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

Details

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Internal ID e32fe3cc-ab03-468d-be61-4f8e25b4c2f7
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
IUPAC Name methyl 2-[(2R,4aR,8aR)-8a-hydroperoxy-4a-methyl-8-methylidene-2,3,4,5,6,7-hexahydro-1H-naphthalen-2-yl]prop-2-enoate
SMILES (Canonical) CC12CCCC(=C)C1(CC(CC2)C(=C)C(=O)OC)OO
SMILES (Isomeric) C[C@]12CCCC(=C)[C@@]1(C[C@@H](CC2)C(=C)C(=O)OC)OO
InChI InChI=1S/C16H24O4/c1-11-6-5-8-15(3)9-7-13(10-16(11,15)20-18)12(2)14(17)19-4/h13,18H,1-2,5-10H2,3-4H3/t13-,15-,16-/m1/s1
InChI Key XSFRJTINOXLAHU-FVQBIDKESA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C16H24O4
Molecular Weight 280.36 g/mol
Exact Mass 280.16745924 g/mol
Topological Polar Surface Area (TPSA) 55.80 Ų
XlogP 2.90
Atomic LogP (AlogP) 3.49
H-Bond Acceptor 4
H-Bond Donor 1
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl 2-[(2R,4aR,8aR)-8a-hydroperoxy-4a-methyl-8-methylidene-2,3,4,5,6,7-hexahydro-1H-naphthalen-2-yl]prop-2-enoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9838 98.38%
Caco-2 + 0.8489 84.89%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability + 0.6857 68.57%
Subcellular localzation Mitochondria 0.7717 77.17%
OATP2B1 inhibitior - 0.8535 85.35%
OATP1B1 inhibitior + 0.8906 89.06%
OATP1B3 inhibitior + 0.8620 86.20%
MATE1 inhibitior - 0.7000 70.00%
OCT2 inhibitior - 0.8071 80.71%
BSEP inhibitior - 0.8969 89.69%
P-glycoprotein inhibitior - 0.9038 90.38%
P-glycoprotein substrate - 0.7807 78.07%
CYP3A4 substrate + 0.6071 60.71%
CYP2C9 substrate - 0.8016 80.16%
CYP2D6 substrate - 0.8532 85.32%
CYP3A4 inhibition - 0.6572 65.72%
CYP2C9 inhibition - 0.8362 83.62%
CYP2C19 inhibition - 0.8204 82.04%
CYP2D6 inhibition - 0.9365 93.65%
CYP1A2 inhibition - 0.6597 65.97%
CYP2C8 inhibition - 0.6657 66.57%
CYP inhibitory promiscuity - 0.9004 90.04%
UGT catelyzed + 0.5362 53.62%
Carcinogenicity (binary) - 0.8663 86.63%
Carcinogenicity (trinary) Non-required 0.6147 61.47%
Eye corrosion - 0.9841 98.41%
Eye irritation - 0.5164 51.64%
Skin irritation - 0.5681 56.81%
Skin corrosion - 0.9347 93.47%
Ames mutagenesis - 0.7074 70.74%
Human Ether-a-go-go-Related Gene inhibition + 0.6758 67.58%
Micronuclear - 0.7400 74.00%
Hepatotoxicity - 0.5269 52.69%
skin sensitisation - 0.6866 68.66%
Respiratory toxicity - 0.5444 54.44%
Reproductive toxicity + 0.8778 87.78%
Mitochondrial toxicity + 0.5875 58.75%
Nephrotoxicity + 0.6894 68.94%
Acute Oral Toxicity (c) III 0.6100 61.00%
Estrogen receptor binding - 0.5363 53.63%
Androgen receptor binding + 0.5650 56.50%
Thyroid receptor binding - 0.5839 58.39%
Glucocorticoid receptor binding + 0.5652 56.52%
Aromatase binding + 0.6007 60.07%
PPAR gamma - 0.5158 51.58%
Honey bee toxicity - 0.8025 80.25%
Biodegradation - 0.6750 67.50%
Crustacea aquatic toxicity + 0.5100 51.00%
Fish aquatic toxicity + 0.9970 99.70%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
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 97.45% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.40% 96.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 90.65% 97.25%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 88.00% 94.45%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.70% 95.89%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 84.68% 91.24%
CHEMBL3267 P48736 PI3-kinase p110-gamma subunit 83.78% 95.71%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 83.57% 94.33%
CHEMBL3437 Q16853 Amine oxidase, copper containing 83.33% 94.00%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 83.04% 93.03%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 83.03% 91.07%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 81.81% 95.50%
CHEMBL3137262 O60341 LSD1/CoREST complex 81.39% 97.09%
CHEMBL340 P08684 Cytochrome P450 3A4 80.31% 91.19%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Eriocephalus pauperrimus
Ursinia eckloniana

Cross-Links

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PubChem 13895705
LOTUS LTS0254905
wikiData Q105341006