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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:20:01 UTC
HMDB IDHMDB0000394
Secondary Accession Numbers
  • HMDB00394
Metabolite Identification
Common Name3-Hydroxytetradecanedioic acid
Description3-Hydroxytetradecanedioic acid is an unusual 3-hydroxydicarboxylic acid human metabolite found occasionally in urine. (PMID 2925825 ) High levels of 3-Hydroxytetradecanedioic acid (and other 3-hydroxydicarboxylic acids) were detected in the urine of a patient with 3-hydroxydicarboxylic aciduria (PMID 1507493 ), due to acute intoxication associated with hopantenate occurs owing to pantothenic acid deficiency or the inhibition of CoA-requiring reactions during stress, i.e., infection, prolonged fasting, or malnutrition (PMID 2026687 ), and in a patient with thanatophoric dysplasia due to enhanced but incomplete oxidation of fatty acid, a consequence of a heterozygous point mutation, S249C in the fibroblast growth factor receptor 3 gene. (PMID 11879084 ).
Structure
Data?1582752128
Synonyms
ValueSource
3-HydroxytetradecanedioateGenerator
3-Hydroxy-tetradecanedioateHMDB
Chemical FormulaC14H26O5
Average Molecular Weight274.3532
Monoisotopic Molecular Weight274.178023942
IUPAC Name3-hydroxytetradecanedioic acid
Traditional Name3-hydroxytetradecanedioic acid
CAS Registry Number73179-89-2
SMILES
OC(CCCCCCCCCCC(O)=O)CC(O)=O
InChI Identifier
InChI=1S/C14H26O5/c15-12(11-14(18)19)9-7-5-3-1-2-4-6-8-10-13(16)17/h12,15H,1-11H2,(H,16,17)(H,18,19)
InChI KeyCEDZIURHISELSQ-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
  • Hydroxy fatty acid
  • Beta-hydroxy acid
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.29 g/LALOGPS
logP10(2.03) g/LALOGPS
logP10(2.82) g/LChemAxon
logS10(-3) g/LALOGPS
pKa (Strongest Acidic)4.49ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity71.06 m³·mol⁻¹ChemAxon
Polarizability31.84 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+168.6531661259
DarkChem[M-H]-165.12931661259
AllCCS[M+H]+167.47432859911
AllCCS[M-H]-168.49832859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Hydroxytetradecanedioic acid,1TMS,#1C[Si](C)(C)OC(CCCCCCCCCCC(=O)O)CC(=O)O2345.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
3-Hydroxytetradecanedioic acid,1TMS,#2C[Si](C)(C)OC(=O)CCCCCCCCCCC(O)CC(=O)O2373.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
3-Hydroxytetradecanedioic acid,1TMS,#3C[Si](C)(C)OC(=O)CC(O)CCCCCCCCCCC(=O)O2360.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
3-Hydroxytetradecanedioic acid,2TMS,#1C[Si](C)(C)OC(=O)CCCCCCCCCCC(CC(=O)O)O[Si](C)(C)C2384.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
3-Hydroxytetradecanedioic acid,2TMS,#2C[Si](C)(C)OC(=O)CC(CCCCCCCCCCC(=O)O)O[Si](C)(C)C2370.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
3-Hydroxytetradecanedioic acid,2TMS,#3C[Si](C)(C)OC(=O)CCCCCCCCCCC(O)CC(=O)O[Si](C)(C)C2431.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
3-Hydroxytetradecanedioic acid,3TMS,#1C[Si](C)(C)OC(=O)CCCCCCCCCCC(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C2445.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
3-Hydroxytetradecanedioic acid,1TBDMS,#1CC(C)(C)[Si](C)(C)OC(CCCCCCCCCCC(=O)O)CC(=O)O2604.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
3-Hydroxytetradecanedioic acid,1TBDMS,#2CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCCC(O)CC(=O)O2629.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
3-Hydroxytetradecanedioic acid,1TBDMS,#3CC(C)(C)[Si](C)(C)OC(=O)CC(O)CCCCCCCCCCC(=O)O2616.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
3-Hydroxytetradecanedioic acid,2TBDMS,#1CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCCC(CC(=O)O)O[Si](C)(C)C(C)(C)C2921.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
3-Hydroxytetradecanedioic acid,2TBDMS,#2CC(C)(C)[Si](C)(C)OC(=O)CC(CCCCCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C2881.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
3-Hydroxytetradecanedioic acid,2TBDMS,#3CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCCC(O)CC(=O)O[Si](C)(C)C(C)(C)C2912.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
3-Hydroxytetradecanedioic acid,3TBDMS,#1CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCCC(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3153.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxytetradecanedioic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9670000000-59c708cd80a1a877c79d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxytetradecanedioic acid GC-MS (3 TMS) - 70eV, Positivesplash10-004i-9367800000-47e5a2287d205a6fa02b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxytetradecanedioic acid 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 - 3-Hydroxytetradecanedioic acid 10V, Positive-QTOFsplash10-0a70-0090000000-d1bf3dd36ae3dbdb51852016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxytetradecanedioic acid 20V, Positive-QTOFsplash10-08i9-0490000000-31021daf233368701f5c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxytetradecanedioic acid 40V, Positive-QTOFsplash10-040d-4910000000-e13f32a9e5177e2e956f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxytetradecanedioic acid 10V, Negative-QTOFsplash10-00di-0090000000-a11f84f48743557a02ab2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxytetradecanedioic acid 20V, Negative-QTOFsplash10-0729-1190000000-d4f10462ec57b05c51712016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxytetradecanedioic acid 40V, Negative-QTOFsplash10-0a4l-9330000000-d55db446d3aebb26fa932016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxytetradecanedioic acid 10V, Negative-QTOFsplash10-00di-0090000000-265d760b412867c1fc5b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxytetradecanedioic acid 20V, Negative-QTOFsplash10-0ab9-4290000000-e6a2a92e8d6e8157fb332021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxytetradecanedioic acid 40V, Negative-QTOFsplash10-0a4i-9230000000-71bfc30db585642857132021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxytetradecanedioic acid 10V, Positive-QTOFsplash10-056r-1290000000-112d6e8e034b7c4a28a82021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxytetradecanedioic acid 20V, Positive-QTOFsplash10-0avi-9520000000-49001720daac9e4dd43a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxytetradecanedioic acid 40V, Positive-QTOFsplash10-0a59-9000000000-01b43981d92af775a9ff2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, 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
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.21(0.068-0.54) uMInfant (0-1 year old)Not SpecifiedNormal details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.90-17.6 uM uMInfant (0-1 year old)Female3-Hydroxydicarboxylic aciduria details
UrineDetected but not QuantifiedNot QuantifiedNot AvailableNot AvailableKetosis details
UrineDetected but not QuantifiedNot QuantifiedNot AvailableNot AvailableCHAD/TFP deficiency details
UrineDetected but not QuantifiedNot QuantifiedNot AvailableNot AvailableHepatocellular disease details
Associated Disorders and Diseases
Disease References
Ketosis
  1. Kumps A, Duez P, Mardens Y: Metabolic, nutritional, iatrogenic, and artifactual sources of urinary organic acids: a comprehensive table. Clin Chem. 2002 May;48(5):708-17. [PubMed:11978597 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022012
KNApSAcK IDNot Available
Chemspider ID13628077
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5383
PubChem Compound20848956
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceHill, Frank Friedrich. Manufacture of 3-hydroxydicarboxylic acids. Ger. Offen. (1986), 14 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lefevere MF, Verhaeghe BJ, Declerck DH, Van Bocxlaer JF, De Leenheer AP, De Sagher RM: Metabolic profiling of urinary organic acids by single and multicolumn capillary gas chromatography. J Chromatogr Sci. 1989 Jan;27(1):23-9. [PubMed:2925825 ]
  2. Matsumoto M, Kuhara T, Inoue Y, Shinka T, Matsumoto I: Abnormal fatty acid metabolism in patients in hopantenate therapy during clinical episodes. J Chromatogr. 1991 Jan 2;562(1-2):139-45. [PubMed:2026687 ]
  3. Okajima K, Asai K, Niwa T, Ohki S, Sobajima H, Tyson J, Malcolm S, Wada Y: Clinical and biochemical findings of a patient with thanatophoric dysplasia type I: additional finding of dicarboxylic aciduria. Cleft Palate Craniofac J. 2002 Mar;39(2):246-8. [PubMed:11879084 ]
  4. Shimizu A, Nakanishi T: [Quantitative analysis of urinary organic acid]. Rinsho Byori. 1992 Jul;40(7):743-50. [PubMed:1507493 ]