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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-07 16:45:27 UTC
HMDB IDHMDB0000872
Secondary Accession Numbers
  • HMDB00872
Metabolite Identification
Common NameTetradecanedioic acid
DescriptionTetradecanedioic acid, also known as 1,14-tetradecanedioate or NSC 9504, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Tetradecanedioic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Structure
Data?1582752161
Synonyms
ValueSource
1,12-Dodecanedicarboxylic acidChEBI
1,14-Tetradecanedioic acidChEBI
Dodecamethylenedicarboxylic acidChEBI
NSC 9504ChEBI
Tetradecane-1,14-dioic acidChEBI
1,12-DodecanedicarboxylateGenerator
1,14-TetradecanedioateGenerator
DodecamethylenedicarboxylateGenerator
Tetradecane-1,14-dioateGenerator
TetradecanedioateGenerator
TetradecanedicarboxylateHMDB
Tetradecanedicarboxylic acidHMDB
Chemical FormulaC14H26O4
Average Molecular Weight258.3538
Monoisotopic Molecular Weight258.18310932
IUPAC Nametetradecanedioic acid
Traditional Nametetradecanedioic acid
CAS Registry Number821-38-5
SMILES
OC(=O)CCCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C14H26O4/c15-13(16)11-9-7-5-3-1-2-4-6-8-10-12-14(17)18/h1-12H2,(H,15,16)(H,17,18)
InChI KeyHQHCYKULIHKCEB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.2 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.036 g/LALOGPS
logP3.63ALOGPS
logP4.05ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity69.55 m³·mol⁻¹ChemAxon
Polarizability31.11 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+165.01231661259
DarkChem[M-H]-163.29631661259
AllCCS[M+H]+163.79932859911
AllCCS[M-H]-166.51332859911
DeepCCS[M+H]+161.21630932474
DeepCCS[M-H]-157.33130932474
DeepCCS[M-2H]-195.14530932474
DeepCCS[M+Na]+170.80830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Tetradecanedioic acidOC(=O)CCCCCCCCCCCCC(O)=O3206.5Standard polar33892256
Tetradecanedioic acidOC(=O)CCCCCCCCCCCCC(O)=O1967.4Standard non polar33892256
Tetradecanedioic acidOC(=O)CCCCCCCCCCCCC(O)=O2150.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Tetradecanedioic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CCCCCCCCCCCCC(=O)O2218.2Semi standard non polar33892256
Tetradecanedioic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CCCCCCCCCCCCC(=O)O[Si](C)(C)C2308.2Semi standard non polar33892256
Tetradecanedioic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCCCCC(=O)O2476.5Semi standard non polar33892256
Tetradecanedioic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2832.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Tetradecanedioic acid GC-MS (2 TMS)splash10-0gea-5931000000-7d708613c692157ca7202014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tetradecanedioic acid GC-MS (Non-derivatized)splash10-0gea-5931000000-7d708613c692157ca7202017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetradecanedioic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-06to-2900000000-09da70a8cbdaf5efb1ee2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetradecanedioic acid GC-MS (2 TMS) - 70eV, Positivesplash10-0079-8792000000-ed152a72b2036b1e463a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetradecanedioic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetradecanedioic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetradecanedioic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetradecanedioic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetradecanedioic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetradecanedioic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-0a4i-0090000000-68cf7f448aa88f51f1fd2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetradecanedioic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-000j-1590000000-617ed9d896a7b93f24b22012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetradecanedioic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-0a4r-7090000000-b1a301623bc52c836e522012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetradecanedioic acid 10V, Positive-QTOFsplash10-052f-0090000000-54e68e29d3fdf7badb462017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetradecanedioic acid 20V, Positive-QTOFsplash10-06r7-1980000000-d0bd64117d133e9670262017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetradecanedioic acid 40V, Positive-QTOFsplash10-0gbl-6900000000-d2da62ee3049acfbecb02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetradecanedioic acid 10V, Negative-QTOFsplash10-0a4i-0090000000-9f8937fcc871a66736d32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetradecanedioic acid 20V, Negative-QTOFsplash10-0a4r-0090000000-832aea5a1ccea7a252412017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetradecanedioic acid 40V, Negative-QTOFsplash10-0a4l-9220000000-d36f64ab6fa1af70a4122017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetradecanedioic acid 10V, Positive-QTOFsplash10-052f-0590000000-3311683356eaf5ac613b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetradecanedioic acid 20V, Positive-QTOFsplash10-05mw-9740000000-800bffa13a66b1ce36342021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetradecanedioic acid 40V, Positive-QTOFsplash10-0aor-9100000000-5ee74e2123cc109c39f62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetradecanedioic acid 10V, Negative-QTOFsplash10-0a4i-0090000000-da808ed15b9927bca9a92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetradecanedioic acid 20V, Negative-QTOFsplash10-000i-0090000000-0e4998477f65560e24b42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetradecanedioic acid 40V, Negative-QTOFsplash10-052o-8920000000-d02f76466c638d0839702021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.11(0.078-0.19) uMInfant (0-1 year old)Not SpecifiedNormal details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.088-3.4 uMInfant (0-1 year old)Female3-Hydroxydicarboxylic aciduria details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022293
KNApSAcK IDC00053820
Chemspider ID12630
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5833
PubChem Compound13185
PDB IDNot Available
ChEBI ID76308
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceChen, Yuandong; Hao, Xiuzhen. Method for producing tetradecanedioic acid by bioconversion of n-tetradecane. Faming Zhuanli Shenqing Gongkai Shuomingshu (2002), 10 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
  2. Ziegler I, Fink M, Wilmanns W: Biopterin level in peripheral blood cells as a marker for hemopoietic cell proliferation during leukemia and polycythemia vera. Blut. 1982 Apr;44(4):231-40. [PubMed:6952953 ]