[(4S,4aR,5S,7R)-7-hydroxy-4a,5-dimethyl-9-oxo-4,5,6,7-tetrahydrobenzo[f][1]benzofuran-4-yl] (Z)-2-methylbut-2-enoate

Details

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Internal ID e263a39d-757e-494e-b910-4ec151a0bddb
Taxonomy Organoheterocyclic compounds > Naphthofurans
IUPAC Name [(4S,4aR,5S,7R)-7-hydroxy-4a,5-dimethyl-9-oxo-4,5,6,7-tetrahydrobenzo[f][1]benzofuran-4-yl] (Z)-2-methylbut-2-enoate
SMILES (Canonical) CC=C(C)C(=O)OC1C2=C(C(=O)C3=CC(CC(C13C)C)O)OC=C2
SMILES (Isomeric) C/C=C(/C)\C(=O)O[C@@H]1C2=C(C(=O)C3=C[C@@H](C[C@@H]([C@@]13C)C)O)OC=C2
InChI InChI=1S/C19H22O5/c1-5-10(2)18(22)24-17-13-6-7-23-16(13)15(21)14-9-12(20)8-11(3)19(14,17)4/h5-7,9,11-12,17,20H,8H2,1-4H3/b10-5-/t11-,12+,17+,19+/m0/s1
InChI Key VWUPQZXUHCYORA-ZEQRYJAYSA-N
Popularity 0 references 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) 76.70 Ų
XlogP 3.00
Atomic LogP (AlogP) 3.36
H-Bond Acceptor 5
H-Bond Donor 1
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(4S,4aR,5S,7R)-7-hydroxy-4a,5-dimethyl-9-oxo-4,5,6,7-tetrahydrobenzo[f][1]benzofuran-4-yl] (Z)-2-methylbut-2-enoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9966 99.66%
Caco-2 + 0.6842 68.42%
Blood Brain Barrier + 0.7500 75.00%
Human oral bioavailability + 0.5143 51.43%
Subcellular localzation Mitochondria 0.6578 65.78%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8739 87.39%
OATP1B3 inhibitior + 0.8814 88.14%
MATE1 inhibitior - 0.8200 82.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior + 0.5824 58.24%
P-glycoprotein inhibitior - 0.6688 66.88%
P-glycoprotein substrate - 0.6257 62.57%
CYP3A4 substrate + 0.6626 66.26%
CYP2C9 substrate - 0.7983 79.83%
CYP2D6 substrate - 0.8642 86.42%
CYP3A4 inhibition - 0.7002 70.02%
CYP2C9 inhibition - 0.7584 75.84%
CYP2C19 inhibition - 0.8182 81.82%
CYP2D6 inhibition - 0.8608 86.08%
CYP1A2 inhibition - 0.5316 53.16%
CYP2C8 inhibition - 0.6054 60.54%
CYP inhibitory promiscuity - 0.7412 74.12%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Danger 0.4098 40.98%
Eye corrosion - 0.9894 98.94%
Eye irritation - 0.9550 95.50%
Skin irritation - 0.5963 59.63%
Skin corrosion - 0.9342 93.42%
Ames mutagenesis - 0.5500 55.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7525 75.25%
Micronuclear + 0.5300 53.00%
Hepatotoxicity + 0.5827 58.27%
skin sensitisation - 0.7222 72.22%
Respiratory toxicity + 0.6222 62.22%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.8375 83.75%
Nephrotoxicity + 0.4936 49.36%
Acute Oral Toxicity (c) III 0.3722 37.22%
Estrogen receptor binding + 0.5416 54.16%
Androgen receptor binding + 0.5974 59.74%
Thyroid receptor binding - 0.6396 63.96%
Glucocorticoid receptor binding - 0.5262 52.62%
Aromatase binding + 0.5620 56.20%
PPAR gamma + 0.6120 61.20%
Honey bee toxicity - 0.5998 59.98%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity - 0.5800 58.00%
Fish aquatic toxicity + 0.9922 99.22%

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 98.17% 91.11%
CHEMBL1806 P11388 DNA topoisomerase II alpha 95.75% 89.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.25% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.18% 86.33%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.03% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.55% 95.56%
CHEMBL2581 P07339 Cathepsin D 89.50% 98.95%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 86.96% 99.23%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.83% 100.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.00% 97.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 82.25% 97.25%
CHEMBL241 Q14432 Phosphodiesterase 3A 80.40% 92.94%

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.
Packera bellidifolia

Cross-Links

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PubChem 162820138
LOTUS LTS0102223
wikiData Q103813534