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Showing metabocard for 2,2,4-Trihydroxybutanoic acid (HMDB0341420)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2022-09-09 21:04:34 UTC
Update Date2022-09-22 18:35:14 UTC
HMDB IDHMDB0341420
Secondary Accession NumbersNone
Metabolite Identification
Common Name2,2,4-Trihydroxybutanoic acid
Description2,2,4-Trihydroxybutanoic acid, also known as 2,2,4-trihydroxybutyrate, 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. 2,2,4-Trihydroxybutanoic 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 very few articles have been published on 2,2,4-Trihydroxybutanoic acid.
Structure
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MOLSDFPDBSMILESInChI

MOL for HMDB0341420 (2,2,4-Trihydroxybutanoic acid)


  Mrv1652309092223422D          

  9  8  0  0  0  0            999 V2000
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
M  END
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3D MOL for HMDB0341420 (2,2,4-Trihydroxybutanoic acid)

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3D SDF for HMDB0341420 (2,2,4-Trihydroxybutanoic acid)

  Mrv1652309092223422D          

  9  8  0  0  0  0            999 V2000
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341420

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H8O5/c5-2-1-4(8,9)3(6)7/h5,8-9H,1-2H2,(H,6,7)

> <INCHI_KEY>
IASCKZVQSNCRPV-UHFFFAOYSA-N

> <FORMULA>
C4H8O5

> <MOLECULAR_WEIGHT>
136.103

> <EXACT_MASS>
136.037173358

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
11.646093090530343

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,2,4-trihydroxybutanoic acid

> <JCHEM_LOGP>
-1.2859311876666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.059382769989476

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.947006689427561

> <JCHEM_PKA_STRONGEST_BASIC>
-2.459231925686302

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
26.3777

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
D-threonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for HMDB0341420 (2,2,4-Trihydroxybutanoic acid)
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PDB for HMDB0341420 (2,2,4-Trihydroxybutanoic acid)
HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       1.540  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.874  -2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.874  -3.850   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.540   1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.206   2.310   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.874   2.310   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       3.080  -0.000   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    3                                                       
CONECT    3    2                                                            
CONECT    4    1    5    8    9                                             
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    4                                                            
CONECT    9    4                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END

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3D PDB for HMDB0341420 (2,2,4-Trihydroxybutanoic acid)
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SMILES for HMDB0341420 (2,2,4-Trihydroxybutanoic acid)
OCCC(O)(O)C(O)=O
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INCHI for HMDB0341420 (2,2,4-Trihydroxybutanoic acid)
InChI=1S/C4H8O5/c5-2-1-4(8,9)3(6)7/h5,8-9H,1-2H2,(H,6,7)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2,2,4-Trihydroxybutyric acidChEBI
2,2,4-TrihydroxybutyrateGenerator
2,2,4-TrihydroxybutanoateGenerator
Chemical FormulaC4H8O5
Average Molecular Weight136.103
Monoisotopic Molecular Weight136.037173358
IUPAC Name2,2,4-trihydroxybutanoic acid
Traditional NameD-threonic acid
CAS Registry NumberNot Available
SMILES
OCCC(O)(O)C(O)=O
InChI Identifier
InChI=1S/C4H8O5/c5-2-1-4(8,9)3(6)7/h5,8-9H,1-2H2,(H,6,7)
InChI KeyIASCKZVQSNCRPV-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
    • 

  • Fatty acid
    • 

  • Carbonyl hydrate
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Polyol
    • 

  • Carbonyl group
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Primary alcohol
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • 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-1.3ChemAxon
pKa (Strongest Acidic)2.95ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity26.38 m³·mol⁻¹ChemAxon
Polarizability11.65 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties
Predicted Retention Times 
Not Available
Predicted Kovats Retention Indices
Not Available
Spectra
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 IDNot Available
KNApSAcK IDNot Available
Chemspider ID4446060  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5282933  
PDB IDNot Available
ChEBI ID73967  
Food Biomarker OntologyNot Available
VMH IDNot Available
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  ]