(3R)-5,7-dihydroxy-3-[(4-hydroxyphenyl)methyl]-6-methoxy-2,3-dihydrochromen-4-one

Details

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Internal ID db4bdf8e-3a34-4c58-bf21-065ed11af8b9
Taxonomy Phenylpropanoids and polyketides > Homoisoflavonoids > Homoisoflavans > Homoisoflavanones
IUPAC Name (3R)-5,7-dihydroxy-3-[(4-hydroxyphenyl)methyl]-6-methoxy-2,3-dihydrochromen-4-one
SMILES (Canonical) COC1=C(C2=C(C=C1O)OCC(C2=O)CC3=CC=C(C=C3)O)O
SMILES (Isomeric) COC1=C(C2=C(C=C1O)OC[C@H](C2=O)CC3=CC=C(C=C3)O)O
InChI InChI=1S/C17H16O6/c1-22-17-12(19)7-13-14(16(17)21)15(20)10(8-23-13)6-9-2-4-11(18)5-3-9/h2-5,7,10,18-19,21H,6,8H2,1H3/t10-/m1/s1
InChI Key CGCVUMRAPMFWDT-SNVBAGLBSA-N
Popularity 5 references in papers

Physical and Chemical Properties

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Molecular Formula C17H16O6
Molecular Weight 316.30 g/mol
Exact Mass 316.09468823 g/mol
Topological Polar Surface Area (TPSA) 96.20 Ų
XlogP 2.80
Atomic LogP (AlogP) 2.25
H-Bond Acceptor 6
H-Bond Donor 3
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (3R)-5,7-dihydroxy-3-[(4-hydroxyphenyl)methyl]-6-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 + 0.9084 90.84%
Caco-2 + 0.7965 79.65%
Blood Brain Barrier - 0.7750 77.50%
Human oral bioavailability - 0.6286 62.86%
Subcellular localzation Mitochondria 0.6222 62.22%
OATP2B1 inhibitior - 0.5801 58.01%
OATP1B1 inhibitior + 0.8956 89.56%
OATP1B3 inhibitior + 0.8476 84.76%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior - 0.4943 49.43%
P-glycoprotein inhibitior - 0.7261 72.61%
P-glycoprotein substrate - 0.7594 75.94%
CYP3A4 substrate + 0.5455 54.55%
CYP2C9 substrate - 0.8046 80.46%
CYP2D6 substrate - 0.7445 74.45%
CYP3A4 inhibition + 0.5267 52.67%
CYP2C9 inhibition + 0.6154 61.54%
CYP2C19 inhibition + 0.6544 65.44%
CYP2D6 inhibition - 0.7474 74.74%
CYP1A2 inhibition + 0.8096 80.96%
CYP2C8 inhibition + 0.5983 59.83%
CYP inhibitory promiscuity + 0.8277 82.77%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.7137 71.37%
Eye corrosion - 0.9674 96.74%
Eye irritation + 0.6810 68.10%
Skin irritation - 0.7114 71.14%
Skin corrosion - 0.9547 95.47%
Ames mutagenesis + 0.5900 59.00%
Human Ether-a-go-go-Related Gene inhibition - 0.6607 66.07%
Micronuclear + 0.7459 74.59%
Hepatotoxicity - 0.6072 60.72%
skin sensitisation - 0.8677 86.77%
Respiratory toxicity + 0.5556 55.56%
Reproductive toxicity + 0.7444 74.44%
Mitochondrial toxicity - 0.5625 56.25%
Nephrotoxicity - 0.7607 76.07%
Acute Oral Toxicity (c) III 0.8189 81.89%
Estrogen receptor binding + 0.9230 92.30%
Androgen receptor binding + 0.8205 82.05%
Thyroid receptor binding - 0.4914 49.14%
Glucocorticoid receptor binding + 0.6945 69.45%
Aromatase binding + 0.6171 61.71%
PPAR gamma + 0.6352 63.52%
Honey bee toxicity - 0.8812 88.12%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity + 0.5100 51.00%
Fish aquatic toxicity + 0.7652 76.52%

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 98.83% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.90% 94.45%
CHEMBL2581 P07339 Cathepsin D 95.96% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.96% 96.09%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 92.35% 94.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.76% 86.33%
CHEMBL5608 Q16288 NT-3 growth factor receptor 88.61% 95.89%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.51% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.92% 95.56%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 86.45% 95.89%
CHEMBL3060 Q9Y345 Glycine transporter 2 86.29% 99.17%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.52% 89.00%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 83.91% 99.15%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 83.63% 92.62%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 82.41% 85.14%
CHEMBL4208 P20618 Proteasome component C5 81.59% 90.00%
CHEMBL3192 Q9BY41 Histone deacetylase 8 80.96% 93.99%
CHEMBL2535 P11166 Glucose transporter 80.79% 98.75%
CHEMBL2107 P61073 C-X-C chemokine receptor type 4 80.10% 93.10%

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 autumnalis
Soymida febrifuga

Cross-Links

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PubChem 638288
NPASS NPC96167
LOTUS LTS0204038
wikiData Q2110317