[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (E)-3-phenylprop-2-enoate

Details

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Internal ID 20932c45-ff42-4db9-9334-5a5bde675cc4
Taxonomy Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Cinnamic acid esters
IUPAC Name [(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (E)-3-phenylprop-2-enoate
SMILES (Canonical) CN1C2CCC1CC(C2)OC(=O)C=CC3=CC=CC=C3
SMILES (Isomeric) CN1[C@@H]2CC[C@H]1CC(C2)OC(=O)/C=C/C3=CC=CC=C3
InChI InChI=1S/C17H21NO2/c1-18-14-8-9-15(18)12-16(11-14)20-17(19)10-7-13-5-3-2-4-6-13/h2-7,10,14-16H,8-9,11-12H2,1H3/b10-7+/t14-,15+,16?
InChI Key WTIWQHQPUWFUPX-NUUMQCRXSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C17H21NO2
Molecular Weight 271.35 g/mol
Exact Mass 271.157228913 g/mol
Topological Polar Surface Area (TPSA) 29.50 Ų
XlogP 3.40
Atomic LogP (AlogP) 2.87
H-Bond Acceptor 3
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 [(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (E)-3-phenylprop-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 + 0.9933 99.33%
Caco-2 + 0.8845 88.45%
Blood Brain Barrier + 0.8858 88.58%
Human oral bioavailability - 0.5857 58.57%
Subcellular localzation Mitochondria 0.4575 45.75%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9440 94.40%
OATP1B3 inhibitior + 0.9485 94.85%
MATE1 inhibitior - 0.7800 78.00%
OCT2 inhibitior + 0.9250 92.50%
BSEP inhibitior - 0.7125 71.25%
P-glycoprotein inhibitior - 0.9173 91.73%
P-glycoprotein substrate - 0.7914 79.14%
CYP3A4 substrate + 0.5414 54.14%
CYP2C9 substrate - 0.6039 60.39%
CYP2D6 substrate - 0.7046 70.46%
CYP3A4 inhibition - 0.9017 90.17%
CYP2C9 inhibition - 0.9114 91.14%
CYP2C19 inhibition - 0.8650 86.50%
CYP2D6 inhibition + 0.6279 62.79%
CYP1A2 inhibition - 0.8979 89.79%
CYP2C8 inhibition - 0.8430 84.30%
CYP inhibitory promiscuity - 0.8420 84.20%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.5643 56.43%
Eye corrosion - 0.9861 98.61%
Eye irritation - 0.9285 92.85%
Skin irritation - 0.7806 78.06%
Skin corrosion - 0.9516 95.16%
Ames mutagenesis - 0.7600 76.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7750 77.50%
Micronuclear - 0.6300 63.00%
Hepatotoxicity - 0.5364 53.64%
skin sensitisation - 0.8777 87.77%
Respiratory toxicity + 0.7667 76.67%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity + 0.8250 82.50%
Nephrotoxicity - 0.8208 82.08%
Acute Oral Toxicity (c) III 0.6522 65.22%
Estrogen receptor binding - 0.7696 76.96%
Androgen receptor binding - 0.6338 63.38%
Thyroid receptor binding - 0.6688 66.88%
Glucocorticoid receptor binding - 0.8454 84.54%
Aromatase binding + 0.6739 67.39%
PPAR gamma - 0.6469 64.69%
Honey bee toxicity - 0.9468 94.68%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.5955 59.55%
Fish aquatic toxicity + 0.7805 78.05%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.67% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 95.12% 95.56%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 94.32% 94.62%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 94.18% 94.23%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 92.83% 94.08%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.46% 86.33%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 91.17% 96.00%
CHEMBL2581 P07339 Cathepsin D 90.95% 98.95%
CHEMBL1899 P46098 Serotonin 3a (5-HT3a) receptor 89.38% 100.00%
CHEMBL3192 Q9BY41 Histone deacetylase 8 84.86% 93.99%
CHEMBL5028 O14672 ADAM10 84.63% 97.50%
CHEMBL3137262 O60341 LSD1/CoREST complex 83.90% 97.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 82.08% 91.11%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.81% 95.89%
CHEMBL4208 P20618 Proteasome component C5 80.64% 90.00%
CHEMBL221 P23219 Cyclooxygenase-1 80.62% 90.17%
CHEMBL245 P20309 Muscarinic acetylcholine receptor M3 80.57% 97.53%
CHEMBL3060 Q9Y345 Glycine transporter 2 80.49% 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.
Erythroxylum coca

Cross-Links

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PubChem 1237281
LOTUS LTS0270454
wikiData Q105312580