Resveratrol

Details

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Internal ID 91b47fd8-bf5b-45d7-b82b-5b3863f04e03
Taxonomy Phenylpropanoids and polyketides > Stilbenes
IUPAC Name 5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol
SMILES (Canonical) C1=CC(=CC=C1C=CC2=CC(=CC(=C2)O)O)O
SMILES (Isomeric) C1=CC(=CC=C1/C=C/C2=CC(=CC(=C2)O)O)O
InChI InChI=1S/C14H12O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h1-9,15-17H/b2-1+
InChI Key LUKBXSAWLPMMSZ-OWOJBTEDSA-N
Popularity 21,415 references in papers

Physical and Chemical Properties

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Molecular Formula C14H12O3
Molecular Weight 228.24 g/mol
Exact Mass 228.078644241 g/mol
Topological Polar Surface Area (TPSA) 60.70 Ų
XlogP 3.10
Atomic LogP (AlogP) 2.97
H-Bond Acceptor 3
H-Bond Donor 3
Rotatable Bonds 2

Synonyms

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501-36-0
trans-resveratrol
3,4',5-Trihydroxystilbene
(E)-5-(4-Hydroxystyryl)benzene-1,3-diol
3,5,4'-Trihydroxystilbene
(E)-resveratrol
Resvida
3,4',5-Stilbenetriol
5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol
3,4',5-Trihydroxy-trans-stilbene
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Resveratrol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9884 98.84%
Caco-2 + 0.8398 83.98%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability - 0.6857 68.57%
Subcellular localzation Mitochondria 0.6615 66.15%
OATP2B1 inhibitior - 0.7145 71.45%
OATP1B1 inhibitior + 0.9414 94.14%
OATP1B3 inhibitior + 0.9479 94.79%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.9088 90.88%
BSEP inhibitior - 0.6594 65.94%
P-glycoprotein inhibitior - 0.9537 95.37%
P-glycoprotein substrate - 0.9899 98.99%
CYP3A4 substrate - 0.7342 73.42%
CYP2C9 substrate - 0.5955 59.55%
CYP2D6 substrate - 0.6927 69.27%
CYP3A4 inhibition + 0.7539 75.39%
CYP2C9 inhibition + 0.7068 70.68%
CYP2C19 inhibition + 0.8052 80.52%
CYP2D6 inhibition - 0.9226 92.26%
CYP1A2 inhibition + 0.9106 91.06%
CYP2C8 inhibition + 0.4709 47.09%
CYP inhibitory promiscuity + 0.8559 85.59%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.6496 64.96%
Carcinogenicity (trinary) Non-required 0.5753 57.53%
Eye corrosion - 0.9581 95.81%
Eye irritation + 0.9960 99.60%
Skin irritation + 0.6257 62.57%
Skin corrosion - 0.7751 77.51%
Ames mutagenesis - 0.7600 76.00%
Human Ether-a-go-go-Related Gene inhibition - 0.8361 83.61%
Micronuclear - 0.5900 59.00%
Hepatotoxicity - 0.6060 60.60%
skin sensitisation + 0.8871 88.71%
Respiratory toxicity - 0.8111 81.11%
Reproductive toxicity - 0.5556 55.56%
Mitochondrial toxicity - 0.8125 81.25%
Nephrotoxicity + 0.5376 53.76%
Acute Oral Toxicity (c) III 0.6825 68.25%
Estrogen receptor binding + 0.9144 91.44%
Androgen receptor binding + 0.7659 76.59%
Thyroid receptor binding + 0.7160 71.60%
Glucocorticoid receptor binding + 0.7722 77.22%
Aromatase binding + 0.9242 92.42%
PPAR gamma + 0.9289 92.89%
Honey bee toxicity - 0.8722 87.22%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity + 0.5600 56.00%
Fish aquatic toxicity + 0.9588 95.88%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL1293255 P15428 15-hydroxyprostaglandin dehydrogenase [NAD+] 25118.9 nM
31622.8 nM
14125.4 nM
10000 nM
25118.9 nM
Potency
Potency
Potency
Potency
Potency
via CMAUP
via CMAUP
via CMAUP
via CMAUP
via CMAUP
CHEMBL3577 P00352 Aldehyde dehydrogenase 1A1 35481.3 nM
39810.7 nM
39810.7 nM
31622.8 nM
Potency
Potency
Potency
Potency
via CMAUP
via CMAUP
via CMAUP
via CMAUP
CHEMBL2096618 P11274 Bcr/Abl fusion protein 28000 nM
IC50
PMID: 16686543
CHEMBL2487 P05067 Beta amyloid A4 protein 15900 nM
15110 nM
4100 nM
2600 nM
IC50
IC50
IC50
IC50
PMID: 23786711
PMID: 23799643
PMID: 27190601
PMID: 27190601
CHEMBL261 P00915 Carbonic anhydrase I 2210 nM
Ki
PMID: 20674354
CHEMBL205 P00918 Carbonic anhydrase II 2770 nM
Ki
PMID: 20674354
CHEMBL2885 P07451 Carbonic anhydrase III 9090 nM
Ki
PMID: 20674354
CHEMBL3729 P22748 Carbonic anhydrase IV 4470 nM
Ki
PMID: 20674354
CHEMBL3594 Q16790 Carbonic anhydrase IX 810 nM
810 nM
Ki
Ki
PMID: 20674354
via Super-PRED
CHEMBL4789 P35218 Carbonic anhydrase VA 4750 nM
Ki
PMID: 20674354
CHEMBL3969 Q9Y2D0 Carbonic anhydrase VB 4640 nM
Ki
PMID: 20674354
CHEMBL3025 P23280 Carbonic anhydrase VI 8070 nM
Ki
PMID: 20674354
CHEMBL2326 P43166 Carbonic anhydrase VII 4350 nM
Ki
PMID: 20674354
CHEMBL3242 O43570 Carbonic anhydrase XII 950 nM
950 nM
Ki
Ki
PMID: 20674354
via Super-PRED
CHEMBL3912 Q8N1Q1 Carbonic anhydrase XIII 4090 nM
Ki
PMID: 20674354
CHEMBL3510 Q9ULX7 Carbonic anhydrase XIV 830 nM
830 nM
Ki
Ki
PMID: 20674354
via Super-PRED
CHEMBL4096 P04637 Cellular tumor antigen p53 10000 nM
10000 nM
Potency
Potency
via CMAUP
via CMAUP
CHEMBL221 P23219 Cyclooxygenase-1 1100 nM
2840 nM
4120 nM
830 nM
625 nM
IC50
IC50
IC50
IC50
IC50
PMID: 11858749
PMID: 16814546
PMID: 18063374
PMID: 18487053
via CMAUP
CHEMBL230 P35354 Cyclooxygenase-2 1300 nM
996 nM
990 nM
750 nM
996 nM
IC50
IC50
IC50
IC50
IC50
PMID: 11858749
PMID: 17604631
PMID: 18487053
PMID: 20527891
PMID: 26850006
CHEMBL1978 P11511 Cytochrome P450 19A1 25000 nM
25000 nM
IC50
IC50
PMID: 22115839
PMID: 22386564
CHEMBL2231 P04798 Cytochrome P450 1A1 34000 nM
IC50
PMID: 27265259
CHEMBL3356 P05177 Cytochrome P450 1A2 3000 nM
IC50
via CMAUP
CHEMBL3622 P33261 Cytochrome P450 2C19 3000 nM
IC50
via CMAUP
CHEMBL3397 P11712 Cytochrome P450 2C9 7000 nM
IC50
via CMAUP
CHEMBL340 P08684 Cytochrome P450 3A4 600 nM
IC50
via CMAUP
CHEMBL284 P27487 Dipeptidyl peptidase IV 0.6 nM
IC50
via Super-PRED
CHEMBL2392 P06746 DNA polymerase beta 44668.4 nM
Potency
via CMAUP
CHEMBL4159 Q99714 Endoplasmic reticulum-associated amyloid beta-peptide-binding protein 31622.8 nM
31622.8 nM
Potency
Potency
via CMAUP
via CMAUP
CHEMBL206 P03372 Estrogen receptor alpha 785 nM
785 nM
Ki
Ki
PMID: 15634023
via Super-PRED
CHEMBL1741189 P55789 FAD-linked sulfhydryl oxidase ALR 4021 nM
AC50
via CMAUP
CHEMBL5514 P42858 Huntingtin 2238.7 nM
Potency
via CMAUP
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 10000 nM
10000 nM
Potency
Potency
via CMAUP
via CMAUP
CHEMBL1293226 B2RXH2 Lysine-specific demethylase 4D-like 39810.7 nM
22387.2 nM
31622.8 nM
25118.9 nM
Potency
Potency
Potency
Potency
via CMAUP
via CMAUP
via CMAUP
via CMAUP
CHEMBL2608 P10253 Lysosomal alpha-glucosidase 39506.8 nM
Potency
via CMAUP
CHEMBL1293224 P10636 Microtubule-associated protein tau 12589.3 nM
8912.5 nM
12589.3 nM
17782.8 nM
15848.9 nM
7079.5 nM
8912.5 nM
5623.4 nM
17782.8 nM
10000 nM
7079.5 nM
22387.2 nM
Potency
Potency
Potency
Potency
Potency
Potency
Potency
Potency
Potency
Potency
Potency
Potency
via CMAUP
via CMAUP
via CMAUP
via CMAUP
via CMAUP
via CMAUP
via CMAUP
via CMAUP
via CMAUP
via CMAUP
via CMAUP
via CMAUP
CHEMBL1951 P21397 Monoamine oxidase A 17410 nM
449 nM
IC50
IC50
DOI: 10.1039/C3MD00376K
via CMAUP
CHEMBL2039 P27338 Monoamine oxidase B 29370 nM
IC50
DOI: 10.1039/C3MD00376K
CHEMBL1293277 O15118 Niemann-Pick C1 protein 5623.4 nM
18356.4 nM
Potency
Potency
via CMAUP
via CMAUP
CHEMBL222 P23975 Norepinephrine transporter 2312 nM
IC50
via CMAUP
CHEMBL5533 Q04206 Nuclear factor NF-kappa-B p65 subunit 20000 nM
IC50
via CMAUP
CHEMBL1869 P11926 Ornithine decarboxylase 19000 nM
IC50
PMID: 10075742
CHEMBL1293298 Q01453 Peripheral myelin protein 22 42561.5 nM
Potency
via CMAUP
CHEMBL4005 P42336 PI3-kinase p110-alpha subunit 250 nM
250 nM
IC50
IC50
DOI: 10.1039/C2MD20044A
via Super-PRED
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 500 nM
500 nM
IC50
IC50
DOI: 10.1039/C2MD20044A
via Super-PRED
CHEMBL1293235 P02545 Prelamin-A/C 5 nM
35481.3 nM
12589.3 nM
Potency
Potency
Potency
via CMAUP
via CMAUP
via CMAUP
CHEMBL3959 P16083 Quinone reductase 2 960 nM
450 nM
450 nM
960 nM
1400 nM
913 nM
54 nM
IC50
IC50
IC50
IC50
IC50
IC50
Kd
PMID: 19265439
PMID: 20036559
PMID: 20356739
PMID: 21261296
PMID: 26854376
PMID: 26854376
via Super-PRED
CHEMBL1293294 P51151 Ras-related protein Rab-9A 3981.1 nM
29092.9 nM
Potency
Potency
via CMAUP
via CMAUP
CHEMBL2842 P42345 Serine/threonine-protein kinase mTOR 3689.8 nM
18492.7 nM
Potency
Potency
via CMAUP
via CMAUP
CHEMBL1293232 Q16637 Survival motor neuron protein 14125.4 nM
12589.3 nM
8912.5 nM
Potency
Potency
Potency
via CMAUP
via CMAUP
via CMAUP
CHEMBL3194 P02766 Transthyretin 470 nM
Kd
via Super-PRED
CHEMBL1075138 Q9NUW8 Tyrosyl-DNA phosphodiesterase 1 1 nM
Potency
via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.52% 91.11%
CHEMBL242 Q92731 Estrogen receptor beta 92.49% 98.35%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.38% 95.56%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 87.44% 96.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.66% 86.33%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 84.13% 91.71%
CHEMBL1951 P21397 Monoamine oxidase A 83.75% 91.49%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 81.12% 94.45%

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.
Acacia adunca
Aconitum heterophylloides
Aconitum seravschanicum
Adansonia grandidieri
Adiantum philippense
Ageratina adenophora
Aldama incana
Alkekengi officinarum
Ammopiptanthus mongolicus
Ampelopsis glandulosa var. brevipedunculata
Ampelopsis japonica
Andrographis lineata
Annona cornifolia
Aphyllocladus denticulatus
Arachis hypogaea
Aristeguietia glutinosa
Artemisia lagocephala
Artemisia pedemontana subsp. assoana
Artocarpus gomezianus
Artocarpus lacucha
Astragalus cibarius
Astragalus sempervirens
Baccharis patagonica
Bagassa guianensis
Bassia muricata
Bauhinia racemosa
Boehmeria nivea
Bolboschoenus fluviatilis
Bolboschoenus maritimus subsp. maritimus
Broussonetia papyrifera
Calamus draco
Calostephane divaricata
Canthium berberidifolium
Caragana aurantiaca
Caragana sinica
Caragana tibetica
Chaenomeles sinensis
Chamaecrista dentata
Chamaecrista greggii
Cinnamosma macrocarpa
Cissus quadrangularis
Coprosma lucida
Crotalaria micans
Croton poilanei
Cyperus longus
Cyphostemma crotalarioides
Dasymaschalon sootepense
Dendriopoterium menendezii
Dianthera secunda
Dictyoloma vandellianum
Dodonaea viscosa
Dracaena cochinchinensis
Dryopteris crassirhizoma
Dumortiera hirsuta
Dysoxylum cumingianum
Echeveria secunda
Elephantorrhiza goetzei
Eleutherococcus sessiliflorus
Enceliopsis argophylla
Eucalyptus melliodora
Eucalyptus pruinosa
Eucalyptus wandoo
Euonymus sachalinensis
Fagopyrum megacarpum
Felicia erigeroides
Festuca argentina
Festuca arundinacea
Flacourtia jangomas
Flueggea virosa subsp. melanthesoides
Fritillaria persica
Galatella sedifolia subsp. sedifolia
Garcinia quaesita
Gnetum gnemon
Gnetum hainanense
Gnetum klossii
Gnetum latifolium
Gnetum macrostachyum
Gnetum montanum
Gnetum parvifolium
Gnetum pendulum
Gnetum venosum
Goniothalamus malayanus
Guatteria megalophylla
Gymnosporia diversifolia
Hedysarum inundatum
Hippophae rhamnoides
Holodiscus discolor
Hopea utilis
Hoya australis
Humulopsis scandens
Humulus lupulus
Hydrangea macrophylla
Hylotelephium telephium
Hypericum laricifolium
Ipomoea digitata
Iris domestica
Iris halophila
Juniperus seravschanica
Larix gmelinii
Lavandula angustifolia subsp. pyrenaica
Lepisorus ussuriensis
Leptactina senegambica
Leptinella filicula
Leucosceptrum canum
Lupinus paniculatus
Lycoris traubii
Lygodium flexuosum
Lysimachia mauritiana
Maackia amurensis
Maclura pomifera
Marrubium anisodon
Maytenus imbricata
Miliusa velutina
Morus alba
Naucleopsis ternstroemiiflora
Neobalanocarpus heimii
Ocotea pittieri
Onobrychis arenaria
Oroxylum indicum
Packera toluccana
Paeonia lactiflora
Paeonia suffruticosa
Panax ginseng
Parthenocissus quinquefolia
Parthenocissus tricuspidata
Pastinaca sativa
Peltostigma guatemalense
Phalaenopsis cornu-cervi
Phoenix dactylifera
Pholidota chinensis
Picea abies
Pinus sibirica
Piper caninum
Polyalthia evecta
Premna odorata
Psychotria stachyoides
Pterolobium hexapetalum
Rauvolfia vomitoria
Reynoutria japonica
Reynoutria multiflora
Rheum officinale
Rheum palmatum
Rheum rhabarbarum
Rheum tanguticum
Rhodanthe chlorocephala subsp. rosea
Rubia cordifolia
Rumex bucephalophorus
Rumex hastatus
Rumex maritimus
Rumex nepalensis
Saccharum spontaneum
Salacia lehmbachii
Salvia syriaca
Schizocarphus nervosus
Scutellaria amoena
Senecio subdentatus
Sideritis chamaedryfolia
Smilax aspera
Smilax bracteata
Smilax china
Smilax corbularia
Smilax excelsa
Smilax glabra
Smilax perfoliata
Solanum laxum
Sorghum bicolor
Spiraea formosana
Spirotropis longifolia
Strychnos staudtii
Stuhlmannia moavi
Swertia franchetiana
Syagrus romanzoffiana
Tanacetum parthenium
Teucrium yemense
Thalictrum speciosissimum
Trichotosia mollis
Trifolium campestre
Trifolium dubium
Trinia scabra
Tsuga mertensiana
Upuna borneensis
Vaccinium macrocarpon
Vaccinium myrtillus
Vaccinium oxycoccos
Vaccinium vitis-idaea
Vasconcellea cauliflora
Vatica rassak
Veratrum dahuricum
Veratrum grandiflorum
Veratrum taliense
Vigna angularis
Vigna umbellata
Vitis amurensis
Vitis chunganensis
Vitis davidi
Vitis riparia
Vitis vinifera
Wikstroemia retusa
Yucca periculosa
Yucca schidigera
Zanthoxylum tetraspermum

Cross-Links

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PubChem 445154
NPASS NPC161571
ChEMBL CHEMBL165
LOTUS LTS0256677
wikiData Q407329