ethyl 3-[(3aS,8R,8aR)-8-hydroxy-6,8-dimethyl-3-methylidene-2-oxo-3a,4,5,8a-tetrahydrocyclohepta[b]furan-7-yl]propanoate

Details

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Internal ID a06b9746-46d3-4af5-beac-130cfc41aa19
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
IUPAC Name ethyl 3-[(3aS,8R,8aR)-8-hydroxy-6,8-dimethyl-3-methylidene-2-oxo-3a,4,5,8a-tetrahydrocyclohepta[b]furan-7-yl]propanoate
SMILES (Canonical) CCOC(=O)CCC1=C(CCC2C(C1(C)O)OC(=O)C2=C)C
SMILES (Isomeric) CCOC(=O)CCC1=C(CC[C@@H]2[C@H]([C@]1(C)O)OC(=O)C2=C)C
InChI InChI=1S/C17H24O5/c1-5-21-14(18)9-8-13-10(2)6-7-12-11(3)16(19)22-15(12)17(13,4)20/h12,15,20H,3,5-9H2,1-2,4H3/t12-,15+,17+/m0/s1
InChI Key UBODNQTWXZCHMY-XGWLTEMNSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C17H24O5
Molecular Weight 308.40 g/mol
Exact Mass 308.16237386 g/mol
Topological Polar Surface Area (TPSA) 72.80 Ų
XlogP 1.10
Atomic LogP (AlogP) 2.29
H-Bond Acceptor 5
H-Bond Donor 1
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of ethyl 3-[(3aS,8R,8aR)-8-hydroxy-6,8-dimethyl-3-methylidene-2-oxo-3a,4,5,8a-tetrahydrocyclohepta[b]furan-7-yl]propanoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9852 98.52%
Caco-2 + 0.6369 63.69%
Blood Brain Barrier + 0.7000 70.00%
Human oral bioavailability - 0.5286 52.86%
Subcellular localzation Mitochondria 0.7500 75.00%
OATP2B1 inhibitior - 0.8558 85.58%
OATP1B1 inhibitior + 0.8515 85.15%
OATP1B3 inhibitior + 0.9421 94.21%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.6364 63.64%
BSEP inhibitior - 0.7818 78.18%
P-glycoprotein inhibitior - 0.5787 57.87%
P-glycoprotein substrate - 0.8326 83.26%
CYP3A4 substrate + 0.6405 64.05%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8958 89.58%
CYP3A4 inhibition + 0.6379 63.79%
CYP2C9 inhibition - 0.5154 51.54%
CYP2C19 inhibition - 0.6195 61.95%
CYP2D6 inhibition - 0.9185 91.85%
CYP1A2 inhibition + 0.5141 51.41%
CYP2C8 inhibition - 0.6677 66.77%
CYP inhibitory promiscuity - 0.8252 82.52%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.6373 63.73%
Eye corrosion - 0.9850 98.50%
Eye irritation - 0.5520 55.20%
Skin irritation + 0.5000 50.00%
Skin corrosion - 0.9364 93.64%
Ames mutagenesis - 0.7900 79.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5675 56.75%
Micronuclear - 0.8000 80.00%
Hepatotoxicity + 0.7218 72.18%
skin sensitisation - 0.8761 87.61%
Respiratory toxicity + 0.6000 60.00%
Reproductive toxicity + 0.6778 67.78%
Mitochondrial toxicity + 0.5625 56.25%
Nephrotoxicity + 0.5000 50.00%
Acute Oral Toxicity (c) III 0.5126 51.26%
Estrogen receptor binding + 0.6534 65.34%
Androgen receptor binding - 0.4881 48.81%
Thyroid receptor binding - 0.6493 64.93%
Glucocorticoid receptor binding + 0.6852 68.52%
Aromatase binding - 0.4886 48.86%
PPAR gamma + 0.5193 51.93%
Honey bee toxicity - 0.8401 84.01%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.5200 52.00%
Fish aquatic toxicity + 0.9950 99.50%

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 94.08% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 93.87% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.07% 97.09%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.72% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.10% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.55% 95.56%
CHEMBL221 P23219 Cyclooxygenase-1 89.26% 90.17%
CHEMBL241 Q14432 Phosphodiesterase 3A 87.87% 92.94%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 87.76% 99.23%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.40% 86.33%
CHEMBL4040 P28482 MAP kinase ERK2 85.24% 83.82%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 84.37% 85.14%
CHEMBL2664 P23526 Adenosylhomocysteinase 84.26% 86.67%
CHEMBL340 P08684 Cytochrome P450 3A4 83.67% 91.19%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 83.19% 94.33%
CHEMBL5255 O00206 Toll-like receptor 4 80.98% 92.50%
CHEMBL3060 Q9Y345 Glycine transporter 2 80.86% 99.17%

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.
Ambrosia tenuifolia

Cross-Links

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PubChem 15143692
LOTUS LTS0211000
wikiData Q104391272