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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 IDHMDB0000424
Secondary Accession Numbers
  • HMDB00424
Metabolite Identification
Common Name2-Hydroxydecanedioic acid
Description2-Hydroxydecanedioic acid, also known as a-hydroxysebasate or 2-hydroxysebacic acid, belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain. 2-Hydroxydecanedioic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 2-hydroxydecanedioic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2-Hydroxydecanedioic acid.
Structure
Data?1582752130
Synonyms
ValueSource
2-HydroxydecanedioateGenerator
2-Hydroxy-decandioateHMDB
2-Hydroxy-decandioic acidHMDB
2-HydroxysebacateHMDB
2-Hydroxysebacic acidHMDB
a-HydroxysebasateHMDB
a-Hydroxysebasic acidHMDB
alpha-HydroxysebasateHMDB
alpha-Hydroxysebasic acidHMDB
2-Hydroxy-decanedioateHMDB
Chemical FormulaC10H18O5
Average Molecular Weight218.2469
Monoisotopic Molecular Weight218.115423686
IUPAC Name2-hydroxydecanedioic acid
Traditional Name2-hydroxysebacic acid
CAS Registry Number103963-71-9
SMILES
OC(CCCCCCCC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C10H18O5/c11-8(10(14)15)6-4-2-1-3-5-7-9(12)13/h8,11H,1-7H2,(H,12,13)(H,14,15)
InChI KeyLPIOYESQKJFWPQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassMedium-chain hydroxy acids and derivatives
Direct ParentMedium-chain hydroxy acids and derivatives
Alternative Parents
Substituents
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Hydroxy fatty acid
  • Alpha-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Monosaccharide
  • Fatty acid
  • Fatty acyl
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point118 - 121 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.42 g/LALOGPS
logP0.87ALOGPS
logP1.4ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)4.16ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity52.64 m³·mol⁻¹ChemAxon
Polarizability23.38 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]+151.45231661259
DarkChem[M-H]-147.53731661259
AllCCS[M+H]+150.05132859911
AllCCS[M-H]-149.74332859911
DeepCCS[M+H]+148.85830932474
DeepCCS[M-H]-144.83430932474
DeepCCS[M-2H]-182.51830932474
DeepCCS[M+Na]+158.18330932474
AllCCS[M+H]+150.132859911
AllCCS[M+H-H2O]+146.532859911
AllCCS[M+NH4]+153.332859911
AllCCS[M+Na]+154.332859911
AllCCS[M-H]-149.732859911
AllCCS[M+Na-2H]-150.632859911
AllCCS[M+HCOO]-151.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Hydroxydecanedioic acidOC(CCCCCCCC(O)=O)C(O)=O2951.3Standard polar33892256
2-Hydroxydecanedioic acidOC(CCCCCCCC(O)=O)C(O)=O1598.7Standard non polar33892256
2-Hydroxydecanedioic acidOC(CCCCCCCC(O)=O)C(O)=O1894.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Hydroxydecanedioic acid,1TMS,isomer #1C[Si](C)(C)OC(CCCCCCCC(=O)O)C(=O)O1928.5Semi standard non polar33892256
2-Hydroxydecanedioic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)CCCCCCCC(O)C(=O)O1912.2Semi standard non polar33892256
2-Hydroxydecanedioic acid,1TMS,isomer #3C[Si](C)(C)OC(=O)C(O)CCCCCCCC(=O)O1908.9Semi standard non polar33892256
2-Hydroxydecanedioic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CCCCCCCC(O[Si](C)(C)C)C(=O)O1984.8Semi standard non polar33892256
2-Hydroxydecanedioic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)C(CCCCCCCC(=O)O)O[Si](C)(C)C1948.2Semi standard non polar33892256
2-Hydroxydecanedioic acid,2TMS,isomer #3C[Si](C)(C)OC(=O)CCCCCCCC(O)C(=O)O[Si](C)(C)C1975.2Semi standard non polar33892256
2-Hydroxydecanedioic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)CCCCCCCC(O[Si](C)(C)C)C(=O)O[Si](C)(C)C2047.3Semi standard non polar33892256
2-Hydroxydecanedioic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(CCCCCCCC(=O)O)C(=O)O2186.2Semi standard non polar33892256
2-Hydroxydecanedioic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCC(O)C(=O)O2157.1Semi standard non polar33892256
2-Hydroxydecanedioic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(O)CCCCCCCC(=O)O2173.9Semi standard non polar33892256
2-Hydroxydecanedioic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCC(O[Si](C)(C)C(C)(C)C)C(=O)O2476.4Semi standard non polar33892256
2-Hydroxydecanedioic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C2457.5Semi standard non polar33892256
2-Hydroxydecanedioic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCC(O)C(=O)O[Si](C)(C)C(C)(C)C2462.8Semi standard non polar33892256
2-Hydroxydecanedioic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCC(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2707.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9710000000-5fe9b8e6d318d5edf2e92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (3 TMS) - 70eV, Positivesplash10-016r-7649300000-ef73b5c677459a4e40322017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (TBDMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxydecanedioic acid 10V, Positive-QTOFsplash10-0uyi-0890000000-b8439c284ac682367d512016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxydecanedioic acid 20V, Positive-QTOFsplash10-0kh9-2920000000-3620dca641969f0dd8a22016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxydecanedioic acid 40V, Positive-QTOFsplash10-0a7m-9300000000-e8753077d260110272f22016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxydecanedioic acid 10V, Negative-QTOFsplash10-014i-1790000000-de7ab953c1ff73d7dc412016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxydecanedioic acid 20V, Negative-QTOFsplash10-00di-1910000000-80317878d8a89b878c502016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxydecanedioic acid 40V, Negative-QTOFsplash10-0a6r-9600000000-7364e1a98ebf405954282016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxydecanedioic acid 10V, Positive-QTOFsplash10-0uxr-2970000000-19a5a07acdba79f72a652021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxydecanedioic acid 20V, Positive-QTOFsplash10-053r-9200000000-15c7825b2a6fd1e91d482021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxydecanedioic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-6eef4b232bf26f42a6a52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxydecanedioic acid 10V, Negative-QTOFsplash10-014i-0290000000-40841675c8e6ee707caf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxydecanedioic acid 20V, Negative-QTOFsplash10-06dj-2920000000-6703bfa04e1a83a7ea8a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxydecanedioic acid 40V, Negative-QTOFsplash10-0a4l-9100000000-0ee8ff6b7d6aeed7288e2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
UrineDetected and Quantified0.39-0.67 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.37-0.55 umol/mmol creatinineAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedNot AvailableNot AvailablePeroxisomal diseases details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022037
KNApSAcK IDC00055623
Chemspider ID113866
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5413
PubChem Compound128458
PDB IDNot Available
ChEBI ID89312
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceChiruta, Chandramouli; Jachak, Santosh; Clive, Derrick L. J. A convenient general method for the synthesis of hydroxy diacids. Tetrahedron Letters (2007), 48(18), 3141-3143.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Rocchiccioli F, Cartier PH, Aubourg P, Bougneres PF: Mass spectrometric identification of 2-hydroxy-sebacic acid in the urines of patients with neonatal adrenoleukodystrophy and Zellweger syndrome. Biomed Environ Mass Spectrom. 1986 Jun;13(6):315-8. [PubMed:2943344 ]
  2. Kajita M, Iwase K, Matsumoto M, Kuhara T, Sinka T, Matsumoto I: [Clinical and biochemical studies in a case of acute encephalopathy associated with calcium hopanthenate administration]. No To Hattatsu. 1990 May;22(3):267-73. [PubMed:2194543 ]
  3. Muth A, Jung J, Bilke S, Scharrer A, Mosandl A, Sewell AC, Bohles H: Simultaneous enantioselective analysis of chiral urinary metabolites in patients with Zellweger syndrome. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 25;792(2):269-77. [PubMed:12860034 ]
  4. Muth A, Mosandl A, Wanders RJ, Nowaczyk MJ, Baric I, Bohles H, Sewell AC: Stereoselective analysis of 2-hydroxysebacic acid in urine of patients with Zellweger syndrome and of premature infants fed with medium-chain triglycerides. J Inherit Metab Dis. 2003;26(6):583-92. [PubMed:14605504 ]