[4]-Shogaol

Details

• Internal ID: fe48479c-887a-407a-a9ff-acf20414659a
• Taxonomy: Benzenoids > Phenols > Methoxyphenols > Shogaols
• IUPAC Name: (E)-1-(4-hydroxy-3-methoxyphenyl)oct-4-en-3-one
• SMILES (Canonical): CCCC=CC(=O)CCC1=CC(=C(C=C1)O)OC
• SMILES (Isomeric): CCC/C=C/C(=O)CCC1=CC(=C(C=C1)O)OC
• InChI: InChI=1S/C15H20O3/c1-3-4-5-6-13(16)9-7-12-8-10-14(17)15(11-12)18-2/h5-6,8,10-11,17H,3-4,7,9H2,1-2H3/b6-5+
• InChI Key: PHHDVGGCTAPBHF-AATRIKPKSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 3.26
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

• 1-(4-hydroxy-3-methoxyphenyl)oct-4-en-3-one
• CHEMBL277440
• SCHEMBL8231268
• PHHDVGGCTAPBHF-AATRIKPKSA-N

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9972	99.72%
Caco-2	+	0.8112	81.12%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8351	83.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8902	89.02%
OATP1B3 inhibitior	+	0.9685	96.85%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6032	60.32%
P-glycoprotein inhibitior	-	0.9630	96.30%
P-glycoprotein substrate	-	0.8157	81.57%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.7929	79.29%
CYP2D6 substrate	-	0.8137	81.37%
CYP3A4 inhibition	-	0.8252	82.52%
CYP2C9 inhibition	-	0.8526	85.26%
CYP2C19 inhibition	-	0.5879	58.79%
CYP2D6 inhibition	-	0.8565	85.65%
CYP1A2 inhibition	+	0.6680	66.80%
CYP2C8 inhibition	+	0.9426	94.26%
CYP inhibitory promiscuity	-	0.7193	71.93%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7686	76.86%
Carcinogenicity (trinary)	Non-required	0.6425	64.25%
Eye corrosion	-	0.7914	79.14%
Eye irritation	+	0.8913	89.13%
Skin irritation	-	0.6933	69.33%
Skin corrosion	-	0.9377	93.77%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5424	54.24%
Micronuclear	-	0.8767	87.67%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	+	0.5789	57.89%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	-	0.5556	55.56%
Mitochondrial toxicity	-	0.9500	95.00%
Nephrotoxicity	-	0.7686	76.86%
Acute Oral Toxicity (c)	III	0.7852	78.52%
Estrogen receptor binding	+	0.7097	70.97%
Androgen receptor binding	-	0.6630	66.30%
Thyroid receptor binding	+	0.6907	69.07%
Glucocorticoid receptor binding	-	0.5674	56.74%
Aromatase binding	-	0.8038	80.38%
PPAR gamma	-	0.5177	51.77%
Honey bee toxicity	-	0.9396	93.96%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5145	51.45%
Fish aquatic toxicity	+	0.9480	94.80%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3060	Q9Y345	Glycine transporter 2	96.69%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.03%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.35%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.70%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.21%	94.45%
CHEMBL2581	P07339	Cathepsin D	87.29%	98.95%
CHEMBL2535	P11166	Glucose transporter	87.21%	98.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.20%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.32%	95.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.37%	92.62%
CHEMBL1255126	O15151	Protein Mdm4	81.34%	90.20%

Plants that contains it

• Zingiber officinale

Cross-Links

• PubChem: 9794897
• NPASS: NPC114298
• ChEMBL: CHEMBL277440
• LOTUS: LTS0079209
• wikiData: Q105302211