Dehydrozingerone

Details

• Internal ID: e2b06fa0-6ebd-48a8-8549-4e37189b29d3
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives
• IUPAC Name: (E)-4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one
• SMILES (Canonical): CC(=O)C=CC1=CC(=C(C=C1)O)OC
• SMILES (Isomeric): CC(=O)/C=C/C1=CC(=C(C=C1)O)OC
• InChI: InChI=1S/C11H12O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h3-7,13H,1-2H3/b4-3+
• InChI Key: AFWKBSMFXWNGRE-ONEGZZNKSA-N
• Popularity: 131 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₂O₃
• Molecular Weight: 192.21 g/mol
• Exact Mass: 192.078644241 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.00
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 1080-12-2
• 4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one
• Feruloylmethane
• Vanillylidenacetone
• 4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one
• Vanillalacetone
• Vanillylidene acetone
• 22214-42-2
• (E)-4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one
• Dehydrogingerone
• Vanylidenacetone
• MHSK
• Vanillidene acetone
• Dehydro(O)-paradol
• 3-Methoxy-4-hydroxybenzalacetone
• 3-BUTEN-2-ONE, 4-(4-HYDROXY-3-METHOXYPHENYL)-
• (O)-Paradol, dehydro-
• (O)-Dehydroparadol
• 4-Hydroxy-3-methoxystyryl methyl ketone
• 4-Hydroxy-3-methoxybenzylideneacetone
• FEMA No. 3738
• NSC 4019
• NSC 5316
• Vanillylideneacetone
• NSC 26613
• NSC 44708
• Methyl-3-methoxy-4-hydroxy styryl ketone
• NSC-4019
• NSC-5316
• (0)-Paradol, dehydro-
• EINECS 214-096-9
• NSC 45411
• NSC-44708
• NSC-45411
• (3E)-4-(4-Hydroxy-3-methoxyphenyl)but-3-en-2-one
• 8CJX5I27B7
• CHEMBL106509
• (E)-2-Methoxy-4-(3-oxo-1-butenyl)phenol
• CHEBI:81361
• (E)-4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one
• NSC-26613
• 3-Buten-2-one, 4-(4-hydroxy-3-methoxyphenyl)-, (E)-
• [0]-Paradol, dehydro-
• Methyl-3-methoxy-4-hydroxystyryl ketone
• (~{E})-4-(3-methoxy-4-oxidanyl-phenyl)but-3-en-2-one
• [0]-Dehydroparadol
• MFCD00012210
• 3-Buten-2-one, 4-(4-hydroxy-3-methoxyphenyl)-, (3E)-
• Dehydro(0)-paradol
• BRN 2049660
• UNII-8CJX5I27B7
• AI3-01934
• GJK
• TRANS-DEHYDROZINGERONE
• 2-08-00-00326 (Beilstein Handbook Reference)
• SCHEMBL498223
• (E)-4-(4-hydroxy-3-methoxy-phenyl)but-3-en-2-one
• Vanillylidenacetone, >=98.5%
• NSC4019
• NSC5316
• NSC26613
• NSC44708
• NSC45411
• XAA21442
• VANILLYLIDENE ACETONE [FHFI]
• AC8555
• BDBM50195679
• AKOS004909556
• DS-4905
• Vanillylidenacetone, analytical standard
• CS-0146520
• CS-0356785
• H0996
• C17840
• 3-Buten-2-one,4-(4-hydroxy-3-methoxyphenyl)-
• EN300-1858829
• 4-(4-Hydroxy-3-methoxy-phenyl)-but-3-en-2-one
• 4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one #
• A895371
• AE-562/43459152
• W-200772
• (E)-4-(4-hydroxy-3-methoxyphenyl) but-3-en-2-one
• Q27155299
• (E)-4-(4-Hydroxy-3-methoxy-phenyl)-but-3-en-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9968	99.68%
Caco-2	+	0.7120	71.20%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8861	88.61%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9636	96.36%
OATP1B3 inhibitior	+	0.9857	98.57%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7023	70.23%
P-glycoprotein inhibitior	-	0.9767	97.67%
P-glycoprotein substrate	-	0.9691	96.91%
CYP3A4 substrate	-	0.6329	63.29%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8042	80.42%
CYP3A4 inhibition	-	0.8021	80.21%
CYP2C9 inhibition	-	0.9550	95.50%
CYP2C19 inhibition	-	0.6309	63.09%
CYP2D6 inhibition	-	0.9267	92.67%
CYP1A2 inhibition	-	0.5704	57.04%
CYP2C8 inhibition	+	0.5466	54.66%
CYP inhibitory promiscuity	-	0.6804	68.04%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7675	76.75%
Carcinogenicity (trinary)	Non-required	0.5972	59.72%
Eye corrosion	+	0.8915	89.15%
Eye irritation	+	0.9885	98.85%
Skin irritation	+	0.8671	86.71%
Skin corrosion	-	0.9052	90.52%
Ames mutagenesis	-	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6951	69.51%
Micronuclear	-	0.5267	52.67%
Hepatotoxicity	-	0.7553	75.53%
skin sensitisation	-	0.5371	53.71%
Respiratory toxicity	-	0.9444	94.44%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	-	0.9875	98.75%
Nephrotoxicity	-	0.6369	63.69%
Acute Oral Toxicity (c)	III	0.8684	86.84%
Estrogen receptor binding	+	0.7458	74.58%
Androgen receptor binding	+	0.5347	53.47%
Thyroid receptor binding	-	0.7521	75.21%
Glucocorticoid receptor binding	-	0.7265	72.65%
Aromatase binding	-	0.6871	68.71%
PPAR gamma	-	0.6053	60.53%
Honey bee toxicity	-	0.9307	93.07%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.6255	62.55%
Fish aquatic toxicity	+	0.9170	91.70%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2487	P05067	Beta amyloid A4 protein	54.24 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.28%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.67%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.54%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.34%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.18%	95.56%
CHEMBL3194	P02766	Transthyretin	91.19%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.12%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.79%	99.17%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.68%	89.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.93%	94.45%
CHEMBL4208	P20618	Proteasome component C5	83.76%	90.00%
CHEMBL1951	P21397	Monoamine oxidase A	82.98%	91.49%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.73%	95.50%
CHEMBL2535	P11166	Glucose transporter	81.37%	98.75%

Plants that contains it

• Aframomum giganteum
• Curcuma longa
• Fibraurea tinctoria

Cross-Links

• PubChem: 5354238
• LOTUS: LTS0197654
• wikiData: Q27155299