Dehydrodieugenol

Details

• Internal ID: d496e78f-158c-4e21-a9b9-1fb49bc07111
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Biphenyls and derivatives
• IUPAC Name: 2-(2-hydroxy-3-methoxy-5-prop-2-enylphenyl)-6-methoxy-4-prop-2-enylphenol
• SMILES (Canonical): COC1=CC(=CC(=C1O)C2=C(C(=CC(=C2)CC=C)OC)O)CC=C
• SMILES (Isomeric): COC1=CC(=CC(=C1O)C2=C(C(=CC(=C2)CC=C)OC)O)CC=C
• InChI: InChI=1S/C20H22O4/c1-5-7-13-9-15(19(21)17(11-13)23-3)16-10-14(8-6-2)12-18(24-4)20(16)22/h5-6,9-12,21-22H,1-2,7-8H2,3-4H3
• InChI Key: KETPSFSOGFKJJY-UHFFFAOYSA-N
• Popularity: 19 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂O₄
• Molecular Weight: 326.40 g/mol
• Exact Mass: 326.15180918 g/mol
• Topological Polar Surface Area (TPSA): 58.90 Ų
• XlogP: 4.90
• Atomic LogP (AlogP): 4.24
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

• Dieugenol
• Bis-Eugenol
• 4433-08-3
• 2,2'-Biphenyldiol, 5,5'-diallyl-3,3'-dimethoxy-
• CHEBI:4361
• 3,3'-dimethoxy-5,5'-di-2-propen-1-yl-[1,1'-biphenyl]-2,2'-diol
• AC1L4WB6
• AC1Q79LE
• Bieugenol
• CHEMBL182629
• SCHEMBL5320878
• DTXSID80196137
• KETPSFSOGFKJJY-UHFFFAOYSA-N
• 2-(2-hydroxy-3-methoxy-5-prop-2-enylphenyl)-6-methoxy-4-prop-2-enylphenol
• AB00115914-01
• SR-01000500269
• SR-01000500269-1
• Q27106349
• 5,5'-Diallyl-3,3'-dimethoxy[1,1'-biphenyl]-2,2'-diol #
• [1,1'-Biphenyl]-2,2'-diol, 3,3'-dimethoxy-5,5'-di-2-propenyl-
• 4-allyl-2-(5-allyl-2-hydroxy-3-methoxy-phenyl)-6-methoxy-phenol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9836	98.36%
Caco-2	+	0.5202	52.02%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8313	83.13%
OATP2B1 inhibitior	-	0.7127	71.27%
OATP1B1 inhibitior	+	0.7364	73.64%
OATP1B3 inhibitior	+	0.9222	92.22%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6537	65.37%
P-glycoprotein inhibitior	+	0.6290	62.90%
P-glycoprotein substrate	-	0.8594	85.94%
CYP3A4 substrate	-	0.5656	56.56%
CYP2C9 substrate	-	0.6092	60.92%
CYP2D6 substrate	+	0.4730	47.30%
CYP3A4 inhibition	+	0.6365	63.65%
CYP2C9 inhibition	+	0.7970	79.70%
CYP2C19 inhibition	+	0.9261	92.61%
CYP2D6 inhibition	-	0.7521	75.21%
CYP1A2 inhibition	+	0.7440	74.40%
CYP2C8 inhibition	+	0.7531	75.31%
CYP inhibitory promiscuity	+	0.8939	89.39%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7338	73.38%
Carcinogenicity (trinary)	Non-required	0.6023	60.23%
Eye corrosion	-	0.9737	97.37%
Eye irritation	+	0.7104	71.04%
Skin irritation	-	0.7927	79.27%
Skin corrosion	-	0.8608	86.08%
Ames mutagenesis	-	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4188	41.88%
Micronuclear	+	0.5959	59.59%
Hepatotoxicity	+	0.7375	73.75%
skin sensitisation	-	0.7261	72.61%
Respiratory toxicity	-	0.7556	75.56%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	-	0.8500	85.00%
Nephrotoxicity	-	0.7502	75.02%
Acute Oral Toxicity (c)	III	0.7496	74.96%
Estrogen receptor binding	+	0.7577	75.77%
Androgen receptor binding	-	0.5376	53.76%
Thyroid receptor binding	+	0.6386	63.86%
Glucocorticoid receptor binding	+	0.7075	70.75%
Aromatase binding	+	0.7592	75.92%
PPAR gamma	+	0.7734	77.34%
Honey bee toxicity	-	0.8662	86.62%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9935	99.35%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.11%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.22%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.41%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.05%	99.17%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	91.98%	95.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.68%	86.33%
CHEMBL3492	P49721	Proteasome Macropain subunit	83.40%	90.24%
CHEMBL4208	P20618	Proteasome component C5	83.32%	90.00%
CHEMBL1255126	O15151	Protein Mdm4	82.48%	90.20%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.67%	89.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.36%	95.56%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	80.35%	98.11%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.05%	95.50%

Plants that contains it

• Catalpa bignonioides
• Cirsium arvense var. integrifolium
• Damburneya purpurea
• Entada phaseoloides
• Erymophyllum tenellum
• Esenbeckia nesiotica
• Eucommia ulmoides
• Hyptis tomentosa
• Illicium dunnianum
• Ipomoea cristulata
• Litsea turfosa
• Myristica fragrans
• Nothofagus menziesii
• Ocimum tenuiflorum
• Pancratium trianthum
• Piper pedicellosum
• Rhodotypos scandens
• Syzygium aromaticum
• Virola surinamensis
• Xanthostemon oppositifolius

Cross-Links

• PubChem: 165225
• NPASS: NPC21563
• LOTUS: LTS0207256
• wikiData: Q27106349