1-(4-HYDROXY-3-METHOXYPHENYL)-DECAN-3-ONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H26O3
Molecular Weight	278.3865
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 1-(4-HYDROXY-3-METHOXYPHENYL)-DECAN-3-ONE

Structure Search

SMILES

CCCCCCCC(=O)CCC1=CC(OC)=C(O)C=C1

InChI

InChIKey=CZNLTCTYLMYLHL-UHFFFAOYSA-N

InChI=1S/C17H26O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h10,12-13,19H,3-9,11H2,1-2H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28869564 | https://www.ncbi.nlm.nih.gov/pubmed/28274629 | https://www.ncbi.nlm.nih.gov/pubmed/25789481

1-(4-hydroxy-3-methoxyphenyl)decan-3-one (Paradol, 6-paradol ), a major constituent of A. melegueta seeds, exhibited potent proliferative and ossification characteristics in bone cells. It enhanced alkaline phosphatase activity and vitamin D content and decreased the osteoporotic marker acid phosphatase. Paradol enhanced the expression of osteocyte and osteoblast-related genes and inhibited osteoclast and RUNX suppressor genes. Paradols are unsaturated ketones produced by biotransformation of shogaols in gingers. Among them, 6-paradol has been investigated as a new drug candidate due to its anti-inflammatory, apoptotic, and neuroprotective activities. 6-paradol exhibited a significant glucose-lowering effect and decreased body weight. 6-paradol possesses good anti-hyperglycemic activity, therefore it may serve as a novel target for the development of anti-obesity and anti-hyperglycemic functional food. 6-paradol effectively protects brain after cerebral ischemia, likely by attenuating neuroinflammation in microglia, suggesting it as a potential therapeutic agent to treat cerebral ischemia.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cytochrome P450 1A2 72 Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28274629	Inhibitor 8297	7.1 µM [IC50]
Cytochrome P450 2C8 18 Target ID: CHEMBL3721 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28274629	Inhibitor 8297	5.1 µM [IC50]
Cyclooxygenase-2 196 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20837112	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Osteoporosis 97 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28869564	Primary	Basic research	Unknown Approved Use Unknown
Diabetes mellitus 91 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28106738	Primary	Phase I 428	Unknown Approved Use Unknown
Focal cerebral ischemia 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25789481	Primary	Preclinical	Unknown Approved Use Unknown
Obesity 203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28106738 https://www.ncbi.nlm.nih.gov/pubmed/24909840	Primary	Preclinical	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21273675 https://www.ncbi.nlm.nih.gov/pubmed/15281225 https://www.ncbi.nlm.nih.gov/pubmed/11809529	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Enzymatic reduction of shogaol: a novel biotransformation pathway for the alpha,beta-unsaturated ketone system.	1992 Jun	1627175
Gingerol and Its Role in Chronic Diseases.	2016	27771925
Inhibition of key enzymes linked to type 2 diabetes by compounds isolated from Aframomum melegueta fruit.	2017 Dec	28176546

Patents

Sample Use Guides

In Vivo Use Guide

Mice: Compared with the HFD group, the treatment with 1-(4-hydroxy-3-methoxyphenyl)decan-3-one (6-paradol) low dose (6.75 mg/kg/day) or high dose (33.75 mg/kg/day), as well as with pioglitazone (6.75 mg/kg/day) significantly lowered the blood glucose at the 30-, 60- and 120-min time points.

Route of Administration: Oral

In Vitro Use Guide

In 3T3-L1 adipocytes, 6-paradol increased glucose utilization by the cells in a concentration-dependent manner, with insulin EC50 53.2 ± 5.5 uM and without insulin EC50 65.4 ± 5.3 uM. The similar effect was also observed in C2C12 myotubes, with insulin EC50 54.2 ± 4.7 uM and without insulin EC50 54.9 ± 3.3 uM. Moreover, our results revealed that 6-paradol inhibited lipid synthesis in 3T3-L1 cells, reducing the cellular lipid accumulation in a concentration-dependent manner, with insulin EC50 13.3 ± 3.3 uM and without insulin EC50 29.8 ± 1.4 uM.

Name

Type

Language

1-(4-HYDROXY-3-METHOXYPHENYL)-DECAN-3-ONE

Systematic Name

English

HEPTYL 4-HYDROXY-3-METHOXYPHENETHYL KETONE

Systematic Name

English

(6)-GINGERONE

Common Name

English

HYDROXYMETHOXYPHENYL DECANONE

Official Name

English

3-DECANONE, 1-(4-HYDROXY-3-METHOXYPHENYL)-

Systematic Name

English

HYDROXYMETHOXYPHENYL DECANONE [INCI]

Common Name

English

6-GINGERONE

Common Name

English

FEMA NO. 4665

Code

English

(6)-PARADOL

Common Name

English

PARADOL

Common Name

English

5-PARADOL

Common Name

English

Code System Code Type Description

MESH

C421614