methyl 2-(8a-hydroperoxy-7-hydroxy-4a-methyl-8-methylidene-2,3,4,5,6,7-hexahydro-1H-naphthalen-2-yl)prop-2-enoate

Details

• Internal ID: 8bd1696e-1858-44fd-bed2-bc3cf47e0180
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: methyl 2-(8a-hydroperoxy-7-hydroxy-4a-methyl-8-methylidene-2,3,4,5,6,7-hexahydro-1H-naphthalen-2-yl)prop-2-enoate
• SMILES (Canonical): CC12CCC(CC1(C(=C)C(CC2)O)OO)C(=C)C(=O)OC
• SMILES (Isomeric): CC12CCC(CC1(C(=C)C(CC2)O)OO)C(=C)C(=O)OC
• InChI: InChI=1S/C16H24O5/c1-10(14(18)20-4)12-5-7-15(3)8-6-13(17)11(2)16(15,9-12)21-19/h12-13,17,19H,1-2,5-9H2,3-4H3
• InChI Key: HYYDXRPFQYGMRO-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₄O₅
• Molecular Weight: 296.36 g/mol
• Exact Mass: 296.16237386 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.46
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9836	98.36%
Caco-2	+	0.7175	71.75%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7425	74.25%
OATP2B1 inhibitior	-	0.8545	85.45%
OATP1B1 inhibitior	+	0.8892	88.92%
OATP1B3 inhibitior	+	0.8591	85.91%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8240	82.40%
BSEP inhibitior	-	0.8849	88.49%
P-glycoprotein inhibitior	-	0.9014	90.14%
P-glycoprotein substrate	-	0.7481	74.81%
CYP3A4 substrate	+	0.6289	62.89%
CYP2C9 substrate	-	0.8176	81.76%
CYP2D6 substrate	-	0.8439	84.39%
CYP3A4 inhibition	-	0.7748	77.48%
CYP2C9 inhibition	-	0.8220	82.20%
CYP2C19 inhibition	-	0.7806	78.06%
CYP2D6 inhibition	-	0.9255	92.55%
CYP1A2 inhibition	-	0.7112	71.12%
CYP2C8 inhibition	-	0.7144	71.44%
CYP inhibitory promiscuity	-	0.9129	91.29%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8543	85.43%
Carcinogenicity (trinary)	Non-required	0.5969	59.69%
Eye corrosion	-	0.9831	98.31%
Eye irritation	-	0.5000	50.00%
Skin irritation	-	0.5967	59.67%
Skin corrosion	-	0.8942	89.42%
Ames mutagenesis	-	0.6274	62.74%
Human Ether-a-go-go-Related Gene inhibition	+	0.6968	69.68%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.7318	73.18%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.8556	85.56%
Acute Oral Toxicity (c)	III	0.3574	35.74%
Estrogen receptor binding	+	0.5291	52.91%
Androgen receptor binding	+	0.6234	62.34%
Thyroid receptor binding	-	0.5644	56.44%
Glucocorticoid receptor binding	+	0.6585	65.85%
Aromatase binding	+	0.6315	63.15%
PPAR gamma	-	0.5364	53.64%
Honey bee toxicity	-	0.7989	79.89%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9947	99.47%

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	96.81%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.13%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	89.49%	90.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.43%	95.89%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	86.66%	91.03%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.67%	97.25%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.76%	91.07%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	84.40%	95.71%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.18%	94.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.50%	97.14%

Plants that contains it

• Eriocephalus pauperrimus

Cross-Links

• PubChem: 13895635
• LOTUS: LTS0148352
• wikiData: Q105035537