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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:02 UTC
HMDB IDHMDB0000413
Secondary Accession Numbers
  • HMDB00413
Metabolite Identification
Common Name3-Hydroxydodecanedioic acid
Description3-Hydroxydodecanedioic 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. In humans, 3-hydroxydodecanedioic acid is involved in the acylcarnitine 3-hydroxydodecanedioylcarnitine pathway. 3-Hydroxydodecanedioic 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 3-hydroxydodecanedioic acid a potential biomarker for the consumption of these foods. 3-Hydroxydodecanedioic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a small amount of articles have been published on 3-Hydroxydodecanedioic acid.
Structure
Data?1582752130
Synonyms
ValueSource
3-HydroxydodecanedioateGenerator
3-Hydroxy-dodecanedioateHMDB
Chemical FormulaC12H22O5
Average Molecular Weight246.3001
Monoisotopic Molecular Weight246.146723814
IUPAC Name3-hydroxydodecanedioic acid
Traditional Name3-hydroxydodecanedioic acid
CAS Registry Number34574-69-1
SMILES
OC(CCCCCCCCC(O)=O)CC(O)=O
InChI Identifier
InChI=1S/C12H22O5/c13-10(9-12(16)17)7-5-3-1-2-4-6-8-11(14)15/h10,13H,1-9H2,(H,14,15)(H,16,17)
InChI KeyFYVQCLGZFXHEGL-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
  • Beta-hydroxy acid
  • Hydroxy fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Fatty acid
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • 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 SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.83 g/LALOGPS
logP1.49ALOGPS
logP1.93ChemAxon
logS-2.5ALOGPS
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 Count11ChemAxon
Refractivity61.86 m³·mol⁻¹ChemAxon
Polarizability27.58 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]+160.89731661259
DarkChem[M-H]-155.56531661259
AllCCS[M+H]+158.48832859911
AllCCS[M-H]-159.62532859911
DeepCCS[M+H]+157.19230932474
DeepCCS[M-H]-153.16930932474
DeepCCS[M-2H]-190.99730932474
DeepCCS[M+Na]+166.66130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Hydroxydodecanedioic acidOC(CCCCCCCCC(O)=O)CC(O)=O3328.0Standard polar33892256
3-Hydroxydodecanedioic acidOC(CCCCCCCCC(O)=O)CC(O)=O1793.1Standard non polar33892256
3-Hydroxydodecanedioic acidOC(CCCCCCCCC(O)=O)CC(O)=O2100.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Hydroxydodecanedioic acid,1TMS,isomer #1C[Si](C)(C)OC(CCCCCCCCC(=O)O)CC(=O)O2137.6Semi standard non polar33892256
3-Hydroxydodecanedioic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)CCCCCCCCC(O)CC(=O)O2164.0Semi standard non polar33892256
3-Hydroxydodecanedioic acid,1TMS,isomer #3C[Si](C)(C)OC(=O)CC(O)CCCCCCCCC(=O)O2156.4Semi standard non polar33892256
3-Hydroxydodecanedioic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CCCCCCCCC(CC(=O)O)O[Si](C)(C)C2201.3Semi standard non polar33892256
3-Hydroxydodecanedioic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)CC(CCCCCCCCC(=O)O)O[Si](C)(C)C2180.9Semi standard non polar33892256
3-Hydroxydodecanedioic acid,2TMS,isomer #3C[Si](C)(C)OC(=O)CCCCCCCCC(O)CC(=O)O[Si](C)(C)C2231.1Semi standard non polar33892256
3-Hydroxydodecanedioic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)CCCCCCCCC(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C2257.8Semi standard non polar33892256
3-Hydroxydodecanedioic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(CCCCCCCCC(=O)O)CC(=O)O2402.8Semi standard non polar33892256
3-Hydroxydodecanedioic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCC(O)CC(=O)O2421.0Semi standard non polar33892256
3-Hydroxydodecanedioic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)CC(O)CCCCCCCCC(=O)O2407.8Semi standard non polar33892256
3-Hydroxydodecanedioic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCC(CC(=O)O)O[Si](C)(C)C(C)(C)C2719.5Semi standard non polar33892256
3-Hydroxydodecanedioic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CC(CCCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C2680.6Semi standard non polar33892256
3-Hydroxydodecanedioic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCC(O)CC(=O)O[Si](C)(C)C(C)(C)C2704.7Semi standard non polar33892256
3-Hydroxydodecanedioic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCC(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2934.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxydodecanedioic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9840000000-ba1d51f5769b6001dfc12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxydodecanedioic acid GC-MS (3 TMS) - 70eV, Positivesplash10-009t-6339200000-6b8f2d46e5131baa2bf82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxydodecanedioic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxydodecanedioic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxydodecanedioic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxydodecanedioic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxydodecanedioic acid GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxydodecanedioic acid GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxydodecanedioic acid GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxydodecanedioic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxydodecanedioic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxydodecanedioic acid GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxydodecanedioic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxydodecanedioic acid GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxydodecanedioic acid GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxydodecanedioic 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 - 3-Hydroxydodecanedioic acid 10V, Positive-QTOFsplash10-01t9-0190000000-56a5ca0692bd052ae94f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxydodecanedioic acid 20V, Positive-QTOFsplash10-02e9-1960000000-e2b23bf3215485b28bba2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxydodecanedioic acid 40V, Positive-QTOFsplash10-029y-9800000000-cdbf0382e047c2655d992017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxydodecanedioic acid 10V, Negative-QTOFsplash10-002b-0190000000-659140900506a85c6c832017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxydodecanedioic acid 20V, Negative-QTOFsplash10-0kea-0590000000-30d125dca29237080fb22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxydodecanedioic acid 40V, Negative-QTOFsplash10-0a4l-9610000000-9f27770ca089c740fe352017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxydodecanedioic acid 10V, Positive-QTOFsplash10-004j-2790000000-8872855000b5f36f50f42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxydodecanedioic acid 20V, Positive-QTOFsplash10-07r9-9510000000-6ac3800480ad36de53642021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxydodecanedioic acid 40V, Positive-QTOFsplash10-0a4i-9100000000-e2e1e808d7a4b61debb42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxydodecanedioic acid 10V, Negative-QTOFsplash10-002b-0090000000-2cc995a8b8c0ea7aebd12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxydodecanedioic acid 20V, Negative-QTOFsplash10-0a4j-5490000000-60cdf4bc23e2a4a49cf02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxydodecanedioic acid 40V, Negative-QTOFsplash10-0a4i-9410000000-7e8cf4471e074c5cf4212021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.61(0.39-1.1) uMInfant (0-1 year old)Not SpecifiedNormal details
UrineDetected and Quantified0 umol/mmol creatinineChildren (1-13 years old)Not Specified
Normal
details
UrineDetected and Quantified0.918 +/- 1.836 umol/mmol creatinineChildren (1-13 years old)Not Specified
Normal
details
UrineDetected and Quantified3.672 +/- 3.213 umol/mmol creatinineChildren (1-13 years old)Not Specified
Normal
details
UrineDetected and Quantified9.181 +/- 3.672 umol/mmol creatinineChildren (1-13 years old)Not Specified
Normal
details
UrineDetected and Quantified20.657 +/- 15.148 umol/mmol creatinineChildren (1-13 years old)Not Specified
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.79-19.2 uM uMInfant (0-1 year old)Female3-Hydroxydicarboxylic aciduria details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Femaleovarian cancer details
UrineDetected and Quantified37.182-550.840 umol/mmol creatinineInfant (0-1 year old)Not Specified3-Hydroxydicarboxylic aciduria details
Associated Disorders and Diseases
Disease References
Ovarian cancer
  1. Gaul DA, Mezencev R, Long TQ, Jones CM, Benigno BB, Gray A, Fernandez FM, McDonald JF: Highly-accurate metabolomic detection of early-stage ovarian cancer. Sci Rep. 2015 Nov 17;5:16351. doi: 10.1038/srep16351. [PubMed:26573008 ]
3-Hydroxydicarboxylic aciduria
  1. Tserng KY, Jin SJ, Kerr DS, Hoppel CL: Urinary 3-hydroxydicarboxylic acids in pathophysiology of metabolic disorders with dicarboxylic aciduria. Metabolism. 1991 Jul;40(7):676-82. [PubMed:1870421 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022029
KNApSAcK IDNot Available
Chemspider ID13628081
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5402
PubChem Compound16663321
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceSchreurs, P. H. M.; Montijn, P. P.; Hoff, S. New synthesis of trans-2-dodecene-1,12-dioic acid (traumatic acid). Recueil des Travaux Chimiques des Pays-Bas (1971), 90(12), 1331-2.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Boulat O, Gradwohl M, Matos V, Guignard JP, Bachmann C: Organic acids in the second morning urine in a healthy Swiss paediatric population. Clin Chem Lab Med. 2003 Dec;41(12):1642-58. [PubMed:14708889 ]
  2. Korman SH, Mandel H, Gutman A: Characteristic urine organic acid profile in peroxisomal biogenesis disorders. J Inherit Metab Dis. 2000 Jun;23(4):425-8. [PubMed:10896310 ]