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Showing metabocard for 2-Hydroxybutanoic acid (HMDB0341410)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2022-09-09 21:00:40 UTC
Update Date2022-09-22 18:35:14 UTC
HMDB IDHMDB0341410
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Hydroxybutanoic acid
Description2-Hydroxybutyric acid, also known as a-hydroxybutyrate, belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon. alpha-Ketobutyrate is produced by amino acid catabolism (threonine and methionine) and glutathione anabolism (cysteine formation pathway) and is metabolized to propionyl-CoA and carbon dioxide (PMID: 20526369 ). 2-Hydroxybutyric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Hydroxybutyric acid exists in all living species, ranging from bacteria to humans. 2-hydroxybutyric acid can be converted into 2-ketobutyric acid through its interaction with the enzyme L-lactate dehydrogenase a-like 6B. In humans, 2-hydroxybutyric acid is involved in the metabolic disorder called methylmalonic aciduria due to cobalamin-related disorders. Outside of the human body, 2-Hydroxybutyric acid has been detected, but not quantified in, milk (cow). This could make 2-hydroxybutyric acid a potential biomarker for the consumption of these foods. It was concluded from studies done in the mid-1970's that an increased NADH2/NAD ratio was the most important factor for the production of 2-hydroxybutyric acid (PMID: 168632 ). Under such metabolic stress conditions, supplies of L-cysteine for glutathione synthesis become limiting, so homocysteine is diverted from the transmethylation pathway forming methionine into the transsulfuration pathway forming cystathionine. 2-Hydroxybutyric acid is a potentially toxic compound. 2-Hydroxybutyric acid, with regard to humans, has been found to be associated with several diseases such as colorectal cancer, dihydrolipoamide dehydrogenase deficiency, alzheimer's disease, and early preeclampsia; 2-hydroxybutyric acid has also been linked to the inborn metabolic disorder pyruvate dehydrogenase deficiency. 2-Hydroxybutyric acid is released as a byproduct when cystathionine is cleaved into cysteine that is incorporated into glutathione. 2-Hydroxybutyric acid is primarily produced in mammalian hepatic tissues that catabolize L-threonine or synthesize glutathione.
Structure
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MOLSDFPDBSMILESInChI

MOL for HMDB0341410 (2-Hydroxybutanoic acid)


  Mrv1652305261923542D          

  7  6  0  0  0  0            999 V2000
 9998.9586 9998.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2439 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5292 9998.7576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2439 9999.9944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6740 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3874 9998.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9586 9997.9323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  6  1  0  0  0  0
M  END
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3D MOL for HMDB0341410 (2-Hydroxybutanoic acid)

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3D SDF for HMDB0341410 (2-Hydroxybutanoic acid)

  Mrv1652305261923542D          

  7  6  0  0  0  0            999 V2000
 9998.9586 9998.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2439 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5292 9998.7576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2439 9999.9944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6740 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3874 9998.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9586 9997.9323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  6  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341410

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7)

> <INCHI_KEY>
AFENDNXGAFYKQO-UHFFFAOYSA-N

> <FORMULA>
C4H8O3

> <MOLECULAR_WEIGHT>
104.1045

> <EXACT_MASS>
104.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
9.975162710656104

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxybutanoic acid

> <ALOGPS_LOGP>
-0.16

> <JCHEM_LOGP>
0.050692876999999914

> <ALOGPS_LOGS>
0.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.293154365104641

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9899988581138763

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7935876935907205

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
23.3638

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.84e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-hydroxybutyric acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for HMDB0341410 (2-Hydroxybutanoic acid)
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PDB for HMDB0341410 (2-Hydroxybutanoic acid)
HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0    8664.7238664.348   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8663.3898665.117   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8662.0558664.348   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8663.3898666.656   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8666.0588665.117   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8667.3908664.348   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8664.7238662.807   0.000  0.00  0.00           O+0
CONECT    1    2    5    7                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    1    6                                                       
CONECT    6    5                                                            
CONECT    7    1                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END

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3D PDB for HMDB0341410 (2-Hydroxybutanoic acid)
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SMILES for HMDB0341410 (2-Hydroxybutanoic acid)
CCC(O)C(O)=O
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INCHI for HMDB0341410 (2-Hydroxybutanoic acid)
InChI=1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2-Hydroxybutanoic acidChEBI
alpha-Hydroxybutanoic acidChEBI
alpha-Hydroxybutyric acidChEBI
2-HydroxybutanoateGenerator
a-HydroxybutanoateGenerator
a-Hydroxybutanoic acidGenerator
alpha-HydroxybutanoateGenerator
Α-hydroxybutanoateGenerator
Α-hydroxybutanoic acidGenerator
a-HydroxybutyrateGenerator
a-Hydroxybutyric acidGenerator
alpha-HydroxybutyrateGenerator
Α-hydroxybutyrateGenerator
Α-hydroxybutyric acidGenerator
2-HydroxybutyrateGenerator
(RS)-2-HydroxybutyrateHMDB
(RS)-2-Hydroxybutyric acidHMDB
2-Hydroxy-butanoateHMDB
2-Hydroxy-butanoic acidHMDB
2-Hydroxy-DL-butyrateHMDB
2-Hydroxy-DL-butyric acidHMDB
2-Hydroxy-N-butyrateHMDB
2-Hydroxy-N-butyric acidHMDB
a-Hydroxy-N-butyrateHMDB
a-Hydroxy-N-butyric acidHMDB
alpha-Hydroxy-N-butyrateHMDB
alpha-Hydroxy-N-butyric acidHMDB
DL-2-HydroxybutanoateHMDB
DL-2-Hydroxybutanoic acidHMDB
DL-a-HydroxybutyrateHMDB
DL-a-Hydroxybutyric acidHMDB
DL-alpha-HydroxybutyrateHMDB
DL-alpha-Hydroxybutyric acidHMDB
2-Hydroxybutyric acid, (R)-isomerHMDB
2-Hydroxybutyric acid, monosodium saltHMDB
2-Hydroxybutyric acid, (+-)-isomerHMDB
2-Hydroxybutyric acid, monosodium salt, (+-)-isomerHMDB
(+/-)a-hydoxy butyrateHMDB
(+/-)a-hydoxy butyric acidHMDB
(+/-)alpha-hydoxy butyrateHMDB
(+/-)α-hydoxy butyrateHMDB
(+/-)α-hydoxy butyric acidHMDB
2-Hydroxybutyric acidMeSH
Chemical FormulaC4H8O3
Average Molecular Weight104.1045
Monoisotopic Molecular Weight104.047344122
IUPAC Name2-hydroxybutanoic acid
Traditional Nameα-hydroxybutyric acid
CAS Registry NumberNot Available
SMILES
CCC(O)C(O)=O
InChI Identifier
InChI=1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7)
InChI KeyAFENDNXGAFYKQO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassHydroxy acids and derivatives  
Sub ClassAlpha hydroxy acids and derivatives  
Direct ParentAlpha hydroxy acids and derivatives  
Alternative Parents
Substituents
  • Fatty acid
    • 

  • Alpha-hydroxy acid
    • 

  • Secondary alcohol
    • 

  • Monocarboxylic acid or derivatives
    • 

  • 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
Not AvailableNot Available
Physical Properties
StateNot Available
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
logP-0.16ALOGPS
logP0.051ChemAxon
logS0.67ALOGPS
pKa (Strongest Acidic)3.99ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.36 m³·mol⁻¹ChemAxon
Polarizability9.98 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties
Predicted Kovats Retention Indices
Not Available
Spectra
GC-MS Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2-Hydroxybutanoic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-001j-0900000000-44dd1bf8072e5731bac42014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Hydroxybutanoic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00e9-9700000000-93eba027d5343e3d6ce12014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Hydroxybutanoic acid GC-MS (2 TMS)splash10-001i-1910000000-3bc9898b26df33cad2442014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Hydroxybutanoic acid EI-B (Non-derivatized)splash10-0a4i-9000000000-4d935da8e593ec61fd962017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Hydroxybutanoic acid GC-EI-TOF (Non-derivatized)splash10-001j-0900000000-44dd1bf8072e5731bac42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Hydroxybutanoic acid GC-EI-TOF (Non-derivatized)splash10-00e9-9700000000-93eba027d5343e3d6ce12017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Hydroxybutanoic acid GC-MS (Non-derivatized)splash10-001i-1910000000-3bc9898b26df33cad2442017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxybutanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6u-9000000000-0d95c1179b1b006506012016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxybutanoic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00v0-9520000000-598a2bd61c303327bd8f2017-10-06Wishart LabView Spectrum
MS/MS Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxybutanoic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-0zfr-9600000000-f688c3e6fdeb5f0270c52012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxybutanoic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-0a4j-9200000000-e3b371c29b9ebed3199b2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxybutanoic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-0zfs-9700000000-bccfada2c97e04d344172012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxybutanoic acid EI-B (HITACHI RMU-7M) , Positive-QTOFsplash10-0a4i-9000000000-4d935da8e593ec61fd962012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxybutanoic acid LC-ESI-IT , negative-QTOFsplash10-0udi-2900000000-3c7915ea71886873f0242017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxybutanoic acid  , negative-QTOFsplash10-0zfr-7900000000-d91c840306a06d4ea5132017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxybutanoic acid  10V, Positive-QTOFsplash10-0a4i-9500000000-8f04a5941997004743d22016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxybutanoic acid  20V, Positive-QTOFsplash10-0a4i-9100000000-cef703dc6f30af7834a82016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxybutanoic acid  40V, Positive-QTOFsplash10-052f-9000000000-1e7e6e8a895c4c1d51db2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxybutanoic acid  10V, Negative-QTOFsplash10-0udi-4900000000-d0907a0b08e0d829ceca2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxybutanoic acid  20V, Negative-QTOFsplash10-0pb9-9200000000-d826b54f814ac185b4db2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxybutanoic acid  40V, Negative-QTOFsplash10-0a4l-9000000000-3727124ed618f038b5142016-09-12Wishart LabView Spectrum
NMR Spectra
Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
    • 

  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma  details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma  details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021867  
KNApSAcK IDNot Available
Chemspider ID10792  
KEGG Compound IDC05984  
BioCyc IDNot Available
BiGG ID47130  
Wikipedia Link2-Hydroxybutyric_acid  
METLIN ID3783  
PubChem Compound11266  
PDB IDNot Available
ChEBI ID1148  
Food Biomarker OntologyNot Available
VMH ID2HB  
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Meister I, Zhang P, Sinha A, Skold CM, Wheelock AM, Izumi T, Chaleckis R, Wheelock CE: High-Precision Automated Workflow for Urinary Untargeted Metabolomic Epidemiology. Anal Chem. 2021 Mar 30;93(12):5248-5258. doi: 10.1021/acs.analchem.1c00203. Epub  2021 Mar 19. [PubMed:33739820  ]