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Showing metabocard for Dehydroacetic acid (HMDB0250943)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 08:06:01 UTC
Update Date2021-09-26 23:02:40 UTC
HMDB IDHMDB0250943
Secondary Accession NumbersNone
Metabolite Identification
Common NameDehydroacetic acid
Descriptiondehydroacetic acid, also known as biocide 470F or methylacetopyronone, belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond. dehydroacetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Dehydroacetic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Dehydroacetic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0250943 (Dehydroacetic acid)

  Mrv1533004261516532D          

 12 12  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   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
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   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  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  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
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  0  0  0  0
M  END
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3D MOL for HMDB0250943 (Dehydroacetic acid)

HMDB0250943
     RDKit          3D
Dehydroacetic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
   -3.2608    0.2822   -0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1802   -0.3027    0.6202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3571   -1.2189    1.4058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8017    0.2272    0.4840 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1621   -0.4682    1.3540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1985   -1.1616    2.3335 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5843   -0.3415    1.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9866   -0.0235   -0.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4042    0.1233   -0.5430 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0270    0.1799   -1.1433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3319    0.0707   -0.9136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1662   -0.1543   -1.8451 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2434    0.2071    0.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4055   -0.2013   -1.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0316    1.3612   -0.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8443    1.3149    0.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3513   -0.4991    1.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0792    0.1778    0.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7110   -0.6638   -1.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5158    1.0907   -1.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11  4  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  7 17  1  0
  9 18  1  0
  9 19  1  0
  9 20  1  0
M  END
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3D SDF for HMDB0250943 (Dehydroacetic acid)

  Mrv1533004261516532D          

 12 12  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   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
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   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  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  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
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250943

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)C1C(=O)OC(C)=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O4/c1-4-3-6(10)7(5(2)9)8(11)12-4/h3,7H,1-2H3

> <INCHI_KEY>
PGRHXDWITVMQBC-UHFFFAOYSA-N

> <FORMULA>
C8H8O4

> <MOLECULAR_WEIGHT>
168.148

> <EXACT_MASS>
168.042258738

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
15.582167640039788

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-acetyl-6-methyl-3,4-dihydro-2H-pyran-2,4-dione

> <ALOGPS_LOGP>
0.11

> <JCHEM_LOGP>
0.4352045773333331

> <ALOGPS_LOGS>
-0.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.091813367855032

> <JCHEM_PKA_STRONGEST_BASIC>
-6.0375869134285365

> <JCHEM_POLAR_SURFACE_AREA>
60.440000000000005

> <JCHEM_REFRACTIVITY>
41.334

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.32e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dehydroacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0250943 (Dehydroacetic acid)

HMDB0250943
     RDKit          3D
Dehydroacetic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
   -3.2608    0.2822   -0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1802   -0.3027    0.6202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3571   -1.2189    1.4058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8017    0.2272    0.4840 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1621   -0.4682    1.3540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1985   -1.1616    2.3335 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5843   -0.3415    1.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9866   -0.0235   -0.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4042    0.1233   -0.5430 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0270    0.1799   -1.1433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3319    0.0707   -0.9136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1662   -0.1543   -1.8451 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2434    0.2071    0.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4055   -0.2013   -1.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0316    1.3612   -0.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8443    1.3149    0.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3513   -0.4991    1.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0792    0.1778    0.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7110   -0.6638   -1.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5158    1.0907   -1.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11  4  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  7 17  1  0
  9 18  1  0
  9 19  1  0
  9 20  1  0
M  END
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PDB for HMDB0250943 (Dehydroacetic acid)

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    8                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for HMDB0250943 (Dehydroacetic acid)

COMPND    HMDB0250943
HETATM    1  C1  UNL     1      -3.261   0.282  -0.179  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.180  -0.303   0.620  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.357  -1.219   1.406  1.00  0.00           O  
HETATM    4  C3  UNL     1      -0.802   0.227   0.484  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.162  -0.468   1.354  1.00  0.00           C  
HETATM    6  O2  UNL     1      -0.199  -1.162   2.334  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.584  -0.341   1.060  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.987  -0.024  -0.168  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.404   0.123  -0.543  1.00  0.00           C  
HETATM   10  O3  UNL     1       1.027   0.180  -1.143  1.00  0.00           O  
HETATM   11  C8  UNL     1      -0.332   0.071  -0.914  1.00  0.00           C  
HETATM   12  O4  UNL     1      -1.166  -0.154  -1.845  1.00  0.00           O  
HETATM   13  H1  UNL     1      -4.243   0.207   0.356  1.00  0.00           H  
HETATM   14  H2  UNL     1      -3.406  -0.201  -1.168  1.00  0.00           H  
HETATM   15  H3  UNL     1      -3.032   1.361  -0.390  1.00  0.00           H  
HETATM   16  H4  UNL     1      -0.844   1.315   0.686  1.00  0.00           H  
HETATM   17  H5  UNL     1       2.351  -0.499   1.818  1.00  0.00           H  
HETATM   18  H6  UNL     1       4.079   0.178   0.335  1.00  0.00           H  
HETATM   19  H7  UNL     1       3.711  -0.664  -1.264  1.00  0.00           H  
HETATM   20  H8  UNL     1       3.516   1.091  -1.113  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    3    4
CONECT    4    5   11   16
CONECT    5    6    6    7
CONECT    7    8    8   17
CONECT    8    9   10
CONECT    9   18   19   20
CONECT   10   11
CONECT   11   12   12
END
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SMILES for HMDB0250943 (Dehydroacetic acid)

CC(=O)C1C(=O)OC(C)=CC1=O
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INCHI for HMDB0250943 (Dehydroacetic acid)

InChI=1S/C8H8O4/c1-4-3-6(10)7(5(2)9)8(11)12-4/h3,7H,1-2H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
Biocide 470FChEBI
MethylacetopyrononeChEBI
DehydroacetateGenerator
DHASMeSH
Dehydroacetic acid, zinc ion (1-)MeSH
DHA-SMeSH
Dehydroacetic acid, potassium ion (1-)MeSH
Sodium dehydroacetateMeSH
Dehydroacetic acid ion (1-)MeSH
Dehydroacetic acid, sodium ion (1-)MeSH
Dihydroxyacetone sulfateMeSH
Dehydroacetic acid, sodium monohydrate ion (1-)MeSH
e265ChEMBL
Chemical FormulaC8H8O4
Average Molecular Weight168.148
Monoisotopic Molecular Weight168.042258738
IUPAC Name3-acetyl-6-methyl-3,4-dihydro-2H-pyran-2,4-dione
Traditional Namedehydroacetic acid
CAS Registry NumberNot Available
SMILES
CC(=O)C1C(=O)OC(C)=CC1=O
InChI Identifier
InChI=1S/C8H8O4/c1-4-3-6(10)7(5(2)9)8(11)12-4/h3,7H,1-2H3
InChI KeyPGRHXDWITVMQBC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrans
Sub ClassPyranones and derivatives
Direct ParentDihydropyranones
Alternative Parents
Substituents
  • Dihydropyranone
  • 1,3-diketone
  • 1,3-dicarbonyl compound
  • Enol ester
  • Cyclic ketone
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
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
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDehydroacetic_acid
METLIN IDNot Available
PubChem Compound122903
PDB IDNot Available
ChEBI ID137426
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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]