Methyl cinnamate

Details

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Internal ID 88bc65ab-eabd-4a6b-899c-831b139eb1da
Taxonomy Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Cinnamic acid esters
IUPAC Name methyl (E)-3-phenylprop-2-enoate
SMILES (Canonical) COC(=O)C=CC1=CC=CC=C1
SMILES (Isomeric) COC(=O)/C=C/C1=CC=CC=C1
InChI InChI=1S/C10H10O2/c1-12-10(11)8-7-9-5-3-2-4-6-9/h2-8H,1H3/b8-7+
InChI Key CCRCUPLGCSFEDV-BQYQJAHWSA-N
Popularity 898 references in papers

Physical and Chemical Properties

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Molecular Formula C10H10O2
Molecular Weight 162.18 g/mol
Exact Mass 162.068079557 g/mol
Topological Polar Surface Area (TPSA) 26.30 Ų
XlogP 2.60
Atomic LogP (AlogP) 1.87
H-Bond Acceptor 2
H-Bond Donor 0
Rotatable Bonds 2

Synonyms

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103-26-4
Methyl trans-cinnamate
1754-62-7
Methyl (E)-cinnamate
Methyl (E)-3-phenylprop-2-enoate
Cinnamic acid methyl ester
Methyl 3-phenylpropenoate
Methyl cinnamylate
Methyl 3-phenylacrylate
Methylcinnamate
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Methyl cinnamate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 1.0000 100.00%
Caco-2 + 0.8860 88.60%
Blood Brain Barrier + 0.8750 87.50%
Human oral bioavailability - 0.5429 54.29%
Subcellular localzation Mitochondria 0.5112 51.12%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9520 95.20%
OATP1B3 inhibitior + 0.9744 97.44%
MATE1 inhibitior - 0.7800 78.00%
OCT2 inhibitior - 1.0000 100.00%
BSEP inhibitior - 0.6700 67.00%
P-glycoprotein inhibitior - 0.9841 98.41%
P-glycoprotein substrate - 0.9820 98.20%
CYP3A4 substrate - 0.6995 69.95%
CYP2C9 substrate - 0.6000 60.00%
CYP2D6 substrate - 0.8653 86.53%
CYP3A4 inhibition - 0.9814 98.14%
CYP2C9 inhibition - 0.9402 94.02%
CYP2C19 inhibition - 0.9081 90.81%
CYP2D6 inhibition - 0.9721 97.21%
CYP1A2 inhibition - 0.5140 51.40%
CYP2C8 inhibition - 0.6670 66.70%
CYP inhibitory promiscuity - 0.8400 84.00%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) + 0.5136 51.36%
Carcinogenicity (trinary) Non-required 0.6419 64.19%
Eye corrosion + 0.8917 89.17%
Eye irritation + 0.9955 99.55%
Skin irritation + 0.8380 83.80%
Skin corrosion - 0.8222 82.22%
Ames mutagenesis - 0.7800 78.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5958 59.58%
Micronuclear - 0.8600 86.00%
Hepatotoxicity - 0.6579 65.79%
skin sensitisation + 0.9033 90.33%
Respiratory toxicity - 0.7889 78.89%
Reproductive toxicity - 0.8667 86.67%
Mitochondrial toxicity - 0.9750 97.50%
Nephrotoxicity + 0.4675 46.75%
Acute Oral Toxicity (c) III 0.9144 91.44%
Estrogen receptor binding - 0.8681 86.81%
Androgen receptor binding + 0.5264 52.64%
Thyroid receptor binding - 0.8627 86.27%
Glucocorticoid receptor binding - 0.7208 72.08%
Aromatase binding - 0.5997 59.97%
PPAR gamma - 0.9285 92.85%
Honey bee toxicity - 0.9659 96.59%
Biodegradation - 0.6250 62.50%
Crustacea aquatic toxicity - 0.5400 54.00%
Fish aquatic toxicity + 0.9143 91.43%

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
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.04% 86.33%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 93.62% 96.00%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.85% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.63% 95.56%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 88.13% 96.09%
CHEMBL221 P23219 Cyclooxygenase-1 87.82% 90.17%
CHEMBL5028 O14672 ADAM10 83.67% 97.50%
CHEMBL2581 P07339 Cathepsin D 83.54% 98.95%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 81.77% 95.50%
CHEMBL3401 O75469 Pregnane X receptor 80.97% 94.73%

Cross-Links

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PubChem 637520
NPASS NPC3672
LOTUS LTS0222336
wikiData Q72460898