5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one

Basic Info

Common Name5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one(F00783)
2D Structure
FRCD IDF00783
CAS Number39886-76-5
PubChem CID3473
FormulaC17H26O4
IUPAC Name

5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one

InChI Key

NLDDIKRKFXEWBK-UHFFFAOYSA-N

InChI

InChI=1S/C17H26O4/c1-3-4-5-6-14(18)12-15(19)9-7-13-8-10-16(20)17(11-13)21-2/h8,10-11,14,18,20H,3-7,9,12H2,1-2H3

Canonical SMILES

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

Isomeric SMILES

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

Synonyms
        
            5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one
        
            39886-76-5
        
            rac-[6]-Gingerol
        
            6G [6]-gingerol
        
            CHEMBL1950582
        
            [6]-Gingerol, Zingiber officinale
        
            3-DECANONE, 5-HYDROXY-1-(4-HYDROXY-3-METHOXYPHENYL)-
        
            1-(4′-Hydroxy-3′-methoxyphenyl)-5-hydroxy-3-decanone
        
            ( inverted exclamation markA)-gingerol
        
            5-Hydroxy-1-(4'-hydroxy-3'-methoxyphenyl)-3-decanone
Classifies
                

                  
                    Predicted: Pesticide
Update DateNov 13, 2018 16:49

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassPhenols
SubclassMethoxyphenols
Intermediate Tree NodesNot available
Direct ParentGingerols
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsGingerol - Fatty alcohol - Phenoxy compound - Anisole - Methoxybenzene - Phenol ether - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Monocyclic benzene moiety - Beta-hydroxy ketone - Fatty acyl - Ketone - Secondary alcohol - Ether - Organic oxide - Hydrocarbon derivative - Carbonyl group - Organic oxygen compound - Alcohol - Organooxygen compound - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as gingerols. These are compounds containing a gingerol moiety, which is structurally characterized by a 4-hydroxy-3-methoxyphenyl group substituted at the C6 carbon atom by a 5-hydroxy-alkane-3-one.

Properties

Property NameProperty Value
Molecular Weight294.391
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count10
Complexity293
Monoisotopic Mass294.183
Exact Mass294.183
XLogP2.5
Formal Charge0
Heavy Atom Count21
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.6072
Human Intestinal AbsorptionHIA+0.9805
Caco-2 PermeabilityCaco2+0.6843
P-glycoprotein SubstrateSubstrate0.7319
P-glycoprotein InhibitorNon-inhibitor0.8440
Inhibitor0.5172
Renal Organic Cation TransporterNon-inhibitor0.8858
Distribution
Subcellular localizationMitochondria0.9052
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8432
CYP450 2D6 SubstrateNon-substrate0.8002
CYP450 3A4 SubstrateSubstrate0.5724
CYP450 1A2 InhibitorInhibitor0.6632
CYP450 2C9 InhibitorNon-inhibitor0.8278
CYP450 2D6 InhibitorNon-inhibitor0.7926
CYP450 2C19 InhibitorNon-inhibitor0.6350
CYP450 3A4 InhibitorNon-inhibitor0.5902
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8581
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9403
Non-inhibitor0.5451
AMES ToxicityNon AMES toxic0.7697
CarcinogensNon-carcinogens0.9121
Fish ToxicityHigh FHMT0.9832
Tetrahymena Pyriformis ToxicityHigh TPT0.9997
Honey Bee ToxicityHigh HBT0.6474
BiodegradationNot ready biodegradable0.6432
Acute Oral ToxicityIII0.6007
Carcinogenicity (Three-class)Non-required0.7188
Model Value Unit
Absorption
Aqueous solubility-3.2344LogS
Caco-2 Permeability1.0418LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.4106LD50, mol/kg
Fish Toxicity0.9306pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.7746pIGC50, ug/L

References

TitleJournalDatePubmed ID
[6]-Gingerol modulates spermatotoxicity associated with ulcerative colitis andbenzo[a]pyrene exposure in BALB/c mice.J Basic Clin Physiol Pharmacol2018 Jun 2729902912
Specific bioactive compounds in ginger and apple alleviate hyperglycemia in mice with high fat diet-induced obesity via Nrf2 mediated pathway.Food Chem2017 Jul 128254022
Quantitation of Gingerols in Human Plasma by Newly Developed Stable IsotopeDilution Assays and Assessment of Their Immunomodulatory Potential.J Agric Food Chem2016 Mar 2326939769
Effect of Pre-treatment and Storage Conditions on the Quality Characteristics of Ginger Paste.Prev Nutr Food Sci2012 Mar24471062
Zingiber officinale extract exhibits antidiabetic potential via modulating glucose uptake, protein glycation and inhibiting adipocyte differentiation: an in vitro study.J Sci Food Agric2012 Jul22261727
6-gingerol prevents patulin-induced genotoxicity in HepG2 cells.Phytother Res2011 Oct21953711
Antibacterial activity of [10]-gingerol and [12]-gingerol isolated from gingerrhizome against periodontal bacteria.Phytother Res2008 Nov18814211
In vitro synthesis of curcuminoids by type III polyketide synthase from Oryzasativa.J Biol Chem2007 Dec 2817932040
Suppressive effects of mioga ginger and ginger constituents on reactive oxygen and nitrogen species generation, and the expression of inducible pro-inflammatory genes in macrophages.Antioxid Redox Signal2005 Nov-Dec16356125
Commercially processed dry ginger (Zingiber officinale): composition and effects on LPS-stimulated PGE2 production.Phytochemistry2005 Jul15996695
Effect of active molluscicidal component of spices on different enzyme activitiesand biogenic amine levels in the nervous tissue of Lymnaea acuminata.Phytother Res1999 Dec10594932