Vanillin

Details

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Internal ID 07936086-832a-4d14-8b0a-cda47dcee894
Taxonomy Benzenoids > Phenols > Methoxyphenols
IUPAC Name 4-hydroxy-3-methoxybenzaldehyde
SMILES (Canonical) COC1=C(C=CC(=C1)C=O)O
SMILES (Isomeric) COC1=C(C=CC(=C1)C=O)O
InChI InChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3
InChI Key MWOOGOJBHIARFG-UHFFFAOYSA-N
Popularity 13,311 references in papers

Physical and Chemical Properties

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Molecular Formula C8H8O3
Molecular Weight 152.15 g/mol
Exact Mass 152.047344113 g/mol
Topological Polar Surface Area (TPSA) 46.50 Ų
XlogP 1.20
Atomic LogP (AlogP) 1.21
H-Bond Acceptor 3
H-Bond Donor 1
Rotatable Bonds 2

Synonyms

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4-Hydroxy-3-methoxybenzaldehyde
121-33-5
Vanillaldehyde
Vanillic aldehyde
p-Vanillin
Lioxin
Vanilline
Vanilla
3-Methoxy-4-hydroxybenzaldehyde
4-Hydroxy-m-anisaldehyde
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Vanillin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9961 99.61%
Caco-2 + 0.8847 88.47%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability + 0.5714 57.14%
Subcellular localzation Mitochondria 0.9328 93.28%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9197 91.97%
OATP1B3 inhibitior + 0.9863 98.63%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 1.0000 100.00%
BSEP inhibitior - 0.9640 96.40%
P-glycoprotein inhibitior - 0.9834 98.34%
P-glycoprotein substrate - 0.9844 98.44%
CYP3A4 substrate - 0.6920 69.20%
CYP2C9 substrate - 0.6165 61.65%
CYP2D6 substrate - 0.6929 69.29%
CYP3A4 inhibition - 0.9561 95.61%
CYP2C9 inhibition - 0.9643 96.43%
CYP2C19 inhibition - 0.7401 74.01%
CYP2D6 inhibition - 0.9662 96.62%
CYP1A2 inhibition - 0.7125 71.25%
CYP2C8 inhibition - 0.7052 70.52%
CYP inhibitory promiscuity - 0.8592 85.92%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.7404 74.04%
Carcinogenicity (trinary) Non-required 0.5099 50.99%
Eye corrosion + 0.9827 98.27%
Eye irritation + 1.0000 100.00%
Skin irritation + 0.9243 92.43%
Skin corrosion - 0.8350 83.50%
Ames mutagenesis - 0.9600 96.00%
Human Ether-a-go-go-Related Gene inhibition - 0.7446 74.46%
Micronuclear + 0.5163 51.63%
Hepatotoxicity + 0.6572 65.72%
skin sensitisation - 0.6802 68.02%
Respiratory toxicity - 0.9556 95.56%
Reproductive toxicity + 0.8333 83.33%
Mitochondrial toxicity - 1.0000 100.00%
Nephrotoxicity + 0.4758 47.58%
Acute Oral Toxicity (c) III 0.8545 85.45%
Estrogen receptor binding - 0.5657 56.57%
Androgen receptor binding - 0.7921 79.21%
Thyroid receptor binding - 0.8177 81.77%
Glucocorticoid receptor binding - 0.8999 89.99%
Aromatase binding - 0.8415 84.15%
PPAR gamma - 0.8274 82.74%
Honey bee toxicity - 0.9483 94.83%
Biodegradation + 0.7500 75.00%
Crustacea aquatic toxicity - 0.5755 57.55%
Fish aquatic toxicity + 0.7544 75.44%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL1293255 P15428 15-hydroxyprostaglandin dehydrogenase [NAD+] 39810.7 nM
Potency
via CMAUP
CHEMBL3577 P00352 Aldehyde dehydrogenase 1A1 25118.9 nM
14125.4 nM
Potency
Potency
via CMAUP
via CMAUP
CHEMBL2176772 Q9UPN9 E3 ubiquitin-protein ligase TRIM33 325.6 nM
IC50
via Super-PRED
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 162 nM
IC50
via Super-PRED
CHEMBL1075138 Q9NUW8 Tyrosyl-DNA phosphodiesterase 1 5011.9 nM
Potency
via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL1163101 O75460 Serine/threonine-protein kinase/endoribonuclease IRE1 97.08% 98.11%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.16% 91.11%
CHEMBL3194 P02766 Transthyretin 93.80% 90.71%
CHEMBL1951 P21397 Monoamine oxidase A 93.18% 91.49%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.39% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.41% 86.33%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 87.99% 96.00%
CHEMBL4208 P20618 Proteasome component C5 85.88% 90.00%
CHEMBL3492 P49721 Proteasome Macropain subunit 84.95% 90.24%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 84.22% 89.62%
CHEMBL3060 Q9Y345 Glycine transporter 2 83.48% 99.17%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 81.99% 94.45%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 81.98% 99.15%
CHEMBL2535 P11166 Glucose transporter 81.33% 98.75%
CHEMBL1255126 O15151 Protein Mdm4 81.16% 90.20%

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 alba
Abies nephrolepis
Abies sachalinensis
Abies sibirica
Acacia pulchella
Acanthophyllum sordidum
Achlys triphylla
Aconitum habaense
Aconitum sajanense
Aconitum tanguticum
Aegle marmelos
Aframomum sulcatum
Ailanthus integrifolia
Alangium platanifolium
Albizia julibrissin
Albizia procera
Alcea rosea
Alkanna hirsutissima
Allagopappus canariensis
Alpinia roxburghii
Alstonia angustiloba
Alstonia rostrata
Amphiachyris dracunculoides
Amsinckia menziesii
Anastatica hierochuntica
Angelica pachycarpa
Angelica sinensis
Annona cherimola
Annona purpurea
Anodendron affine
Antidesma montanum var. montanum
Aphelandra chamissoniana
Aquilaria malaccensis
Aquilaria sinensis
Arabidopsis thaliana
Aralia bipinnata
Araucaria angustifolia
Arcangelisia flava
Aristolochia asclepiadifolia
Aristolochia kaempferi
Aristolochia tomentosa
Artemisia afra
Artemisia annua
Artemisia arbuscula
Artemisia capillaris
Artemisia giraldii
Artemisia jacutica
Artemisia japonica
Artemisia scoparia
Asplenium normale
Aster indicus
Asteriscus aquaticus
Austrobaileya scandens
Avena sativa
Baccharis grandicapitulata
Balanops australiana
Basella alba
Beesia calthifolia
Begonia nantoensis
Beilschmiedia erithrophloia
Beilschmiedia tsangii
Bersama abyssinica
Beta vulgaris
Betula pendula subsp. mandshurica
Boschniakia rossica
Bosistoa floydii
Botrychium ternatum
Bougainvillea glabra
Brassica napus
Brucea javanica
Buddleja davidii
Bulbophyllum protractum
Bupleurum chinense
Bursera kerberi
Calea megacephala
Calystegia pubescens
Cannabis sativa
Capparis spinosa var. ovata
Capsicum annuum var. glabriusculum
Carissa spinarum
Carpobrotus edulis
Carya cathayensis
Cassytha filiformis
Castanea crenata
Cedrela salvadorensis
Centaurea calcitrapa
Centaurea ornata
Centaurea scoparia
Centrolobium tomentosum
Ceratophyllum submersum
Ceratozamia kuesteriana
Chaerophyllum hirsutum
Chamaecrista flexuosa
Chamaecyparis pisifera
Charpentiera obovata
Chlorophytum inornatum
Chuquiraga atacamensis
Cinnamomum kotoense
Cinnamomum subavenium
Cinnamomum verum
Citrus × aurantium
Citrus limon
Clerodendrum trichotomum
Clinacanthus nutans
Colchicum kotschyi
Colchicum manissadjianii
Conioselinum anthriscoides
Cordyline indivisa
Cornus officinalis
Corydalis cornuta
Cremastra appendiculata
Crotalaria stolzii
Croton montevidensis
Croton penduliflorus
Cryptocarya chinensis
Curcuma aeruginosa
Curcuma comosa
Curcuma longa
Cypripedium calceolus
Cyrtocymura scorpioides
Dacrycarpus imbricatus
Damnacanthus major
Datisca glomerata
Davallia perdurans
Decalepis hamiltonii
Deguelia urucu
Delphinium campylocentrum
Delphinium giraldii
Dioscorea olfersiana
Diospyros japonica
Disepalum plagioneurum
Dracocephalum kotschyi
Duhaldea cappa
Ecballium elaterium
Echinacea purpurea
Elaeodendron papillosum
Eleutherococcus senticosus
Eleutherococcus spinosus
Engelhardia roxburghiana
Epipactis palustris
Eremophila serrulata
Eschweilera coriacea
Eucalyptus albens
Eucalyptus cladocalyx
Euchresta formosana
Euonymus fortunei
Euonymus tingens
Euphorbia cornigera
Euphorbia esula subsp. tommasiniana
Euphorbia quinquecostata
Euploca racemosa
Ferula assa-foetida
Festuca arundinacea
Fibraurea tinctoria
Ficus nervosa
Galium latoramosum
Galium odoratum
Garcinia gummi-gutta
Garcinia lateriflora
Gastrodia elata
Geijera balansae
Gonzalezia decurrens
Gossypium hirsutum
Grindelia hirsutula
Gynura elliptica
Gynura japonica
Hakea salicifolia
Haloxylon salicornicum
Handroanthus impetiginosus
Haplopteris anguste-elongata
Hedysarum gmelinii
Hedysarum sachalinense
Helenium integrifolium
Helianthus annuus
Helianthus heterophyllus
Helianthus petiolaris
Helichrysum auriceps
Hemionitis opposita
Heptapleurum divaricatum
Hertia cheirifolia
Hibiscus cannabinus
Hibiscus taiwanensis
Hortonia floribunda
Houttuynia cordata
Hubertia tomentosa
Hylocomium splendens
Hymenoxys ambigens var. floribunda
Hyoscyamus niger
Ilex pubescens
Imperata cylindrica
Jasminum grandiflorum
Juniperus communis
Juniperus scopulorum
Kokoona reflexa
Lactuca sativa
Lagochilus leiacanthus
Lagotis yunnanensis
Lampranthus sociorum
Lasianthaea podocephala
Leionema dentatum
Lepechinia caulescens
Lepidothamnus intermedius
Leucanthemum maximum
Levisticum officinale
Licaria chrysophylla
Licaria triandra
Ligularia dentata
Ligusticum officinale
Ligusticum striatum
Ligustrum obtusifolium
Lippia carviodora
Liquidambar orientalis
Lonicera microphylla
Lotus ucrainicus
Lupinus cosentinii
Lychnophora salicifolia
Machilus zuihoensis
Maesa ramentacea
Magnolia ovata
Malus pumila
Maprounea guianensis
Melaleuca uncinata
Melampodium leucanthum
Melia azedarach
Melicope semecarpifolia
Mentha arvensis
Micromelum integerrimum
Microtropis japonica
Mikania rimachii
Millettia ichthyochtona
Millettia laurentii
Mondia whitei
Monodora tenuifolia
Morinda citrifolia
Myriactis humilis
Myrica nana
Myrica pensylvanica
Myristica argentea
Myristica cagayanensis
Nectandra oppositifolia
Neolitsea hiiranensis
Neolitsea konishii
Neopallasia pectinata
Nicotiana tabacum
Nothofagus fusca
Ocimum tenuiflorum
Olea europaea
Onobrychis meschetica
Ormosia hosiei
Ornithoglossum viride
Paeonia clusii
Panax ginseng
Panax japonicus
Panax notoginseng
Panax quinquefolius
Pandanus tectorius
Papaver glaucum
Papaver pseudocanescens
Pedalium murex
Pellacalyx axillaris
Peltodon longipes
Peperomia filiformis
Periploca sepium
Peritassa campestris
Persea indica
Perymenium mendezii
Petasites formosanus
Petasites radiatus
Phegopteris microstegia
Phlomis crinita
Phoebe formosana
Phyllanthus oligospermus
Picea glauca
Picea obovata
Picris asplenioides subsp. asplenioides
Pimenta dioica
Pinus strobus
Pinus sylvestris
Pinus wallichiana
Piper aequale
Piper attenuatum
Piptocarpha opaca
Pisonia aculeata
Pleione bulbocodioides
Pleione yunnanensis
Pluchea odorata
Pojarkovia pojarkovae
Polyalthia stenopetala
Polygonum pubescens
Pongamia pinnata
Populus deltoides
Populus euphratica
Populus grandidentata
Populus tomentosa
Posidonia oceanica
Primula hirsuta
Protium tonkinense
Prunus persica
Psephellus dealbatus
Pseudostellaria heterophylla
Pseudotsuga japonica
Pseudotsuga sinensis var. sinensis
Pseudowintera colorata
Psidium acutangulum
Psilostrophe cooperi
Pteris altissima
Putranjiva roxburghii
Pyrolirion flavum
Quercus imbricaria
Quercus laurifolia
Quercus petraea subsp. petraea
Quercus pyrenaica
Quercus suber
Radermachera sinica
Rehmannia glutinosa
Renealmia alpinia
Reynoutria multiflora
Rhododendron ferrugineum
Rhododendron mucronulatum
Rhus chinensis
Robinsonia thurifera
Rodgersia podophylla
Roemeria refracta
Rolandra fruticosa
Rubus idaeus
Rubus sanctus
Rumex obtusifolius
Salacia lehmbachii
Salvadora persica
Salvia divaricata
Salvia nubicola
Salvia yosgadensis
Santalum album
Saussurea cordifolia
Scapania nemorea
Schizanthus tricolor
Schlumbergera truncata
Scrophularia buergeriana
Scrophularia koelzii
Scrophularia ningpoensis
Scutellaria baicalensis
Scutellaria chaematochlora
Secale cereale
Senecio scandens
Senna artemisioides
Senna santanderensis
Seriphidium porrectum
Sesamum indicum
Seseli libanotis
Sideritis brevibracteata
Sideritis dasygnaphala
Sideritis tragoriganum
Sideroxylon cubense
Solanum jamaicense
Solanum melongena
Spartina cynosuroides
Sphaeranthus confertifolius
Spiracantha cornifolia
Stauntonia hexaphylla
Stellaria dichotoma
Stellaria media
Strophanthus hispidus
Strychnos henningsii
Strychnos trinervis
Styrax
Styrax benzoin
Styrax tonkinensis
Syzygium aromaticum
Tabebuia angustata
Tabernaemontana glandulosa
Taraxacum coreanum
Taraxacum mongolicum
Taraxacum officinale
Taraxacum platycarpum
Taraxacum sinicum
Tarchonanthus camphoratus
Taxus wallichiana
Tephroseris kirilowii
Tephroseris palustris
Tetracentron sinense
Tetradium glabrifolium
Thapsia garganica
Theobroma cacao
Tinospora crispa
Tithonia rotundifolia
Tolpis webbii
Tribulus terrestris
Trifolium alexandrinum
Uncaria rhynchophylla
Urtica dioica
Uvariopsis tripetala
Vallaris solanacea
Vanilla planifolia
Vanilla pompona
Vepris louisii
Vernonanthura chamaedrys
Veronica intercedens
Vincetoxicum tanakae
Viscum articulatum
Viscum coloratum
Vitex trifolia
Vitis vinifera
Vouacapoua macropetala
Wurfbainia neoaurantiaca
Xanthium spinosum
Xanthium strumarium
Zanthoxylum ailanthoides
Zanthoxylum beecheyanum
Zanthoxylum integrifoliolum
Zanthoxylum wutaiense
Zea mays
Zingiber officinale
Zingiber zerumbet
Zizania aquatica

Cross-Links

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PubChem 1183
NPASS NPC203719
ChEMBL CHEMBL13883
LOTUS LTS0136163
wikiData Q33495