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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 17:42:00 UTC
Update Date2023-02-21 17:20:14 UTC
HMDB IDHMDB0031266
Secondary Accession Numbers
  • HMDB0013822
  • HMDB13822
  • HMDB31266
Metabolite Identification
Common Name2-Nonanone
Description2-Nonanone, also known as beta-nonanone or N-C7H15COCH3, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Thus, 2-nonanone is considered to be an oxygenated hydrocarbon. 2-Nonanone exists in all living species, ranging from bacteria to plants to humans. 2-Nonanone is a sweet, earthy, and fishy tasting compound. 2-Nonanone is found, on average, in the highest concentration within a few different foods, such as corns (Zea mays), gingers (Zingiber officinale), and cloves (Syzygium aromaticum) and in a lower concentration in beer. 2-Nonanone has also been detected, but not quantified in, several different foods, such as asparagus (Asparagus officinalis), garden tomatoes (Solanum lycopersicum), anatidaes (Anatidae), alcoholic beverages, and fruits. This could make 2-nonanone a potential biomarker for the consumption of these foods. 2-Nonanone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 2-Nonanone, with regard to humans, has been found to be associated with several diseases such as ulcerative colitis, crohn's disease, and nonalcoholic fatty liver disease; 2-nonanone has also been linked to the inborn metabolic disorder celiac disease. Based on a literature review a significant number of articles have been published on 2-Nonanone.
Structure
Data?1677000014
Synonyms
ValueSource
beta-NonanoneChEBI
Heptyl methyl ketoneChEBI
Methyl heptyl ketoneChEBI
Methyl N-heptyl ketoneChEBI
N-C7H15COCH3ChEBI
NONANONE-2ChEBI
NSC 14760ChEBI
b-NonanoneGenerator
Β-nonanoneGenerator
Nonan-2-oneHMDB
2-NonanoneChEBI
Chemical FormulaC9H18O
Average Molecular Weight142.2386
Monoisotopic Molecular Weight142.135765198
IUPAC Namenonan-2-one
Traditional Name2-nonanone
CAS Registry Number821-55-6
SMILES
CCCCCCCC(C)=O
InChI Identifier
InChI=1S/C9H18O/c1-3-4-5-6-7-8-9(2)10/h3-8H2,1-2H3
InChI KeyVKCYHJWLYTUGCC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentKetones
Alternative Parents
Substituents
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-15 °CNot Available
Boiling Point192.00 °C. @ 743.00 mm HgThe Good Scents Company Information System
Water Solubility0.37 mg/mL at 25 °CNot Available
LogP3.14Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP3.08ALOGPS
logP3.03ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)19.64ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity43.83 m³·mol⁻¹ChemAxon
Polarizability18.45 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.92731661259
DarkChem[M-H]-130.48931661259
DeepCCS[M+H]+143.61430932474
DeepCCS[M-H]-141.00130932474
DeepCCS[M-2H]-177.75930932474
DeepCCS[M+Na]+152.6530932474
AllCCS[M+H]+136.532859911
AllCCS[M+H-H2O]+132.432859911
AllCCS[M+NH4]+140.332859911
AllCCS[M+Na]+141.432859911
AllCCS[M-H]-138.732859911
AllCCS[M+Na-2H]-141.132859911
AllCCS[M+HCOO]-143.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-NonanoneCCCCCCCC(C)=O1382.7Standard polar33892256
2-NonanoneCCCCCCCC(C)=O1066.8Standard non polar33892256
2-NonanoneCCCCCCCC(C)=O1091.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Nonanone,1TMS,isomer #1CCCCCCC=C(C)O[Si](C)(C)C1281.6Semi standard non polar33892256
2-Nonanone,1TMS,isomer #1CCCCCCC=C(C)O[Si](C)(C)C1244.0Standard non polar33892256
2-Nonanone,1TMS,isomer #2C=C(CCCCCCC)O[Si](C)(C)C1245.9Semi standard non polar33892256
2-Nonanone,1TMS,isomer #2C=C(CCCCCCC)O[Si](C)(C)C1249.6Standard non polar33892256
2-Nonanone,1TBDMS,isomer #1CCCCCCC=C(C)O[Si](C)(C)C(C)(C)C1497.7Semi standard non polar33892256
2-Nonanone,1TBDMS,isomer #1CCCCCCC=C(C)O[Si](C)(C)C(C)(C)C1436.0Standard non polar33892256
2-Nonanone,1TBDMS,isomer #2C=C(CCCCCCC)O[Si](C)(C)C(C)(C)C1454.6Semi standard non polar33892256
2-Nonanone,1TBDMS,isomer #2C=C(CCCCCCC)O[Si](C)(C)C(C)(C)C1438.6Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2-Nonanone EI-B (Non-derivatized)splash10-0a4l-9000000000-0fe4be17f047f1cbaf582017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Nonanone EI-B (Non-derivatized)splash10-0a4l-9000000000-d4d90ed2a739f3ba43a22017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Nonanone EI-B (Non-derivatized)splash10-0a4i-9000000000-2a497da6778b253c580d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Nonanone EI-B (Non-derivatized)splash10-0a4l-9000000000-0fe4be17f047f1cbaf582018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Nonanone EI-B (Non-derivatized)splash10-0a4l-9000000000-d4d90ed2a739f3ba43a22018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Nonanone EI-B (Non-derivatized)splash10-0a4i-9000000000-2a497da6778b253c580d2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Nonanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-18cf9f4d8e442b44587a2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Nonanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-052f-9000000000-66af6754da6b5ba929482015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Nonanone 10V, Positive-QTOFsplash10-002f-1900000000-b52f5c512f325c11c6ba2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Nonanone 20V, Positive-QTOFsplash10-004l-9800000000-33619c294c6393ac19692016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Nonanone 40V, Positive-QTOFsplash10-052f-9000000000-725f3e8a97e5c68c351e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Nonanone 10V, Negative-QTOFsplash10-0006-0900000000-e13c834dc0e63fb726202016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Nonanone 20V, Negative-QTOFsplash10-0006-4900000000-de2b3a74f2f11e17dd722016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Nonanone 40V, Negative-QTOFsplash10-0a4l-9200000000-08b8f165dbc8896c20682016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Nonanone 10V, Negative-QTOFsplash10-0006-0900000000-31a4c0b614cfbc7c31562021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Nonanone 20V, Negative-QTOFsplash10-0006-1900000000-1876fcaf8a524c0ed06e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Nonanone 40V, Negative-QTOFsplash10-0006-9000000000-4fd075076315784e420a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Nonanone 10V, Positive-QTOFsplash10-0aor-9000000000-3c0d0ece6940e9b3808a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Nonanone 20V, Positive-QTOFsplash10-0a4l-9000000000-16ea4b859f3f879e23882021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Nonanone 40V, Positive-QTOFsplash10-052f-9000000000-2c2279aa10ada5dc60b82021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected and Quantified0-23950.367 nmol/g wet fecesChildren (1-13 years old)Not Specified
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal
    • Zhang, S., Liu, L...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothUlcerative colitis details
FecesDetected and Quantified0-141733.678 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease
details
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. 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 ]
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Crohn's disease
  1. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Ulcerative colitis
  1. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003308
KNApSAcK IDC00029463
Chemspider ID12632
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNonanone
METLIN IDNot Available
PubChem Compound13187
PDB IDNot Available
ChEBI ID77927
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1008331
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .