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Showing metabocard for Acetoxyacetone (HMDB0034466)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:18:33 UTC
Update Date2023-02-21 17:24:17 UTC
HMDB IDHMDB0034466
Secondary Accession Numbers
  • HMDB34466
Metabolite Identification
Common NameAcetoxyacetone
DescriptionAcetoxyacetone belongs to the class of organic compounds known as alpha-acyloxy ketones. These are ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom). Acetoxyacetone is a buttery and fruity tasting compound. Acetoxyacetone has been detected, but not quantified in, pineapples (Ananas comosus). This could make acetoxyacetone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Acetoxyacetone.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0034466 (Acetoxyacetone)

  Mrv0541 05061307502D          

  8  7  0  0  0  0            999 V2000
   -1.8414   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  2  0  0  0  0
  7  5  2  0  0  0  0
  8  3  1  0  0  0  0
  8  5  1  0  0  0  0
M  END
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3D MOL for HMDB0034466 (Acetoxyacetone)

HMDB0034466
     RDKit          3D
Acetoxyacetone
 16 15  0  0  0  0  0  0  0  0999 V2000
   -2.7131   -0.1441    0.7309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2746    0.1811    0.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401    0.3841    1.4688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7367    0.2582   -0.8629 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188    0.5717   -0.8599 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5745   -0.2166   -0.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0184    0.0810   -0.2206 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1765   -1.2581    0.3289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9870    0.0673    1.7905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2951    0.5336    0.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9670   -1.1803    0.4409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8687   -0.7249   -1.3698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2872    0.9921   -1.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2886    0.9469   -0.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6062   -0.8175   -0.5673 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3866    0.3256    0.8134 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  1  0
  6  7  1  0
  6  8  2  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  4 12  1  0
  4 13  1  0
  7 14  1  0
  7 15  1  0
  7 16  1  0
M  END
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3D SDF for HMDB0034466 (Acetoxyacetone)

  Mrv0541 05061307502D          

  8  7  0  0  0  0            999 V2000
   -1.8414   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  2  0  0  0  0
  7  5  2  0  0  0  0
  8  3  1  0  0  0  0
  8  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034466

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)COC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O3/c1-4(6)3-8-5(2)7/h3H2,1-2H3

> <INCHI_KEY>
DBERHVIZRVGDFO-UHFFFAOYSA-N

> <FORMULA>
C5H8O3

> <MOLECULAR_WEIGHT>
116.1152

> <EXACT_MASS>
116.047344122

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
11.355232742665137

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-oxopropyl acetate

> <ALOGPS_LOGP>
-0.27

> <JCHEM_LOGP>
-0.2698428273333332

> <ALOGPS_LOGS>
0.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.511874819256313

> <JCHEM_PKA_STRONGEST_BASIC>
-6.95085678457926

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
27.048500000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.49e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-propanone, 1-(acetyloxy)-

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0034466 (Acetoxyacetone)

HMDB0034466
     RDKit          3D
Acetoxyacetone
 16 15  0  0  0  0  0  0  0  0999 V2000
   -2.7131   -0.1441    0.7309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2746    0.1811    0.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401    0.3841    1.4688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7367    0.2582   -0.8629 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188    0.5717   -0.8599 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5745   -0.2166   -0.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0184    0.0810   -0.2206 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1765   -1.2581    0.3289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9870    0.0673    1.7905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2951    0.5336    0.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9670   -1.1803    0.4409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8687   -0.7249   -1.3698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2872    0.9921   -1.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2886    0.9469   -0.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6062   -0.8175   -0.5673 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3866    0.3256    0.8134 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  1  0
  6  7  1  0
  6  8  2  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  4 12  1  0
  4 13  1  0
  7 14  1  0
  7 15  1  0
  7 16  1  0
M  END
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PDB for HMDB0034466 (Acetoxyacetone)

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -3.437  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.231  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.104  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.897  -1.334   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.104   0.976   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.897  -2.874   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.564  -0.564   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3    4    8                                                       
CONECT    4    1    3    6                                                  
CONECT    5    2    7    8                                                  
CONECT    6    4                                                            
CONECT    7    5                                                            
CONECT    8    3    5                                                       
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for HMDB0034466 (Acetoxyacetone)

COMPND    HMDB0034466
HETATM    1  C1  UNL     1      -2.713  -0.144   0.731  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.275   0.181   0.510  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.540   0.384   1.469  1.00  0.00           O  
HETATM    4  C3  UNL     1      -0.737   0.258  -0.863  1.00  0.00           C  
HETATM    5  O2  UNL     1       0.619   0.572  -0.860  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.575  -0.217  -0.246  1.00  0.00           C  
HETATM    7  C5  UNL     1       3.018   0.081  -0.221  1.00  0.00           C  
HETATM    8  O3  UNL     1       1.177  -1.258   0.329  1.00  0.00           O  
HETATM    9  H1  UNL     1      -2.987   0.067   1.791  1.00  0.00           H  
HETATM   10  H2  UNL     1      -3.295   0.534   0.066  1.00  0.00           H  
HETATM   11  H3  UNL     1      -2.967  -1.180   0.441  1.00  0.00           H  
HETATM   12  H4  UNL     1      -0.869  -0.725  -1.370  1.00  0.00           H  
HETATM   13  H5  UNL     1      -1.287   0.992  -1.490  1.00  0.00           H  
HETATM   14  H6  UNL     1       3.289   0.947  -0.847  1.00  0.00           H  
HETATM   15  H7  UNL     1       3.606  -0.818  -0.567  1.00  0.00           H  
HETATM   16  H8  UNL     1       3.387   0.326   0.813  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    3    4
CONECT    4    5   12   13
CONECT    5    6
CONECT    6    7    8    8
CONECT    7   14   15   16
END
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SMILES for HMDB0034466 (Acetoxyacetone)

CC(=O)COC(C)=O
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INCHI for HMDB0034466 (Acetoxyacetone)

InChI=1S/C5H8O3/c1-4(6)3-8-5(2)7/h3H2,1-2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC5H8O3
Average Molecular Weight116.1152
Monoisotopic Molecular Weight116.047344122
IUPAC Name2-oxopropyl acetate
Traditional Name2-propanone, 1-(acetyloxy)-
CAS Registry Number592-20-1
SMILES
CC(=O)COC(C)=O
InChI Identifier
InChI=1S/C5H8O3/c1-4(6)3-8-5(2)7/h3H2,1-2H3
InChI KeyDBERHVIZRVGDFO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-acyloxy ketones. These are ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-acyloxy ketones
Alternative Parents
Substituents
  • Alpha-acyloxy ketone
  • Ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Biological role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point66.00 °C. @ 12.00 mm HgThe Good Scents Company Information System
Water Solubility0The Good Scents Company Information System
LogP-0.296 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB012876
KNApSAcK IDNot Available
Chemspider ID11105
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11593
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1053041
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .