Apigenin 7,4'-dimethyl ether

Details

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Internal ID 4b3ec14d-5afb-4bce-9014-cd3b6fc51e14
Taxonomy Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 7-O-methylated flavonoids
IUPAC Name 5-hydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one
SMILES (Canonical) COC1=CC=C(C=C1)C2=CC(=O)C3=C(C=C(C=C3O2)OC)O
SMILES (Isomeric) COC1=CC=C(C=C1)C2=CC(=O)C3=C(C=C(C=C3O2)OC)O
InChI InChI=1S/C17H14O5/c1-20-11-5-3-10(4-6-11)15-9-14(19)17-13(18)7-12(21-2)8-16(17)22-15/h3-9,18H,1-2H3
InChI Key LZERJKGWTQYMBB-UHFFFAOYSA-N
Popularity 120 references in papers

Physical and Chemical Properties

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Molecular Formula C17H14O5
Molecular Weight 298.29 g/mol
Exact Mass 298.08412354 g/mol
Topological Polar Surface Area (TPSA) 65.00 Ų
XlogP 2.40
Atomic LogP (AlogP) 3.18
H-Bond Acceptor 5
H-Bond Donor 1
Rotatable Bonds 3

Synonyms

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7,4'-Di-O-methylapigenin
Apigenin 7,4'-dimethyl ether
Apigenin dimethylether
Genkwanin 4'-methyl ether
5-Hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one
4',7-DIMETHOXY-5-HYDROXYFLAVONE
4',7-Dimethylapigenin
Apigenin 4',7-dimethyl ether
5-Hydroxy-4',7-dimethoxyflavone
5-hydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-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 Apigenin 7,4'-dimethyl ether

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9895 98.95%
Caco-2 + 0.9405 94.05%
Blood Brain Barrier - 0.7500 75.00%
Human oral bioavailability - 0.5857 58.57%
Subcellular localzation Mitochondria 0.7557 75.57%
OATP2B1 inhibitior - 0.7127 71.27%
OATP1B1 inhibitior + 0.9361 93.61%
OATP1B3 inhibitior + 0.9904 99.04%
MATE1 inhibitior + 0.5400 54.00%
OCT2 inhibitior - 0.9750 97.50%
BSEP inhibitior + 0.5958 59.58%
P-glycoprotein inhibitior + 0.8605 86.05%
P-glycoprotein substrate - 0.9411 94.11%
CYP3A4 substrate - 0.5050 50.50%
CYP2C9 substrate - 0.6401 64.01%
CYP2D6 substrate - 0.8296 82.96%
CYP3A4 inhibition + 0.8398 83.98%
CYP2C9 inhibition + 0.7864 78.64%
CYP2C19 inhibition + 0.8233 82.33%
CYP2D6 inhibition - 0.8645 86.45%
CYP1A2 inhibition + 0.8793 87.93%
CYP2C8 inhibition + 0.6209 62.09%
CYP inhibitory promiscuity + 0.6296 62.96%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9113 91.13%
Carcinogenicity (trinary) Non-required 0.5508 55.08%
Eye corrosion - 0.9568 95.68%
Eye irritation + 0.7307 73.07%
Skin irritation - 0.6844 68.44%
Skin corrosion - 0.9875 98.75%
Ames mutagenesis - 0.5100 51.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5596 55.96%
Micronuclear + 0.8800 88.00%
Hepatotoxicity - 0.7500 75.00%
skin sensitisation - 0.9674 96.74%
Respiratory toxicity - 0.6222 62.22%
Reproductive toxicity + 0.7444 74.44%
Mitochondrial toxicity + 0.5375 53.75%
Nephrotoxicity - 0.6816 68.16%
Acute Oral Toxicity (c) III 0.8081 80.81%
Estrogen receptor binding + 0.9545 95.45%
Androgen receptor binding + 0.9447 94.47%
Thyroid receptor binding + 0.6894 68.94%
Glucocorticoid receptor binding + 0.8949 89.49%
Aromatase binding + 0.9265 92.65%
PPAR gamma + 0.8988 89.88%
Honey bee toxicity - 0.9009 90.09%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5500 55.00%
Fish aquatic toxicity + 0.8044 80.44%

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 98.54% 91.11%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 97.66% 85.14%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 96.60% 94.00%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 96.55% 99.15%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.94% 95.56%
CHEMBL2581 P07339 Cathepsin D 92.56% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.15% 86.33%
CHEMBL3194 P02766 Transthyretin 88.09% 90.71%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.93% 89.00%
CHEMBL1907 P15144 Aminopeptidase N 87.76% 93.31%
CHEMBL3401 O75469 Pregnane X receptor 84.72% 94.73%
CHEMBL4208 P20618 Proteasome component C5 84.72% 90.00%
CHEMBL3192 Q9BY41 Histone deacetylase 8 84.52% 93.99%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 84.42% 94.45%
CHEMBL5409 Q8TDU6 G-protein coupled bile acid receptor 1 83.62% 93.65%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 82.66% 86.92%
CHEMBL3060 Q9Y345 Glycine transporter 2 82.27% 99.17%
CHEMBL1951 P21397 Monoamine oxidase A 82.11% 91.49%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 80.41% 90.71%

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.
Aconitum variegatum
Afrocarpus gracilior
Agave xylonacantha
Alpinia oxyphylla
Amorphophallus konjac
Andrographis paniculata
Angelica saxatilis
Aniba santalodora
Anthemis cretica
Antiphiona pinnatisecta
Artabotrys hexapetalus
Artemisia pontica
Astragalus circassicus
Baccharis conferta
Baccharis rhomboidalis
Baccharis tola
Beilschmiedia madang
Bethencourtia palmensis
Betula nigra
Betula pendula
Betula pendula subsp. mandshurica
Boesenbergia rotunda
Bombax anceps
Boswellia ovalifoliolata
Breonia chinensis
Calea crocinervosa
Calea jamaicensis
Callicarpa americana
Calophyllum inophyllum
Campanula bayerniana
Campylotropis hirtella
Caucasalia pontica
Centaurea scoparia
Centaurea sphaerocephala subsp. sphaerocephala
Ceropegia dichotoma
Chrysanthemum indicum
Cistus clusii
Colchicum filifolium
Cota palaestina
Crinum moorei
Crotalaria candicans
Cryptomeria japonica
Dacrycarpus dacrydioides
Daphne genkwa
Dendrobium loddigesii
Dialium excelsum
Distephanus angulifolius
Drymaria cordata
Erythrina subumbrans
Eucalyptus apodophylla
Euphorbia hylonoma
Euphorbia laurifolia
Glycosmis macrophylla
Gymnocarpium robertianum
Gypsophila perfoliata
Hardenbergia violacea
Heliotropium marifolium
Helleborus niger subsp. macranthus
Hemionitis pteridioides
Hypericum polyanthemum
Hyptis capitata
Isodon flavidus
Juniperus drupacea
Kaempferia parviflora
Lepechinia urbanii
Leucas cephalotes
Lindelofia anchusoides subsp. macrostyla
Lonchocarpus chiricanus
Lophostemon confertus
Lycopodium japonicum
Lycopus virginicus
Maackia tashiroi
Maclura cochinchinensis
Marchesinia brachiata
Mentha × gentilis
Mentzelia decapetala
Metanarthecium luteoviride
Mimosa pigra
Mirabilis viscosa
Monoclea gottschei
Monoon cupulare
Montanoa leucantha
Mucuna holtonii
Nuxia sphaerocephala
Ocimum basilicum
Oncosiphon sabulosus
Ononis spinosa
Ophryosporus heptanthus
Orbivestus karaguensis
Origanum dictamnus
Origanum pampaninii
Oroxylum indicum
Ostrya carpinifolia
Pandanus tectorius
Pentaclethra macrophylla
Peperomia blanda
Periploca sepium
Pinalia japonica
Piper falconeri
Platycladus orientalis
Plectranthus fruticosus
Plectranthus hereroensis
Podocarpus fasciculus
Polytrichastrum alpinum
Pongamia pinnata
Pongamia pinnata var. pinnata
Pteris pulchra
Pterocaulon serrulatum
Pterocaulon virgatum
Pulsatilla chinensis
Quercus marilandica
Reboulia hemisphaerica
Rhodiola semenovii
Rosmarinus officinalis
Rubia argyi
Salix rosmarinifolia
Salvia bucharica
Salvia hydrangea
Salvia lavanduloides
Salvia patens
Salvia sessei
Salvia staminea
Salvia syriaca
Salvia texana
Salvia virgata
Salvia yosgadensis
Sarcococca saligna
Scutellaria barbata
Seriphidium diffusum
Sideritis marmorea
Sonneratia caseolaris
Stephania dielsiana
Stephania zippeliana
Teucrium heterophyllum
Teucrium ramosissimum
Thelypteris esquirolii
Thymus vulgaris
Turnera diffusa
Vangueria agrestis
Veratrum dahuricum
Veronica polita
Xanthorrhoea australis

Cross-Links

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PubChem 5281601
NPASS NPC29353
LOTUS LTS0208774
wikiData Q23050245