[5-ethenyl-1-oxo-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl] (2E,6Z)-8-hydroxy-2,6-dimethylocta-2,6-dienoate

Details

• Internal ID: 86be1cdf-ff71-41ab-89ac-f8001904aa1c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [5-ethenyl-1-oxo-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl] (2E,6Z)-8-hydroxy-2,6-dimethylocta-2,6-dienoate
• SMILES (Canonical): CC(=CCO)CCC=C(C)C(=O)OC1CC2C(C(OC=C2C(=O)O1)OC3C(C(C(C(O3)CO)O)O)O)C=C
• SMILES (Isomeric): C/C(=C/CO)/CC/C=C(\C)/C(=O)OC1CC2C(C(OC=C2C(=O)O1)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C=C
• InChI: InChI=1S/C26H36O12/c1-4-15-16-10-19(36-23(32)14(3)7-5-6-13(2)8-9-27)37-24(33)17(16)12-34-25(15)38-26-22(31)21(30)20(29)18(11-28)35-26/h4,7-8,12,15-16,18-22,25-31H,1,5-6,9-11H2,2-3H3/b13-8-,14-7+/t15?,16?,18-,19?,20-,21+,22-,25?,26+/m1/s1
• InChI Key: BGEODRYTLBLROB-WVKCPNKLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₆O₁₂
• Molecular Weight: 540.60 g/mol
• Exact Mass: 540.22067658 g/mol
• Topological Polar Surface Area (TPSA): 181.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): -0.06
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5587	55.87%
Caco-2	-	0.8678	86.78%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8482	84.82%
OATP2B1 inhibitior	-	0.8628	86.28%
OATP1B1 inhibitior	+	0.8117	81.17%
OATP1B3 inhibitior	+	0.8359	83.59%
MATE1 inhibitior	-	0.8812	88.12%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.7620	76.20%
P-glycoprotein inhibitior	-	0.4671	46.71%
P-glycoprotein substrate	-	0.6443	64.43%
CYP3A4 substrate	+	0.6816	68.16%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8822	88.22%
CYP3A4 inhibition	-	0.7502	75.02%
CYP2C9 inhibition	-	0.9082	90.82%
CYP2C19 inhibition	-	0.8800	88.00%
CYP2D6 inhibition	-	0.9206	92.06%
CYP1A2 inhibition	-	0.7826	78.26%
CYP2C8 inhibition	+	0.5309	53.09%
CYP inhibitory promiscuity	-	0.9495	94.95%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7081	70.81%
Eye corrosion	-	0.9870	98.70%
Eye irritation	-	0.9202	92.02%
Skin irritation	-	0.6629	66.29%
Skin corrosion	-	0.9459	94.59%
Ames mutagenesis	-	0.6170	61.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6883	68.83%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.7267	72.67%
skin sensitisation	-	0.9019	90.19%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.7120	71.20%
Acute Oral Toxicity (c)	III	0.6324	63.24%
Estrogen receptor binding	+	0.7939	79.39%
Androgen receptor binding	+	0.5955	59.55%
Thyroid receptor binding	-	0.5748	57.48%
Glucocorticoid receptor binding	-	0.4682	46.82%
Aromatase binding	+	0.5438	54.38%
PPAR gamma	+	0.6654	66.54%
Honey bee toxicity	-	0.7350	73.50%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9825	98.25%

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	96.48%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.07%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.00%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.89%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.77%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.47%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	90.03%	94.73%
CHEMBL2581	P07339	Cathepsin D	87.60%	98.95%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	87.03%	93.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.71%	91.24%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.60%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.97%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.78%	97.25%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.20%	99.17%
CHEMBL340	P08684	Cytochrome P450 3A4	83.66%	91.19%
CHEMBL5255	O00206	Toll-like receptor 4	83.33%	92.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.82%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.36%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.85%	94.45%

Plants that contains it

• Foeniculum vulgare
• Menyanthes trifoliata

Cross-Links

• PubChem: 5317365
• NPASS: NPC120590
• LOTUS: LTS0082644
• wikiData: Q105100661