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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:43:33 UTC
Update Date2022-03-07 02:52:59 UTC
HMDB IDHMDB0031476
Secondary Accession Numbers
  • HMDB31476
Metabolite Identification
Common Name2,3-Heptanedione
Description2,3-Heptanedione, also known as heptane-23-dione or 2,3-dioxoheptane, belongs to the class of organic compounds known as alpha-diketones. These are organic compounds containing two ketone groups on two adjacent carbon atoms. Thus, 2,3-heptanedione is considered to be an oxygenated hydrocarbon lipid molecule. 2,3-Heptanedione is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 2,3-Heptanedione is a butter, cheese, and oily tasting compound. 2,3-Heptanedione has been detected, but not quantified, in several different foods, such as alcoholic beverages, garden tomato, mushrooms, and pulses. This could make 2,3-heptanedione a potential biomarker for the consumption of these foods.
Structure
Data?1563862131
Synonyms
ValueSource
Heptane-23-dioneChEMBL, HMDB
2,3-DioxoheptaneHMDB
Acetyl pentanoylHMDB
Acetyl valerylHMDB
Benzil-related compound, 47HMDB
FEMA 2543HMDB
ValerylacetylHMDB
Chemical FormulaC7H12O2
Average Molecular Weight128.169
Monoisotopic Molecular Weight128.083729628
IUPAC Nameheptane-2,3-dione
Traditional Nameheptane-2,3-dione
CAS Registry Number96-04-8
SMILES
CCCCC(=O)C(C)=O
InChI Identifier
InChI=1S/C7H12O2/c1-3-4-5-7(9)6(2)8/h3-5H2,1-2H3
InChI KeyFJPGAMCQJNLTJC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-diketones. These are organic compounds containing two ketone groups on two adjacent carbon atoms.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-diketones
Alternative Parents
Substituents
  • Alpha-diketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point64.00 °C. @ 18.00 mm HgThe Good Scents Company Information System
Water Solubility0The Good Scents Company Information System
LogP0.188 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.83 g/LALOGPS
logP1.48ALOGPS
logP1.99ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)16.22ChemAxon
pKa (Strongest Basic)-8.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity35.37 m³·mol⁻¹ChemAxon
Polarizability14.32 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]+129.59231661259
DarkChem[M-H]-125.59631661259
DeepCCS[M+H]+133.08630932474
DeepCCS[M-H]-130.51630932474
DeepCCS[M-2H]-167.09930932474
DeepCCS[M+Na]+141.63330932474
AllCCS[M+H]+130.832859911
AllCCS[M+H-H2O]+126.632859911
AllCCS[M+NH4]+134.832859911
AllCCS[M+Na]+135.932859911
AllCCS[M-H]-130.632859911
AllCCS[M+Na-2H]-133.332859911
AllCCS[M+HCOO]-136.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2,3-HeptanedioneCCCCC(=O)C(C)=O1231.5Standard polar33892256
2,3-HeptanedioneCCCCC(=O)C(C)=O827.7Standard non polar33892256
2,3-HeptanedioneCCCCC(=O)C(C)=O868.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2,3-Heptanedione,1TMS,isomer #1CCCC=C(O[Si](C)(C)C)C(C)=O1171.5Semi standard non polar33892256
2,3-Heptanedione,1TMS,isomer #1CCCC=C(O[Si](C)(C)C)C(C)=O1107.2Standard non polar33892256
2,3-Heptanedione,1TMS,isomer #2C=C(O[Si](C)(C)C)C(=O)CCCC1168.1Semi standard non polar33892256
2,3-Heptanedione,1TMS,isomer #2C=C(O[Si](C)(C)C)C(=O)CCCC1125.9Standard non polar33892256
2,3-Heptanedione,2TMS,isomer #1C=C(O[Si](C)(C)C)C(=CCCC)O[Si](C)(C)C1317.2Semi standard non polar33892256
2,3-Heptanedione,2TMS,isomer #1C=C(O[Si](C)(C)C)C(=CCCC)O[Si](C)(C)C1271.8Standard non polar33892256
2,3-Heptanedione,1TBDMS,isomer #1CCCC=C(O[Si](C)(C)C(C)(C)C)C(C)=O1409.2Semi standard non polar33892256
2,3-Heptanedione,1TBDMS,isomer #1CCCC=C(O[Si](C)(C)C(C)(C)C)C(C)=O1318.5Standard non polar33892256
2,3-Heptanedione,1TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)C(=O)CCCC1370.6Semi standard non polar33892256
2,3-Heptanedione,1TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)C(=O)CCCC1306.9Standard non polar33892256
2,3-Heptanedione,2TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)C(=CCCC)O[Si](C)(C)C(C)(C)C1761.3Semi standard non polar33892256
2,3-Heptanedione,2TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)C(=CCCC)O[Si](C)(C)C(C)(C)C1662.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2,3-Heptanedione GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-8ac8c67781a56a80f63c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,3-Heptanedione GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-054o-9000000000-388f37bf3237397b5b752015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Heptanedione 10V, Positive-QTOFsplash10-01t9-2900000000-efd72e067859f956ab882016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Heptanedione 20V, Positive-QTOFsplash10-0bvl-9500000000-4f9562374cc653a1151b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Heptanedione 40V, Positive-QTOFsplash10-052f-9000000000-17bcc43d964248c37c8e2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Heptanedione 10V, Negative-QTOFsplash10-004i-1900000000-970ce84ef1fc4cd15f842016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Heptanedione 20V, Negative-QTOFsplash10-003i-9400000000-320d78373fc8c67bb1032016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Heptanedione 40V, Negative-QTOFsplash10-00ko-9100000000-33a158e0fb098b2278912016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Heptanedione 10V, Positive-QTOFsplash10-052u-9000000000-93e034289386e5fd12592021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Heptanedione 20V, Positive-QTOFsplash10-052f-9000000000-4592240fd574c6c857d22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Heptanedione 40V, Positive-QTOFsplash10-052f-9000000000-db8f97af0edda748d78a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Heptanedione 10V, Negative-QTOFsplash10-004i-0900000000-28e0e9380275f577d79b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Heptanedione 20V, Negative-QTOFsplash10-0006-9200000000-e14ea248d70670acd3232021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Heptanedione 40V, Negative-QTOFsplash10-00kf-9000000000-b6f1af0ba0e6e67151c92021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
  • Saliva
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)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
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 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008049
KNApSAcK IDNot Available
Chemspider ID54944
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound60983
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1025601
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.. .