Apigetrin

Details

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Internal ID af02b497-38d9-4871-8c27-9ba85e9e8cf3
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
IUPAC Name 5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
SMILES (Canonical) C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O
SMILES (Isomeric) C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O
InChI InChI=1S/C21H20O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-11-5-12(24)17-13(25)7-14(30-15(17)6-11)9-1-3-10(23)4-2-9/h1-7,16,18-24,26-28H,8H2/t16-,18-,19+,20-,21-/m1/s1
InChI Key KMOUJOKENFFTPU-QNDFHXLGSA-N
Popularity 407 references in papers

Physical and Chemical Properties

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Molecular Formula C21H20O10
Molecular Weight 432.40 g/mol
Exact Mass 432.10564683 g/mol
Topological Polar Surface Area (TPSA) 166.00 Ų
XlogP -0.10
Atomic LogP (AlogP) 0.05
H-Bond Acceptor 10
H-Bond Donor 6
Rotatable Bonds 4

Synonyms

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578-74-5
COSMOSIIN
Apigenin 7-glucoside
Cosmosioside
Cosmosiine
Apigenin 7-O-beta-D-glucoside
APIGENIN-7-GLUCOSIDE
Cosmetin
Cosemetin
Cosmoside
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Apigetrin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.5548 55.48%
Caco-2 - 0.9236 92.36%
Blood Brain Barrier - 0.7000 70.00%
Human oral bioavailability - 0.8286 82.86%
Subcellular localzation Mitochondria 0.6433 64.33%
OATP2B1 inhibitior - 0.5298 52.98%
OATP1B1 inhibitior + 0.9514 95.14%
OATP1B3 inhibitior + 0.9480 94.80%
MATE1 inhibitior - 0.8400 84.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior - 0.4704 47.04%
P-glycoprotein inhibitior - 0.8532 85.32%
P-glycoprotein substrate - 0.8587 85.87%
CYP3A4 substrate + 0.5537 55.37%
CYP2C9 substrate - 0.6762 67.62%
CYP2D6 substrate - 0.8575 85.75%
CYP3A4 inhibition - 0.9192 91.92%
CYP2C9 inhibition - 0.9435 94.35%
CYP2C19 inhibition - 0.9426 94.26%
CYP2D6 inhibition - 0.9501 95.01%
CYP1A2 inhibition - 0.9203 92.03%
CYP2C8 inhibition + 0.6928 69.28%
CYP inhibitory promiscuity - 0.7833 78.33%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6688 66.88%
Eye corrosion - 0.9926 99.26%
Eye irritation - 0.8716 87.16%
Skin irritation - 0.8111 81.11%
Skin corrosion - 0.9715 97.15%
Ames mutagenesis + 0.5200 52.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5745 57.45%
Micronuclear + 0.6133 61.33%
Hepatotoxicity - 0.8696 86.96%
skin sensitisation - 0.9256 92.56%
Respiratory toxicity - 0.5111 51.11%
Reproductive toxicity + 0.6667 66.67%
Mitochondrial toxicity - 0.5125 51.25%
Nephrotoxicity - 0.7945 79.45%
Acute Oral Toxicity (c) III 0.4522 45.22%
Estrogen receptor binding + 0.6847 68.47%
Androgen receptor binding + 0.7434 74.34%
Thyroid receptor binding + 0.5224 52.24%
Glucocorticoid receptor binding + 0.5840 58.40%
Aromatase binding + 0.6524 65.24%
PPAR gamma + 0.8225 82.25%
Honey bee toxicity - 0.6936 69.36%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.6450 64.50%
Fish aquatic toxicity + 0.7773 77.73%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL1825 P01375 TNF-alpha 200 nM
Kd
via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.32% 91.11%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 95.74% 94.00%
CHEMBL2581 P07339 Cathepsin D 95.39% 98.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 94.51% 89.00%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 93.74% 99.15%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 91.90% 86.92%
CHEMBL3194 P02766 Transthyretin 91.80% 90.71%
CHEMBL1951 P21397 Monoamine oxidase A 89.31% 91.49%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.73% 97.09%
CHEMBL3401 O75469 Pregnane X receptor 88.56% 94.73%
CHEMBL242 Q92731 Estrogen receptor beta 87.75% 98.35%
CHEMBL5339 Q5NUL3 G-protein coupled receptor 120 87.54% 95.78%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 86.44% 94.45%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 86.10% 96.21%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.28% 86.33%
CHEMBL1293255 P15428 15-hydroxyprostaglandin dehydrogenase [NAD+] 84.61% 83.57%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 83.41% 95.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.50% 95.89%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 82.44% 91.71%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 81.74% 90.71%
CHEMBL3060 Q9Y345 Glycine transporter 2 81.42% 99.17%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 81.32% 85.14%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 80.77% 95.89%

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.
Abies veitchii
Acaena pinnatifida
Acanthus ebracteatus
Achillea atrata
Achillea collina
Achillea fragrantissima
Achillea ligustica
Achillea millefolium
Achillea pannonica
Achillea roseo-alba
Acmella oleracea
Aconitum leucostomum
Afrocarpus gracilior
Agastache scrophulariifolia
Agave xylonacantha
Agrimonia eupatoria
Ailanthus altissima
Ainsliaea macrocephala
Aiouea montana
Allium rotundum
Aloe castellorum
Alstroemeria pulchra
Ammoides pusilla
Andrographis paniculata
Anisomeles indica
Annona rensoniana
Antennaria dioica
Anthemis cretica
Anthemis pseudocotula
Antiphiona pinnatisecta
Apium graveolens
Aquilegia ecalcarata
Archidendron clypearia
Aristolochia maxima
Arnica acaulis
Arnica angustifolia
Arnica chamissonis
Arnica gracilis
Arnica longifolia
Arnica mollis
Arrhenatherum elatius
Artemisia austriaca
Artemisia judaica
Artemisia szowitziana
Artemisia tridentata
Asphodeline globifera
Asphodelus ramosus
Aster koraiensis
Astilbe rubra
Astragalus kadshorensis
Astragalus verrucosus
Asystasia gangetica
Atroxima liberica
Aureolaria virginica
Azadirachta indica
Baccharis thesioides
Ballota hirsuta
Baptisia australis
Barbarea vulgaris
Bellis perennis
Bergenia crassifolia
Bergenia purpurascens
Betula pendula subsp. mandshurica
Biebersteinia orphanidis
Bischofia javanica
Blasia pusilla
Blepharis ciliaris
Blumea axillaris
Bombax ceiba
Bonnetia paniculata
Boronia ternata
Broussonetia papyrifera
Bryum argenteum
Bryum pseudotriquetrum
Buddleja globosa
Buddleja officinalis
Bunias orientalis
Buxus microphylla
Buxus sempervirens
Callistephus chinensis
Calophyllum inophyllum
Cannabis sativa
Capparis flavicans
Capsicum annuum
Caragana tibetica
Carduus nutans
Carex fraseriana
Casearia membranacea
Ceanothus velutinus
Centaurea cyanus
Centaurea furfuracea
Centaurea horrida
Centaurea sphaerocephala
Centaurea urvillei
Centrosema molle
Cephalaria ambrosioides
Chaerophyllum aureum
Chamaecytisus ratisbonensis
Chamaemelum nobile
Chlorophytum borivilianum
Christisonia bicolor
Chrozophora tinctoria
Chrysanthemum indicum
Chrysanthemum morifolium
Cichorium intybus
Cichorium pumilum
Cinnamomum kotoense
Cirsium oleraceum
Clinopodium laxiflorum
Codonopsis clematidea
Codonopsis ovata
Colchicum robustum
Colchicum soboliferum
Colchicum speciosum
Conioselinum anthriscoides
Conocephalum conicum
Conospermum teretifolium
Convallaria majalis
Coreopsis grandiflora
Corynanthe pachyceras
Cosmos bipinnatus
Cotoneaster horizontalis
Crataegus monogyna
Crataegus orientalis
Crataegus sinaica
Crepidiastrum sonchifolium subsp. sonchifolium
Crocus chrysanthus
Crotalaria orixensis
Cryptocarya triplinervis
Cryptomeria japonica
Cryptotaenia japonica
Cynara cardunculus
Cynara cornigera
Daphne genkwa
Daphne gnidioides
Daphne gnidium
Daphne sericea
Daucus carota
Dermatophyllum secundiflorum
Dicliptera chinensis
Dicoma anomala
Digitalis chalcantha
Dipterocarpus dyeri
Discaria chacaye
Dracocephalum multicaule
Dracocephalum nutans
Dracocephalum tanguticum
Echinops echinatus
Elsholtzia bodinieri
Elsholtzia ciliata
Elsholtzia rugulosa
Ephedra foeminea
Epidendrum rigidum
Erica cinerea
Euphorbia ferganensis
Euphorbia humifusa
Farsetia aegyptia
Fragaria vesca
Fraxinus malacophylla
Fuchsia perscandens
Galeopsis bifida
Galeopsis speciosa
Galeopsis tetrahit
Galinsoga parviflora
Galium album subsp. prusense
Galium verum subsp. verum
Gamblea innovans
Garcinia quaesita
Garcinia scortechinii
Gardenia jasminoides
Gardenia tubifera
Gentiana dahurica
Gerbera jamesonii
Ginkgo biloba
Glebionis coronaria
Glechoma grandis
Glechoma longituba
Globularia davisiana
Glycosmis ovoidea
Gonocaryum calleryanum
Helichrysum arenarium
Helichrysum armenium
Hibiscus cannabinus
Hieracium gymnocephalum
Hornschuchia citriodora
Humulopsis scandens
Humulus scandens
Hydnocarpus venenata
Hypericum perforatum
Hyssopus officinalis
Ipomoea cairica
Isodon angustifolius
Isodon lophanthoides
Isodon rubescens
Itoa orientalis
Ixeridium laevigatum
Jasminum officinale
Kniphofia pumila
Kopsia grandifolia
Kummerowia striata
Lactuca perennis
Lamyropsis cynaroides
Lasianthus fordii
Lasiocephalus ovatus
Launaea arborescens
Launaea aspleniifolia
Lavandula angustifolia subsp. angustifolia
Lavandula dentata
Lawsonia inermis
Ledebouria floribunda
Ledebouria socialis
Leontodon taraxacoides
Leontopodium ochroleucum
Leonurus cardiaca
Lepidothamnus laxifolius
Leptactina senegambica
Leucas cephalotes
Leucophyllum ambiguum
Licaria brasiliensis
Ligularia platyglossa
Ligusticum officinale
Ligustrum robustum
Ligustrum vulgare
Linaria macroura
Linum salsoloides
Lippia origanoides
Lobelia chinensis
Lonicera gracilipes
Lonicera japonica
Luculia pinceana
Luetkea pectinata
Lupinus albus
Lupinus polyphyllus
Lupinus texensis
Lycianthes synanthera
Lycopodium casuarinoides
Lycopodium japonicum
Lycopus europaeus
Lycopus lucidus
Lycopus virginicus
Lygodium japonicum
Maackia tashiroi
Macleaya cordata
Macrotyloma axillare
Malus asiatica
Marrubium vulgare
Mentha arvensis
Mentha canadensis
Mikania obtusata
Mimosa pudica
Monarda punctata
Monoon cupulare
Montrouziera sphaeroidea
Morinda morindoides
Mosla chinensis
Myrtopsis novae-caledoniae
Nardostachys jatamansi
Nepeta cataria
Nepeta tenuifolia
Nepeta velutina
Notobasis syriaca
Ocimum tenuiflorum
Oenothera triangulata
Olea europaea
Onosma hispida
Origanum vulgare
Osmanthus fragrans
Osmanthus heterophyllus
Ostericum maximowiczii
Pachyrhizus tuberosus
Palafoxia texana
Pallenis hierochuntica
Passiflora foetida
Passiflora palmeri
Passiflora sanguinolenta
Perilla frutescens
Persea barbujana
Petroselinum crispum
Phagnalon rupestre
Phillyrea latifolia
Phlomis aurea
Phlomis bovei
Phlomis herba-venti
Phlomis nissolii
Phlomoides rotata
Phyllocladus aspleniifolius
Physocarpus capitatus
Picea neoveitchii
Pimpinella saxifraga
Pinus mugo
Pityrogramma ebenea
Platycodon grandiflorus
Plectranthus ovatus
Podocarpus nivalis
Pogostemon cablin
Pogostemon stellatus
Polygala myrtifolia
Polystichum deltodon
Prosopis farcta
Prostanthera melissifolia
Pseudodictamnus acetabulosus
Psorothamnus spinosus
Pteris multifida
Pteris splendens
Pyrrhopappus carolinianus
Ramirezella strobilophora
Raukaua simplex
Reichardia picroides
Retama raetam
Reynoutria japonica
Rhodiola rosea
Rhodiola stephani
Riella americana
Rosa rugosa
Rosulabryum capillare
Rubus amabilis
Salix arbusculoides
Salix gilgiana
Salix lindleyana
Salix viminalis
Salvia albimaculata
Salvia atropatana
Salvia bucharica
Salvia fruticosa
Salvia limbata
Salvia palaestina
Salvia pinnata
Salvia pratensis
Salvia staminea
Sambucus nigra
Sanguisorba officinalis
Sarcomelicope argyrophylla
Saussurea gossipiphora
Saussurea involucrata
Saussurea medusa
Scandix pecten-veneris
Scorzonera laciniata
Scrophularia wattii
Scutellaria albida
Scutellaria barbata
Scutellaria immaculata
Scutellaria phyllostachya
Scutellaria schachristanica
Scutellaria sieberi
Sedum sarmentosum
Senecio angulatus
Senegalia tenuifolia
Senna italica
Seriphidium vachanicum
Sideritis raeseri
Silybum marianum
Smilax bracteata
Solanum bahamense
Sonchus asper
Sophora flavescens
Spartium junceum
Spiraea canescens
Spirodela polyrhiza
Stachys aegyptiaca
Stachys byzantina
Stachys germanica
Stevia rebaudiana
Strychnos camptoneura
Swertia paniculata
Tanacetum vulgare
Teucrium gnaphalodes
Teucrium polium
Thelypteris esquirolii
Thymus membranaceus
Thymus nummularius
Thymus piperella
Thymus quinquecostatus
Thymus vulgaris
Tinospora crispa
Tinospora smilacina
Trachelospermum asiaticum
Trachelospermum jasminoides
Trichomanes lucens
Trichosanthes kirilowii
Trichosanthes rosthornii
Trigonostemon reidioides
Tropaeolum speciosum
Turnera diffusa
Tynanthus panurensis
Uvaria chamae
Valeriana amurensis
Valeriana cardamines
Valeriana rossica
Vatica diospyroides
Vellozia nivea
Vepris nobilis
Veratrum grandiflorum
Verbascum letourneuxii
Verbascum salviifolium
Verbena officinalis
Veronica chamaedrys
Veronica strictissima
Viburnum wrightii
Vicia sativa
Vitex agnus-castus
Vitex negundo
Vitis cinerea
Zanthoxylum ailanthoides
Ziziphus spina-christi

Cross-Links

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PubChem 5280704
NPASS NPC210003
ChEMBL CHEMBL487017
LOTUS LTS0252743
wikiData Q2858304