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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2013-03-04 20:35:59 UTC
Update Date2021-09-14 15:47:54 UTC
HMDB IDHMDB0059808
Secondary Accession Numbers
  • HMDB59808
Metabolite Identification
Common NameAcetyl citrate
DescriptionAcetyl citrate belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. Acetyl citrate is an extremely weak basic (essentially neutral) compound (based on its pKa). These are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
Structure
Data?1563865977
Synonyms
ValueSource
Acetyl citric acidGenerator
2-[2-(Acetyloxy)-2-oxoethyl]-2-hydroxybutanedioateGenerator
Chemical FormulaC8H10O8
Average Molecular Weight234.16
Monoisotopic Molecular Weight234.037567282
IUPAC Name2-[2-(acetyloxy)-2-oxoethyl]-2-hydroxybutanedioic acid
Traditional Name2-[2-(acetyloxy)-2-oxoethyl]-2-hydroxybutanedioic acid
CAS Registry NumberNot Available
SMILES
CC(=O)OC(=O)CC(O)(CC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C8H10O8/c1-4(9)16-6(12)3-8(15,7(13)14)2-5(10)11/h15H,2-3H2,1H3,(H,10,11)(H,13,14)
InChI KeyWWXUGNUFCNYMFK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTetracarboxylic acids and derivatives
Direct ParentTetracarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tetracarboxylic acid or derivatives
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Tertiary alcohol
  • Carboxylic acid anhydride
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility19.1 g/LALOGPS
logP-1ALOGPS
logP-1.4ChemAxon
logS-0.51ALOGPS
pKa (Strongest Acidic)3.09ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area138.2 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity45.06 m³·mol⁻¹ChemAxon
Polarizability19.69 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+152.55731661259
DarkChem[M-H]-148.40731661259
DeepCCS[M+H]+142.53930932474
DeepCCS[M-H]-140.14430932474
DeepCCS[M-2H]-174.41930932474
DeepCCS[M+Na]+148.98730932474
AllCCS[M+H]+149.432859911
AllCCS[M+H-H2O]+146.032859911
AllCCS[M+NH4]+152.632859911
AllCCS[M+Na]+153.532859911
AllCCS[M-H]-145.532859911
AllCCS[M+Na-2H]-146.132859911
AllCCS[M+HCOO]-146.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Acetyl citrateCC(=O)OC(=O)CC(O)(CC(O)=O)C(O)=O3108.7Standard polar33892256
Acetyl citrateCC(=O)OC(=O)CC(O)(CC(O)=O)C(O)=O1420.2Standard non polar33892256
Acetyl citrateCC(=O)OC(=O)CC(O)(CC(O)=O)C(O)=O1831.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Acetyl citrate,1TMS,isomer #1CC(=O)OC(=O)CC(CC(=O)O)(O[Si](C)(C)C)C(=O)O1761.3Semi standard non polar33892256
Acetyl citrate,1TMS,isomer #2CC(=O)OC(=O)CC(O)(CC(=O)O[Si](C)(C)C)C(=O)O1724.1Semi standard non polar33892256
Acetyl citrate,1TMS,isomer #3CC(=O)OC(=O)CC(O)(CC(=O)O)C(=O)O[Si](C)(C)C1679.1Semi standard non polar33892256
Acetyl citrate,2TMS,isomer #1CC(=O)OC(=O)CC(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O1794.9Semi standard non polar33892256
Acetyl citrate,2TMS,isomer #2CC(=O)OC(=O)CC(CC(=O)O)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1784.8Semi standard non polar33892256
Acetyl citrate,2TMS,isomer #3CC(=O)OC(=O)CC(O)(CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1768.4Semi standard non polar33892256
Acetyl citrate,3TMS,isomer #1CC(=O)OC(=O)CC(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1876.8Semi standard non polar33892256
Acetyl citrate,1TBDMS,isomer #1CC(=O)OC(=O)CC(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O1987.8Semi standard non polar33892256
Acetyl citrate,1TBDMS,isomer #2CC(=O)OC(=O)CC(O)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O1962.4Semi standard non polar33892256
Acetyl citrate,1TBDMS,isomer #3CC(=O)OC(=O)CC(O)(CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C1945.4Semi standard non polar33892256
Acetyl citrate,2TBDMS,isomer #1CC(=O)OC(=O)CC(CC(=O)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C(=O)O2254.3Semi standard non polar33892256
Acetyl citrate,2TBDMS,isomer #2CC(=O)OC(=O)CC(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2229.4Semi standard non polar33892256
Acetyl citrate,2TBDMS,isomer #3CC(=O)OC(=O)CC(O)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2226.9Semi standard non polar33892256
Acetyl citrate,3TBDMS,isomer #1CC(=O)OC(=O)CC(CC(=O)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2496.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Acetyl citrate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl citrate 10V, Positive-QTOFsplash10-0170-0920000000-7567fd17430dd029d7312019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl citrate 20V, Positive-QTOFsplash10-0zi0-4900000000-ab3e4d09833ec463ae2b2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl citrate 40V, Positive-QTOFsplash10-0573-8900000000-21b4ccdf82a0a18264202019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl citrate 10V, Negative-QTOFsplash10-00el-4910000000-1b5e60837b715e3034cb2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl citrate 20V, Negative-QTOFsplash10-0a4i-8900000000-5c582058c2a59dd5d89d2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl citrate 40V, Negative-QTOFsplash10-0a4l-9300000000-4682f667d2f4c8234c7b2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl citrate 10V, Positive-QTOFsplash10-016s-1950000000-bf4b16c0266f7990de252021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl citrate 20V, Positive-QTOFsplash10-052f-9200000000-579a650509f00d5c546d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl citrate 40V, Positive-QTOFsplash10-0006-9000000000-bc4d06b8b59a03b2af5c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl citrate 10V, Negative-QTOFsplash10-00b9-1900000000-fe52b213995f06cfddd52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl citrate 20V, Negative-QTOFsplash10-004i-3900000000-bd73bc8dd50d8227ac722021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl citrate 40V, Negative-QTOFsplash10-0a4i-9000000000-200e9366e2e327119b752021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNot Available details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound54454045
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available