(4betaH)-5alpha-hydroxy-8alpha-(2-methylbut-2-enoyloxy)-2-oxo-1(10),11(13)-guaiadien-12,6alpha-olide

Details

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Internal ID 99edb0eb-4221-4744-96a1-60ddc0f7b683
Taxonomy Lipids and lipid-like molecules > Fatty Acyls > Fatty acid esters
IUPAC Name [(3aR,4S,9R,9aR,9bS)-9a-hydroxy-6,9-dimethyl-3-methylidene-2,7-dioxo-3a,4,5,8,9,9b-hexahydroazuleno[4,5-b]furan-4-yl] (E)-2-methylbut-2-enoate
SMILES (Canonical) CC=C(C)C(=O)OC1CC(=C2C(=O)CC(C2(C3C1C(=C)C(=O)O3)O)C)C
SMILES (Isomeric) C/C=C(\C)/C(=O)O[C@H]1CC(=C2C(=O)C[C@H]([C@@]2([C@@H]3[C@@H]1C(=C)C(=O)O3)O)C)C
InChI InChI=1S/C20H24O6/c1-6-9(2)18(22)25-14-7-10(3)16-13(21)8-11(4)20(16,24)17-15(14)12(5)19(23)26-17/h6,11,14-15,17,24H,5,7-8H2,1-4H3/b9-6+/t11-,14+,15-,17+,20-/m1/s1
InChI Key SKWQNPANRJEPQJ-JTOVZCNQSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C20H24O6
Molecular Weight 360.40 g/mol
Exact Mass 360.15728848 g/mol
Topological Polar Surface Area (TPSA) 89.90 Ų
XlogP 1.50
Atomic LogP (AlogP) 2.02
H-Bond Acceptor 6
H-Bond Donor 1
Rotatable Bonds 2

Synonyms

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CHEBI:65832
DTXSID301100412
Q27134325
(3aR)-3-Methylene-4beta-(2-methyl-2-butenoyloxy)-6,9beta-dimethyl-9abeta-hydroxy-2,3,3abeta,4,5,7,8,9,9a,9balpha-decahydroazuleno[4,5-b]furan-2,7-dione
(3aR,4S,9R,9aR,9bS)-2,3,3a,4,5,7,8,9,9a,9b-Decahydro-9a-hydroxy-6,9-dimethyl-3-methylene-2,7-dioxoazuleno[4,5-b]furan-4-yl (2E)-2-methyl-2-butenoate
(3aR,4S,9R,9aR,9bS)-9a-hydroxy-6,9-dimethyl-3-methylidene-2,7-dioxo-2,3,3a,4,5,7,8,9,9a,9b-decahydroazuleno[4,5-b]furan-4-yl (2E)-2-methylbut-2-enoate
[(3aR,4S,9R,9aR,9bS)-9a-hydroxy-6,9-dimethyl-3-methylidene-2,7-dioxo-3a,4,5,8,9,9b-hexahydroazuleno[4,5-b]furan-4-yl] (E)-2-methylbut-2-enoate
1039025-72-3

2D Structure

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2D Structure of (4betaH)-5alpha-hydroxy-8alpha-(2-methylbut-2-enoyloxy)-2-oxo-1(10),11(13)-guaiadien-12,6alpha-olide

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9738 97.38%
Caco-2 + 0.6475 64.75%
Blood Brain Barrier + 0.6500 65.00%
Human oral bioavailability - 0.5429 54.29%
Subcellular localzation Mitochondria 0.6533 65.33%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9170 91.70%
OATP1B3 inhibitior - 0.2270 22.70%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.8250 82.50%
BSEP inhibitior + 0.5588 55.88%
P-glycoprotein inhibitior - 0.5088 50.88%
P-glycoprotein substrate - 0.5928 59.28%
CYP3A4 substrate + 0.6305 63.05%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9119 91.19%
CYP3A4 inhibition - 0.6357 63.57%
CYP2C9 inhibition - 0.7245 72.45%
CYP2C19 inhibition - 0.7213 72.13%
CYP2D6 inhibition - 0.9527 95.27%
CYP1A2 inhibition - 0.5335 53.35%
CYP2C8 inhibition - 0.8362 83.62%
CYP inhibitory promiscuity - 0.9175 91.75%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9443 94.43%
Carcinogenicity (trinary) Non-required 0.4892 48.92%
Eye corrosion - 0.9759 97.59%
Eye irritation - 0.8693 86.93%
Skin irritation - 0.5993 59.93%
Skin corrosion - 0.9169 91.69%
Ames mutagenesis - 0.5500 55.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4332 43.32%
Micronuclear - 0.6200 62.00%
Hepatotoxicity + 0.7699 76.99%
skin sensitisation - 0.7532 75.32%
Respiratory toxicity + 0.6556 65.56%
Reproductive toxicity + 0.7333 73.33%
Mitochondrial toxicity + 0.7250 72.50%
Nephrotoxicity + 0.5807 58.07%
Acute Oral Toxicity (c) II 0.4384 43.84%
Estrogen receptor binding + 0.7095 70.95%
Androgen receptor binding - 0.5199 51.99%
Thyroid receptor binding + 0.5394 53.94%
Glucocorticoid receptor binding + 0.7168 71.68%
Aromatase binding - 0.4892 48.92%
PPAR gamma + 0.6717 67.17%
Honey bee toxicity - 0.6641 66.41%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity + 0.5100 51.00%
Fish aquatic toxicity + 0.9781 97.81%

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 93.65% 91.11%
CHEMBL221 P23219 Cyclooxygenase-1 92.25% 90.17%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.24% 95.56%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.72% 94.45%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 90.78% 99.23%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.78% 86.33%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 88.28% 97.21%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 88.18% 96.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.63% 89.00%
CHEMBL2581 P07339 Cathepsin D 84.40% 98.95%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 83.08% 85.14%
CHEMBL253 P34972 Cannabinoid CB2 receptor 82.58% 97.25%
CHEMBL5028 O14672 ADAM10 82.47% 97.50%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 82.10% 93.00%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 81.55% 93.03%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 80.62% 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.
Elephantopus mollis

Cross-Links

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PubChem 24814493
NPASS NPC197523
LOTUS LTS0203100
wikiData Q27134325