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Showing metabocard for triacetate lactone (HMDB0341406)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2022-09-09 20:59:07 UTC
Update Date2022-09-22 18:34:54 UTC
HMDB IDHMDB0341406
Secondary Accession NumbersNone
Metabolite Identification
Common Nametriacetate lactone
Descriptiontriacetate lactone belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. triacetate lactone is an extremely weak basic (essentially neutral) compound (based on its pKa). Triacetic acid lactone (TAL; 4-hydroxy-6-methyl-2-pyrone) is an organic compound derived enzymatically from glucose. This enzyme catalyzes the synthesis of triacetic acid lactone from acetyl-CoA via two subsequent condensations with malonyl-CoA. The tautomer on the left, featuring a 4-hydroxy group, the C4 carbon, is dominant. It is also a precursor to sorbic acid, dienoic acid, and hexenoic acid. The microbial synthesis of triacetic acid lactone requires the enzyme 2-pyrone synthase (2-PS).
Structure
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MOLSDFPDBSMILESInChI

MOL for HMDB0341406 (triacetate lactone)


  Mrv1533004241504232D          

  9  9  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  2  8  1  0  0  0  0
  4  9  1  0  0  0  0
M  END
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3D MOL for HMDB0341406 (triacetate lactone)

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3D SDF for HMDB0341406 (triacetate lactone)

  Mrv1533004241504232D          

  9  9  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  2  8  1  0  0  0  0
  4  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341406

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(O)=CC(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C6H6O3/c1-4-2-5(7)3-6(8)9-4/h2-3,7H,1H3

> <INCHI_KEY>
NSYSSMYQPLSPOD-UHFFFAOYSA-N

> <FORMULA>
C6H6O3

> <MOLECULAR_WEIGHT>
126.111

> <EXACT_MASS>
126.031694053

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
11.711635153042744

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-6-methyl-2H-pyran-2-one

> <ALOGPS_LOGP>
-0.03

> <JCHEM_LOGP>
0.5490816496666666

> <ALOGPS_LOGS>
-0.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.6675492052298395

> <JCHEM_PKA_STRONGEST_BASIC>
-6.006013977634546

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
33.8069

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.63e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
triacetic acid lactone

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for HMDB0341406 (triacetate lactone)
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PDB for HMDB0341406 (triacetate lactone)
HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    2                                                       
CONECT    9    4                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END

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3D PDB for HMDB0341406 (triacetate lactone)
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SMILES for HMDB0341406 (triacetate lactone)
CC1=CC(O)=CC(=O)O1
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INCHI for HMDB0341406 (triacetate lactone)
InChI=1S/C6H6O3/c1-4-2-5(7)3-6(8)9-4/h2-3,7H,1H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
4-Hydroxy-6-methyl-2-pyroneChEBI
Triacetic acid lactoneGenerator
Chemical FormulaC6H6O3
Average Molecular Weight126.111
Monoisotopic Molecular Weight126.031694053
IUPAC Name4-hydroxy-6-methyl-2H-pyran-2-one
Traditional Nametriacetic acid lactone
CAS Registry NumberNot Available
SMILES
CC1=CC(O)=CC(=O)O1
InChI Identifier
InChI=1S/C6H6O3/c1-4-2-5(7)3-6(8)9-4/h2-3,7H,1H3
InChI KeyNSYSSMYQPLSPOD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyrans  
Sub ClassPyranones and derivatives  
Direct ParentPyranones and derivatives  
Alternative Parents
Substituents
  • Pyranone
    • 

  • Heteroaromatic compound
    • 

  • Vinylogous acid
    • 

  • Lactone
    • 

  • Oxacycle
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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-0.03ALOGPS
logP0.55ChemAxon
logS-0.22ALOGPS
pKa (Strongest Acidic)7.67ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity33.81 m³·mol⁻¹ChemAxon
Polarizability11.71 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties
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 QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation  details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation  details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00037933  
Chemspider IDNot Available
KEGG Compound IDC02752  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTriacetic acid lactone  
METLIN IDNot Available
PubChem Compound54675757  
PDB IDNot Available
ChEBI ID16458  
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. Simon-Manso Y, Marupaka R, Yan X, Liang Y, Telu KH, Mirokhin Y, Stein SE: Mass Spectrometry Fingerprints of Small-Molecule Metabolites in Biofluids: Building a Spectral Library of Recurrent Spectra for Urine Analysis. Anal Chem. 2019 Sep 17;91(18):12021-12029. doi: 10.1021/acs.analchem.9b02977. Epub 2019 Aug 30. [PubMed:31424920  ]