2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3,4-dihydroxy-2-methylbutanoic acid

Details

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Internal ID ccd39401-23cb-480b-bddc-0dac5b3999f1
Taxonomy Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
IUPAC Name 2-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-3,4-dihydroxy-2-methylbutanoic acid
SMILES (Canonical) CC(C(CO)O)(C(=O)O)OC(=O)C=CC1=CC(=C(C=C1)O)O
SMILES (Isomeric) CC(C(CO)O)(C(=O)O)OC(=O)C=CC1=CC(=C(C=C1)O)O
InChI InChI=1S/C14H16O8/c1-14(13(20)21,11(18)7-15)22-12(19)5-3-8-2-4-9(16)10(17)6-8/h2-6,11,15-18H,7H2,1H3,(H,20,21)
InChI Key VFNQXFLXWICPJF-UHFFFAOYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C14H16O8
Molecular Weight 312.27 g/mol
Exact Mass 312.08451746 g/mol
Topological Polar Surface Area (TPSA) 145.00 Ų
XlogP 0.00
Atomic LogP (AlogP) -0.15
H-Bond Acceptor 7
H-Bond Donor 5
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3,4-dihydroxy-2-methylbutanoic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8594 85.94%
Caco-2 - 0.8218 82.18%
Blood Brain Barrier - 0.6750 67.50%
Human oral bioavailability - 0.6714 67.14%
Subcellular localzation Mitochondria 0.7787 77.87%
OATP2B1 inhibitior - 0.7177 71.77%
OATP1B1 inhibitior + 0.9329 93.29%
OATP1B3 inhibitior + 0.9565 95.65%
MATE1 inhibitior - 0.8000 80.00%
OCT2 inhibitior - 0.8338 83.38%
BSEP inhibitior - 0.5874 58.74%
P-glycoprotein inhibitior - 0.9646 96.46%
P-glycoprotein substrate - 0.8689 86.89%
CYP3A4 substrate - 0.5380 53.80%
CYP2C9 substrate + 0.6032 60.32%
CYP2D6 substrate - 0.8741 87.41%
CYP3A4 inhibition - 0.8163 81.63%
CYP2C9 inhibition - 0.8414 84.14%
CYP2C19 inhibition - 0.9079 90.79%
CYP2D6 inhibition - 0.8974 89.74%
CYP1A2 inhibition - 0.7662 76.62%
CYP2C8 inhibition - 0.6792 67.92%
CYP inhibitory promiscuity - 0.9441 94.41%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.8032 80.32%
Carcinogenicity (trinary) Non-required 0.7355 73.55%
Eye corrosion - 0.9920 99.20%
Eye irritation - 0.8884 88.84%
Skin irritation - 0.6595 65.95%
Skin corrosion - 0.9224 92.24%
Ames mutagenesis - 0.7700 77.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5702 57.02%
Micronuclear - 0.6227 62.27%
Hepatotoxicity - 0.7571 75.71%
skin sensitisation - 0.5313 53.13%
Respiratory toxicity + 0.5333 53.33%
Reproductive toxicity + 0.6222 62.22%
Mitochondrial toxicity - 0.5000 50.00%
Nephrotoxicity - 0.8942 89.42%
Acute Oral Toxicity (c) III 0.7452 74.52%
Estrogen receptor binding + 0.7806 78.06%
Androgen receptor binding + 0.7422 74.22%
Thyroid receptor binding + 0.5580 55.80%
Glucocorticoid receptor binding + 0.6225 62.25%
Aromatase binding + 0.7366 73.66%
PPAR gamma - 0.6142 61.42%
Honey bee toxicity - 0.8951 89.51%
Biodegradation - 0.6750 67.50%
Crustacea aquatic toxicity - 0.7600 76.00%
Fish aquatic toxicity + 0.9398 93.98%

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 98.69% 91.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 96.75% 86.33%
CHEMBL2581 P07339 Cathepsin D 96.41% 98.95%
CHEMBL1951 P21397 Monoamine oxidase A 96.04% 91.49%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 93.36% 96.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.99% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.70% 95.56%
CHEMBL3060 Q9Y345 Glycine transporter 2 88.76% 99.17%
CHEMBL3401 O75469 Pregnane X receptor 88.10% 94.73%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 87.03% 94.45%
CHEMBL2085 P14174 Macrophage migration inhibitory factor 85.73% 80.78%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 85.16% 99.15%
CHEMBL1907591 P30926 Neuronal acetylcholine receptor; alpha4/beta4 84.26% 100.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.10% 89.00%
CHEMBL3194 P02766 Transthyretin 83.08% 90.71%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 82.99% 95.50%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 82.90% 94.62%
CHEMBL3359 P21462 Formyl peptide receptor 1 80.87% 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.
Bidens pilosa

Cross-Links

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PubChem 74095085
LOTUS LTS0263756
wikiData Q105285470