5,3',4'-Trihydroxy-7-methoxy-4-phenylcoumarin

Details

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Internal ID a3d166ed-9eb4-4196-8a76-38c9e05d44f0
Taxonomy Phenylpropanoids and polyketides > Neoflavonoids > Neoflavones
IUPAC Name 4-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxychromen-2-one
SMILES (Canonical) COC1=CC(=C2C(=CC(=O)OC2=C1)C3=CC(=C(C=C3)O)O)O
SMILES (Isomeric) COC1=CC(=C2C(=CC(=O)OC2=C1)C3=CC(=C(C=C3)O)O)O
InChI InChI=1S/C16H12O6/c1-21-9-5-13(19)16-10(7-15(20)22-14(16)6-9)8-2-3-11(17)12(18)4-8/h2-7,17-19H,1H3
InChI Key DEVKCCHIUHLHCF-UHFFFAOYSA-N
Popularity 8 references in papers

Physical and Chemical Properties

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Molecular Formula C16H12O6
Molecular Weight 300.26 g/mol
Exact Mass 300.06338810 g/mol
Topological Polar Surface Area (TPSA) 96.20 Ų
XlogP 2.00
Atomic LogP (AlogP) 2.59
H-Bond Acceptor 6
H-Bond Donor 3
Rotatable Bonds 2

Synonyms

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CHEMBL486219
4-(3,4-DIHYDROXYPHENYL)-5-HYDROXY-7-METHOXYCHROMEN-2-ONE
112078-72-5
DTXSID30432350
CHEBI:183610
BDBM50430024
LMPK12100045
7-methoxy-5,3',4'-trihydroxy-4-phenylcoumarin

2D Structure

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2D Structure of 5,3',4'-Trihydroxy-7-methoxy-4-phenylcoumarin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9320 93.20%
Caco-2 + 0.5281 52.81%
Blood Brain Barrier - 0.8500 85.00%
Human oral bioavailability + 0.5429 54.29%
Subcellular localzation Mitochondria 0.7787 77.87%
OATP2B1 inhibitior - 0.5637 56.37%
OATP1B1 inhibitior + 0.9413 94.13%
OATP1B3 inhibitior + 0.9857 98.57%
MATE1 inhibitior - 0.7800 78.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior - 0.6093 60.93%
P-glycoprotein inhibitior - 0.7578 75.78%
P-glycoprotein substrate - 0.9168 91.68%
CYP3A4 substrate + 0.5171 51.71%
CYP2C9 substrate - 0.8321 83.21%
CYP2D6 substrate - 0.8219 82.19%
CYP3A4 inhibition - 0.8662 86.62%
CYP2C9 inhibition - 0.6942 69.42%
CYP2C19 inhibition - 0.6144 61.44%
CYP2D6 inhibition - 0.9444 94.44%
CYP1A2 inhibition + 0.7339 73.39%
CYP2C8 inhibition + 0.7787 77.87%
CYP inhibitory promiscuity - 0.6181 61.81%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.5627 56.27%
Eye corrosion - 0.9777 97.77%
Eye irritation + 0.9129 91.29%
Skin irritation - 0.6127 61.27%
Skin corrosion - 0.9531 95.31%
Ames mutagenesis + 0.6300 63.00%
Human Ether-a-go-go-Related Gene inhibition - 0.8204 82.04%
Micronuclear + 0.9300 93.00%
Hepatotoxicity - 0.6375 63.75%
skin sensitisation - 0.9432 94.32%
Respiratory toxicity - 0.5667 56.67%
Reproductive toxicity + 0.8556 85.56%
Mitochondrial toxicity + 0.7125 71.25%
Nephrotoxicity - 0.6178 61.78%
Acute Oral Toxicity (c) III 0.6219 62.19%
Estrogen receptor binding + 0.8482 84.82%
Androgen receptor binding + 0.9308 93.08%
Thyroid receptor binding + 0.6861 68.61%
Glucocorticoid receptor binding + 0.9289 92.89%
Aromatase binding + 0.7822 78.22%
PPAR gamma + 0.8447 84.47%
Honey bee toxicity - 0.8199 81.99%
Biodegradation - 0.9250 92.50%
Crustacea aquatic toxicity + 0.5200 52.00%
Fish aquatic toxicity + 0.9327 93.27%

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 98.50% 91.11%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 97.22% 99.15%
CHEMBL2581 P07339 Cathepsin D 96.15% 98.95%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 94.56% 94.00%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 93.51% 85.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.57% 95.56%
CHEMBL1951 P21397 Monoamine oxidase A 91.52% 91.49%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.98% 86.33%
CHEMBL2085 P14174 Macrophage migration inhibitory factor 89.43% 80.78%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.29% 89.00%
CHEMBL3194 P02766 Transthyretin 86.74% 90.71%
CHEMBL4940 P07195 L-lactate dehydrogenase B chain 85.65% 95.53%
CHEMBL3060 Q9Y345 Glycine transporter 2 85.63% 99.17%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 85.62% 99.23%
CHEMBL3401 O75469 Pregnane X receptor 85.34% 94.73%
CHEMBL5409 Q8TDU6 G-protein coupled bile acid receptor 1 84.85% 93.65%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 84.80% 96.09%
CHEMBL1907 P15144 Aminopeptidase N 84.20% 93.31%
CHEMBL3922 P50579 Methionine aminopeptidase 2 83.13% 97.28%
CHEMBL4208 P20618 Proteasome component C5 82.79% 90.00%
CHEMBL3438 Q05513 Protein kinase C zeta 82.62% 88.48%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 82.55% 95.50%

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.
Exostema caribaeum
Hintonia latiflora

Cross-Links

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PubChem 9882773
LOTUS LTS0079318
wikiData Q82246423