Isoeugenyl methyl ether

Details

• Internal ID: aebe55b3-5e2e-4aad-a27c-2dcd9ae1387c
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Methoxybenzenes > Dimethoxybenzenes
• IUPAC Name: 1,2-dimethoxy-4-[(Z)-prop-1-enyl]benzene
• SMILES (Canonical): CC=CC1=CC(=C(C=C1)OC)OC
• SMILES (Isomeric): C/C=C\C1=CC(=C(C=C1)OC)OC
• InChI: InChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4-8H,1-3H3/b5-4-
• InChI Key: NNWHUJCUHAELCL-PLNGDYQASA-N
• Popularity: 31 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₄O₂
• Molecular Weight: 178.23 g/mol
• Exact Mass: 178.099379685 g/mol
• Topological Polar Surface Area (TPSA): 18.50 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.74
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• cis-Methyl isoeugenol
• 6380-24-1
• O-Methylisoeugenol
• Isoeugenyl methyl ether
• Isomethyleugenol
• Methylisoeugenol, (Z)-
• cis-4-Propenyl veratrole
• Methyl isoeugenol
• 4-Propenyl veratrole
• (Z)-Methylisoeugenol
• Isohomogenol
• 1,3,4-Isoeugenol methyl ether
• 4-Propenyl-1,2-dimethoxybenzene
• 4-Propenylveratrole
• 1-(3,4-Dimethoxyphenyl)-1-propene
• FEMA No. 2476
• 1-Veratryl-1-propene
• Isoeugenol methyl ether
• (Z)-methyl isoeugenol
• 1,2-dimethoxy-4-[(Z)-prop-1-enyl]benzene
• 3,4-Dimethoxypropenylbenzene (VAN)
• EINECS 202-224-6
• NSC 46111
• UNII-64DPK8DS6F
• Benzene, 1,2-dimethoxy-4-(1-propenyl)-, (Z)-
• BRN 0880472
• 64DPK8DS6F
• UNII-46RN7Q97DE
• 1-Propene, 1-(3,4-dimethoxyphenyl)-
• 4-Prop-1-enylveratrole
• 1,2-Dimethoxy-4-(1-propen-1-yl)benzene
• AI3-20967
• 1,2-Dimethoxy-4-propenylbenzene
• 1,2-DIMETHOXY-4-(1-PROPENYL)BENZENE
• Benzene, 1,2-dimethoxy-4-propenyl-, (Z)-
• CHEBI:50550
• BRN 1911284
• Benzene, 1,2-dimethoxy-4-propenyl-
• 1,2-dimethoxy-4-[(1Z)-prop-1-en-1-yl]benzene
• 2-06-00-00918 (Beilstein Handbook Reference)
• 3-06-00-04995 (Beilstein Handbook Reference)
• 4-prop-1-enylveratrol
• cis-isomethyleugenol
• Benzene, 1,2-dimethoxy-4-(1-propen-1-yl)-
• 4 - prop - 1 - enylveratrole
• (e)-methyl eugenol
• Benceno, 1,2-dimetoxi-4-(1-propen-1-il)-
• trans-Methyl isoeugenol
• cis-isoeugenolmethylether
• 4-(1-Propenyl)veratrole
• cis-isoeugenol methyl ether
• ghl.PD_Mitscher_leg0.375
• (Z)-O-METHYLISOEUGENOL
• 4-CIS-PROPENYLVERATROLE
• 46RN7Q97DE
• SCHEMBL1760676
• CHEMBL1164609
• FEMA 2476
• NNWHUJCUHAELCL-PLNGDYQASA-N
• DTXSID101026531
• 1,2-Dimethoxy-4-propenyl-Benzene
• FEMA NO. 2476, Z-
• ISOEUGENYL METHYL ETHER, CIS-
• 1,2-dimethoxy-4-cis-propenyl-benzene
• AKOS025287899
• LS-2861
• VERATROLE, 4-PROPENYL-, CIS-
• 1,2-Dimethoxy-4-propenyl-(E)-Benzene
• 1,2-Dimethoxy-4-(1-propenyl)benzene, 9CI
• (Z)-3,4-DIMETHOXY-.BETA.-METHYLSTYRENE
• 1,2-DIMETHOXY-4-(1-CIS-PROPENYL)BENZENE
• Q27122111
• BENZENE, 1,2-DIMETHOXY-4-(1Z)-1-PROPEN-1-YL-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.9115	91.15%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.8571	85.71%
Subcellular localzation	Mitochondria	0.7470	74.70%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9337	93.37%
OATP1B3 inhibitior	+	0.9822	98.22%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7845	78.45%
P-glycoprotein inhibitior	-	0.9763	97.63%
P-glycoprotein substrate	-	0.8902	89.02%
CYP3A4 substrate	-	0.6717	67.17%
CYP2C9 substrate	+	0.6036	60.36%
CYP2D6 substrate	-	0.6859	68.59%
CYP3A4 inhibition	-	0.8461	84.61%
CYP2C9 inhibition	-	0.9709	97.09%
CYP2C19 inhibition	-	0.6790	67.90%
CYP2D6 inhibition	-	0.9295	92.95%
CYP1A2 inhibition	+	0.6061	60.61%
CYP2C8 inhibition	-	0.5861	58.61%
CYP inhibitory promiscuity	+	0.5947	59.47%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7309	73.09%
Carcinogenicity (trinary)	Non-required	0.4544	45.44%
Eye corrosion	+	0.7002	70.02%
Eye irritation	+	0.9824	98.24%
Skin irritation	+	0.5923	59.23%
Skin corrosion	-	0.8915	89.15%
Ames mutagenesis	-	0.8600	86.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6446	64.46%
Micronuclear	-	0.8367	83.67%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	+	0.7489	74.89%
Respiratory toxicity	-	0.9111	91.11%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	-	0.9375	93.75%
Nephrotoxicity	-	0.6540	65.40%
Acute Oral Toxicity (c)	III	0.8765	87.65%
Estrogen receptor binding	-	0.7393	73.93%
Androgen receptor binding	-	0.6015	60.15%
Thyroid receptor binding	-	0.8071	80.71%
Glucocorticoid receptor binding	-	0.8781	87.81%
Aromatase binding	-	0.8301	83.01%
PPAR gamma	-	0.8714	87.14%
Honey bee toxicity	-	0.8964	89.64%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	+	0.8400	84.00%
Fish aquatic toxicity	+	0.8848	88.48%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.57%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.39%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.72%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.04%	95.56%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.55%	89.62%
CHEMBL1255126	O15151	Protein Mdm4	84.11%	90.20%
CHEMBL2535	P11166	Glucose transporter	83.71%	98.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.45%	91.11%
CHEMBL3492	P49721	Proteasome Macropain subunit	82.20%	90.24%
CHEMBL2487	P05067	Beta amyloid A4 protein	82.19%	96.74%
CHEMBL3194	P02766	Transthyretin	80.87%	90.71%
CHEMBL4208	P20618	Proteasome component C5	80.36%	90.00%

Plants that contains it

• Acorus calamus
• Acorus calamus var. angustatus
• Acorus gramineus
• Asarum rigescens
• Catalpa bignonioides
• Cirsium arvense var. integrifolium
• Daucus carota
• Entada phaseoloides
• Erymophyllum tenellum
• Esenbeckia nesiotica
• Foeniculum vulgare
• Hyptis tomentosa
• Illicium difengpi
• Illicium verum
• Ipomoea cristulata
• Myristica fragrans
• Nothofagus menziesii
• Pancratium trianthum
• Piper pedicellosum
• Platostoma africanum
• Rhodotypos scandens
• Xanthostemon oppositifolius
• Zingiber officinale

Cross-Links

• PubChem: 1549045
• NPASS: NPC301043
• LOTUS: LTS0036071
• wikiData: Q27122111