(3S,5S,8R,9S,10S,12R,13S,14S,17R)-3-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-methoxy-6-methyloxan-2-yl]oxy-5,12,14-trihydroxy-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: 607c5840-00ca-4547-b08b-a58f49d58f9d
• 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,12R,13S,14S,17R)-3-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-methoxy-6-methyloxan-2-yl]oxy-5,12,14-trihydroxy-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(C4CC(C5(C(CCC5(C4CCC3(C2)O)O)C6=CC(=O)OC6)C)O)C=O)OC)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]4C[C@H]([C@@]5([C@H](CC[C@@]5([C@@H]4CC[C@@]3(C2)O)O)C6=CC(=O)OC6)C)O)C=O)OC)O)O
• InChI: InChI=1S/C30H44O11/c1-15-23(34)24(35)25(38-3)26(40-15)41-17-4-7-28(14-31)20-11-21(32)27(2)18(16-10-22(33)39-13-16)6-9-30(27,37)19(20)5-8-29(28,36)12-17/h10,14-15,17-21,23-26,32,34-37H,4-9,11-13H2,1-3H3/t15-,17+,18-,19-,20+,21-,23-,24-,25-,26+,27+,28+,29+,30+/m1/s1
• InChI Key: WUAYGHQTMPWDRU-LBJUOORFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₄O₁₁
• Molecular Weight: 580.70 g/mol
• Exact Mass: 580.28836222 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): 0.37
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8773	87.73%
Caco-2	-	0.8498	84.98%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8179	81.79%
OATP2B1 inhibitior	-	0.7343	73.43%
OATP1B1 inhibitior	+	0.9247	92.47%
OATP1B3 inhibitior	+	0.9747	97.47%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.5706	57.06%
P-glycoprotein inhibitior	+	0.6081	60.81%
P-glycoprotein substrate	+	0.7662	76.62%
CYP3A4 substrate	+	0.6978	69.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8975	89.75%
CYP3A4 inhibition	-	0.9409	94.09%
CYP2C9 inhibition	-	0.9118	91.18%
CYP2C19 inhibition	-	0.9370	93.70%
CYP2D6 inhibition	-	0.9374	93.74%
CYP1A2 inhibition	-	0.9285	92.85%
CYP2C8 inhibition	-	0.6238	62.38%
CYP inhibitory promiscuity	-	0.9569	95.69%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5473	54.73%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9380	93.80%
Skin irritation	-	0.5736	57.36%
Skin corrosion	-	0.9317	93.17%
Ames mutagenesis	-	0.5070	50.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7948	79.48%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8928	89.28%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.8426	84.26%
Acute Oral Toxicity (c)	I	0.7173	71.73%
Estrogen receptor binding	+	0.7971	79.71%
Androgen receptor binding	+	0.8084	80.84%
Thyroid receptor binding	-	0.5844	58.44%
Glucocorticoid receptor binding	+	0.6758	67.58%
Aromatase binding	+	0.6697	66.97%
PPAR gamma	+	0.5496	54.96%
Honey bee toxicity	-	0.7103	71.03%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9348	93.48%

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	98.82%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.69%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.05%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.09%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.82%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.62%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.59%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.39%	85.14%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.14%	97.36%
CHEMBL226	P30542	Adenosine A1 receptor	89.63%	95.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.24%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.99%	89.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.78%	82.69%
CHEMBL4208	P20618	Proteasome component C5	86.21%	90.00%
CHEMBL1871	P10275	Androgen Receptor	85.54%	96.43%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.17%	99.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.21%	96.00%
CHEMBL3492	P49721	Proteasome Macropain subunit	83.04%	90.24%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.57%	92.94%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.38%	97.14%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.74%	94.80%
CHEMBL1937	Q92769	Histone deacetylase 2	81.53%	94.75%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	81.17%	86.00%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	80.95%	92.88%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.79%	95.89%
CHEMBL2581	P07339	Cathepsin D	80.51%	98.95%

Plants that contains it

• Antiaris toxicaria

Cross-Links

• PubChem: 154496158
• LOTUS: LTS0136656
• wikiData: Q105312940