P30542	Adenosine A1 receptor	81.15%	95.93%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	80.11%	94.78%
CHEMBL1871	P10275	Androgen Receptor	80.04%	96.43%

Plants that contains it

• Antiaris toxicaria
• Convallaria majalis
• Erysimum cheiri

Cross-Links

• PubChem: 16401455
• LOTUS: LTS0002016
• wikiData: Q104388059