[(1R,2R,4aS,5R,7R,8aR)-5-hydroxy-1,8a-dimethyl-6-oxo-7-prop-1-en-2-yl-1,2,3,4,4a,5,7,8-octahydronaphthalen-2-yl] 3-methylbut-2-enoate

Details

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Internal ID 543dca53-eb54-45c7-970a-ff1793c3ef3d
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
IUPAC Name [(1R,2R,4aS,5R,7R,8aR)-5-hydroxy-1,8a-dimethyl-6-oxo-7-prop-1-en-2-yl-1,2,3,4,4a,5,7,8-octahydronaphthalen-2-yl] 3-methylbut-2-enoate
SMILES (Canonical) CC1C(CCC2C1(CC(C(=O)C2O)C(=C)C)C)OC(=O)C=C(C)C
SMILES (Isomeric) C[C@H]1[C@@H](CC[C@H]2[C@@]1(C[C@@H](C(=O)[C@@H]2O)C(=C)C)C)OC(=O)C=C(C)C
InChI InChI=1S/C20H30O4/c1-11(2)9-17(21)24-16-8-7-15-19(23)18(22)14(12(3)4)10-20(15,6)13(16)5/h9,13-16,19,23H,3,7-8,10H2,1-2,4-6H3/t13-,14+,15+,16+,19+,20+/m0/s1
InChI Key ULEDMRZYWPXVFM-XTPGNIOPSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C20H30O4
Molecular Weight 334.40 g/mol
Exact Mass 334.21440943 g/mol
Topological Polar Surface Area (TPSA) 63.60 Ų
XlogP 4.50
Atomic LogP (AlogP) 3.44
H-Bond Acceptor 4
H-Bond Donor 1
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1R,2R,4aS,5R,7R,8aR)-5-hydroxy-1,8a-dimethyl-6-oxo-7-prop-1-en-2-yl-1,2,3,4,4a,5,7,8-octahydronaphthalen-2-yl] 3-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 + 0.9872 98.72%
Caco-2 + 0.5863 58.63%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.8796 87.96%
OATP2B1 inhibitior - 0.8622 86.22%
OATP1B1 inhibitior + 0.8999 89.99%
OATP1B3 inhibitior - 0.4265 42.65%
MATE1 inhibitior - 0.8000 80.00%
OCT2 inhibitior - 0.6071 60.71%
BSEP inhibitior - 0.5654 56.54%
P-glycoprotein inhibitior - 0.6857 68.57%
P-glycoprotein substrate - 0.7027 70.27%
CYP3A4 substrate + 0.6711 67.11%
CYP2C9 substrate - 0.7735 77.35%
CYP2D6 substrate - 0.9017 90.17%
CYP3A4 inhibition - 0.6447 64.47%
CYP2C9 inhibition - 0.8501 85.01%
CYP2C19 inhibition - 0.8142 81.42%
CYP2D6 inhibition - 0.9449 94.49%
CYP1A2 inhibition - 0.7576 75.76%
CYP2C8 inhibition - 0.7571 75.71%
CYP inhibitory promiscuity - 0.9442 94.42%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9743 97.43%
Carcinogenicity (trinary) Non-required 0.6720 67.20%
Eye corrosion - 0.9920 99.20%
Eye irritation - 0.9361 93.61%
Skin irritation + 0.5751 57.51%
Skin corrosion - 0.9608 96.08%
Ames mutagenesis - 0.7200 72.00%
Human Ether-a-go-go-Related Gene inhibition - 0.7113 71.13%
Micronuclear - 0.7400 74.00%
Hepatotoxicity + 0.6213 62.13%
skin sensitisation - 0.5591 55.91%
Respiratory toxicity + 0.5222 52.22%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.6250 62.50%
Nephrotoxicity + 0.7625 76.25%
Acute Oral Toxicity (c) III 0.7123 71.23%
Estrogen receptor binding + 0.8368 83.68%
Androgen receptor binding + 0.5571 55.71%
Thyroid receptor binding + 0.5197 51.97%
Glucocorticoid receptor binding + 0.7343 73.43%
Aromatase binding + 0.5645 56.45%
PPAR gamma - 0.5783 57.83%
Honey bee toxicity - 0.6403 64.03%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity + 0.6500 65.00%
Fish aquatic toxicity + 1.0000 100.00%

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 95.53% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.66% 96.09%
CHEMBL340 P08684 Cytochrome P450 3A4 91.94% 91.19%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 89.17% 85.14%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 88.70% 94.45%
CHEMBL1994 P08235 Mineralocorticoid receptor 88.27% 100.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.75% 95.56%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 85.99% 91.07%
CHEMBL1951 P21397 Monoamine oxidase A 85.10% 91.49%
CHEMBL241 Q14432 Phosphodiesterase 3A 83.44% 92.94%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.24% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 82.99% 86.33%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 82.97% 95.89%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 82.61% 94.33%
CHEMBL253 P34972 Cannabinoid CB2 receptor 82.58% 97.25%
CHEMBL2581 P07339 Cathepsin D 82.55% 98.95%
CHEMBL1902 P62942 FK506-binding protein 1A 80.73% 97.05%
CHEMBL3137262 O60341 LSD1/CoREST complex 80.71% 97.09%

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.
Senecio sylvaticus

Cross-Links

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PubChem 163037656
LOTUS LTS0117100
wikiData Q105275051