Showing Compound Card for Decanal (CDB000588)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2) Show 5 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:45:19 UTC
Updated at2020-12-07 19:07:33 UTC
CannabisDB IDCDB000588
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameDecanal
DescriptionDecanal, also known as n-decyl aldehyde or caprinaldehyde, 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. Thus, decanal is considered to be a fatty aldehyde lipid molecule. Decanal is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Decanal is a sweet, aldehydic, and citrus tasting compound. Decanal is found, on average, in the highest concentration within a few different foods, such as corianders, dills, and gingers and in a lower concentration in limes, sweet oranges, and safflowers. Decanal has also been detected, but not quantified in, several different foods, such as fishes, cauliflowers, citrus, fats and oils, and lemon grass. This could make decanal a potential biomarker for the consumption of these foods. Decanal is a potentially toxic compound. Decanal, with regard to humans, has been found to be associated with several diseases such as uremia, asthma, and perillyl alcohol administration for cancer treatment; decanal has also been linked to the inborn metabolic disorder celiac disease. Decanal occurs naturally and is used in fragrances and flavoring. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Decanal is one of several aldehydes that are found in cannabis plants (PMID: 6991645 ). 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.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-DecanalChEBI
1-Decyl aldehydeChEBI
CapraldehydeChEBI
CaprinaldehydeChEBI
DecanaldehydeChEBI
N-DecaldehydeChEBI
N-DecanalChEBI
N-Decyl aldehydeChEBI
1-Decanal(mixed isomers)HMDB
Aldehyde C10HMDB
C-10 AldehydeHMDB
Capric aldehydeHMDB
Caprinic aldehydeHMDB
DecaldehydeHMDB
Decanal (acd/name 4.0)HMDB
Decyl aldehydeHMDB
Decylic aldehydeHMDB
N-Decanal (capric aldehyde)HMDB
DecanalMeSH
Chemical FormulaC10H20O
Average Molecular Weight156.27
Monoisotopic Molecular Weight156.1514
IUPAC Namedecanal
Traditional Namedecanal
CAS Registry Number112-31-2
SMILES
CCCCCCCCCC=O
InChI Identifier
InChI=1S/C10H20O/c1-2-3-4-5-6-7-8-9-10-11/h10H,2-9H2,1H3
InChI KeyKSMVZQYAVGTKIV-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentMedium-chain aldehydes
Alternative Parents
Substituents
  • Medium-chain aldehyde
  • Alpha-hydrogen aldehyde
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point-5 °CNot Available
Boiling Point207 to 209 °CWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.44ALOGPS
logP3.43ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)17.79ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity48.55 m³·mol⁻¹ChemAxon
Polarizability20.66 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-052f-9000000000-5c4742446d704137c4cd2014-09-20View Spectrum
GC-MSDecanal, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-7749bc046eaf4c263d51Spectrum
GC-MSDecanal, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-87164b5c9889aeaf6447Spectrum
GC-MSDecanal, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-68c403b2d9fe194c1c55Spectrum
GC-MSDecanal, non-derivatized, GC-MS Spectrumsplash10-05mo-9100000000-d33aea8d64934a73baadSpectrum
GC-MSDecanal, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-7749bc046eaf4c263d51Spectrum
GC-MSDecanal, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-87164b5c9889aeaf6447Spectrum
GC-MSDecanal, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-68c403b2d9fe194c1c55Spectrum
GC-MSDecanal, non-derivatized, GC-MS Spectrumsplash10-05mo-9100000000-d33aea8d64934a73baadSpectrum
Predicted GC-MSDecanal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05g3-9100000000-74578afa9afd554784e5Spectrum
Predicted GC-MSDecanal, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDecanal, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-052f-9000000000-27a6eb7adbde8b4df4eb2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-052f-9000000000-6583e86a6ea49f8016782012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HP 5970) , Positivesplash10-052f-9000000000-68c403b2d9fe194c1c552012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-05mo-9100000000-d33aea8d64934a73baad2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0a4i-6900000000-e1d9d4a1d621cdb8e7832021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1900000000-2364cb822acc74394aa52016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-8900000000-a60793d40772b1ee39172016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-13163f941fae3335f3dc2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-f8919934fe6be4ffd0fa2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2900000000-96f0e3848fdde9ff60262016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-3a8fd3c6c088c5e11ca62016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-f6034c6a8245c68a37ac2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-e8b015c2539ebca0f9212021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mo-9000000000-37e48635ff257cb68c232021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0aou-9000000000-1723af53a3cc3d7ba5d52021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9000000000-e15457d7e27d24aee44b2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-c777b63c4ee6c891865e2021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 50.18 MHz, CDCl3, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Retinal dehydrogenase 2ALDH1A215q21.3O94788 details
Aldehyde dehydrogenase family 8 member A1ALDH8A16q23.2Q9H2A2 details
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Retinal dehydrogenase 2ALDH1A215q21.3O94788 details
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0011623
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012768
KNApSAcK IDC00030804
Chemspider ID7883
KEGG Compound IDC12307
BioCyc IDCPD-8490
BiGG IDNot Available
Wikipedia LinkDecanal
METLIN IDNot Available
PubChem Compound8175
PDB IDNot Available
ChEBI ID31457
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]

Enzymes

Enzyme Details
1. Retinal dehydrogenase 2
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Does metabolize octanal and decanal but does not metabolize citral, benzaldehyde, acetaldehyde and propanal efficiently (By similarity).
Gene Name:
ALDH1A2
Uniprot ID:
O94788
Molecular weight:
54672.24
Enzyme Details
2. Aldehyde dehydrogenase family 8 member A1
General function:
Involved in oxidoreductase activity
Specific function:
Converts 9-cis-retinal to 9-cis-retinoic acid. Has lower activity towards 13-cis-retinal. Has much lower activity towards all-trans-retinal. Has highest activity with benzaldehyde and decanal (in vitro). Has a preference for NAD, but shows considerable activity with NADP (in vitro)
Gene Name:
ALDH8A1
Uniprot ID:
Q9H2A2
Molecular weight:
53400.9