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Showing metabocard for Threonolactone (HMDB0000940)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:19 UTC
HMDB IDHMDB0000940
Secondary Accession Numbers
  • HMDB00940
Metabolite Identification
Common NameThreonolactone
DescriptionThreonolactone belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Threonolactone 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 threonolactone a potential biomarker for the consumption of these foods. Threonolactone 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 significant number of articles have been published on Threonolactone.
Structure
Data?1676999719
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000940 (Threonolactone)

  Mrv0541 02231218502D          

  8  8  0  0  1  0            999 V2000
   10.6802   -7.1439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9369   -7.9280    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.7619   -7.9261    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.0151   -7.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7991   -6.8842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3466   -6.6575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4535   -8.5965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2484   -8.5924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  7  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  6  0  0  0
  4  6  1  0  0  0  0
  4  5  2  0  0  0  0
M  END
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3D MOL for HMDB0000940 (Threonolactone)

HMDB0000940
     RDKit          3D
Threonolactone
 14 14  0  0  0  0  0  0  0  0999 V2000
    1.0758    1.7059   -1.7877 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7188    0.7002   -1.0875 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2282   -0.5220   -1.5229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8330   -0.8965   -0.6320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4398   -0.3028    0.6937 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4689    0.4644    1.2091 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7426    0.5911    0.4068 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8826   -0.0568    0.8537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7607   -0.4058   -1.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9260   -1.9882   -0.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1978   -1.1081    1.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6873    1.2281    0.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6882    1.5680    0.9002 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9776   -0.9775    0.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  2  1  0
  4  9  1  0
  4 10  1  0
  5 11  1  1
  6 12  1  0
  7 13  1  1
  8 14  1  0
M  END
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3D SDF for HMDB0000940 (Threonolactone)

  Mrv0541 02231218502D          

  8  8  0  0  1  0            999 V2000
   10.6802   -7.1439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9369   -7.9280    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.7619   -7.9261    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.0151   -7.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7991   -6.8842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3466   -6.6575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4535   -8.5965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2484   -8.5924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  7  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  6  0  0  0
  4  6  1  0  0  0  0
  4  5  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000940

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@H]1COC(=O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C4H6O4/c5-2-1-8-4(7)3(2)6/h2-3,5-6H,1H2/t2-,3+/m0/s1

> <INCHI_KEY>
SGMJBNSHAZVGMC-STHAYSLISA-N

> <FORMULA>
C4H6O4

> <MOLECULAR_WEIGHT>
118.088

> <EXACT_MASS>
118.02660868

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
9.870077369784436

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,4S)-3,4-dihydroxyoxolan-2-one

> <ALOGPS_LOGP>
-1.72

> <JCHEM_LOGP>
-1.484603302

> <ALOGPS_LOGS>
1.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.000796211703818

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.66159827209987

> <JCHEM_PKA_STRONGEST_BASIC>
-3.608833819644188

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
22.8538

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e+03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4S)-3,4-dihydroxyoxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0000940 (Threonolactone)

HMDB0000940
     RDKit          3D
Threonolactone
 14 14  0  0  0  0  0  0  0  0999 V2000
    1.0758    1.7059   -1.7877 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7188    0.7002   -1.0875 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2282   -0.5220   -1.5229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8330   -0.8965   -0.6320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4398   -0.3028    0.6937 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4689    0.4644    1.2091 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7426    0.5911    0.4068 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8826   -0.0568    0.8537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7607   -0.4058   -1.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9260   -1.9882   -0.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1978   -1.1081    1.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6873    1.2281    0.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6882    1.5680    0.9002 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9776   -0.9775    0.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  2  1  0
  4  9  1  0
  4 10  1  0
  5 11  1  1
  6 12  1  0
  7 13  1  1
  8 14  1  0
M  END
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PDB for HMDB0000940 (Threonolactone)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      19.936 -13.335   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.416 -14.799   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.956 -14.795   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.428 -13.330   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      23.892 -12.851   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      21.180 -12.427   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      19.513 -16.047   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      22.864 -16.039   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    7    3                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    6    5                                                  
CONECT    5    4                                                            
CONECT    6    1    4                                                       
CONECT    7    2                                                            
CONECT    8    3                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
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3D PDB for HMDB0000940 (Threonolactone)

COMPND    HMDB0000940
HETATM    1  O1  UNL     1       1.076   1.706  -1.788  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.719   0.700  -1.087  1.00  0.00           C  
HETATM    3  O2  UNL     1       0.228  -0.522  -1.523  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.833  -0.897  -0.632  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.440  -0.303   0.694  1.00  0.00           C  
HETATM    6  O3  UNL     1      -1.469   0.464   1.209  1.00  0.00           O  
HETATM    7  C4  UNL     1       0.743   0.591   0.407  1.00  0.00           C  
HETATM    8  O4  UNL     1       1.883  -0.057   0.854  1.00  0.00           O  
HETATM    9  H1  UNL     1      -1.761  -0.406  -1.007  1.00  0.00           H  
HETATM   10  H2  UNL     1      -0.926  -1.988  -0.595  1.00  0.00           H  
HETATM   11  H3  UNL     1      -0.198  -1.108   1.407  1.00  0.00           H  
HETATM   12  H4  UNL     1      -1.687   1.228   0.631  1.00  0.00           H  
HETATM   13  H5  UNL     1       0.688   1.568   0.900  1.00  0.00           H  
HETATM   14  H6  UNL     1       1.978  -0.978   0.531  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    7
CONECT    3    4
CONECT    4    5    9   10
CONECT    5    6    7   11
CONECT    6   12
CONECT    7    8   13
CONECT    8   14
END
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SMILES for HMDB0000940 (Threonolactone)

O[C@H]1COC(=O)[C@@H]1O
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INCHI for HMDB0000940 (Threonolactone)

InChI=1S/C4H6O4/c5-2-1-8-4(7)3(2)6/h2-3,5-6H,1H2/t2-,3+/m0/s1
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View in JSmolView Stereo Labels
Synonyms
ValueSource
L-Threonic acid-1,4-lactoneChEBI
Threonic acid-1,4-lactoneChEBI
L-Threonate-1,4-lactoneGenerator
Threonate-1,4-lactoneGenerator
3,4-Bis[(trimethylsilyl)oxy]dihydro-cis-2(3H)-furanoneHMDB
Bis-TMS-threono-1,4-lactoneHMDB
cis-Dihydro-3,4-bis[(trimethylsilyl)oxy]-2(3H)-furanoneHMDB
Di-TMS-threono-1,4-lactoneHMDB
Chemical FormulaC4H6O4
Average Molecular Weight118.088
Monoisotopic Molecular Weight118.02660868
IUPAC Name(3R,4S)-3,4-dihydroxyoxolan-2-one
Traditional Name(3R,4S)-3,4-dihydroxyoxolan-2-one
CAS Registry Number21730-93-8
SMILES
O[C@H]1COC(=O)[C@@H]1O
InChI Identifier
InChI=1S/C4H6O4/c5-2-1-8-4(7)3(2)6/h2-3,5-6H,1H2/t2-,3+/m0/s1
InChI KeySGMJBNSHAZVGMC-STHAYSLISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassGamma butyrolactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Secondary alcohol
  • Carboxylic acid ester
  • 1,2-diol
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
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
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022328
KNApSAcK IDNot Available
Chemspider ID2006913
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5888
PubChem Compound2724794
PDB IDNot Available
ChEBI ID71176
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNakaminami, Gen; Edo, Haruo; Nakagawa, Masazumi. Syntheses of L-threose and methyl di-O-acetyl-L-threuronate from (+)-tartaric acid. Bulletin of the Chemical Society of Japan (1973), 46(1), 266-9.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Kurata, T; Miyake, N; Otsuka, Y. Formation of L-threonolactone and oxalic acid in the autoxidation reaction of L-ascorbic acid - Possible involvement of singlet oxygen. Bioscience, Biotechnology, and Biochemistry, Volume 60, Issue 7, pp. 1212-1214. . .