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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-09-22 17:43:42 UTC
HMDB IDHMDB0000387
Secondary Accession Numbers
  • HMDB00387
Metabolite Identification
Common Name3-Hydroxydodecanoic acid
Description3-Hydroxydodecanoic acid (CAS: 1883-13-2) is a medium-chain fatty acid associated with fatty acid metabolic disorders (PMID: 11948802 ). Deficiency of medium-chain acyl-CoA dehydrogenase is characterized by an intolerance to prolonged fasting, recurrent episodes of hypoglycemic coma with medium-chain dicarboxylic aciduria, impaired ketogenesis, and low plasma and tissue carnitine levels (OMIM: 201450 ). 3-Hydroxydodecanoic acid is also a microbial metabolite found in Acinetobacter, Moraxella, and Pseudomonas (PMID: 21687748 ). 3-Hydroxydodecanoic acid has been identified in the human placenta (PMID: 32033212 ).
Structure
Data?1582752128
Synonyms
ValueSource
(S)-3-Hydroxydodecanoic acidChEBI
(S)-3-OH Dodecanoic acidChEBI
(S)-3-OH Lauric acidChEBI
(S)-beta-Hydroxydodecanoic acidChEBI
(S)-beta-Hydroxylauric acidChEBI
(S)-beta-OH Dodecanoic acidChEBI
(S)-beta-OH Lauric acidChEBI
(S)-3-HydroxydodecanoateGenerator
(S)-3-OH DodecanoateGenerator
(S)-3-OH LaateGenerator
(S)-3-OH Laic acidGenerator
(S)-b-HydroxydodecanoateGenerator
(S)-b-Hydroxydodecanoic acidGenerator
(S)-beta-HydroxydodecanoateGenerator
(S)-Β-hydroxydodecanoateGenerator
(S)-Β-hydroxydodecanoic acidGenerator
(S)-b-HydroxylaateGenerator
(S)-b-Hydroxylaic acidGenerator
(S)-beta-HydroxylaateGenerator
(S)-beta-Hydroxylaic acidGenerator
(S)-Β-hydroxylaateGenerator
(S)-Β-hydroxylaic acidGenerator
(S)-b-OH DodecanoateGenerator
(S)-b-OH Dodecanoic acidGenerator
(S)-beta-OH DodecanoateGenerator
(S)-Β-OH dodecanoateGenerator
(S)-Β-OH dodecanoic acidGenerator
(S)-b-OH LaateGenerator
(S)-b-OH Laic acidGenerator
(S)-beta-OH LaateGenerator
(S)-beta-OH Laic acidGenerator
(S)-Β-OH laateGenerator
(S)-Β-OH laic acidGenerator
3-HydroxydodecanoateGenerator
(S)-3-HydroxylaateHMDB
(S)-3-Hydroxylaic acidHMDB
(3S)-3-HydroxydodecanoateHMDB
(3S)-3-Hydroxydodecanoic acidHMDB
(±)-3-hydroxydodecanoateHMDB
(±)-3-hydroxydodecanoic acidHMDB
3-HydroxylaurateHMDB
3-Hydroxylauric acidHMDB
DL-beta-HydroxydodecanoateHMDB
DL-beta-Hydroxydodecanoic acidHMDB
DL-Β-hydroxydodecanoateHMDB
DL-Β-hydroxydodecanoic acidHMDB
FA(12:0(3-OH))HMDB
FA(12:0(3S-OH))HMDB
L-3-HydroxydodecanoateHMDB
L-3-Hydroxydodecanoic acidHMDB
beta-HydroxydodecanoateHMDB
beta-Hydroxydodecanoic acidHMDB
beta-HydroxylaurateHMDB
beta-Hydroxylauric acidHMDB
Β-hydroxydodecanoateHMDB
Β-hydroxydodecanoic acidHMDB
Β-hydroxylaurateHMDB
Β-hydroxylauric acidHMDB
3-Hydroxydodecanoic acidHMDB
Chemical FormulaC12H24O3
Average Molecular Weight216.321
Monoisotopic Molecular Weight216.172544633
IUPAC Name(3S)-3-hydroxydodecanoic acid
Traditional Name(S)-3-hydroxylauric acid
CAS Registry Number45162-48-9
SMILES
CCCCCCCCC[C@H](O)CC(O)=O
InChI Identifier
InChI=1S/C12H24O3/c1-2-3-4-5-6-7-8-9-11(13)10-12(14)15/h11,13H,2-10H2,1H3,(H,14,15)/t11-/m0/s1
InChI KeyMUCMKTPAZLSKTL-NSHDSACASA-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
  • Fatty acyl
  • Fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Biological locationSource
Process
Role
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 Solubility0.34 g/LALOGPS
logP3.63ALOGPS
logP3.25ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)4.67ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity60.2 m³·mol⁻¹ChemAxon
Polarizability26.38 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
DeepCCS[M+H]+157.76930932474
DeepCCS[M-H]-153.74630932474
DeepCCS[M-2H]-191.3230932474
DeepCCS[M+Na]+166.98530932474
AllCCS[M+H]+156.632859911
AllCCS[M+H-H2O]+153.032859911
AllCCS[M+NH4]+159.832859911
AllCCS[M+Na]+160.832859911
AllCCS[M-H]-156.032859911
AllCCS[M+Na-2H]-157.132859911
AllCCS[M+HCOO]-158.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Hydroxydodecanoic acidCCCCCCCCC[C@H](O)CC(O)=O2842.7Standard polar33892256
3-Hydroxydodecanoic acidCCCCCCCCC[C@H](O)CC(O)=O1679.3Standard non polar33892256
3-Hydroxydodecanoic acidCCCCCCCCC[C@H](O)CC(O)=O1772.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Hydroxydodecanoic acid,1TMS,isomer #1CCCCCCCCC[C@@H](CC(=O)O)O[Si](C)(C)C1780.9Semi standard non polar33892256
3-Hydroxydodecanoic acid,1TMS,isomer #2CCCCCCCCC[C@H](O)CC(=O)O[Si](C)(C)C1767.4Semi standard non polar33892256
3-Hydroxydodecanoic acid,2TMS,isomer #1CCCCCCCCC[C@@H](CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1855.5Semi standard non polar33892256
3-Hydroxydodecanoic acid,1TBDMS,isomer #1CCCCCCCCC[C@@H](CC(=O)O)O[Si](C)(C)C(C)(C)C2007.2Semi standard non polar33892256
3-Hydroxydodecanoic acid,1TBDMS,isomer #2CCCCCCCCC[C@H](O)CC(=O)O[Si](C)(C)C(C)(C)C2000.8Semi standard non polar33892256
3-Hydroxydodecanoic acid,2TBDMS,isomer #1CCCCCCCCC[C@@H](CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2314.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3-Hydroxydodecanoic acid GC-MS (2 TMS)splash10-001i-5930000000-267beffaa56f4c3885ab2019-10-24HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Hydroxydodecanoic acid GC-MS (Non-derivatized)splash10-001i-5930000000-267beffaa56f4c3885ab2019-10-24HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxydodecanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxydodecanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxydodecanoic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxydodecanoic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxydodecanoic acid GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxydodecanoic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxydodecanoic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxydodecanoic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxydodecanoic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-0aor-9050000000-f8825f9349ee9a2ec34e2019-10-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxydodecanoic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-0a4i-9000000000-3d142f4358076fbe51922019-10-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxydodecanoic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-0a4i-9000000000-54e9a813b1c73a4dee862019-10-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxydodecanoic acid 10V, Positive-QTOFsplash10-014i-9640000000-6ae3522b4ab714ac01d92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxydodecanoic acid 20V, Positive-QTOFsplash10-0ab9-9000000000-f44f1941ba69e47860fb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxydodecanoic acid 40V, Positive-QTOFsplash10-0a4l-9000000000-7aa76d51356623cc325f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxydodecanoic acid 10V, Negative-QTOFsplash10-066r-7090000000-c136666cfe0af2c7d0442021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxydodecanoic acid 20V, Negative-QTOFsplash10-0a4i-9000000000-918089033fd82836fb6f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxydodecanoic acid 40V, Negative-QTOFsplash10-0006-9000000000-efd0e0c3d7b6aa45f62c2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2019-10-24Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental)2019-10-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.3 (0.2-0.6) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.4 (0.2-1.4) uMNot AvailableNot Available
Normal
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 Quantified0.4 (0.2-1.4) uMAdult (>18 years old)BothFatty Acid Oxidation disorder with supplementation of MCT formula details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease References
Fatty Acid Oxidation disorder
  1. Jones PM, Quinn R, Fennessey PV, Tjoa S, Goodman SI, Fiore S, Burlina AB, Rinaldo P, Boriack RL, Bennett MJ: Improved stable isotope dilution-gas chromatography-mass spectrometry method for serum or plasma free 3-hydroxy-fatty acids and its utility for the study of disorders of mitochondrial fatty acid beta-oxidation. Clin Chem. 2000 Feb;46(2):149-55. [PubMed:10657369 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022005
KNApSAcK IDNot Available
Chemspider ID4472230
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5376
PubChem Compound5312805
PDB IDNot Available
ChEBI ID36210
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceIwata, Tsutomu; Iwamoto, Osamu; Sugiyama, Haruhiko. Process for preparing b-hydroxy fatty acid. Eur. Pat. Appl. (1990), 6 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Chickos JS, Way BA, Wilson J, Shaharuzzaman M, Laird J, Landt M: Analysis of 3-hydroxydodecanedioic acid for studies of fatty acid metabolic disorders: preparation of stable isotope standards. J Clin Lab Anal. 2002;16(2):115-20. [PubMed:11948802 ]
  2. Jones PM, Quinn R, Fennessey PV, Tjoa S, Goodman SI, Fiore S, Burlina AB, Rinaldo P, Boriack RL, Bennett MJ: Improved stable isotope dilution-gas chromatography-mass spectrometry method for serum or plasma free 3-hydroxy-fatty acids and its utility for the study of disorders of mitochondrial fatty acid beta-oxidation. Clin Chem. 2000 Feb;46(2):149-55. [PubMed:10657369 ]
  3. Jones PM, Moffitt M, Joseph D, Harthcock PA, Boriack RL, Ibdah JA, Strauss AW, Bennett MJ: Accumulation of free 3-hydroxy fatty acids in the culture media of fibroblasts from patients deficient in long-chain l-3-hydroxyacyl-CoA dehydrogenase: a useful diagnostic aid. Clin Chem. 2001;47(7):1190-4. [PubMed:11427448 ]
  4. Ktsoyan ZA, Beloborodova NV, Sedrakyan AM, Osipov GA, Khachatryan ZA, Kelly D, Manukyan GP, Arakelova KA, Hovhannisyan AI, Olenin AY, Arakelyan AA, Ghazaryan KA, Aminov RI: Profiles of Microbial Fatty Acids in the Human Metabolome are Disease-Specific. Front Microbiol. 2011 Jan 20;1:148. doi: 10.3389/fmicb.2010.00148. eCollection 2010. [PubMed:21687748 ]
  5. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]