2alpha,3beta-[Oxycarbonyl[(2S)-3-hydroxy-5beta-methyltetrahydrofuran-3beta,2beta-diyl]oxy]-14-hydroxy-19-oxo-5alpha-carda-20(22)-enolide

Details

• Internal ID: 48e6cbed-0c82-4b82-af87-039aa5cabdcc
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives
• IUPAC Name: (1S,3R,5S,7R,9R,12R,14R,15S,18R,19R,22S,23R)-9,22-dihydroxy-7,18-dimethyl-10-oxo-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.03,12.05,9.015,23.018,22]pentacosane-14-carbaldehyde
• SMILES (Canonical): CC1CC2(C(O1)OC3CC4CCC5C(C4(CC3OC2=O)C=O)CCC6(C5(CCC6C7=CC(=O)OC7)O)C)O
• SMILES (Isomeric): C[C@@H]1C[C@]2([C@@H](O1)O[C@@H]3C[C@@H]4CC[C@@H]5[C@@H]([C@]4(C[C@H]3OC2=O)C=O)CC[C@]6([C@@]5(CC[C@@H]6C7=CC(=O)OC7)O)C)O
• InChI: InChI=1S/C29H38O9/c1-15-11-28(33)24(32)37-22-12-27(14-30)17(10-21(22)38-25(28)36-15)3-4-20-19(27)5-7-26(2)18(6-8-29(20,26)34)16-9-23(31)35-13-16/h9,14-15,17-22,25,33-34H,3-8,10-13H2,1-2H3/t15-,17+,18-,19+,20-,21-,22-,25+,26-,27-,28+,29+/m1/s1
• InChI Key: VVJSEPMKQSGCHB-OLEQQPCLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₈O₉
• Molecular Weight: 530.60 g/mol
• Exact Mass: 530.25158279 g/mol
• Topological Polar Surface Area (TPSA): 129.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 2.21
• H-Bond Acceptor: 9
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9865	98.65%
Caco-2	-	0.7786	77.86%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8479	84.79%
OATP2B1 inhibitior	-	0.7162	71.62%
OATP1B1 inhibitior	+	0.8993	89.93%
OATP1B3 inhibitior	+	0.9725	97.25%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7316	73.16%
BSEP inhibitior	+	0.8777	87.77%
P-glycoprotein inhibitior	+	0.6291	62.91%
P-glycoprotein substrate	+	0.7198	71.98%
CYP3A4 substrate	+	0.7078	70.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9053	90.53%
CYP3A4 inhibition	-	0.8233	82.33%
CYP2C9 inhibition	-	0.8691	86.91%
CYP2C19 inhibition	-	0.9334	93.34%
CYP2D6 inhibition	-	0.9509	95.09%
CYP1A2 inhibition	-	0.9183	91.83%
CYP2C8 inhibition	+	0.4817	48.17%
CYP inhibitory promiscuity	-	0.9543	95.43%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Danger	0.4245	42.45%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9396	93.96%
Skin irritation	+	0.5270	52.70%
Skin corrosion	-	0.9238	92.38%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6563	65.63%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.6552	65.52%
skin sensitisation	-	0.9042	90.42%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.6038	60.38%
Acute Oral Toxicity (c)	I	0.5773	57.73%
Estrogen receptor binding	+	0.8039	80.39%
Androgen receptor binding	+	0.8082	80.82%
Thyroid receptor binding	-	0.5367	53.67%
Glucocorticoid receptor binding	+	0.7353	73.53%
Aromatase binding	+	0.7081	70.81%
PPAR gamma	-	0.4931	49.31%
Honey bee toxicity	-	0.7638	76.38%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	+	0.9911	99.11%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.58%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.27%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	94.78%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.28%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.75%	97.25%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.94%	82.69%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.41%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.82%	94.45%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	90.60%	93.40%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.96%	91.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.17%	95.89%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	87.09%	93.04%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.61%	97.09%
CHEMBL4208	P20618	Proteasome component C5	86.59%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.14%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.00%	97.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.06%	96.77%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.78%	92.94%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.41%	93.00%
CHEMBL1871	P10275	Androgen Receptor	83.06%	96.43%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.96%	97.36%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	81.58%	81.11%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	80.91%	94.42%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	80.75%	82.38%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.07%	89.00%

Plants that contains it

• Anemone narcissiflora
• Asclepias curassavica
• Hyperbaena columbica
• Viburnum lantanoides

Cross-Links

• PubChem: 102408526
• NPASS: NPC302087
• LOTUS: LTS0140404
• wikiData: Q105297697