methyl (1S,2S,4R,7E,9S,10S,11R)-9-hydroxy-4-methyl-10-[(Z)-2-methylbut-2-enoyl]oxy-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-ene-8-carboxylate

Details

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Internal ID 9e7bff5b-bcf9-4eb4-932b-0986175eb9b7
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
IUPAC Name methyl (1S,2S,4R,7E,9S,10S,11R)-9-hydroxy-4-methyl-10-[(Z)-2-methylbut-2-enoyl]oxy-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-ene-8-carboxylate
SMILES (Canonical) CC=C(C)C(=O)OC1C2C(C3C(O3)(CCC=C(C1O)C(=O)OC)C)OC(=O)C2=C
SMILES (Isomeric) C/C=C(/C)\C(=O)O[C@H]1[C@@H]2[C@@H]([C@H]3[C@](O3)(CC/C=C(\[C@@H]1O)/C(=O)OC)C)OC(=O)C2=C
InChI InChI=1S/C21H26O8/c1-6-10(2)18(23)27-15-13-11(3)19(24)28-16(13)17-21(4,29-17)9-7-8-12(14(15)22)20(25)26-5/h6,8,13-17,22H,3,7,9H2,1-2,4-5H3/b10-6-,12-8+/t13-,14+,15+,16+,17+,21-/m1/s1
InChI Key JXROUJXCPKQFHH-NMZRPUQVSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C21H26O8
Molecular Weight 406.40 g/mol
Exact Mass 406.16276778 g/mol
Topological Polar Surface Area (TPSA) 112.00 Ų
XlogP 2.20
Atomic LogP (AlogP) 1.37
H-Bond Acceptor 8
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 (1S,2S,4R,7E,9S,10S,11R)-9-hydroxy-4-methyl-10-[(Z)-2-methylbut-2-enoyl]oxy-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-ene-8-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9572 95.72%
Caco-2 - 0.5312 53.12%
Blood Brain Barrier + 0.7500 75.00%
Human oral bioavailability - 0.6571 65.71%
Subcellular localzation Mitochondria 0.6094 60.94%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8366 83.66%
OATP1B3 inhibitior + 0.9112 91.12%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.7771 77.71%
BSEP inhibitior - 0.6922 69.22%
P-glycoprotein inhibitior + 0.6596 65.96%
P-glycoprotein substrate - 0.5726 57.26%
CYP3A4 substrate + 0.6783 67.83%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8752 87.52%
CYP3A4 inhibition - 0.6662 66.62%
CYP2C9 inhibition - 0.8517 85.17%
CYP2C19 inhibition - 0.8566 85.66%
CYP2D6 inhibition - 0.9216 92.16%
CYP1A2 inhibition - 0.5514 55.14%
CYP2C8 inhibition - 0.5974 59.74%
CYP inhibitory promiscuity - 0.9368 93.68%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.8800 88.00%
Carcinogenicity (trinary) Non-required 0.4344 43.44%
Eye corrosion - 0.9752 97.52%
Eye irritation - 0.9073 90.73%
Skin irritation - 0.6088 60.88%
Skin corrosion - 0.8715 87.15%
Ames mutagenesis - 0.6000 60.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5989 59.89%
Micronuclear - 0.6300 63.00%
Hepatotoxicity + 0.5250 52.50%
skin sensitisation - 0.7660 76.60%
Respiratory toxicity + 0.6889 68.89%
Reproductive toxicity + 0.6778 67.78%
Mitochondrial toxicity + 0.7250 72.50%
Nephrotoxicity + 0.8715 87.15%
Acute Oral Toxicity (c) III 0.3924 39.24%
Estrogen receptor binding + 0.7758 77.58%
Androgen receptor binding + 0.5436 54.36%
Thyroid receptor binding + 0.6179 61.79%
Glucocorticoid receptor binding + 0.7816 78.16%
Aromatase binding + 0.5470 54.70%
PPAR gamma + 0.6701 67.01%
Honey bee toxicity - 0.5629 56.29%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5500 55.00%
Fish aquatic toxicity + 0.8900 89.00%

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 98.83% 91.11%
CHEMBL221 P23219 Cyclooxygenase-1 98.09% 90.17%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.75% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.90% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.42% 86.33%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 87.29% 99.23%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 87.28% 91.07%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.43% 95.89%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 84.24% 95.56%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 83.95% 97.14%
CHEMBL5028 O14672 ADAM10 83.71% 97.50%
CHEMBL340 P08684 Cytochrome P450 3A4 82.72% 91.19%
CHEMBL2581 P07339 Cathepsin D 82.61% 98.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.14% 89.00%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 80.98% 95.50%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 80.92% 93.03%
CHEMBL3401 O75469 Pregnane X receptor 80.64% 94.73%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 80.28% 94.08%

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.
Melampodium longipilum

Cross-Links

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PubChem 163193201
LOTUS LTS0005515
wikiData Q105136746