(3R)-7-hydroxy-3-[(4-hydroxyphenyl)methyl]-5-methoxy-2,3-dihydrochromen-4-one

Details

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Internal ID 33401a18-589b-48a2-9af3-d713742cb5b8
Taxonomy Phenylpropanoids and polyketides > Homoisoflavonoids > Homoisoflavans > Homoisoflavanones
IUPAC Name (3R)-7-hydroxy-3-[(4-hydroxyphenyl)methyl]-5-methoxy-2,3-dihydrochromen-4-one
SMILES (Canonical) COC1=CC(=CC2=C1C(=O)C(CO2)CC3=CC=C(C=C3)O)O
SMILES (Isomeric) COC1=CC(=CC2=C1C(=O)[C@@H](CO2)CC3=CC=C(C=C3)O)O
InChI InChI=1S/C17H16O5/c1-21-14-7-13(19)8-15-16(14)17(20)11(9-22-15)6-10-2-4-12(18)5-3-10/h2-5,7-8,11,18-19H,6,9H2,1H3/t11-/m1/s1
InChI Key COVYMSXAVAIXCI-LLVKDONJSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C17H16O5
Molecular Weight 300.30 g/mol
Exact Mass 300.09977361 g/mol
Topological Polar Surface Area (TPSA) 76.00 Ų
XlogP 2.60
Atomic LogP (AlogP) 2.54
H-Bond Acceptor 5
H-Bond Donor 2
Rotatable Bonds 3

Synonyms

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27245-81-4
(-)-2,3-Dihydro-7-hydroxy-3-[(4-hydroxyphenyl)methyl]-5-methoxy-4H-1-benzopyran-4-one

2D Structure

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2D Structure of (3R)-7-hydroxy-3-[(4-hydroxyphenyl)methyl]-5-methoxy-2,3-dihydrochromen-4-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9741 97.41%
Caco-2 + 0.8822 88.22%
Blood Brain Barrier - 0.8000 80.00%
Human oral bioavailability - 0.6000 60.00%
Subcellular localzation Mitochondria 0.8643 86.43%
OATP2B1 inhibitior - 0.7228 72.28%
OATP1B1 inhibitior + 0.9353 93.53%
OATP1B3 inhibitior + 0.9468 94.68%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior - 0.4909 49.09%
P-glycoprotein inhibitior - 0.4932 49.32%
P-glycoprotein substrate - 0.6526 65.26%
CYP3A4 substrate + 0.5443 54.43%
CYP2C9 substrate - 0.8074 80.74%
CYP2D6 substrate + 0.3454 34.54%
CYP3A4 inhibition - 0.6821 68.21%
CYP2C9 inhibition + 0.7741 77.41%
CYP2C19 inhibition + 0.8994 89.94%
CYP2D6 inhibition - 0.7621 76.21%
CYP1A2 inhibition + 0.9295 92.95%
CYP2C8 inhibition + 0.6546 65.46%
CYP inhibitory promiscuity + 0.8049 80.49%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9213 92.13%
Carcinogenicity (trinary) Non-required 0.6628 66.28%
Eye corrosion - 0.9636 96.36%
Eye irritation + 0.7806 78.06%
Skin irritation - 0.7324 73.24%
Skin corrosion - 0.9793 97.93%
Ames mutagenesis + 0.5500 55.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5000 50.00%
Micronuclear + 0.7600 76.00%
Hepatotoxicity - 0.5916 59.16%
skin sensitisation - 0.9289 92.89%
Respiratory toxicity - 0.5556 55.56%
Reproductive toxicity + 0.6889 68.89%
Mitochondrial toxicity - 0.5750 57.50%
Nephrotoxicity + 0.5120 51.20%
Acute Oral Toxicity (c) III 0.7857 78.57%
Estrogen receptor binding + 0.7897 78.97%
Androgen receptor binding + 0.8632 86.32%
Thyroid receptor binding + 0.5909 59.09%
Glucocorticoid receptor binding + 0.7089 70.89%
Aromatase binding + 0.6071 60.71%
PPAR gamma + 0.6053 60.53%
Honey bee toxicity - 0.8379 83.79%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity + 0.5600 56.00%
Fish aquatic toxicity + 0.8514 85.14%

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
CHEMBL4040 P28482 MAP kinase ERK2 98.40% 83.82%
CHEMBL2581 P07339 Cathepsin D 96.83% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.30% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.29% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.99% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.30% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.73% 95.56%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 89.77% 94.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 89.48% 95.89%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 88.82% 95.89%
CHEMBL3060 Q9Y345 Glycine transporter 2 87.42% 99.17%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.70% 97.09%
CHEMBL2535 P11166 Glucose transporter 86.32% 98.75%
CHEMBL4208 P20618 Proteasome component C5 85.36% 90.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.07% 89.00%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 82.66% 92.62%

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.
Eucomis comosa

Cross-Links

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PubChem 92446293
LOTUS LTS0270538
wikiData Q104967336