(8)-Shogaol

Details

• Internal ID: eb616cd7-49d7-46ab-9a15-a73c43200a08
• Taxonomy: Benzenoids > Phenols > Methoxyphenols > Shogaols
• IUPAC Name: (E)-1-(4-hydroxy-3-methoxyphenyl)dodec-4-en-3-one
• SMILES (Canonical): CCCCCCCC=CC(=O)CCC1=CC(=C(C=C1)O)OC
• SMILES (Isomeric): CCCCCCC/C=C/C(=O)CCC1=CC(=C(C=C1)O)OC
• InChI: InChI=1S/C19H28O3/c1-3-4-5-6-7-8-9-10-17(20)13-11-16-12-14-18(21)19(15-16)22-2/h9-10,12,14-15,21H,3-8,11,13H2,1-2H3/b10-9+
• InChI Key: LGZSMXJRMTYABD-MDZDMXLPSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₈O₃
• Molecular Weight: 304.40 g/mol
• Exact Mass: 304.20384475 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 4.82
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 11

Synonyms

• (8)-Shogaol
• 36700-45-5
• [8]-Shogaol
• (E)-1-(4-hydroxy-3-methoxyphenyl)dodec-4-en-3-one
• trans-(8)-Shogaol
• (E)-(8)-Shogaol
• 104186-07-4
• AV4IK2HCNT
• UNII-AV4IK2HCNT
• cis-[8]-Shogaol
• 4-Dodecen-3-one, 1-(4-hydroxy-3-methoxyphenyl)-
• SHOGAOL, 8-(P)
• CHEMBL25893
• 8-Shogaol (constituent of ginger) [DSC]
• 4-Dodecen-3-one, 1-(4-hydroxy-3-methoxyphenyl)-, (4E)-
• 1-(4-Hydroxy-3-methoxyphenyl)dodec-4-en-3-one
• CIS-8-SHOGAOL
• MEGxp0_001220
• SCHEMBL4886648
• SCHEMBL4886657
• ACon1_001127
• CHEBI:174643
• LGZSMXJRMTYABD-MDZDMXLPSA-N
• 8-Shogaol (constituent of ginger)
• HY-N2435
• BDBM50317424
• MFCD21333718
• AKOS030530374
• NCGC00169651-01
• AC-34352
• MS-24401
• CS-0022653
• 4-Dodecen-3-one, 1-(4-hydroxy-3-methoxyphenyl)
• BRD-K03628532-001-01-5
• Q27274135
• (4e)-1-(4-hydroxy-3-methoxyphenyl)dodec-4-en-3-one
• (E)-1-(4-Hydroxy-3-methoxy-phenyl)-dodec-4-en-3-one
• (e)-1-(4-hydroxy-3-methoxyphenyl) dodec-4-en-3-one
• NCGC00169651-02!(E)-1-(4-hydroxy-3-methoxyphenyl)dodec-4-en-3-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8414	84.14%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8042	80.42%
OATP2B1 inhibitior	-	0.8549	85.49%
OATP1B1 inhibitior	+	0.8493	84.93%
OATP1B3 inhibitior	+	0.9500	95.00%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.7805	78.05%
P-glycoprotein inhibitior	-	0.7953	79.53%
P-glycoprotein substrate	-	0.7143	71.43%
CYP3A4 substrate	+	0.5444	54.44%
CYP2C9 substrate	-	0.7929	79.29%
CYP2D6 substrate	-	0.8137	81.37%
CYP3A4 inhibition	-	0.7130	71.30%
CYP2C9 inhibition	-	0.9117	91.17%
CYP2C19 inhibition	-	0.5831	58.31%
CYP2D6 inhibition	-	0.8292	82.92%
CYP1A2 inhibition	+	0.6002	60.02%
CYP2C8 inhibition	+	0.9826	98.26%
CYP inhibitory promiscuity	-	0.7155	71.55%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7986	79.86%
Carcinogenicity (trinary)	Non-required	0.6917	69.17%
Eye corrosion	-	0.9265	92.65%
Eye irritation	+	0.7243	72.43%
Skin irritation	-	0.6501	65.01%
Skin corrosion	-	0.9374	93.74%
Ames mutagenesis	-	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7216	72.16%
Micronuclear	-	0.9700	97.00%
Hepatotoxicity	-	0.8092	80.92%
skin sensitisation	+	0.5787	57.87%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	-	0.6222	62.22%
Mitochondrial toxicity	-	0.9625	96.25%
Nephrotoxicity	-	0.8105	81.05%
Acute Oral Toxicity (c)	III	0.6916	69.16%
Estrogen receptor binding	+	0.6863	68.63%
Androgen receptor binding	+	0.5214	52.14%
Thyroid receptor binding	+	0.6950	69.50%
Glucocorticoid receptor binding	+	0.6195	61.95%
Aromatase binding	-	0.7403	74.03%
PPAR gamma	+	0.6100	61.00%
Honey bee toxicity	-	0.9651	96.51%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	+	0.8624	86.24%
Fish aquatic toxicity	+	0.9912	99.12%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL214	P08908	Serotonin 1a (5-HT1a) receptor	13050 nM	Ki	PMID: 20363635

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3060	Q9Y345	Glycine transporter 2	99.01%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.04%	91.11%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	96.54%	92.08%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.16%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.76%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.50%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.45%	86.33%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	89.67%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.99%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.93%	96.95%
CHEMBL2535	P11166	Glucose transporter	84.77%	98.75%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.60%	95.50%
CHEMBL1255126	O15151	Protein Mdm4	83.62%	90.20%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.55%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	80.89%	94.73%

Plants that contains it

• Zingiber officinale

Cross-Links

• PubChem: 6442560
• NPASS: NPC242372
• ChEMBL: CHEMBL25893
• LOTUS: LTS0203092
• wikiData: Q27274135