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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:45:10 UTC
HMDB IDHMDB0000360
Secondary Accession Numbers
  • HMDB00360
Metabolite Identification
Common Name2,4-Dihydroxybutanoic acid
Description2,4-Dihydroxybutanoic acid, also known as 2,4-dihydroxybutyrate or 3-deoxytetronate, belongs to the class of organic compounds known as short-chain hydroxy acids and derivatives. These are hydroxy acids with an alkyl chain the contains less than 6 carbon atoms. 2,4-Dihydroxybutanoic 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 2,4-dihydroxybutanoic acid a potential biomarker for the consumption of these foods. 2,4-Dihydroxybutanoic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on 2,4-Dihydroxybutanoic acid.
Structure
Data?1582752126
Synonyms
ValueSource
2,4-Dihydroxybutyric acidChEBI
2,4-DihydroxybutyrateGenerator
2,4-DihydroxybutanoateGenerator
2,4-Dihydroxy-butyrateHMDB
2,4-Dihydroxy-butyric acidHMDB
3-DeoxytetronateHMDB
3-Deoxytetronic acidHMDB
2,4-Dihydroxy-butanoateHMDB
Chemical FormulaC4H8O4
Average Molecular Weight120.1039
Monoisotopic Molecular Weight120.042258744
IUPAC Name2,4-dihydroxybutanoic acid
Traditional Name2,4-dihydroxybutyric acid
CAS Registry Number1518-62-3
SMILES
OCCC(O)C(O)=O
InChI Identifier
InChI=1S/C4H8O4/c5-2-1-3(6)4(7)8/h3,5-6H,1-2H2,(H,7,8)
InChI KeyUFYGCFHQAXXBCF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as short-chain hydroxy acids and derivatives. These are hydroxy acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassShort-chain hydroxy acids and derivatives
Direct ParentShort-chain hydroxy acids and derivatives
Alternative Parents
Substituents
  • Short-chain hydroxy acid
  • Alpha-hydroxy acid
  • Monosaccharide
  • Fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
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 Solubility700 g/LALOGPS
logP-1.5ALOGPS
logP-1.5ChemAxon
logS0.77ALOGPS
pKa (Strongest Acidic)3.67ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity25.25 m³·mol⁻¹ChemAxon
Polarizability10.93 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+124.61431661259
DarkChem[M-H]-117.61231661259
AllCCS[M+H]+129.45232859911
AllCCS[M-H]-122.48732859911
DeepCCS[M+H]+130.69930932474
DeepCCS[M-H]-127.90130932474
DeepCCS[M-2H]-164.31130932474
DeepCCS[M+Na]+138.90330932474
AllCCS[M+H]+129.532859911
AllCCS[M+H-H2O]+125.332859911
AllCCS[M+NH4]+133.432859911
AllCCS[M+Na]+134.532859911
AllCCS[M-H]-122.532859911
AllCCS[M+Na-2H]-125.732859911
AllCCS[M+HCOO]-129.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2,4-Dihydroxybutanoic acidOCCC(O)C(O)=O2424.0Standard polar33892256
2,4-Dihydroxybutanoic acidOCCC(O)C(O)=O1111.9Standard non polar33892256
2,4-Dihydroxybutanoic acidOCCC(O)C(O)=O1217.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2,4-Dihydroxybutanoic acid,1TMS,isomer #1C[Si](C)(C)OCCC(O)C(=O)O1278.0Semi standard non polar33892256
2,4-Dihydroxybutanoic acid,1TMS,isomer #2C[Si](C)(C)OC(CCO)C(=O)O1286.2Semi standard non polar33892256
2,4-Dihydroxybutanoic acid,1TMS,isomer #3C[Si](C)(C)OC(=O)C(O)CCO1220.5Semi standard non polar33892256
2,4-Dihydroxybutanoic acid,2TMS,isomer #1C[Si](C)(C)OCCC(O[Si](C)(C)C)C(=O)O1384.7Semi standard non polar33892256
2,4-Dihydroxybutanoic acid,2TMS,isomer #2C[Si](C)(C)OCCC(O)C(=O)O[Si](C)(C)C1330.1Semi standard non polar33892256
2,4-Dihydroxybutanoic acid,2TMS,isomer #3C[Si](C)(C)OC(=O)C(CCO)O[Si](C)(C)C1327.8Semi standard non polar33892256
2,4-Dihydroxybutanoic acid,3TMS,isomer #1C[Si](C)(C)OCCC(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1427.5Semi standard non polar33892256
2,4-Dihydroxybutanoic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCC(O)C(=O)O1506.5Semi standard non polar33892256
2,4-Dihydroxybutanoic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(CCO)C(=O)O1521.0Semi standard non polar33892256
2,4-Dihydroxybutanoic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(O)CCO1451.9Semi standard non polar33892256
2,4-Dihydroxybutanoic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCC(O[Si](C)(C)C(C)(C)C)C(=O)O1813.1Semi standard non polar33892256
2,4-Dihydroxybutanoic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCCC(O)C(=O)O[Si](C)(C)C(C)(C)C1757.7Semi standard non polar33892256
2,4-Dihydroxybutanoic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(CCO)O[Si](C)(C)C(C)(C)C1764.1Semi standard non polar33892256
2,4-Dihydroxybutanoic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCC(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2041.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2,4-Dihydroxybutanoic acid GC-MS (3 TMS)splash10-0udi-1910000000-557fbb6f2bb47435373c2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,4-Dihydroxybutanoic acid GC-MS (Non-derivatized)splash10-0udi-1910000000-557fbb6f2bb47435373c2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,4-Dihydroxybutanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-5931f2477d1676167be72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,4-Dihydroxybutanoic acid GC-MS (3 TMS) - 70eV, Positivesplash10-00xr-9282000000-e2143c66feff878c4f922017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,4-Dihydroxybutanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,4-Dihydroxybutanoic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,4-Dihydroxybutanoic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,4-Dihydroxybutanoic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,4-Dihydroxybutanoic acid GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,4-Dihydroxybutanoic acid GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,4-Dihydroxybutanoic acid GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,4-Dihydroxybutanoic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,4-Dihydroxybutanoic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,4-Dihydroxybutanoic acid GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,4-Dihydroxybutanoic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,4-Dihydroxybutanoic acid GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,4-Dihydroxybutanoic acid GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,4-Dihydroxybutanoic acid GC-MS (TBDMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,4-Dihydroxybutanoic acid 10V, Negative-QTOFsplash10-014l-9600000000-98ebced22dbf15b80cb82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,4-Dihydroxybutanoic acid 20V, Negative-QTOFsplash10-0006-9000000000-4c467029adb1b5e5f7822021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,4-Dihydroxybutanoic acid 40V, Positive-QTOFsplash10-0gbl-9000000000-653e6cf390301b272d9a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,4-Dihydroxybutanoic acid 40V, Negative-QTOFsplash10-0006-9000000000-44c3a0a6ba4d6c9ce4122021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,4-Dihydroxybutanoic acid 10V, Positive-QTOFsplash10-01b9-9300000000-f018bcfb60b80347a4e52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,4-Dihydroxybutanoic acid 20V, Positive-QTOFsplash10-01b9-9200000000-887aecc630864c37bd742021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Dihydroxybutanoic acid 10V, Positive-QTOFsplash10-0uk9-7900000000-3d1731c289c7fe2655492016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Dihydroxybutanoic acid 20V, Positive-QTOFsplash10-0f6t-9200000000-24bce363159074dbdc002016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Dihydroxybutanoic acid 40V, Positive-QTOFsplash10-0a4j-9000000000-aa7e1aa11c5f98b28b112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Dihydroxybutanoic acid 10V, Negative-QTOFsplash10-014i-9700000000-94ff900476f71827e9aa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Dihydroxybutanoic acid 20V, Negative-QTOFsplash10-00dr-9100000000-ea29f47da5ae8add20c62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Dihydroxybutanoic acid 40V, Negative-QTOFsplash10-0007-9000000000-bc3515dda55b1fc1dcd22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Dihydroxybutanoic acid 10V, Positive-QTOFsplash10-0pb9-9300000000-c5ce677fbdb9fa2b95cd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Dihydroxybutanoic acid 20V, Positive-QTOFsplash10-0a4i-9000000000-a862ec05bec556659baa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Dihydroxybutanoic acid 40V, Positive-QTOFsplash10-0a4j-9000000000-4b9f0fd04ed39eae13562021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Dihydroxybutanoic acid 10V, Negative-QTOFsplash10-106r-6900000000-c22b52896a96201a00512021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Dihydroxybutanoic acid 20V, Negative-QTOFsplash10-05fr-9000000000-5aace9fbc0c6bc57cfdb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Dihydroxybutanoic acid 40V, Negative-QTOFsplash10-0006-9000000000-46eff8db713c6a03d0092021-09-22Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.0 (0.0-7.0) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified84 uMChildren (1-13 years old)BothNormal details
UrineDetected and Quantified1.0 (0.3-1.8) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified2.0 +/- 2.0 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified7.8 (1.9-18.4) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified8.1 (4.9-19.3) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified5.4 (2.5-7.3) umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified4.0 (1.9-15.2) umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified4.3 (3.3-1.3) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021980
KNApSAcK IDC00052108
Chemspider ID167259
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5349
PubChem Compound192742
PDB IDNot Available
ChEBI ID86348
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceRadej, Z.; Kristofova, Z. Hydroxy acid and lactone fraction of black liquor. Papir a Celuloza (1964), 19(6), 152-3.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
  2. Thompson JA, Markey SP, Fennessey PV: Gas-chromatographic/mass-spectrometric identification and quantitation of tetronic and deoxytetronic acids in urine from normal adults and neonates. Clin Chem. 1975 Dec;21(13):1892-8. [PubMed:1192581 ]
  3. Brown GK, Cromby CH, Manning NJ, Pollitt RJ: Urinary organic acids in succinic semialdehyde dehydrogenase deficiency: evidence of alpha-oxidation of 4-hydroxybutyric acid, interaction of succinic semialdehyde with pyruvate dehydrogenase and possible secondary inhibition of mitochondrial beta-oxidation. J Inherit Metab Dis. 1987;10(4):367-75. [PubMed:3126356 ]