Anethole

Details

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Internal ID bb4f4adf-2209-4796-8c8f-9196f5d61c6b
Taxonomy Benzenoids > Phenol ethers > Anisoles
IUPAC Name 1-methoxy-4-[(E)-prop-1-enyl]benzene
SMILES (Canonical) CC=CC1=CC=C(C=C1)OC
SMILES (Isomeric) C/C=C/C1=CC=C(C=C1)OC
InChI InChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3/b4-3+
InChI Key RUVINXPYWBROJD-ONEGZZNKSA-N
Popularity 1,458 references in papers

Physical and Chemical Properties

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Molecular Formula C10H12O
Molecular Weight 148.20 g/mol
Exact Mass 148.088815002 g/mol
Topological Polar Surface Area (TPSA) 9.20 Ų
XlogP 3.30
Atomic LogP (AlogP) 2.73
H-Bond Acceptor 1
H-Bond Donor 0
Rotatable Bonds 2

Synonyms

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trans-Anethole
4180-23-8
104-46-1
(E)-Anethole
p-Propenylanisole
(E)-1-Methoxy-4-(prop-1-en-1-yl)benzene
Anise camphor
Isoestragole
4-Propenylanisole
Monasirup
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Anethole

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9975 99.75%
Caco-2 + 0.9047 90.47%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability + 0.6857 68.57%
Subcellular localzation Mitochondria 0.7035 70.35%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9413 94.13%
OATP1B3 inhibitior + 0.9817 98.17%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.9500 95.00%
BSEP inhibitior - 0.8103 81.03%
P-glycoprotein inhibitior - 0.9832 98.32%
P-glycoprotein substrate - 0.9698 96.98%
CYP3A4 substrate - 0.6926 69.26%
CYP2C9 substrate + 0.6036 60.36%
CYP2D6 substrate - 0.6859 68.59%
CYP3A4 inhibition - 0.8875 88.75%
CYP2C9 inhibition - 0.9385 93.85%
CYP2C19 inhibition - 0.6657 66.57%
CYP2D6 inhibition - 0.9186 91.86%
CYP1A2 inhibition + 0.8091 80.91%
CYP2C8 inhibition - 0.8756 87.56%
CYP inhibitory promiscuity - 0.5787 57.87%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.5729 57.29%
Carcinogenicity (trinary) Non-required 0.5912 59.12%
Eye corrosion + 0.8829 88.29%
Eye irritation + 0.9948 99.48%
Skin irritation + 0.6558 65.58%
Skin corrosion - 0.8578 85.78%
Ames mutagenesis - 0.9500 95.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4775 47.75%
Micronuclear - 0.9300 93.00%
Hepatotoxicity - 0.5342 53.42%
skin sensitisation + 0.9333 93.33%
Respiratory toxicity - 0.9222 92.22%
Reproductive toxicity + 0.5667 56.67%
Mitochondrial toxicity - 0.9875 98.75%
Nephrotoxicity + 0.4768 47.68%
Acute Oral Toxicity (c) III 0.9174 91.74%
Estrogen receptor binding - 0.7777 77.77%
Androgen receptor binding + 0.5586 55.86%
Thyroid receptor binding - 0.8235 82.35%
Glucocorticoid receptor binding - 0.7901 79.01%
Aromatase binding - 0.8515 85.15%
PPAR gamma - 0.8780 87.80%
Honey bee toxicity - 0.9402 94.02%
Biodegradation - 0.6750 67.50%
Crustacea aquatic toxicity + 0.9300 93.00%
Fish aquatic toxicity + 0.8223 82.23%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL3577 P00352 Aldehyde dehydrogenase 1A1 39810.7 nM
Potency
via CMAUP
CHEMBL4096 P04637 Cellular tumor antigen p53 5 nM
Potency
via Super-PRED
CHEMBL1293226 B2RXH2 Lysine-specific demethylase 4D-like 35481.3 nM
Potency
via CMAUP
CHEMBL1293235 P02545 Prelamin-A/C 316.2 nM
Potency
via Super-PRED
CHEMBL1963 P16473 Thyroid stimulating hormone receptor 794.3 nM
Potency
via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 93.45% 96.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.91% 95.56%
CHEMBL1907 P15144 Aminopeptidase N 91.13% 93.31%
CHEMBL2039 P27338 Monoamine oxidase B 90.08% 92.51%
CHEMBL3192 Q9BY41 Histone deacetylase 8 89.40% 93.99%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 89.02% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 87.53% 96.09%
CHEMBL4208 P20618 Proteasome component C5 87.12% 90.00%
CHEMBL3492 P49721 Proteasome Macropain subunit 86.39% 90.24%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.67% 86.33%
CHEMBL2487 P05067 Beta amyloid A4 protein 84.58% 96.74%

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.
Achillea abrotanoides
Actaea cimicifuga
Actaea dahurica
Actaea simplex
Agastache foeniculum
Agastache rugosa
Agrimonia pilosa
Akebia quinata
Akebia trifoliata
Albizia julibrissin
Anacardium occidentale
Anchusa officinalis
Anemopsis californica
Anthriscus cerefolium
Arnebia euchroma
Arnebia guttata
Artemisia annua
Asarum epigynum
Asarum heterotropoides
Aster tataricus
Aucklandia costus
Baccharis dracunculifolia
Basella alba
Bellis perennis
Blepharocalyx salicifolius
Cannabis sativa
Caryopteris mongholica
Chaerophyllum bulbosum
Chaerophyllum macrospermum
Chamaecyparis lawsoniana
Cinnamomum aromaticum
Clausena anisata
Clausena heptaphylla
Clematis chinensis
Coriandrum sativum
Cornus officinalis
Croton essequiboensis
Croton lachnostachyus
Cryptocarya agathophylla
Cryptomeria japonica
Curcuma kwangsiensis
Curcuma phaeocaulis
Curcuma wenyujin
Curcuma zedoaria
Dalbergia ecastaphyllum
Dalbergia rubiginosa
Erucaria microcarpa
Eryngium foetidum
Euphorbia kansui
Foeniculum vulgare
Glycyrrhiza
Glycyrrhiza glabra
Glycyrrhiza inflata
Glycyrrhiza uralensis
Gundelia tournefortii
Hamamelis virginiana
Helichrysum arenarium
Hexalobus monopetalus
Homalomena occulta
Ifloga spicata
Illicium lanceolatum
Illicium verum
Kaempferia galanga
Laurus nobilis
Limnophila rugosa
Lithospermum erythrorhizon
Magnolia salicifolia
Mappia nimmoniana
Mesembryanthemum tortuosum
Monopteryx uauca
Myrrhis odorata
Myrtus communis
Nigella sativa
Ocimum basilicum
Ocimum tenuiflorum
Origanum × adanense
Origanum dictamnus
Osmorhiza aristata
Passiflora incarnata
Paullinia cupana
Pimenta racemosa
Pimpinella anisum
Piper regnellii
Platostoma africanum
Pogostemon cablin
Polygala senega
Porophyllum ruderale
Salvia fruticosa
Satureja atropatana
Scaligeria lazica
Scandix australis
Scutellaria barbata
Senna alexandrina
Solidago odora
Spatholobus suberectus
Stevia rebaudiana
Swertia japonica
Syzygium anisatum
Syzygium aromaticum
Tagetes filifolia
Tagetes lucida
Thapsia garganica
Thymus vulgaris
Trachyspermum ammi
Uncaria macrophylla
Uncaria rhynchophylla
Uncaria sinensis
Vitex agnus-castus
Zanthoxylum bungeanum
Zanthoxylum dipetalum
Zanthoxylum schinifolium

Cross-Links

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PubChem 637563
NPASS NPC99886
ChEMBL CHEMBL452630
LOTUS LTS0033696
wikiData Q255564