Showing Compound Card for Nonanal (CDB000076)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencestransporters (1) Show 3 proteinsXML
Record Information
Version1.0
Created at2020-03-18 23:23:53 UTC
Updated at2020-12-07 19:07:04 UTC
CannabisDB IDCDB000076
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameNonanal
DescriptionNonanal, also known as nonyl aldehyde or pelargonaldehyde, 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. It is a fatty aldehyde lipid molecule. Nonanal, a colourless, oily liquid, is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Nonanal exists in all eukaryotes, from yeast to humans. Nonanal has an aldehydic, citrus, and fat taste. Nonanal is found in highest concentration in corns, tea, and gingers and in lower concentrations in sweet oranges, carrots, and limes. It has also been detected in olives, cereals and cereal products, Chinese cinnamons, common grapes, and oats, making nonanal a potential biomarker for the consumption of these foods. Nonanal is also a component of cannabis plants (PMID: 6991645 ). Although it occurs in several natural oils, it is produced commercially by hydroformylation of 1-octene (doi:10.1002/14356007.a01_321.pub2). Nonanal, an odorant of humans and birds, attracts Culex mosquitoes, which have extremely sensitive olfactory neurons in their antennae ( PMID: 19858490 ) for nonanal. Nonanal has been associated with several diseases such as pervasive developmental disorder not otherwise specified, autism (PMID: 24130822 ), Crohn's disease (PMID: 26071410 ), ulcerative colitis and non-alcoholic fatty liver disease (PMID: 23454028 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
N-NonaldehydeChEBI
Nonanoic aldehydeChEBI
Nonyl aldehydeChEBI
NonylaldehydeChEBI
Nonylic aldehydeChEBI
PelargonaldehydeChEBI
Pelargonic aldehydeChEBI
N-NonylaldehydeHMDB
NonanalMeSH
Chemical FormulaC9H18O
Average Molecular Weight142.24
Monoisotopic Molecular Weight142.1358
IUPAC Namenonanal
Traditional Namenonanal
CAS Registry NumberNot Available
SMILES
CCCCCCCCC=O
InChI Identifier
InChI=1S/C9H18O/c1-2-3-4-5-6-7-8-9-10/h9H,2-8H2,1H3
InChI KeyGYHFUZHODSMOHU-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:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point−18 °CWikipedia
Boiling Point191 °CWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.81ALOGPS
logP2.99ChemAxon
logS-3.4ALOGPS
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 Count7ChemAxon
Refractivity43.95 m³·mol⁻¹ChemAxon
Polarizability18.54 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-9000000000-945f6bb4a733637d5cf82014-10-20View Spectrum
GC-MSNonanal, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-7bfee629e196af9e810aSpectrum
GC-MSNonanal, non-derivatized, GC-MS Spectrumsplash10-0a4l-9000000000-7a91b8574f3d51d4856aSpectrum
GC-MSNonanal, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-373d544eb5629e680bc4Spectrum
GC-MSNonanal, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-858f5f7c138a343dc472Spectrum
GC-MSNonanal, non-derivatized, GC-MS Spectrumsplash10-0a4l-9000000000-6653261e95803e235236Spectrum
GC-MSNonanal, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-7bfee629e196af9e810aSpectrum
GC-MSNonanal, non-derivatized, GC-MS Spectrumsplash10-0a4l-9000000000-7a91b8574f3d51d4856aSpectrum
GC-MSNonanal, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-373d544eb5629e680bc4Spectrum
GC-MSNonanal, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-858f5f7c138a343dc472Spectrum
GC-MSNonanal, non-derivatized, GC-MS Spectrumsplash10-0a4l-9000000000-6653261e95803e235236Spectrum
Predicted GC-MSNonanal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-062l-9000000000-b8472e31e5bcec84f30cSpectrum
Predicted GC-MSNonanal, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1900000000-f0ef344b71801c87bae22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9700000000-6646461d0ed7f00c97322016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-e9cf39f812a5e37b32532016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-f0a7779f3ceded55079f2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-2900000000-8a94df0d859760c12b512016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-c476311d08e1bd1d53df2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-31a4c0b614cfbc7c31562021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-fc1333865a778fe314522021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-3e15d73ab7b0a83b0b4d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0aor-9000000000-15622cc20ddbb14ed88c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9000000000-bacbd1e7d4f6be160b212021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-796b68d98dc297622b772021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
Transporters
Protein NameGene NameLocusUniprot IDDetails
Platelet glycoprotein 4CD367q11.2P16671 details
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Free fatty acid receptor 1FFAR119q13.1O14842 details
Free fatty acid receptor 4FFAR410q23.33Q5NUL3 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0059835
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003303
KNApSAcK IDC00030828
Chemspider ID29029
KEGG Compound IDNot Available
BioCyc IDCPD-8491
BiGG IDNot Available
Wikipedia LinkNonanal
METLIN IDNot Available
PubChem Compound31289
PDB IDNot Available
ChEBI ID84268
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 ]
  2. Syed Z, Leal WS: Acute olfactory response of Culex mosquitoes to a human- and bird-derived attractant. Proc Natl Acad Sci U S A. 2009 Nov 3;106(44):18803-8. doi: 10.1073/pnas.0906932106. Epub 2009 Oct 26. [PubMed:19858490 ]
  3. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
  4. Hicks LC, Huang J, Kumar S, Powles ST, Orchard TR, Hanna GB, Williams HR: Analysis of Exhaled Breath Volatile Organic Compounds in Inflammatory Bowel Disease: A Pilot Study. J Crohns Colitis. 2015 Sep;9(9):731-7. doi: 10.1093/ecco-jcc/jjv102. Epub 2015 Jun 12. [PubMed:26071410 ]
  5. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]

Transporters

Enzyme Details
1. Platelet glycoprotein 4
General function:
Not Available
Specific function:
Seems to have numerous potential physiological functions. Binds to collagen, thrombospondin, anionic phospholipids and oxidized LDL. May function as a cell adhesion molecule. Directly mediates cytoadherence of Plasmodium falciparum parasitized erythrocytes. Binds long chain fatty acids and may function in the transport and/or as a regulator of fatty acid transport
Gene Name:
CD36
Uniprot ID:
P16671
Molecular weight:
53054.0