[5-formyl-4,8-dihydroxy-3-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-2,3,4,4a,5,6,7,8-octahydro-1H-naphthalen-2-yl] 2-(hydroxymethyl)prop-2-enoate

Details

• Internal ID: 91898351-e52e-4a0f-b8c3-69369073ab3d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: [5-formyl-4,8-dihydroxy-3-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-2,3,4,4a,5,6,7,8-octahydro-1H-naphthalen-2-yl] 2-(hydroxymethyl)prop-2-enoate
• SMILES (Canonical): CC12CC(C(C(C1C(CCC2O)C=O)O)C(=C)C(=O)OC)OC(=O)C(=C)CO
• SMILES (Isomeric): CC12CC(C(C(C1C(CCC2O)C=O)O)C(=C)C(=O)OC)OC(=O)C(=C)CO
• InChI: InChI=1S/C20H28O8/c1-10(8-21)18(25)28-13-7-20(3)14(23)6-5-12(9-22)16(20)17(24)15(13)11(2)19(26)27-4/h9,12-17,21,23-24H,1-2,5-8H2,3-4H3
• InChI Key: AXTHWXPLSBCNCK-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₈
• Molecular Weight: 396.40 g/mol
• Exact Mass: 396.17841785 g/mol
• Topological Polar Surface Area (TPSA): 130.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.15
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9814	98.14%
Caco-2	-	0.6936	69.36%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8586	85.86%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8931	89.31%
OATP1B3 inhibitior	+	0.8752	87.52%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.5815	58.15%
BSEP inhibitior	-	0.7569	75.69%
P-glycoprotein inhibitior	-	0.6790	67.90%
P-glycoprotein substrate	+	0.5359	53.59%
CYP3A4 substrate	+	0.6958	69.58%
CYP2C9 substrate	-	0.8111	81.11%
CYP2D6 substrate	-	0.8801	88.01%
CYP3A4 inhibition	-	0.5799	57.99%
CYP2C9 inhibition	-	0.8504	85.04%
CYP2C19 inhibition	-	0.8796	87.96%
CYP2D6 inhibition	-	0.9371	93.71%
CYP1A2 inhibition	-	0.7781	77.81%
CYP2C8 inhibition	-	0.6000	60.00%
CYP inhibitory promiscuity	-	0.9211	92.11%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7146	71.46%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.9486	94.86%
Skin irritation	-	0.5857	58.57%
Skin corrosion	-	0.9628	96.28%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6465	64.65%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.6325	63.25%
skin sensitisation	-	0.8827	88.27%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.6499	64.99%
Acute Oral Toxicity (c)	III	0.5541	55.41%
Estrogen receptor binding	+	0.8038	80.38%
Androgen receptor binding	+	0.5614	56.14%
Thyroid receptor binding	-	0.4926	49.26%
Glucocorticoid receptor binding	+	0.6951	69.51%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.5783	57.83%
Honey bee toxicity	-	0.7293	72.93%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9922	99.22%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.40%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.15%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	90.79%	95.93%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	89.90%	94.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.12%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	88.89%	91.19%
CHEMBL204	P00734	Thrombin	88.25%	96.01%
CHEMBL1871	P10275	Androgen Receptor	88.24%	96.43%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.10%	99.17%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	87.07%	92.88%
CHEMBL2243	O00519	Anandamide amidohydrolase	86.75%	97.53%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.19%	95.50%
CHEMBL3437	Q16853	Amine oxidase, copper containing	85.66%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.29%	100.00%
CHEMBL5028	O14672	ADAM10	85.25%	97.50%
CHEMBL221	P23219	Cyclooxygenase-1	85.13%	90.17%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	84.13%	95.71%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	83.93%	97.47%
CHEMBL2581	P07339	Cathepsin D	83.40%	98.95%
CHEMBL2664	P23526	Adenosylhomocysteinase	83.21%	86.67%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.72%	95.89%
CHEMBL5600	P27448	Serine/threonine-protein kinase c-TAK1	82.62%	88.81%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.45%	91.24%
CHEMBL203	P00533	Epidermal growth factor receptor erbB1	82.21%	97.34%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.81%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.21%	95.89%

Plants that contains it

• Onopordum carmanicum
• Onopordum illyricum

Cross-Links

• PubChem: 14287841
• LOTUS: LTS0269814
• wikiData: Q104920779