(3aR,4aS,8R,8aR,9aS)-8-hydroxy-5,8a-dimethyl-3-methylidene-3a,4,4a,8,9,9a-hexahydrobenzo[f][1]benzofuran-2,7-dione

Details

Top
Internal ID 6767eb30-60fc-4a6d-8303-02fab5d3d002
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
IUPAC Name (3aR,4aS,8R,8aR,9aS)-8-hydroxy-5,8a-dimethyl-3-methylidene-3a,4,4a,8,9,9a-hexahydrobenzo[f][1]benzofuran-2,7-dione
SMILES (Canonical) CC1=CC(=O)C(C2(C1CC3C(C2)OC(=O)C3=C)C)O
SMILES (Isomeric) CC1=CC(=O)[C@@H]([C@]2([C@H]1C[C@H]3[C@H](C2)OC(=O)C3=C)C)O
InChI InChI=1S/C15H18O4/c1-7-4-11(16)13(17)15(3)6-12-9(5-10(7)15)8(2)14(18)19-12/h4,9-10,12-13,17H,2,5-6H2,1,3H3/t9-,10+,12+,13+,15-/m1/s1
InChI Key XAFJIIZCMNHLRS-LAEDSOSDSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C15H18O4
Molecular Weight 262.30 g/mol
Exact Mass 262.12050905 g/mol
Topological Polar Surface Area (TPSA) 63.60 Ų
XlogP 1.20
Atomic LogP (AlogP) 1.39
H-Bond Acceptor 4
H-Bond Donor 1
Rotatable Bonds 0

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of (3aR,4aS,8R,8aR,9aS)-8-hydroxy-5,8a-dimethyl-3-methylidene-3a,4,4a,8,9,9a-hexahydrobenzo[f][1]benzofuran-2,7-dione

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9872 98.72%
Caco-2 + 0.5745 57.45%
Blood Brain Barrier + 0.6250 62.50%
Human oral bioavailability - 0.5286 52.86%
Subcellular localzation Mitochondria 0.7422 74.22%
OATP2B1 inhibitior - 0.8580 85.80%
OATP1B1 inhibitior + 0.8653 86.53%
OATP1B3 inhibitior + 0.8829 88.29%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior - 0.9775 97.75%
P-glycoprotein inhibitior - 0.9289 92.89%
P-glycoprotein substrate - 0.8284 82.84%
CYP3A4 substrate + 0.6052 60.52%
CYP2C9 substrate - 0.7829 78.29%
CYP2D6 substrate - 0.8959 89.59%
CYP3A4 inhibition + 0.5486 54.86%
CYP2C9 inhibition - 0.9039 90.39%
CYP2C19 inhibition - 0.8765 87.65%
CYP2D6 inhibition - 0.9405 94.05%
CYP1A2 inhibition - 0.7287 72.87%
CYP2C8 inhibition - 0.8214 82.14%
CYP inhibitory promiscuity - 0.8674 86.74%
UGT catelyzed - 0.5638 56.38%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.4970 49.70%
Eye corrosion - 0.9872 98.72%
Eye irritation - 0.7864 78.64%
Skin irritation + 0.5252 52.52%
Skin corrosion - 0.8534 85.34%
Ames mutagenesis - 0.7570 75.70%
Human Ether-a-go-go-Related Gene inhibition - 0.5858 58.58%
Micronuclear - 0.6000 60.00%
Hepatotoxicity + 0.7244 72.44%
skin sensitisation - 0.6940 69.40%
Respiratory toxicity + 0.7778 77.78%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.8750 87.50%
Nephrotoxicity + 0.4916 49.16%
Acute Oral Toxicity (c) III 0.5309 53.09%
Estrogen receptor binding + 0.5984 59.84%
Androgen receptor binding + 0.5529 55.29%
Thyroid receptor binding - 0.5307 53.07%
Glucocorticoid receptor binding - 0.5936 59.36%
Aromatase binding - 0.7952 79.52%
PPAR gamma - 0.5824 58.24%
Honey bee toxicity - 0.8227 82.27%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5000 50.00%
Fish aquatic toxicity + 0.9966 99.66%

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
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.66% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.12% 95.56%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.86% 91.11%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 90.95% 85.14%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.27% 97.09%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 86.83% 99.23%
CHEMBL253 P34972 Cannabinoid CB2 receptor 84.30% 97.25%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.13% 100.00%
CHEMBL221 P23219 Cyclooxygenase-1 84.08% 90.17%
CHEMBL1951 P21397 Monoamine oxidase A 82.29% 91.49%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 82.04% 96.09%
CHEMBL2996 Q05655 Protein kinase C delta 81.30% 97.79%
CHEMBL1293249 Q13887 Kruppel-like factor 5 81.06% 86.33%

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.
Helianthus grosseserratus

Cross-Links

Top
PubChem 163005093
LOTUS LTS0266183
wikiData Q105323896