cis-6-Shogaol

Details

• Internal ID: 2fb6ba04-2ef9-47d2-b8ee-dfdd6fd27484
• Taxonomy: Benzenoids > Phenols > Methoxyphenols > Shogaols
• IUPAC Name: (Z)-1-(4-hydroxy-3-methoxyphenyl)dec-4-en-3-one
• SMILES (Canonical): CCCCCC=CC(=O)CCC1=CC(=C(C=C1)O)OC
• SMILES (Isomeric): CCCCC/C=C\C(=O)CCC1=CC(=C(C=C1)O)OC
• InChI: InChI=1S/C17H24O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h7-8,10,12-13,19H,3-6,9,11H2,1-2H3/b8-7-
• InChI Key: OQWKEEOHDMUXEO-FPLPWBNLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₄O₃
• Molecular Weight: 276.40 g/mol
• Exact Mass: 276.17254462 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 4.04
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 9

Synonyms

• SCHEMBL10523393

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.7765	77.65%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8042	80.42%
OATP2B1 inhibitior	-	0.8536	85.36%
OATP1B1 inhibitior	+	0.8299	82.99%
OATP1B3 inhibitior	+	0.9500	95.00%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.7638	76.38%
P-glycoprotein inhibitior	-	0.8852	88.52%
P-glycoprotein substrate	-	0.7294	72.94%
CYP3A4 substrate	+	0.5317	53.17%
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	+	0.9817	98.17%
CYP inhibitory promiscuity	-	0.7155	71.55%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7986	79.86%
Carcinogenicity (trinary)	Non-required	0.6917	69.17%
Eye corrosion	-	0.9265	92.65%
Eye irritation	+	0.9292	92.92%
Skin irritation	-	0.6501	65.01%
Skin corrosion	-	0.9374	93.74%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4031	40.31%
Micronuclear	-	0.9700	97.00%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	+	0.5787	57.87%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	-	0.6222	62.22%
Mitochondrial toxicity	-	0.9625	96.25%
Nephrotoxicity	-	0.8118	81.18%
Acute Oral Toxicity (c)	III	0.6916	69.16%
Estrogen receptor binding	+	0.8009	80.09%
Androgen receptor binding	-	0.5224	52.24%
Thyroid receptor binding	+	0.6741	67.41%
Glucocorticoid receptor binding	+	0.6619	66.19%
Aromatase binding	-	0.7182	71.82%
PPAR gamma	+	0.8083	80.83%
Honey bee toxicity	-	0.9650	96.50%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.7000	70.00%
Fish aquatic toxicity	+	0.9912	99.12%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4794	Q8NER1	Vanilloid receptor	290 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3060	Q9Y345	Glycine transporter 2	98.83%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.49%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.53%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.72%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.69%	94.45%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	94.01%	92.08%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.45%	86.33%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	87.58%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.18%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.93%	96.95%
CHEMBL2535	P11166	Glucose transporter	85.46%	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	80.74%	94.73%

Plants that contains it

• Zingiber officinale

Cross-Links

• PubChem: 12315512
• NPASS: NPC38724