4-Allyl-2,6-dimethoxyphenol

Details

• Internal ID: 45583663-aa60-454e-bfd4-baee251df36b
• Taxonomy: Benzenoids > Phenols > Methoxyphenols
• IUPAC Name: 2,6-dimethoxy-4-prop-2-enylphenol
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)CC=C
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)CC=C
• InChI: InChI=1S/C11H14O3/c1-4-5-8-6-9(13-2)11(12)10(7-8)14-3/h4,6-7,12H,1,5H2,2-3H3
• InChI Key: FWMPKHMKIJDEMJ-UHFFFAOYSA-N
• Popularity: 201 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₄O₃
• Molecular Weight: 194.23 g/mol
• Exact Mass: 194.094294304 g/mol
• Topological Polar Surface Area (TPSA): 38.70 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.14
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• 6627-88-9
• Methoxyeugenol
• 2,6-dimethoxy-4-prop-2-enylphenol
• 4-Allylsyringol
• Phenol, 2,6-dimethoxy-4-(2-propenyl)-
• 2,6-Dimethoxychavicol
• Phenol, 4-allyl-2,6-dimethoxy-
• 2,6-Dimethoxy-4-allylphenol
• 4-Hydroxy-3,5-dimethoxyallylbenzene
• FEMA No. 3655
• CHEBI:86562
• UNII-8VF00YWP89
• 4-Allyl-2,6-dimetoxyphenol
• 2,6-dimethoxy-4-(prop-2-en-1-yl)phenol
• 8VF00YWP89
• Phenol,2,6-dimethoxy-4-(2-propen-1-yl)-
• EINECS 229-600-2
• NSC 16953
• NSC 60246
• NSC-16953
• NSC-60246
• 2,6-dimethoxy-4-(2-propenyl)phenol
• Phenol,6-dimethoxy-
• Phenol, 4-(2-propenyl)-2,6-dimethoxy
• AI3-23057
• Phenol,6-dimethoxy-4-(2-propenyl)-
• 6-methoxyeugenol
• bmse010054
• SCHEMBL293977
• 4-allyl-2,6-dimethoxy-phenol
• 4-(2-PROPENYL)SYRINGOL
• CHEMBL2059292
• DTXSID30216470
• FWMPKHMKIJDEMJ-UHFFFAOYSA-N
• CHAVICOL, 2,6-DIMETHOXY-
• NSC16953
• NSC60246
• 4-Allyl-2,6-dimethoxyphenol, 8CI
• BDBM50242963
• MFCD00008655
• 2,6-dimethoxy-4-prop-2-enyl-phenol
• 4-(2-Propenyl)-2,6-dimethoxyphenol
• AKOS015888171
• 2,6-dimethoxy-4-(2-propenyl)-phenol
• 4-Allyl-2,6-dimethoxyphenol, >=95%
• AS-36789
• BP-10517
• Phenol, 4-allyl-2,6-dimethoxy- (8CI)
• 2,6-Dimethoxy-4-(2-propenyl)phenol, 9CI
• 4-ALLYL-2,6-DIMETHOXYPHENOL [FHFI]
• 4-Allyl-2,6-dimethoxyphenol, >=95%, FG
• CS-0158007
• FT-0636204
• A835401
• Phenol, 2,6-dimethoxy-4-(2-propenyl)- (9CI)
• PHENOL, 2,6-DIMETHOXY-4-(2-PROPEN-1-YL)-
• Q27159248
• 4-(2-Propenyl)-2,6-dimethoxyphenol (4-allylsyringol)
• InChI=1/C11H14O3/c1-4-5-8-6-9(13-2)11(12)10(7-8)14-3/h4,6-7,12H,1,5H2,2-3H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9919	99.19%
Caco-2	+	0.5856	58.56%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7978	79.78%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7389	73.89%
OATP1B3 inhibitior	+	0.9811	98.11%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8882	88.82%
P-glycoprotein inhibitior	-	0.9575	95.75%
P-glycoprotein substrate	-	0.8918	89.18%
CYP3A4 substrate	-	0.6142	61.42%
CYP2C9 substrate	-	0.6092	60.92%
CYP2D6 substrate	+	0.4730	47.30%
CYP3A4 inhibition	-	0.6694	66.94%
CYP2C9 inhibition	-	0.9487	94.87%
CYP2C19 inhibition	-	0.5090	50.90%
CYP2D6 inhibition	-	0.8761	87.61%
CYP1A2 inhibition	-	0.5552	55.52%
CYP2C8 inhibition	+	0.6431	64.31%
CYP inhibitory promiscuity	-	0.5128	51.28%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7661	76.61%
Carcinogenicity (trinary)	Non-required	0.6545	65.45%
Eye corrosion	+	0.6453	64.53%
Eye irritation	+	0.9759	97.59%
Skin irritation	+	0.6601	66.01%
Skin corrosion	-	0.7765	77.65%
Ames mutagenesis	-	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7672	76.72%
Micronuclear	-	0.6708	67.08%
Hepatotoxicity	+	0.7000	70.00%
skin sensitisation	+	0.7052	70.52%
Respiratory toxicity	-	0.7667	76.67%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	-	0.9500	95.00%
Nephrotoxicity	-	0.7629	76.29%
Acute Oral Toxicity (c)	III	0.8439	84.39%
Estrogen receptor binding	-	0.6793	67.93%
Androgen receptor binding	-	0.8006	80.06%
Thyroid receptor binding	-	0.6690	66.90%
Glucocorticoid receptor binding	-	0.8114	81.14%
Aromatase binding	-	0.7157	71.57%
PPAR gamma	-	0.6518	65.18%
Honey bee toxicity	-	0.8831	88.31%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9385	93.85%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.36%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.48%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.87%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.09%	99.17%
CHEMBL2581	P07339	Cathepsin D	88.03%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.83%	94.45%
CHEMBL1255126	O15151	Protein Mdm4	84.86%	90.20%
CHEMBL4208	P20618	Proteasome component C5	82.72%	90.00%

Plants that contains it

• Asarum asperum var. geaster
• Catalpa bignonioides
• Cirsium arvense var. integrifolium
• Cocculus orbiculatus
• Entada phaseoloides
• Erymophyllum tenellum
• Esenbeckia nesiotica
• Houttuynia cordata
• Hyptis tomentosa
• Illicium dunnianum
• Illicium verum
• Ipomoea cristulata
• Myristica fragrans
• Nothofagus menziesii
• Pancratium trianthum
• Pimenta racemosa
• Piper aduncum
• Piper auritum
• Piper pedicellosum
• Prunus mume
• Rhodotypos scandens
• Spathiphyllum cannifolium
• Xanthostemon oppositifolius

Cross-Links

• PubChem: 226486
• NPASS: NPC20674
• LOTUS: LTS0015297
• wikiData: Q27159248