Zingerone

Details

• Internal ID: 939ea6e5-d062-4dfd-b17c-8d27738bdfaa
• Taxonomy: Benzenoids > Phenols > Methoxyphenols
• IUPAC Name: 4-(4-hydroxy-3-methoxyphenyl)butan-2-one
• SMILES (Canonical): CC(=O)CCC1=CC(=C(C=C1)O)OC
• SMILES (Isomeric): CC(=O)CCC1=CC(=C(C=C1)O)OC
• InChI: InChI=1S/C11H14O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h5-7,13H,3-4H2,1-2H3
• InChI Key: OJYLAHXKWMRDGS-UHFFFAOYSA-N
• Popularity: 633 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): 46.50 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.92
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• Vanillylacetone
• 122-48-5
• 4-(4-Hydroxy-3-methoxyphenyl)butan-2-one
• Zingiberone
• 4-(4-Hydroxy-3-methoxyphenyl)-2-butanone
• Zingherone
• Gingerone
• Vanillyl acetone
• 2-Butanone, 4-(4-hydroxy-3-methoxyphenyl)-
• [0]-Paradol
• 4-Hydroxy-3-methoxybenzylacetone
• (4-Hydroxy-3-methoxyphenyl)ethyl methyl ketone
• (0)-Paradol
• NSC 15335
• 4-(3-Methoxy-4-hydroxyphenyl)-2-butanone
• 3-Methoxy-4-hydroxybenzylacetone
• FEMA No. 3124
• 2-(4-Hydroxy-3-methoxyphenyl)ethyl methyl ketone
• 3-Methoxy-4-hydroxy-benzylacetone
• (O)-Paradol
• CCRIS 2036
• UNII-4MMW850892
• HSDB 1064
• Vanillylacetone;Gingerone
• EINECS 204-548-3
• BRN 2051099
• CHEMBL25894
• AI3-31837
• DTXSID8047420
• 4-(4-hydroxy-3-methoxy-phenyl)-butan-2-one
• CHEBI:68657
• MFCD00048232
• NSC-15335
• 4MMW850892
• 4-08-00-01866 (Beilstein Handbook Reference)
• vanillylaceton
• [0]Paradol
• ZINGERONE [FCC]
• ZINGERONE [MI]
• ZINGERONE [FHFI]
• ZINGERONE [HSDB]
• ZINGERONE [INCI]
• SCHEMBL119051
• Vanillylacetone, >=96%, FG
• VANILLYLACETON [WHO-DD]
• DTXCID6027420
• FEMA 3124
• 4-(4-hydroxy-3-methoxyphenyl)-
• HMS3651E22
• NSC15335
• Tox21_302493
• BDBM50304073
• s2371
• STL564783
• AKOS009462778
• CCG-208511
• DB15589
• LS-2368
• Vanillylacetone, >=98%, natural, FG
• Zingerone, analytical reference material
• NCGC00256663-01
• AC-34331
• AS-65368
• CAS-122-48-5
• HY-14621
• SY017980
• 4(4-Hydroxy-3-methoxyphenyl)-2-butanone
• 4-(3-methoxy-4-hydroxyphenyl)butan-2-one
• CS-0003480
• FT-0616634
• H1314
• SW219618-1
• C17497
• EN300-1721864
• A891122
• SR-05000013705
• Q1064625
• SR-05000013705-1
• W-108429
• BUTAN-2-ONE, 4-(4-HYDROXY-3-METHOXYPHENYL)-
• 4-(4-Hydroxy-3-methoxyphenyl)-2-butanone, 9CI, 8CI
• Z1255442373
• 4 - (4 - hydroxy - 3 - methoxyphenyl)butan - 2 - one
• InChI=1/C11H14O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h5-7,13H,3-4H2,1-2H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9960	99.60%
Caco-2	+	0.7782	77.82%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.9229	92.29%
OATP2B1 inhibitior	-	0.8616	86.16%
OATP1B1 inhibitior	+	0.9446	94.46%
OATP1B3 inhibitior	+	0.9646	96.46%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7717	77.17%
P-glycoprotein inhibitior	-	0.9849	98.49%
P-glycoprotein substrate	-	0.8638	86.38%
CYP3A4 substrate	-	0.5832	58.32%
CYP2C9 substrate	-	0.5963	59.63%
CYP2D6 substrate	+	0.3653	36.53%
CYP3A4 inhibition	-	0.9322	93.22%
CYP2C9 inhibition	-	0.9274	92.74%
CYP2C19 inhibition	-	0.7111	71.11%
CYP2D6 inhibition	-	0.8489	84.89%
CYP1A2 inhibition	+	0.6701	67.01%
CYP2C8 inhibition	+	0.7992	79.92%
CYP inhibitory promiscuity	-	0.8882	88.82%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7654	76.54%
Carcinogenicity (trinary)	Non-required	0.6489	64.89%
Eye corrosion	-	0.5764	57.64%
Eye irritation	+	0.9778	97.78%
Skin irritation	+	0.5892	58.92%
Skin corrosion	-	0.8848	88.48%
Ames mutagenesis	-	0.9600	96.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5789	57.89%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.5540	55.40%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	-	0.9000	90.00%
Nephrotoxicity	-	0.7722	77.22%
Acute Oral Toxicity (c)	III	0.8801	88.01%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	-	0.7439	74.39%
Thyroid receptor binding	-	0.8320	83.20%
Glucocorticoid receptor binding	-	0.8035	80.35%
Aromatase binding	-	0.8293	82.93%
PPAR gamma	-	0.7102	71.02%
Honey bee toxicity	-	0.9219	92.19%
Biodegradation	+	0.5250	52.50%
Crustacea aquatic toxicity	-	0.6704	67.04%
Fish aquatic toxicity	+	0.8342	83.42%

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	97.79%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.53%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.31%	99.17%
CHEMBL2581	P07339	Cathepsin D	94.07%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.95%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.43%	86.33%
CHEMBL2535	P11166	Glucose transporter	87.89%	98.75%
CHEMBL1255126	O15151	Protein Mdm4	84.46%	90.20%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.72%	95.50%
CHEMBL4208	P20618	Proteasome component C5	81.24%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.23%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.15%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.65%	96.95%

Plants that contains it

• Aframomum melegueta
• Alpinia officinarum
• Pinus contorta
• Trivalvaria costata
• Zingiber officinale

Cross-Links

• PubChem: 31211
• NPASS: NPC299406
• LOTUS: LTS0266587
• wikiData: Q1064625