4-(3,4-Dihydroxyphenyl)-5-(beta-D-glucopyranosyloxy)-7-methoxy-2H-1-benzopyran-2-one

Details

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Internal ID 1e7e01d6-59ab-4742-934d-e0ac15e911b2
Taxonomy Phenylpropanoids and polyketides > Coumarins and derivatives > Coumarin glycosides
IUPAC Name 4-(3,4-dihydroxyphenyl)-7-methoxy-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one
SMILES (Canonical) COC1=CC2=C(C(=CC(=O)O2)C3=CC(=C(C=C3)O)O)C(=C1)OC4C(C(C(C(O4)CO)O)O)O
SMILES (Isomeric) COC1=CC2=C(C(=CC(=O)O2)C3=CC(=C(C=C3)O)O)C(=C1)OC4C(C(C(C(O4)CO)O)O)O
InChI InChI=1S/C22H22O11/c1-30-10-5-14-18(11(7-17(26)31-14)9-2-3-12(24)13(25)4-9)15(6-10)32-22-21(29)20(28)19(27)16(8-23)33-22/h2-7,16,19-25,27-29H,8H2,1H3
InChI Key JZBHUVGJBWDUSA-UHFFFAOYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C22H22O11
Molecular Weight 462.40 g/mol
Exact Mass 462.11621151 g/mol
Topological Polar Surface Area (TPSA) 175.00 Ų
XlogP 0.20
Atomic LogP (AlogP) 0.06
H-Bond Acceptor 11
H-Bond Donor 6
Rotatable Bonds 5

Synonyms

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116310-58-8

2D Structure

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2D Structure of 4-(3,4-Dihydroxyphenyl)-5-(beta-D-glucopyranosyloxy)-7-methoxy-2H-1-benzopyran-2-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.4855 48.55%
Caco-2 - 0.8680 86.80%
Blood Brain Barrier - 0.8500 85.00%
Human oral bioavailability - 0.6143 61.43%
Subcellular localzation Mitochondria 0.6190 61.90%
OATP2B1 inhibitior + 0.5830 58.30%
OATP1B1 inhibitior + 0.9092 90.92%
OATP1B3 inhibitior + 0.9740 97.40%
MATE1 inhibitior - 0.8000 80.00%
OCT2 inhibitior - 0.8000 80.00%
BSEP inhibitior + 0.7455 74.55%
P-glycoprotein inhibitior - 0.6620 66.20%
P-glycoprotein substrate - 0.7706 77.06%
CYP3A4 substrate + 0.5938 59.38%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8507 85.07%
CYP3A4 inhibition - 0.9108 91.08%
CYP2C9 inhibition - 0.9071 90.71%
CYP2C19 inhibition - 0.9173 91.73%
CYP2D6 inhibition - 0.9514 95.14%
CYP1A2 inhibition - 0.9045 90.45%
CYP2C8 inhibition + 0.6868 68.68%
CYP inhibitory promiscuity - 0.7292 72.92%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6890 68.90%
Eye corrosion - 0.9896 98.96%
Eye irritation - 0.8951 89.51%
Skin irritation - 0.8153 81.53%
Skin corrosion - 0.9600 96.00%
Ames mutagenesis + 0.7100 71.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4474 44.74%
Micronuclear + 0.6633 66.33%
Hepatotoxicity - 0.8071 80.71%
skin sensitisation - 0.9373 93.73%
Respiratory toxicity - 0.5222 52.22%
Reproductive toxicity + 0.7667 76.67%
Mitochondrial toxicity - 0.5250 52.50%
Nephrotoxicity - 0.7997 79.97%
Acute Oral Toxicity (c) III 0.6624 66.24%
Estrogen receptor binding + 0.7183 71.83%
Androgen receptor binding + 0.7717 77.17%
Thyroid receptor binding + 0.5395 53.95%
Glucocorticoid receptor binding + 0.7536 75.36%
Aromatase binding + 0.5520 55.20%
PPAR gamma + 0.6599 65.99%
Honey bee toxicity - 0.7435 74.35%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.6349 63.49%
Fish aquatic toxicity + 0.7079 70.79%

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 99.39% 91.11%
CHEMBL2581 P07339 Cathepsin D 97.53% 98.95%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 95.92% 85.14%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 95.87% 94.00%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 95.66% 99.15%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.15% 96.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 92.25% 89.00%
CHEMBL220 P22303 Acetylcholinesterase 91.99% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.53% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.43% 86.33%
CHEMBL3060 Q9Y345 Glycine transporter 2 88.62% 99.17%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 87.66% 86.92%
CHEMBL3401 O75469 Pregnane X receptor 87.52% 94.73%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 87.19% 96.00%
CHEMBL2085 P14174 Macrophage migration inhibitory factor 85.55% 80.78%
CHEMBL1951 P21397 Monoamine oxidase A 85.38% 91.49%
CHEMBL4940 P07195 L-lactate dehydrogenase B chain 83.55% 95.53%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.14% 95.89%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 82.05% 96.21%
CHEMBL1907 P15144 Aminopeptidase N 81.97% 93.31%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 81.83% 95.83%
CHEMBL5339 Q5NUL3 G-protein coupled receptor 120 81.51% 95.78%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 81.50% 95.50%
CHEMBL4208 P20618 Proteasome component C5 81.36% 90.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 81.35% 97.09%
CHEMBL3194 P02766 Transthyretin 80.85% 90.71%
CHEMBL3714130 P46095 G-protein coupled receptor 6 80.39% 97.36%

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.
Coutarea hexandra
Hintonia latiflora

Cross-Links

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PubChem 13962181
LOTUS LTS0033982
wikiData Q105137328