Helenalin methacrylate

Details

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Internal ID f832b9bc-63a7-4a3d-84ee-6a58f425efc5
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones
IUPAC Name [(3aR,5R,5aR,8aR,9S,9aR)-5,8a-dimethyl-1-methylidene-2,8-dioxo-3a,4,5,5a,9,9a-hexahydroazuleno[6,5-b]furan-9-yl] 2-methylprop-2-enoate
SMILES (Canonical) CC1CC2C(C(C3(C1C=CC3=O)C)OC(=O)C(=C)C)C(=C)C(=O)O2
SMILES (Isomeric) C[C@@H]1C[C@@H]2[C@H]([C@@H]([C@]3([C@H]1C=CC3=O)C)OC(=O)C(=C)C)C(=C)C(=O)O2
InChI InChI=1S/C19H22O5/c1-9(2)17(21)24-16-15-11(4)18(22)23-13(15)8-10(3)12-6-7-14(20)19(12,16)5/h6-7,10,12-13,15-16H,1,4,8H2,2-3,5H3/t10-,12+,13-,15-,16+,19+/m1/s1
InChI Key USRAFFQOAADTTD-SVAVSBTGSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C19H22O5
Molecular Weight 330.40 g/mol
Exact Mass 330.14672380 g/mol
Topological Polar Surface Area (TPSA) 69.70 Ų
XlogP 3.00
Atomic LogP (AlogP) 2.37
H-Bond Acceptor 5
H-Bond Donor 0
Rotatable Bonds 2

Synonyms

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68798-43-6
[(3aR,5R,5aR,8aR,9S,9aR)-5,8a-Dimethyl-1-methylidene-2,8-dioxo-3a,4,5,5a,9,9a-hexahydroazuleno[6,5-b]furan-9-yl] Methacrylate
DTXSID20218908
[(3aR,5R,5aR,8aR,9S,9aR)-5,8a-dimethyl-1-methylidene-2,8-dioxo-3a,4,5,5a,9,9a-hexahydroazuleno[6,5-b]furan-9-yl] 2-methylprop-2-enoate
2-Propenoic acid, 2-methyl-, 2,3,3a,4,4a,5,7a,8,9,9a-decahydro-4a,8-dimethyl-3-methylene-2,5-dioxoazuleno(6,5-b)furan-4-yl ester, (3aR-(3aalpha,4alpha,4abeta,7aalpha,8alpha,9aalpha))-

2D Structure

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2D Structure of Helenalin methacrylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9859 98.59%
Caco-2 + 0.5199 51.99%
Blood Brain Barrier + 0.6500 65.00%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.4760 47.60%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9039 90.39%
OATP1B3 inhibitior + 0.8659 86.59%
MATE1 inhibitior - 0.8000 80.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior - 0.8548 85.48%
P-glycoprotein inhibitior - 0.5762 57.62%
P-glycoprotein substrate - 0.6857 68.57%
CYP3A4 substrate + 0.6402 64.02%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9134 91.34%
CYP3A4 inhibition - 0.5991 59.91%
CYP2C9 inhibition - 0.8777 87.77%
CYP2C19 inhibition - 0.8422 84.22%
CYP2D6 inhibition - 0.9674 96.74%
CYP1A2 inhibition - 0.6352 63.52%
CYP2C8 inhibition - 0.6368 63.68%
CYP inhibitory promiscuity - 0.8489 84.89%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.8943 89.43%
Carcinogenicity (trinary) Non-required 0.4685 46.85%
Eye corrosion - 0.9488 94.88%
Eye irritation - 0.8236 82.36%
Skin irritation - 0.6261 62.61%
Skin corrosion - 0.8939 89.39%
Ames mutagenesis - 0.7454 74.54%
Human Ether-a-go-go-Related Gene inhibition - 0.5507 55.07%
Micronuclear - 0.5600 56.00%
Hepatotoxicity + 0.8750 87.50%
skin sensitisation - 0.5520 55.20%
Respiratory toxicity + 0.7222 72.22%
Reproductive toxicity + 0.5556 55.56%
Mitochondrial toxicity + 0.6875 68.75%
Nephrotoxicity + 0.7373 73.73%
Acute Oral Toxicity (c) II 0.4805 48.05%
Estrogen receptor binding + 0.7289 72.89%
Androgen receptor binding - 0.4877 48.77%
Thyroid receptor binding + 0.5306 53.06%
Glucocorticoid receptor binding + 0.5765 57.65%
Aromatase binding + 0.6086 60.86%
PPAR gamma + 0.6735 67.35%
Honey bee toxicity - 0.6988 69.88%
Biodegradation - 0.6750 67.50%
Crustacea aquatic toxicity - 0.5200 52.00%
Fish aquatic toxicity + 0.9713 97.13%

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 97.27% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.44% 97.25%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.06% 94.45%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 90.92% 99.23%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.66% 86.33%
CHEMBL221 P23219 Cyclooxygenase-1 88.96% 90.17%
CHEMBL2996 Q05655 Protein kinase C delta 88.86% 97.79%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 88.20% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.21% 95.56%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 83.88% 85.14%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 83.27% 91.07%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 82.20% 95.50%
CHEMBL241 Q14432 Phosphodiesterase 3A 82.06% 92.94%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.88% 89.00%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 80.30% 97.14%

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.
Arnica acaulis
Monactis macbridei

Cross-Links

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PubChem 173069
LOTUS LTS0239878
wikiData Q83095829