Dihydroisorhamnetin

Details

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Internal ID 4c3845d6-da63-41c0-8d91-1934f7aa5b1a
Taxonomy Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 3-O-methylated flavonoids
IUPAC Name 3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydrochromen-4-one
SMILES (Canonical) COC1=C(C=CC(=C1)C2C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O
SMILES (Isomeric) COC1=C(C=CC(=C1)C2C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O
InChI InChI=1S/C16H14O7/c1-22-11-4-7(2-3-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,15-19,21H,1H3
InChI Key JWYULKXTGMJKKM-UHFFFAOYSA-N
Popularity 3 references in papers

Physical and Chemical Properties

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Molecular Formula C16H14O7
Molecular Weight 318.28 g/mol
Exact Mass 318.07395278 g/mol
Topological Polar Surface Area (TPSA) 116.00 Ų
XlogP 1.80
Atomic LogP (AlogP) 1.49
H-Bond Acceptor 7
H-Bond Donor 4
Rotatable Bonds 2

Synonyms

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3,4',5,7-Tetrahydroxy-3'-methoxyflavanone
4',5,7-Trihydroxy-3'-methoxydihydroflavonol
3'-O-methyl taxifolin
2,3-dihydroisorhamnetin
taxifolin 3'-methyl ether
CHEMBL1822704
SCHEMBL16887921
CHEBI:175075
3'-methoxy-4',5,7-trihydroxy-dihydroflavonol
3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydrochromen-4-one
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Dihydroisorhamnetin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9524 95.24%
Caco-2 - 0.7136 71.36%
Blood Brain Barrier - 0.8000 80.00%
Human oral bioavailability - 0.7714 77.14%
Subcellular localzation Mitochondria 0.6494 64.94%
OATP2B1 inhibitior - 0.5712 57.12%
OATP1B1 inhibitior + 0.9500 95.00%
OATP1B3 inhibitior + 0.9480 94.80%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior - 0.7361 73.61%
P-glycoprotein inhibitior - 0.7591 75.91%
P-glycoprotein substrate - 0.9406 94.06%
CYP3A4 substrate + 0.5375 53.75%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.7873 78.73%
CYP3A4 inhibition + 0.7348 73.48%
CYP2C9 inhibition + 0.7560 75.60%
CYP2C19 inhibition + 0.8648 86.48%
CYP2D6 inhibition - 0.6993 69.93%
CYP1A2 inhibition + 0.9218 92.18%
CYP2C8 inhibition + 0.5287 52.87%
CYP inhibitory promiscuity + 0.8546 85.46%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6176 61.76%
Eye corrosion - 0.9767 97.67%
Eye irritation + 0.8540 85.40%
Skin irritation - 0.5841 58.41%
Skin corrosion - 0.9319 93.19%
Ames mutagenesis - 0.6300 63.00%
Human Ether-a-go-go-Related Gene inhibition - 0.7528 75.28%
Micronuclear + 0.9100 91.00%
Hepatotoxicity + 0.7250 72.50%
skin sensitisation - 0.9240 92.40%
Respiratory toxicity - 0.5444 54.44%
Reproductive toxicity + 0.8444 84.44%
Mitochondrial toxicity + 0.6500 65.00%
Nephrotoxicity + 0.6448 64.48%
Acute Oral Toxicity (c) III 0.7362 73.62%
Estrogen receptor binding + 0.7461 74.61%
Androgen receptor binding + 0.5442 54.42%
Thyroid receptor binding + 0.5833 58.33%
Glucocorticoid receptor binding + 0.7756 77.56%
Aromatase binding + 0.5884 58.84%
PPAR gamma + 0.6132 61.32%
Honey bee toxicity - 0.8649 86.49%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5600 56.00%
Fish aquatic toxicity + 0.8321 83.21%

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 98.21% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.29% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.94% 95.56%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 92.92% 85.14%
CHEMBL1806 P11388 DNA topoisomerase II alpha 91.39% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.48% 86.33%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 89.16% 99.23%
CHEMBL2535 P11166 Glucose transporter 88.42% 98.75%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 88.22% 99.15%
CHEMBL2581 P07339 Cathepsin D 88.00% 98.95%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 87.34% 94.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 85.62% 94.45%
CHEMBL3194 P02766 Transthyretin 85.16% 90.71%
CHEMBL3060 Q9Y345 Glycine transporter 2 84.65% 99.17%
CHEMBL3401 O75469 Pregnane X receptor 83.26% 94.73%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 81.91% 97.14%
CHEMBL3137262 O60341 LSD1/CoREST complex 81.21% 97.09%

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.
Anastatica hierochuntica
Beta vulgaris
Larrea tridentata
Urospermum dalechampii

Cross-Links

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PubChem 56658060
LOTUS LTS0142049
wikiData Q105136465