Luteolin 7-O-glucoside

Details

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Internal ID f1c9554d-fc30-4545-aea7-4fe35bcb130d
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
IUPAC Name 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
SMILES (Canonical) C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O)O
SMILES (Isomeric) C1=CC(=C(C=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)O
InChI InChI=1S/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)30-9-4-12(25)17-13(26)6-14(31-15(17)5-9)8-1-2-10(23)11(24)3-8/h1-6,16,18-25,27-29H,7H2/t16-,18-,19+,20-,21-/m1/s1
InChI Key PEFNSGRTCBGNAN-QNDFHXLGSA-N
Popularity 791 references in papers

Physical and Chemical Properties

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Molecular Formula C21H20O11
Molecular Weight 448.40 g/mol
Exact Mass 448.10056145 g/mol
Topological Polar Surface Area (TPSA) 186.00 Ų
XlogP 0.50
Atomic LogP (AlogP) -0.24
H-Bond Acceptor 11
H-Bond Donor 7
Rotatable Bonds 4

Synonyms

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Luteoloside
5373-11-5
Luteolin 7-glucoside
Cinaroside
Luteolin-7-glucoside
Luteolin 7-O-glucoside
Luteolin-7-O-glucoside
Glucoluteolin
7-Glucoluteolin
7-Glucosylluteolin
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Luteolin 7-O-glucoside

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.5116 51.16%
Caco-2 - 0.9372 93.72%
Blood Brain Barrier - 0.7750 77.50%
Human oral bioavailability - 0.7571 75.71%
Subcellular localzation Mitochondria 0.6068 60.68%
OATP2B1 inhibitior + 0.5978 59.78%
OATP1B1 inhibitior + 0.9622 96.22%
OATP1B3 inhibitior + 0.9265 92.65%
MATE1 inhibitior - 0.7800 78.00%
OCT2 inhibitior - 0.7750 77.50%
BSEP inhibitior - 0.5553 55.53%
P-glycoprotein inhibitior - 0.8236 82.36%
P-glycoprotein substrate - 0.8293 82.93%
CYP3A4 substrate + 0.5518 55.18%
CYP2C9 substrate - 0.6709 67.09%
CYP2D6 substrate - 0.8582 85.82%
CYP3A4 inhibition - 0.9193 91.93%
CYP2C9 inhibition - 0.9296 92.96%
CYP2C19 inhibition - 0.9289 92.89%
CYP2D6 inhibition - 0.9513 95.13%
CYP1A2 inhibition - 0.9084 90.84%
CYP2C8 inhibition + 0.7081 70.81%
CYP inhibitory promiscuity - 0.7728 77.28%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.7144 71.44%
Eye corrosion - 0.9930 99.30%
Eye irritation - 0.8660 86.60%
Skin irritation - 0.8036 80.36%
Skin corrosion - 0.9691 96.91%
Ames mutagenesis + 0.6436 64.36%
Human Ether-a-go-go-Related Gene inhibition - 0.4890 48.90%
Micronuclear + 0.6533 65.33%
Hepatotoxicity - 0.8946 89.46%
skin sensitisation - 0.9122 91.22%
Respiratory toxicity + 0.5444 54.44%
Reproductive toxicity + 0.7222 72.22%
Mitochondrial toxicity + 0.5125 51.25%
Nephrotoxicity - 0.8103 81.03%
Acute Oral Toxicity (c) III 0.4045 40.45%
Estrogen receptor binding + 0.6902 69.02%
Androgen receptor binding + 0.7058 70.58%
Thyroid receptor binding + 0.5588 55.88%
Glucocorticoid receptor binding + 0.6151 61.51%
Aromatase binding + 0.5408 54.08%
PPAR gamma + 0.8127 81.27%
Honey bee toxicity - 0.6503 65.03%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.6250 62.50%
Fish aquatic toxicity + 0.8218 82.18%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL5880 P60568 Interleukin-2 20 nM
Kd
via Super-PRED
CHEMBL1287622 Q9Y468 Lethal(3)malignant brain tumor-like protein 1 3981.1 nM
Potency
via CMAUP
CHEMBL1825 P01375 TNF-alpha 790 nM
Kd
via Super-PRED
CHEMBL1075138 Q9NUW8 Tyrosyl-DNA phosphodiesterase 1 7079.5 nM
Potency
via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.63% 91.11%
CHEMBL1951 P21397 Monoamine oxidase A 97.48% 91.49%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 96.15% 99.15%
CHEMBL2581 P07339 Cathepsin D 94.74% 98.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 94.63% 89.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 94.06% 94.00%
CHEMBL3194 P02766 Transthyretin 91.20% 90.71%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 91.16% 86.92%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.56% 97.09%
CHEMBL3401 O75469 Pregnane X receptor 89.09% 94.73%
CHEMBL5339 Q5NUL3 G-protein coupled receptor 120 86.65% 95.78%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.98% 86.33%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 84.53% 94.45%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 84.37% 85.14%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 84.30% 96.21%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 83.81% 95.56%
CHEMBL3060 Q9Y345 Glycine transporter 2 82.33% 99.17%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 81.74% 90.71%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.10% 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
Acacia aulacocarpa
Achillea collina
Achillea fragrantissima
Achillea micrantha
Achillea millefolium
Achillea pannonica
Achillea roseo-alba
Acilepis saligna
Aconitum leucostomum
Aconitum seravschanicum
Adansonia grandidieri
Adenia globosa
Adenia volkensii
Adonis mongolica
Agastache parvifolia
Ageratina areolaris
Aglaia elliptica
Aglaia grandis
Agrimonia eupatoria
Agrimonia pilosa
Ailanthus altissima
Ainsliaea macrocephala
Aiouea montana
Ajuga lupulina
Alangium ridleyi
Alchemilla speciosa
Alkekengi officinarum
Allium rotundum
Aloysia citrodora
Ammannia coccinea
Ammodendron bifolium
Amsinckia tessellata
Anaphalis busua
Anastatica hierochuntica
Anemonastrum flaccidum
Angelica keiskei
Annona rensoniana
Annona tomentosa
Antennaria dioica
Anthemis auriculata
Aphyllocladus denticulatus
Apium graveolens
Aquilegia ecalcarata
Archidendron clypearia
Ardisia neriifolia
Aristolochia maxima
Arnica acaulis
Arnica angustifolia
Arnica chamissonis
Arnica cordifolia
Arnica gracilis
Arnica longifolia
Arnica mollis
Arnica sororia
Arrhenatherum elatius
Artabotrys hexapetalus
Artemisia annua
Artemisia palustris
Artemisia pedemontana subsp. assoana
Artemisia rupestris
Artemisia szowitziana
Artemisia xerophytica
Arum maculatum
Aspalathus linearis
Asphodeline globifera
Asphodelus ramosus
Aspidosperma subincanum
Asplenium normale
Asteriscus graveolens
Astragalus circassicus
Asyneuma campanuloides
Aucuba chinensis
Baccharis angustifolia
Bacopa monnieri
Bahiopsis tomentosa
Ballota hirsuta
Bartsia alpina
Bassia muricata
Begonia erythrophylla
Bergenia purpurascens
Betula nigra
Betula pendula subsp. mandshurica
Bhesa nitidissima
Bidens frondosa
Bidens tripartita
Biebersteinia multifida
Biebersteinia orphanidis
Bischofia javanica
Blechnum minus
Blumea axillaris
Boronia ternata
Brandisia hancei
Brickellia vernicosa
Broussonetia papyrifera
Brucea javanica
Bryum argenteum
Bryum pseudotriquetrum
Buddleja officinalis
Bunias orientalis
Buphthalmum salicifolium
Buxus microphylla
Buxus sempervirens
Calicotome villosa
Calycanthus floridus
Campanula armena
Campanula lactiflora
Campanula ossetica
Campanula pendula
Campanula persicifolia
Canarium album
Capsicum annuum
Caragana tibetica
Carallia brachiata
Carduus acanthoides
Carex fraseriana
Carpobrotus edulis
Carthamus lanatus
Carthamus tinctorius
Caryopteris tangutica
Casearia membranacea
Castanea crenata
Catalpa speciosa
Catananche caerulea
Catunaregam tomentosa
Ceanothus velutinus
Cedronella canariensis
Centaurea cyanus
Centaurea hermannii
Centaurea pseudoscabiosa
Centrolobium tomentosum
Centrosema molle
Cephalaria ambrosioides
Cephalaria gigantea
Cephalaria pastricensis
Cephalaria procera
Cephalotus follicularis
Ceratophyllum submersum
Chaerophyllum aureum
Chaerophyllum hirsutum
Chamaecytisus ratisbonensis
Chamaemelum nobile
Chiliadenus candicans
Chlorophytum borivilianum
Chondrilla juncea
Chrozophora tinctoria
Chrysanthemum × morifolium
Chrysanthemum indicum
Chrysanthemum morifolium
Chrysanthemum naktongense
Cinnamomum kotoense
Cirsium heterophyllum
Cirsium japonicum
Cirsium palustre
Cirsium wallichii
Citrus × aurantium
Clinopodium laxiflorum
Clinopodium umbrosum
Codonopsis clematidea
Codonopsis foetens subsp. nervosa
Codonopsis lanceolata
Codonopsis ovata
Colchicum robustum
Colchicum soboliferum
Colchicum speciosum
Conocephalum conicum
Conospermum teretifolium
Coreopsis auriculata
Cornulaca monacantha
Corydalis calliantha
Cotoneaster horizontalis
Crassothonna sedifolia
Crataegus microphylla
Crataegus monogyna
Crataegus sinaica
Crepidiastrum denticulatum subsp. denticulatum
Crepidiastrum sonchifolium subsp. sonchifolium
Crithmum maritimum
Crocus minimus
Cryptocarya aschersoniana
Cunonia macrophylla
Cuphea wrightii
Curculigo pilosa
Cyanthillium cinereum
Cyanthillium patulum
Cynara cardunculus
Cynara humilis
Cynometra lujae
Cynomorium coccineum subsp. songaricum
Cyrtocymura scorpioides
Daphne gnidioides
Daphne gnidium
Daphne oleoides
Daucus carota
Dendriopoterium menendezii
Dianthera secunda
Dicoma anomala
Digitalis chalcantha
Dimorphotheca fruticosa
Dipterocarpus dyeri
Discaria chacaye
Dodonaea viscosa
Dracocephalum kotschyi
Dracocephalum multicaule
Dracocephalum nutans
Dracocephalum peregrinum
Dracocephalum tanguticum
Dysoxylum cumingianum
Dystaenia takesimana
Eclipta prostrata
Elsholtzia ciliata
Elsholtzia rugulosa
Enceliopsis argophylla
Entada rheedei
Epidendrum rigidum
Epimedium pubescens
Episcia cupreata
Equisetum arvense
Eryngium campestre
Eupatorium argentinum
Euphorbia clarkeana
Euphorbia ferganensis
Euphorbia humifusa
Ferula assa-foetida
Ferula varia
Flacourtia jangomas
Fragaria vesca
Fritillaria cirrhosa
Frullania muscicola
Fuchsia perscandens
Fuchsia splendens
Galatella sedifolia subsp. sedifolia
Galega officinalis
Galeopsis bifida
Galeopsis tetrahit
Galinsoga parviflora
Galium heldreichii
Galium verum subsp. verum
Gamblea innovans
Gamochaeta malvinensis
Garcinia madruno
Garcinia quaesita
Garcinia scortechinii
Gardenia jasminoides
Gardenia tubifera
Genista corsica
Genista lydia
Genista morisii
Genista pichisermolliana
Genista sessilifolia
Gentiana arisanensis
Gentiana depressa
Gentiana pedicellata
Gerbera jamesonii
Glebionis coronaria
Glechoma grandis
Glechoma hederacea
Glechoma longituba
Gleditsia caspica
Glinus oppositifolius
Globularia davisiana
Guatteria ucayalina
Gutierrezia grandis
Gutierrezia microcephala
Gutierrezia wrightii
Gymnanthemum amygdalinum
Gymnarrhena micrantha
Habropetalum dawei
Halenia corniculata
Halleria lucida
Haplophyllum ramosissimum
Hedysarum denticulatum
Helichrysum arenarium
Helichrysum mixtum
Helichrysum nitens
Helichrysum stoechas
Heteromera fuscata
Hieracium guentheri-beckii
Hieracium gymnocephalum
Humulus lupulus
Humulus scandens
Hydrocotyle ranunculoides
Hyparrhenia hirta
Hypericum reflexum
Impatiens edgeworthii
Inula japonica
Ipomoea cairica
Ipomoea muricata
Isodon lophanthoides
Isodon rubescens
Itoa orientalis
Ixeridium laevigatum
Ixeris chinensis
Ixeris tamagawaensis
Jacaratia spinosa
Jasminum officinale
Juniperus brevifolia
Kopsia grandifolia
Lactuca formosana
Lactuca indica
Lactuca quercina
Lactuca serriola
Lactuca viminea
Lagotis brevituba
Lamyropsis cynaroides
Lasianthus fordii
Lasiocephalus ovatus
Launaea aspleniifolia
Launaea lanifera
Lavandula angustifolia subsp. pyrenaica
Lavandula dentata
Lawsonia inermis
Ledebouria socialis
Leiothrix curvifolia
Lepidothamnus intermedius
Leptactina senegambica
Libocedrus plumosa
Ligularia platyglossa
Ligularia songarica
Ligustrum lucidum
Ligustrum vulgare
Limonium axillare
Linaria macroura
Linum grandiflorum
Lippia alba
Lippia carviodora
Lippia origanoides
Liriodendron tulipifera
Lomatium dissectum
Lomelosia caucasica
Lomelosia olgae
Lonicera confusa
Lonicera gracilipes
Lonicera hypoglauca
Lonicera japonica
Lonicera macrantha
Lotus pedunculatus
Luculia pinceana
Luetkea pectinata
Lupinus texensis
Lycopus asper
Lycopus europaeus
Lycopus lucidus
Lysiana subfalcata
Macaranga peltata
Macaranga vedeliana
Macrotyloma axillare
Malus asiatica
Markhamia stipulata
Marrubium cylleneum
Marrubium vulgare
Mayaca fluviatilis
Medicago arborea
Meehania urticifolia
Mentha arvensis
Mentha canadensis
Mentha longifolia
Mentha spicata
Mikania obtusata
Miliusa velutina
Montrouziera sphaeroidea
Morinda morindoides
Mosla chinensis
Myoporum tenuifolium
Myrica nana
Nelumbo nucifera
Neobalanocarpus heimii
Nepeta cataria
Nepeta tenuifolia
Nepeta velutina
Neurolaena macrophylla
Nicotiana alata
Ocimum tenuiflorum
Oenothera triangulata
Olea europaea
Onobrychis arenaria
Onychium lucidum
Origanum vulgare
Orostachys japonica
Osmanthus fragrans
Osmanthus heterophyllus
Osteospermum muricatum
Ostericum sieboldii
Pallenis hierochuntica
Panzerina lanata
Parodiodoxa chionophila
Passiflora foetida
Passiflora menispermifolia
Passiflora palmeri
Passiflora pavonis
Passiflora pittieri
Passiflora sanguinolenta
Passiflora sexflora
Pedicularis rex
Pediomelum esculentum
Pelargonium reniforme
Penstemon serrulatus
Pentanema britannicum
Peperomia vulcanica
Perilla frutescens
Peritassa compta
Persea barbujana
Persicaria orientalis
Persicaria vivipara
Petasites hybridus subsp. hybridus
Phagnalon rupestre
Phebalium whitei
Phedimus kamtschaticus
Phlomis aurea
Phlomis brunneogaleata
Phlomis nissolii
Phlomoides rotata
Phlomoides tuberosa
Phoenix loureiroi var. loureiroi
Phoenix loureiroi var. pedunculata
Phyllocladus toatoa
Phyllostachys nigra
Physalis peruviana
Pilosella officinarum
Pimpinella saxifraga
Pinus mugo
Pityrogramma ebenea
Plantago lagopus
Plantago major
Platycarya strobilacea
Platycodon grandiflorus
Plectranthus ovatus
Podocarpus fasciculus
Podocarpus nivalis
Polygala myrtifolia
Polygonum aviculare
Polystichum deltodon
Populus suaveolens
Portulaca oleracea
Potentilla anserina
Premna tomentosa
Prunella vulgaris
Prunus arborea var. montana
Prunus mume
Psephellus huber-morathii
Pseudodictamnus acetabulosus
Psiadia dentata
Psilostrophe cooperi
Psorothamnus spinosus
Psychotria stachyoides
Pteris cretica
Pteris decurrens
Pteris multifida
Pterocarpus officinalis
Pyrrhopappus carolinianus
Pyrrosia serpens
Quassia indica
Quercus macrocarpa
Ramirezella strobilophora
Ranzania japonica
Reichardia tingitana
Reseda luteola
Retama raetam
Reynoutria japonica
Rhodiola stephani
Riccia fluitans
Ridsdalea wittii
Robinsonia masafuerae
Rosa agrestis
Rosulabryum capillare
Rubus amabilis
Rumex acetosella
Rumex nepalensis
Sagittaria sagittifolia
Salix acutifolia
Salix caprea
Salix cheilophila
Salix gilgiana
Salix gracilistyla
Salix purpurea
Salix viminalis
Salvia albimaculata
Salvia candelabrum
Salvia fruticosa
Salvia limbata
Salvia officinalis
Salvia palaestina
Salvia seravschanica
Salvia tomentosa
Salvia urolepis
Salvia verticillata
Sandersonia aurantiaca
Santolina pinnata
Sarcomelicope argyrophylla
Satureja cuneifolia
Saussurea amara
Saussurea involucrata
Saussurea medusa
Scoparia dulcis
Scorzonera laciniata
Scrophularia wattii
Scutellaria barbata
Scutellaria oreophila
Sedum sarmentosum
Senecio nemorensis
Senecio sandersonii
Senecio subdentatus
Seriphidium kurramense
Seriphidium vachanicum
Sicyos edulis
Sideritis euboea
Sideritis soluta
Sideritis tragoriganum
Sideritis trojana
Sidneya tenuifolia
Sigesbeckia glabrescens
Sigesbeckia pubescens
Silybum marianum
Sisyrinchium californicum
Smilax riparia
Solanum bahamense
Solanum incanum
Solanum jamaicense
Solanum tuberosum
Sonchus arvensis
Sonchus arvensis subsp. arvensis
Sonchus asper
Sonchus erzincanicus
Sonchus oleraceus
Sonneratia caseolaris
Sophora flavescens
Sorbus tianschanica
Spiraea brahuica
Spiraea hypericifolia
Spirodela polyrhiza
Stachys aegyptiaca
Stachys candida
Stephania elegans
Stevia microchaeta
Stevia rebaudiana
Stevia suaveolens
Strychnos camptoneura
Strychnos lucida
Swertia swertopsis
Syagrus romanzoffiana
Tabebuia aurea
Tabebuia ochracea
Tagetes rupestris
Tanacetum corymbosum subsp. corymbosum
Tanacetum parthenium
Tanacetum vulgare
Taraxacum coreanum
Taraxacum hallaisanense
Taraxacum mongolicum
Taraxacum officinale
Taraxacum platycarpum
Taraxacum sinicum
Taxus brevifolia
Tecoma capensis
Tetrapanax papyrifer
Teucrium gnaphalodes
Teucrium hircanicum
Teucrium polium
Teucrium yemense
Thelesperma megapotamicum
Thermopsis alterniflora
Thermopsis dolichocarpa
Thymus membranaceus
Thymus piperella
Tinospora crispa
Tinospora smilacina
Trachelospermum asiaticum
Trachelospermum jasminoides
Trachycarpus fortunei
Tragopogon pratensis
Trichomanes reptans
Trichosanthes kirilowii
Trichosanthes rosthornii
Trichotosia mollis
Trifolium alexandrinum
Trifolium canescens
Trifolium pannonicum
Trifolium trichocephalum
Trigonostemon reidioides
Tropaeolum speciosum
Tsuga chinensis
Turgenia latifolia
Urospermum picroides
Utricularia australis
Valeriana cardamines
Valeriana ficariifolia
Valeriana rossica
Vatica diospyroides
Vellozia nivea
Veratrum grandiflorum
Verbascum eremobium
Verbascum lychnitis
Verbascum phlomoides
Verbascum pyroliforme subsp. dudleyanum
Verbascum songaricum
Verbena officinalis
Veronica fuhsii
Veronica officinalis
Veronica polita
Veronica spicata
Veronica strictissima
Veronica thymoides
Veronicastrum sibiricum
Vicia lens
Vicia sativa
Vicia subvillosa
Vinca minor
Viola reichenbachiana
Virgilia divaricata
Vitex altissima
Vitex negundo
Vitis aestivalis
Vitis betulifolia
Xyris obtusiuscula
Youngia japonica
Zanthoxylum ailanthoides
Zanthoxylum myriacanthum
Zostera marina

Cross-Links

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PubChem 5280637
NPASS NPC189142
ChEMBL CHEMBL233929
LOTUS LTS0227450
wikiData Q2317288