Basic Info

Common NameDecanal(F05267)
2D Structure
Description

Decanal is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
Decanal is an organic compound with the chemical formula C9H19CHO. It is the simplest ten-carbon aldehyde. Decanal occurs naturally and is used in fragrances and flavoring. Decanal occurs in nature and is an important component in citrus along with octanal, citral, and sinensal. Decanal is also an important component of buckwheat odour .

FRCD IDF05267
CAS Number112-31-2
PubChem CID8175
FormulaC10H20O
IUPAC Name

decanal

InChI Key

KSMVZQYAVGTKIV-UHFFFAOYSA-N

InChI

InChI=1S/C10H20O/c1-2-3-4-5-6-7-8-9-10-11/h10H,2-9H2,1H3

Canonical SMILES

CCCCCCCCCC=O

Isomeric SMILES

CCCCCCCCCC=O

WikipediaDecanal
Synonyms
        
            Decyl aldehyde
        
            n-Decyl aldehyde
        
            Decanal
        
            112-31-2
        
            Capraldehyde
        
            Caprinaldehyde
        
            Decanaldehyde
        
            Capric aldehyde
        
            1-Decanal
        
            n-Decanal
        
Classifies
                

                  
                    Predicted: Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds
SubclassCarbonyl compounds
Intermediate Tree NodesAldehydes
Direct ParentMedium-chain aldehydes
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsMedium-chain aldehyde - Alpha-hydrogen aldehyde - Organic oxide - Hydrocarbon derivative - Aliphatic acyclic compound
DescriptionThis compound belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms.

Properties

Property NameProperty Value
Molecular Weight156.269
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count8
Complexity78.9
Monoisotopic Mass156.151
Exact Mass156.151
XLogP3.8
Formal Charge0
Heavy Atom Count11
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9851
Human Intestinal AbsorptionHIA+0.9953
Caco-2 PermeabilityCaco2+0.8562
P-glycoprotein SubstrateNon-substrate0.6717
P-glycoprotein InhibitorNon-inhibitor0.8894
Non-inhibitor0.8900
Renal Organic Cation TransporterNon-inhibitor0.8839
Distribution
Subcellular localizationMitochondria0.3433
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8205
CYP450 2D6 SubstrateNon-substrate0.8595
CYP450 3A4 SubstrateNon-substrate0.7271
CYP450 1A2 InhibitorInhibitor0.7096
CYP450 2C9 InhibitorNon-inhibitor0.9372
CYP450 2D6 InhibitorNon-inhibitor0.9645
CYP450 2C19 InhibitorNon-inhibitor0.9645
CYP450 3A4 InhibitorNon-inhibitor0.9876
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9015
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8058
Non-inhibitor0.8444
AMES ToxicityNon AMES toxic0.9812
CarcinogensCarcinogens 0.5807
Fish ToxicityHigh FHMT0.8899
Tetrahymena Pyriformis ToxicityHigh TPT0.9961
Honey Bee ToxicityHigh HBT0.6964
BiodegradationReady biodegradable0.7513
Acute Oral ToxicityIII0.8649
Carcinogenicity (Three-class)Non-required0.7426

Model Value Unit
Absorption
Aqueous solubility-2.7656LogS
Caco-2 Permeability1.3690LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.5199LD50, mol/kg
Fish Toxicity-0.0883pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.7013pIGC50, ug/L

References

TitleJournalDatePubmed ID
The use of factorial design to evaluate the oxidation of oils containing different types of omega-3 fatty acids.J Sci Food Agric2018 May29023751
Investigation on Key Molecules of Huanglongbing (HLB)-Induced Orange JuiceOff-flavor.J Agric Food Chem2018 Mar 1428285516
Changes in the Key Odorants and Aroma Profiles of Hamlin and Valencia OrangeJuices Not from Concentrate (NFC) during Chilled Storage.J Agric Food Chem2018 Jul 1829889522
Differentiation between Flavors of Sweet Orange (Citrus sinensis) and Mandarin(Citrus reticulata).J Agric Food Chem2018 Jan 1029237265
Volatile molecular markers of VOO Thermo-oxidation: Effect of heating processes, macronutrients composition, and olive ripeness on the new emitted aldehydic compounds.Food Res Int2018 Apr29579972
Characterization of the Key Aroma Compounds in Five Varieties of Mandarins by GasChromatography-Olfactometry, Odor Activity Values, Aroma Recombination, andOmission Analysis.J Agric Food Chem2017 Sep 2728885016
Chemical Composition and Allelopathic, Antibacterial, Antifungal, andAntiacetylcholinesterase Activity of Fish-mint (Houttuynia cordataThunb.) fromIndia.Chem Biodivers2017 Oct28636756
Natural Occurrence of Aldol Condensation Products in Valencia Orange Oil.J Food Sci2017 Dec29095499
Growth media affect the volatilome and antimicrobial activity against Phytophthora infestans in four Lysobacter type strains.Microbiol Res2017 Aug28602402
Major components of orange oil inhibit Staphylococcus aureus growth and biofilm formation, and alter its virulence factors.J Med Microbiol2016 Jul27259704
Green tea flavour determinants and their changes over manufacturing processes.Food Chem2016 Dec 127374591
The effect of acidification of liquid whey protein concentrate on the flavor ofspray-dried powder.J Dairy Sci2014 Jul24792804
The effect of feed solids concentration and inlet temperature on the flavor ofspray dried whey protein concentrate.J Food Sci2014 Jan24329978
Identification of characteristic flavour precursors from enzymatichydrolysis-mild thermal oxidation tallow by descriptive sensory analysis and gas chromatography-olfactometry and partial least squares regression.J Chromatogr B Analyt Technol Biomed Life Sci2013 Jan 1523270941
Isolation and biological activities of decanal, linalool, valencene, and octanal from sweet orange oil.J Food Sci2012 Nov23106968
In vitro anthelmintic activity of the essential oils of Zanthoxylumzanthoxyloides and Newbouldia laevis against Strongyloides ratti.Parasitol Res2012 Apr21960378
Efficacy of cold-pressed terpeneless Valencia oil and its primary components oninhibition of Listeria species by direct contact and exposure to vapors.J Food Sci2011 Sep22417555
The effect of starter culture and annatto on the flavor and functionality of wheyprotein concentrate.J Dairy Sci2011 Mar21338784
Volatile analysis of ground almonds contaminated with naturally occurring fungi.J Agric Food Chem2011 Jun 821528918
Iron is an essential cause of fishy aftertaste formation in wine and seafoodpairing.J Agric Food Chem2009 Sep 2319708656

Targets

General Function:
Vitamin d binding
Specific Function:
May have weak glycosidase activity towards glucuronylated steroids. However, it lacks essential active site Glu residues at positions 239 and 872, suggesting it may be inactive as a glycosidase in vivo. May be involved in the regulation of calcium and phosphorus homeostasis by inhibiting the synthesis of active vitamin D (By similarity). Essential factor for the specific interaction between FGF23 and FGFR1 (By similarity).The Klotho peptide generated by cleavage of the membrane-bound isoform may be an anti-aging circulating hormone which would extend life span by inhibiting insulin/IGF1 signaling.
Gene Name:
KL
Uniprot ID:
Q9UEF7
Molecular Weight:
116179.815 Da
References
  1. Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
General Function:
Superoxide-generating nadph oxidase activity
Specific Function:
Constitutive NADPH oxidase which generates superoxide intracellularly upon formation of a complex with CYBA/p22phox. Regulates signaling cascades probably through phosphatases inhibition. May function as an oxygen sensor regulating the KCNK3/TASK-1 potassium channel and HIF1A activity. May regulate insulin signaling cascade. May play a role in apoptosis, bone resorption and lipolysaccharide-mediated activation of NFKB. May produce superoxide in the nucleus and play a role in regulating gene expression upon cell stimulation. Isoform 3 is not functional. Isoform 5 and isoform 6 display reduced activity.Isoform 4: Involved in redox signaling in vascular cells. Constitutively and NADPH-dependently generates reactive oxygen species (ROS). Modulates the nuclear activation of ERK1/2 and the ELK1 transcription factor, and is capable of inducing nuclear DNA damage. Displays an increased activity relative to isoform 1.
Gene Name:
NOX4
Uniprot ID:
Q9NPH5
Molecular Weight:
66930.995 Da
References
  1. Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
Gene Name:
SLC22A8
Uniprot ID:
Q8TCC7
Molecular Weight:
59855.585 Da
References
  1. Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]