PlantaeDB Logo
Login Sign-up

[(1R,2S,6R,7R,8R,11S,12R,14R)-11-acetyloxy-1,7-dihydroxy-9,14-dimethyl-5-methylidene-4-oxo-3,13-dioxatetracyclo[8.4.0.02,6.012,14]tetradec-9-en-8-yl] (Z)-2-methylbut-2-enoate

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

Top
Internal ID f372078b-a218-4f22-bec8-218e4eb320bf
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
IUPAC Name [(1R,2S,6R,7R,8R,11S,12R,14R)-11-acetyloxy-1,7-dihydroxy-9,14-dimethyl-5-methylidene-4-oxo-3,13-dioxatetracyclo[8.4.0.02,6.012,14]tetradec-9-en-8-yl] (Z)-2-methylbut-2-enoate
SMILES (Canonical) CC=C(C)C(=O)OC1C(C2C(C3(C(=C1C)C(C4C3(O4)C)OC(=O)C)O)OC(=O)C2=C)O
SMILES (Isomeric) C/C=C(/C)\C(=O)O[C@H]1[C@@H]([C@@H]2[C@@H]([C@@]3(C(=C1C)[C@@H]([C@@H]4[C@]3(O4)C)OC(=O)C)O)OC(=O)C2=C)O
InChI InChI=1S/C22H26O9/c1-7-8(2)19(25)29-15-10(4)13-16(28-11(5)23)18-21(6,31-18)22(13,27)17-12(14(15)24)9(3)20(26)30-17/h7,12,14-18,24,27H,3H2,1-2,4-6H3/b8-7-/t12-,14-,15-,16+,17+,18-,21-,22-/m1/s1
InChI Key WGZVUXQFHASBJA-NOZUZWHMSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C22H26O9
Molecular Weight 434.40 g/mol
Exact Mass 434.15768240 g/mol
Topological Polar Surface Area (TPSA) 132.00 Ų
XlogP -0.60
Atomic LogP (AlogP) 0.49
H-Bond Acceptor 9
H-Bond Donor 2
Rotatable Bonds 3

Synonyms

Top
90734-99-9
2-Butenoic acid, 2-methyl-, (3aR,4R,5R,7S,7aR,8aR,8bR,8cS)-7-(acetyloxy)-2,3,3a,4,5,7,7a,8a,8b,8c-decahydro-4,8b-dihydroxy-6,8a-dimethyl-3-methylene-2-oxooxireno[2,3]azuleno[4,5-b]furan-5-yl ester, (2Z)-

2D Structure

Top
2D Structure of [(1R,2S,6R,7R,8R,11S,12R,14R)-11-acetyloxy-1,7-dihydroxy-9,14-dimethyl-5-methylidene-4-oxo-3,13-dioxatetracyclo[8.4.0.02,6.012,14]tetradec-9-en-8-yl] (Z)-2-methylbut-2-enoate

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9535 95.35%
Caco-2 - 0.7108 71.08%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability - 0.6286 62.86%
Subcellular localzation Mitochondria 0.6908 69.08%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8776 87.76%
OATP1B3 inhibitior + 0.9135 91.35%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior - 0.5515 55.15%
P-glycoprotein inhibitior + 0.6241 62.41%
P-glycoprotein substrate - 0.5646 56.46%
CYP3A4 substrate + 0.6550 65.50%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9043 90.43%
CYP3A4 inhibition - 0.6603 66.03%
CYP2C9 inhibition - 0.8965 89.65%
CYP2C19 inhibition - 0.8262 82.62%
CYP2D6 inhibition - 0.9371 93.71%
CYP1A2 inhibition - 0.8514 85.14%
CYP2C8 inhibition - 0.5962 59.62%
CYP inhibitory promiscuity - 0.8299 82.99%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9400 94.00%
Carcinogenicity (trinary) Danger 0.4526 45.26%
Eye corrosion - 0.9699 96.99%
Eye irritation - 0.8335 83.35%
Skin irritation - 0.6047 60.47%
Skin corrosion - 0.9077 90.77%
Ames mutagenesis + 0.5200 52.00%
Human Ether-a-go-go-Related Gene inhibition - 0.6072 60.72%
Micronuclear + 0.6000 60.00%
Hepatotoxicity + 0.5783 57.83%
skin sensitisation - 0.7243 72.43%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.7000 70.00%
Mitochondrial toxicity + 0.7375 73.75%
Nephrotoxicity + 0.8201 82.01%
Acute Oral Toxicity (c) III 0.3514 35.14%
Estrogen receptor binding + 0.7305 73.05%
Androgen receptor binding + 0.6503 65.03%
Thyroid receptor binding + 0.5535 55.35%
Glucocorticoid receptor binding + 0.6830 68.30%
Aromatase binding - 0.5205 52.05%
PPAR gamma + 0.6783 67.83%
Honey bee toxicity - 0.5749 57.49%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity + 0.5300 53.00%
Fish aquatic toxicity + 0.9440 94.40%

Targets

Top

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 96.90% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.57% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.11% 95.56%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 87.94% 95.50%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.65% 89.00%
CHEMBL221 P23219 Cyclooxygenase-1 87.26% 90.17%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 85.89% 94.62%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 85.69% 94.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 84.54% 96.09%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.42% 99.23%
CHEMBL2581 P07339 Cathepsin D 84.10% 98.95%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 82.51% 81.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 81.89% 86.33%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 81.37% 91.07%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 80.10% 94.08%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 80.07% 97.14%

Plants that contains it

Top
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.
Montanoa tomentosa

Cross-Links

Top
PubChem 101293642
LOTUS LTS0064279
wikiData Q104396868