methyl (1E,3R,5Z,8Z)-3-acetyloxy-4,4,8-trimethyl-7-oxocycloundeca-1,5,8-triene-1-carboxylate

Details

• Internal ID: e50a9333-e655-4f9a-ad45-fb07c0df4268
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: methyl (1E,3R,5Z,8Z)-3-acetyloxy-4,4,8-trimethyl-7-oxocycloundeca-1,5,8-triene-1-carboxylate
• SMILES (Canonical): CC1=CCCC(=CC(C(C=CC1=O)(C)C)OC(=O)C)C(=O)OC
• SMILES (Isomeric): C/C/1=C/CC/C(=C\[C@H](C(/C=C\C1=O)(C)C)OC(=O)C)/C(=O)OC
• InChI: InChI=1S/C18H24O5/c1-12-7-6-8-14(17(21)22-5)11-16(23-13(2)19)18(3,4)10-9-15(12)20/h7,9-11,16H,6,8H2,1-5H3/b10-9-,12-7-,14-11+/t16-/m1/s1
• InChI Key: CLNDAYOHEVNSFF-JSMVRMJPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₄O₅
• Molecular Weight: 320.40 g/mol
• Exact Mass: 320.16237386 g/mol
• Topological Polar Surface Area (TPSA): 69.70 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.91
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9892	98.92%
Caco-2	+	0.9050	90.50%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7577	75.77%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9188	91.88%
OATP1B3 inhibitior	+	0.9356	93.56%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5557	55.57%
P-glycoprotein inhibitior	-	0.6446	64.46%
P-glycoprotein substrate	-	0.8168	81.68%
CYP3A4 substrate	+	0.6595	65.95%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9059	90.59%
CYP3A4 inhibition	-	0.8425	84.25%
CYP2C9 inhibition	-	0.8533	85.33%
CYP2C19 inhibition	-	0.8375	83.75%
CYP2D6 inhibition	-	0.9195	91.95%
CYP1A2 inhibition	-	0.7523	75.23%
CYP2C8 inhibition	-	0.7111	71.11%
CYP inhibitory promiscuity	-	0.8840	88.40%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7496	74.96%
Carcinogenicity (trinary)	Non-required	0.6219	62.19%
Eye corrosion	-	0.9552	95.52%
Eye irritation	-	0.7874	78.74%
Skin irritation	-	0.5900	59.00%
Skin corrosion	-	0.9733	97.33%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8230	82.30%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.7125	71.25%
skin sensitisation	+	0.5000	50.00%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	-	0.5889	58.89%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	+	0.7141	71.41%
Acute Oral Toxicity (c)	III	0.7948	79.48%
Estrogen receptor binding	+	0.7369	73.69%
Androgen receptor binding	-	0.7305	73.05%
Thyroid receptor binding	-	0.6225	62.25%
Glucocorticoid receptor binding	-	0.5181	51.81%
Aromatase binding	+	0.5367	53.67%
PPAR gamma	+	0.5624	56.24%
Honey bee toxicity	-	0.8722	87.22%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	+	0.9538	95.38%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	97.39%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.79%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.50%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.70%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.07%	94.45%
CHEMBL2581	P07339	Cathepsin D	87.34%	98.95%
CHEMBL4208	P20618	Proteasome component C5	86.22%	90.00%
CHEMBL340	P08684	Cytochrome P450 3A4	85.44%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.82%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.23%	99.23%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.13%	93.40%
CHEMBL5028	O14672	ADAM10	80.88%	97.50%

Plants that contains it

• Asteriscus graveolens

Cross-Links

• PubChem: 163003405
• LOTUS: LTS0063258
• wikiData: Q104963647