methyl 2-(3-acetyloxy-5-hydroxy-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-2-yl)prop-2-enoate

Details

• Internal ID: 7256b682-c79d-4ef4-80af-6b1b1601b8b5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: methyl 2-(3-acetyloxy-5-hydroxy-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-2-yl)prop-2-enoate
• SMILES (Canonical): CC1=CCC(C2(C1CC(C(C2)OC(=O)C)C(=C)C(=O)OC)C)O
• SMILES (Isomeric): CC1=CCC(C2(C1CC(C(C2)OC(=O)C)C(=C)C(=O)OC)C)O
• InChI: InChI=1S/C18H26O5/c1-10-6-7-16(20)18(4)9-15(23-12(3)19)13(8-14(10)18)11(2)17(21)22-5/h6,13-16,20H,2,7-9H2,1,3-5H3
• InChI Key: JNQCIRWNUNNIAF-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₆O₅
• Molecular Weight: 322.40 g/mol
• Exact Mass: 322.17802393 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.39
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9925	99.25%
Caco-2	+	0.6919	69.19%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8034	80.34%
OATP2B1 inhibitior	-	0.8595	85.95%
OATP1B1 inhibitior	+	0.9095	90.95%
OATP1B3 inhibitior	+	0.7978	79.78%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.7788	77.88%
P-glycoprotein inhibitior	-	0.7026	70.26%
P-glycoprotein substrate	-	0.6722	67.22%
CYP3A4 substrate	+	0.6824	68.24%
CYP2C9 substrate	-	0.8074	80.74%
CYP2D6 substrate	-	0.8798	87.98%
CYP3A4 inhibition	+	0.5111	51.11%
CYP2C9 inhibition	-	0.8767	87.67%
CYP2C19 inhibition	-	0.8694	86.94%
CYP2D6 inhibition	-	0.9560	95.60%
CYP1A2 inhibition	-	0.8455	84.55%
CYP2C8 inhibition	-	0.7187	71.87%
CYP inhibitory promiscuity	-	0.9589	95.89%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	0.9256	92.56%
Carcinogenicity (trinary)	Non-required	0.6611	66.11%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.8604	86.04%
Skin irritation	+	0.4941	49.41%
Skin corrosion	-	0.9641	96.41%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3751	37.51%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.6801	68.01%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.5119	51.19%
Acute Oral Toxicity (c)	III	0.5845	58.45%
Estrogen receptor binding	+	0.7145	71.45%
Androgen receptor binding	+	0.5347	53.47%
Thyroid receptor binding	+	0.5432	54.32%
Glucocorticoid receptor binding	+	0.6935	69.35%
Aromatase binding	-	0.7221	72.21%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.6163	61.63%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	97.56%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.45%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.03%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.38%	85.14%
CHEMBL340	P08684	Cytochrome P450 3A4	89.79%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.45%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.21%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.69%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.63%	96.95%
CHEMBL221	P23219	Cyclooxygenase-1	81.40%	90.17%
CHEMBL5028	O14672	ADAM10	81.17%	97.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.51%	99.23%
CHEMBL4208	P20618	Proteasome component C5	80.33%	90.00%

Plants that contains it

• Inula japonica

Cross-Links

• PubChem: 163089611
• LOTUS: LTS0115662
• wikiData: Q105132065