[(4S,4aR,5S,8aR)-3,4a,5-trimethyl-9-oxo-4,5,6,7,8,8a-hexahydrobenzo[f][1]benzofuran-4-yl] (2R)-2-methylbutanoate

Details

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Internal ID 034ccecf-6748-44d8-96cd-a3e58747c50b
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
IUPAC Name [(4S,4aR,5S,8aR)-3,4a,5-trimethyl-9-oxo-4,5,6,7,8,8a-hexahydrobenzo[f][1]benzofuran-4-yl] (2R)-2-methylbutanoate
SMILES (Canonical) CCC(C)C(=O)OC1C2=C(C(=O)C3C1(C(CCC3)C)C)OC=C2C
SMILES (Isomeric) CC[C@@H](C)C(=O)O[C@@H]1C2=C(C(=O)[C@H]3[C@]1([C@H](CCC3)C)C)OC=C2C
InChI InChI=1S/C20H28O4/c1-6-11(2)19(22)24-18-15-12(3)10-23-17(15)16(21)14-9-7-8-13(4)20(14,18)5/h10-11,13-14,18H,6-9H2,1-5H3/t11-,13+,14+,18-,20-/m1/s1
InChI Key CMCOPWASESUDRF-JCLXGSSSSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C20H28O4
Molecular Weight 332.40 g/mol
Exact Mass 332.19875937 g/mol
Topological Polar Surface Area (TPSA) 56.50 Ų
XlogP 5.00
Atomic LogP (AlogP) 4.86
H-Bond Acceptor 4
H-Bond Donor 0
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(4S,4aR,5S,8aR)-3,4a,5-trimethyl-9-oxo-4,5,6,7,8,8a-hexahydrobenzo[f][1]benzofuran-4-yl] (2R)-2-methylbutanoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9929 99.29%
Caco-2 + 0.8467 84.67%
Blood Brain Barrier + 0.7000 70.00%
Human oral bioavailability - 0.5429 54.29%
Subcellular localzation Mitochondria 0.6223 62.23%
OATP2B1 inhibitior - 0.8584 85.84%
OATP1B1 inhibitior + 0.8572 85.72%
OATP1B3 inhibitior + 0.9239 92.39%
MATE1 inhibitior - 0.6200 62.00%
OCT2 inhibitior - 0.6250 62.50%
BSEP inhibitior - 0.6509 65.09%
P-glycoprotein inhibitior - 0.5354 53.54%
P-glycoprotein substrate - 0.8244 82.44%
CYP3A4 substrate + 0.6029 60.29%
CYP2C9 substrate + 0.6194 61.94%
CYP2D6 substrate - 0.8700 87.00%
CYP3A4 inhibition - 0.7445 74.45%
CYP2C9 inhibition - 0.5929 59.29%
CYP2C19 inhibition - 0.5718 57.18%
CYP2D6 inhibition - 0.9495 94.95%
CYP1A2 inhibition - 0.5218 52.18%
CYP2C8 inhibition - 0.7182 71.82%
CYP inhibitory promiscuity - 0.5940 59.40%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9300 93.00%
Carcinogenicity (trinary) Non-required 0.5857 58.57%
Eye corrosion - 0.9868 98.68%
Eye irritation - 0.9529 95.29%
Skin irritation - 0.6994 69.94%
Skin corrosion - 0.8964 89.64%
Ames mutagenesis - 0.7009 70.09%
Human Ether-a-go-go-Related Gene inhibition - 0.3619 36.19%
Micronuclear - 0.7900 79.00%
Hepatotoxicity + 0.5623 56.23%
skin sensitisation - 0.8413 84.13%
Respiratory toxicity + 0.6889 68.89%
Reproductive toxicity + 0.6333 63.33%
Mitochondrial toxicity + 0.5875 58.75%
Nephrotoxicity - 0.9138 91.38%
Acute Oral Toxicity (c) III 0.5313 53.13%
Estrogen receptor binding + 0.7385 73.85%
Androgen receptor binding + 0.7197 71.97%
Thyroid receptor binding + 0.5868 58.68%
Glucocorticoid receptor binding + 0.6364 63.64%
Aromatase binding - 0.4863 48.63%
PPAR gamma + 0.6537 65.37%
Honey bee toxicity - 0.9047 90.47%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity + 0.5100 51.00%
Fish aquatic toxicity + 0.9965 99.65%

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
CHEMBL2581 P07339 Cathepsin D 96.02% 98.95%
CHEMBL4040 P28482 MAP kinase ERK2 95.91% 83.82%
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.45% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.69% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.08% 97.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 92.11% 94.45%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 91.16% 96.38%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.16% 95.56%
CHEMBL5255 O00206 Toll-like receptor 4 88.34% 92.50%
CHEMBL221 P23219 Cyclooxygenase-1 87.98% 90.17%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 87.07% 96.09%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 86.74% 96.21%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.71% 86.33%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 84.71% 92.62%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 84.37% 96.47%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 81.91% 99.23%
CHEMBL3359 P21462 Formyl peptide receptor 1 80.57% 93.56%

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.
Jacobaea auricula
Roldana aschenborniana

Cross-Links

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PubChem 162985148
LOTUS LTS0100193
wikiData Q104964325