6-Ethenyl-4-hydroxy-7-(3-hydroxyprop-1-en-2-yl)-3,6-dimethyl-3,3a,4,5,7,7a-hexahydro-1-benzofuran-2-one

Details

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Internal ID f723240c-6c05-48f6-a42c-d70656b24e68
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
IUPAC Name 6-ethenyl-4-hydroxy-7-(3-hydroxyprop-1-en-2-yl)-3,6-dimethyl-3,3a,4,5,7,7a-hexahydro-1-benzofuran-2-one
SMILES (Canonical) CC1C2C(CC(C(C2OC1=O)C(=C)CO)(C)C=C)O
SMILES (Isomeric) CC1C2C(CC(C(C2OC1=O)C(=C)CO)(C)C=C)O
InChI InChI=1S/C15H22O4/c1-5-15(4)6-10(17)11-9(3)14(18)19-13(11)12(15)8(2)7-16/h5,9-13,16-17H,1-2,6-7H2,3-4H3
InChI Key BJNRYKWHTCAVLA-UHFFFAOYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C15H22O4
Molecular Weight 266.33 g/mol
Exact Mass 266.15180918 g/mol
Topological Polar Surface Area (TPSA) 66.80 Ų
XlogP 1.90
Atomic LogP (AlogP) 1.29
H-Bond Acceptor 4
H-Bond Donor 2
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 6-Ethenyl-4-hydroxy-7-(3-hydroxyprop-1-en-2-yl)-3,6-dimethyl-3,3a,4,5,7,7a-hexahydro-1-benzofuran-2-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9843 98.43%
Caco-2 - 0.5916 59.16%
Blood Brain Barrier + 0.6750 67.50%
Human oral bioavailability + 0.5857 58.57%
Subcellular localzation Mitochondria 0.5583 55.83%
OATP2B1 inhibitior - 0.8582 85.82%
OATP1B1 inhibitior + 0.9009 90.09%
OATP1B3 inhibitior + 0.9342 93.42%
MATE1 inhibitior - 0.9412 94.12%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior - 0.9447 94.47%
P-glycoprotein inhibitior - 0.9334 93.34%
P-glycoprotein substrate - 0.7826 78.26%
CYP3A4 substrate + 0.5807 58.07%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8480 84.80%
CYP3A4 inhibition - 0.7447 74.47%
CYP2C9 inhibition - 0.9158 91.58%
CYP2C19 inhibition - 0.8940 89.40%
CYP2D6 inhibition - 0.9515 95.15%
CYP1A2 inhibition - 0.8034 80.34%
CYP2C8 inhibition - 0.9401 94.01%
CYP inhibitory promiscuity - 0.8746 87.46%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9200 92.00%
Carcinogenicity (trinary) Non-required 0.5526 55.26%
Eye corrosion - 0.9833 98.33%
Eye irritation - 0.8801 88.01%
Skin irritation - 0.6104 61.04%
Skin corrosion - 0.9310 93.10%
Ames mutagenesis - 0.6654 66.54%
Human Ether-a-go-go-Related Gene inhibition - 0.7722 77.22%
Micronuclear - 0.7600 76.00%
Hepatotoxicity + 0.5274 52.74%
skin sensitisation - 0.6872 68.72%
Respiratory toxicity + 0.5111 51.11%
Reproductive toxicity + 0.6778 67.78%
Mitochondrial toxicity + 0.7375 73.75%
Nephrotoxicity + 0.7348 73.48%
Acute Oral Toxicity (c) III 0.4918 49.18%
Estrogen receptor binding - 0.6377 63.77%
Androgen receptor binding - 0.5093 50.93%
Thyroid receptor binding - 0.6083 60.83%
Glucocorticoid receptor binding - 0.5311 53.11%
Aromatase binding - 0.7520 75.20%
PPAR gamma - 0.7284 72.84%
Honey bee toxicity - 0.7501 75.01%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.6200 62.00%
Fish aquatic toxicity + 0.9277 92.77%

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 96.82% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 90.52% 96.09%
CHEMBL1951 P21397 Monoamine oxidase A 89.54% 91.49%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 89.26% 85.14%
CHEMBL4040 P28482 MAP kinase ERK2 88.21% 83.82%
CHEMBL1994 P08235 Mineralocorticoid receptor 88.08% 100.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.34% 95.56%
CHEMBL253 P34972 Cannabinoid CB2 receptor 85.84% 97.25%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.73% 89.00%
CHEMBL2581 P07339 Cathepsin D 81.68% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 81.40% 94.45%

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.
Centaurea aspera
Centaurea napifolia
Centaurea pullata

Cross-Links

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PubChem 14162546
LOTUS LTS0180326
wikiData Q104937207