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Showing metabocard for 2,3-Pentanedione (HMDB0031598)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:44:16 UTC
Update Date2023-02-21 17:20:57 UTC
HMDB IDHMDB0031598
Secondary Accession Numbers
  • HMDB31598
Metabolite Identification
Common Name2,3-Pentanedione
Description2,3-Pentanedione, also known as acetyl propionyl or pentan-2,3-dione, belongs to the class of organic compounds known as alpha-diketones. These are organic compounds containing two ketone groups on two adjacent carbon atoms. 2,3-Pentanedione is a sweet, butter, and caramel tasting compound. 2,3-Pentanedione has been detected, but not quantified, in several different foods, such as coffee and coffee products, tamarinds, cauliflowers, green beans, and cereals and cereal products.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031598 (2,3-Pentanedione)

Structure #1
  Mrv1652305261923562D          

  7  6  0  0  0  0            999 V2000
    0.8250   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   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
    2.0625    0.7145    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  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  5  7  2  0  0  0  0
M  END
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3D MOL for HMDB0031598 (2,3-Pentanedione)

HMDB0031598
     RDKit          3D
2,3-Pentanedione
 15 14  0  0  0  0  0  0  0  0999 V2000
   -2.1846    0.0105   -0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0869    0.5910    0.7975 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1633   -0.1904    0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2616   -1.2912    1.1068 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1683    0.3105   -0.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3699   -0.5116   -0.6334 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0588    1.3997   -0.9891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5790    0.7996   -0.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8336   -0.8357   -0.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0579   -0.2815    0.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2840    0.5550    1.8937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9262    1.6569    0.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0012   -1.5212   -0.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0413   -0.0856   -1.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8879   -0.6061    0.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  5  7  2  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  6 13  1  0
  6 14  1  0
  6 15  1  0
M  END
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3D SDF for HMDB0031598 (2,3-Pentanedione)

Structure #1
  Mrv1652305261923562D          

  7  6  0  0  0  0            999 V2000
    0.8250   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   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
    2.0625    0.7145    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  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  5  7  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031598

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O2/c1-3-5(7)4(2)6/h3H2,1-2H3

> <INCHI_KEY>
TZMFJUDUGYTVRY-UHFFFAOYSA-N

> <FORMULA>
C5H8O2

> <MOLECULAR_WEIGHT>
100.1158

> <EXACT_MASS>
100.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
10.296518384548499

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
pentane-2,3-dione

> <ALOGPS_LOGP>
0.33

> <JCHEM_LOGP>
1.0960353230000002

> <ALOGPS_LOGS>
-0.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.160616491779

> <JCHEM_PKA_STRONGEST_BASIC>
-8.373102181448367

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
26.1677

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.90e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetyl propionyl

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0031598 (2,3-Pentanedione)

HMDB0031598
     RDKit          3D
2,3-Pentanedione
 15 14  0  0  0  0  0  0  0  0999 V2000
   -2.1846    0.0105   -0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0869    0.5910    0.7975 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1633   -0.1904    0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2616   -1.2912    1.1068 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1683    0.3105   -0.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3699   -0.5116   -0.6334 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0588    1.3997   -0.9891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5790    0.7996   -0.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8336   -0.8357   -0.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0579   -0.2815    0.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2840    0.5550    1.8937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9262    1.6569    0.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0012   -1.5212   -0.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0413   -0.0856   -1.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8879   -0.6061    0.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  5  7  2  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  6 13  1  0
  6 14  1  0
  6 15  1  0
M  END
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PDB for HMDB0031598 (2,3-Pentanedione)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0       1.540  -2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.850   1.334   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2    5    6                                                  
CONECT    5    3    4    7                                                  
CONECT    6    4                                                            
CONECT    7    5                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for HMDB0031598 (2,3-Pentanedione)

COMPND    HMDB0031598
HETATM    1  C1  UNL     1      -2.185   0.011  -0.028  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.087   0.591   0.798  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.163  -0.190   0.507  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.262  -1.291   1.107  1.00  0.00           O  
HETATM    5  C4  UNL     1       1.168   0.311  -0.401  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.370  -0.512  -0.633  1.00  0.00           C  
HETATM    7  O2  UNL     1       1.059   1.400  -0.989  1.00  0.00           O  
HETATM    8  H1  UNL     1      -2.579   0.800  -0.737  1.00  0.00           H  
HETATM    9  H2  UNL     1      -1.834  -0.836  -0.684  1.00  0.00           H  
HETATM   10  H3  UNL     1      -3.058  -0.281   0.592  1.00  0.00           H  
HETATM   11  H4  UNL     1      -1.284   0.555   1.894  1.00  0.00           H  
HETATM   12  H5  UNL     1      -0.926   1.657   0.526  1.00  0.00           H  
HETATM   13  H6  UNL     1       2.001  -1.521  -0.958  1.00  0.00           H  
HETATM   14  H7  UNL     1       3.041  -0.086  -1.421  1.00  0.00           H  
HETATM   15  H8  UNL     1       2.888  -0.606   0.349  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3   11   12
CONECT    3    4    4    5
CONECT    5    6    7    7
CONECT    6   13   14   15
END
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SMILES for HMDB0031598 (2,3-Pentanedione)

CCC(=O)C(C)=O
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INCHI for HMDB0031598 (2,3-Pentanedione)

InChI=1S/C5H8O2/c1-3-5(7)4(2)6/h3H2,1-2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
Acetyl propionylChEBI
AcetylpropionylChEBI
Ethyl methyl diketoneChEBI
2,3-PentadioneHMDB
2,3-PentandioneHMDB
2,3-Pentane-dioneHMDB
23-PENTANEDIONEHMDB
Benzil-related compound, 43HMDB
CH3C(O)C(O)C2H5HMDB
FEMA 2841HMDB
Pentan-2,3-dioneHMDB
Pentane-2,3-dioneHMDB
2,3-PentanedioneChEBI
Chemical FormulaC5H8O2
Average Molecular Weight100.1158
Monoisotopic Molecular Weight100.0524295
IUPAC Namepentane-2,3-dione
Traditional Nameacetyl propionyl
CAS Registry Number600-14-6
SMILES
CCC(=O)C(C)=O
InChI Identifier
InChI=1S/C5H8O2/c1-3-5(7)4(2)6/h3H2,1-2H3
InChI KeyTZMFJUDUGYTVRY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-diketones. These are organic compounds containing two ketone groups on two adjacent carbon atoms.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-diketones
Alternative Parents
Substituents
  • Alpha-diketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-52 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility66.7 mg/mL at 15 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
  2. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Crohn's disease
  1. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008229
KNApSAcK IDNot Available
Chemspider ID11254
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcetylpropionyl
METLIN IDNot Available
PubChem Compound11747
PDB IDNot Available
ChEBI ID52774
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .