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Showing metabocard for Hydroxyacetone (HMDB0006961)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2008-09-11 00:41:42 UTC
Update Date2023-02-21 17:17:24 UTC
HMDB IDHMDB0006961
Secondary Accession Numbers
  • HMDB06961
Metabolite Identification
Common NameHydroxyacetone
DescriptionHydroxyacetone, also known as acetol or acetone alcohol, belongs to the class of organic compounds known as alpha-hydroxy ketones. These are organic compounds containing a carboxylic acid, and an amine group attached to the alpha carbon atom, relative to the C=O group. Hydroxyacetone exists in all living organisms, ranging from bacteria to humans. Hydroxyacetone is a sweet, caramel, and ethereal tasting compound. hydroxyacetone has been detected, but not quantified in several different foods, such as bog bilberries, cardoons, amaranths, black salsifies, and komatsuna. This could make hydroxyacetone a potential biomarker for the consumption of these foods. Hydroxyacetone is an intermediate in glycine, serine, and threonine metabolism.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0006961 (Hydroxyacetone)

  Mrv1652309042000332D          

  5  4  0  0  0  0            999 V2000
   -0.9590   -0.7617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2445   -0.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2445    0.4758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699   -0.7617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1845   -0.3491    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
M  END
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3D MOL for HMDB0006961 (Hydroxyacetone)

HMDB0006961
     RDKit          3D
Hydroxyacetone
 11 10  0  0  0  0  0  0  0  0999 V2000
    1.5249    0.1575    0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0803    0.4479    0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2912    1.5908    0.3542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9486   -0.6193   -0.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2337   -0.0911    0.0821 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195    0.1129   -0.9452 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1385    0.8800    0.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092   -0.8378    0.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8913   -1.0509   -1.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8565   -1.4230    0.7352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1511    0.8330    0.4289 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
  1  6  1  0
  1  7  1  0
  1  8  1  0
  4  9  1  0
  4 10  1  0
  5 11  1  0
M  END
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3D SDF for HMDB0006961 (Hydroxyacetone)

  Mrv1652309042000332D          

  5  4  0  0  0  0            999 V2000
   -0.9590   -0.7617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2445   -0.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2445    0.4758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699   -0.7617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1845   -0.3491    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006961

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C3H6O2/c1-3(5)2-4/h4H,2H2,1H3

> <INCHI_KEY>
XLSMFKSTNGKWQX-UHFFFAOYSA-N

> <FORMULA>
C3H6O2

> <MOLECULAR_WEIGHT>
74.0785

> <EXACT_MASS>
74.036779436

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
7.262209790221975

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-hydroxypropan-2-one

> <ALOGPS_LOGP>
-1.02

> <JCHEM_LOGP>
-0.7109682376666667

> <ALOGPS_LOGS>
0.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.938330218134272

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.88249458963422

> <JCHEM_PKA_STRONGEST_BASIC>
-3.287527368936204

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
17.897

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.80e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetone alcohol

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0006961 (Hydroxyacetone)

HMDB0006961
     RDKit          3D
Hydroxyacetone
 11 10  0  0  0  0  0  0  0  0999 V2000
    1.5249    0.1575    0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0803    0.4479    0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2912    1.5908    0.3542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9486   -0.6193   -0.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2337   -0.0911    0.0821 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195    0.1129   -0.9452 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1385    0.8800    0.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092   -0.8378    0.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8913   -1.0509   -1.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8565   -1.4230    0.7352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1511    0.8330    0.4289 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
  1  6  1  0
  1  7  1  0
  1  8  1  0
  4  9  1  0
  4 10  1  0
  5 11  1  0
M  END
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PDB for HMDB0006961 (Hydroxyacetone)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      -1.790  -1.422   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.456  -0.652   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.456   0.888   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.877  -1.422   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.211  -0.652   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for HMDB0006961 (Hydroxyacetone)

COMPND    HMDB0006961
HETATM    1  C1  UNL     1       1.525   0.158   0.079  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.080   0.448   0.148  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.291   1.591   0.354  1.00  0.00           O  
HETATM    4  C3  UNL     1      -0.949  -0.619  -0.027  1.00  0.00           C  
HETATM    5  O2  UNL     1      -2.234  -0.091   0.082  1.00  0.00           O  
HETATM    6  H1  UNL     1       1.920   0.113  -0.945  1.00  0.00           H  
HETATM    7  H2  UNL     1       2.139   0.880   0.651  1.00  0.00           H  
HETATM    8  H3  UNL     1       1.709  -0.838   0.576  1.00  0.00           H  
HETATM    9  H4  UNL     1      -0.891  -1.051  -1.068  1.00  0.00           H  
HETATM   10  H5  UNL     1      -0.857  -1.423   0.735  1.00  0.00           H  
HETATM   11  H6  UNL     1      -2.151   0.833   0.429  1.00  0.00           H  
CONECT    1    2    6    7    8
CONECT    2    3    3    4
CONECT    4    5    9   10
CONECT    5   11
END
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SMILES for HMDB0006961 (Hydroxyacetone)

CC(=O)CO
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INCHI for HMDB0006961 (Hydroxyacetone)

InChI=1S/C3H6O2/c1-3(5)2-4/h4H,2H2,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC3H6O2
Average Molecular Weight74.0785
Monoisotopic Molecular Weight74.036779436
IUPAC Name1-hydroxypropan-2-one
Traditional Nameacetone alcohol
CAS Registry Number116-09-6
SMILES
CC(=O)CO
InChI Identifier
InChI=1S/C3H6O2/c1-3(5)2-4/h4H,2H2,1H3
InChI KeyXLSMFKSTNGKWQX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-hydroxy ketones. These are organic compounds containing a carboxylic acid, and an amine group attached to the alpha carbon atom, relative to the C=O group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-hydroxy ketones
Alternative Parents
Substituents
  • Alpha-hydroxy ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-17 °CNot Available
Boiling Point145.00 to 146.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000000 mg/L @ 20 °C (exp)The Good Scents Company Information System
LogP-0.780 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified3 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
Associated Disorders and Diseases
Disease References
Autosomal dominant polycystic kidney disease
  1. Gronwald W, Klein MS, Zeltner R, Schulze BD, Reinhold SW, Deutschmann M, Immervoll AK, Boger CA, Banas B, Eckardt KU, Oefner PJ: Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Kidney Int. 2011 Jun;79(11):1244-53. doi: 10.1038/ki.2011.30. Epub 2011 Mar 9. [PubMed:21389975 ]
Associated OMIM IDs
  • 601313 (Autosomal dominant polycystic kidney disease)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012041
KNApSAcK IDC00019558
Chemspider ID21106125
KEGG Compound IDC05235
BioCyc IDACETOL
BiGG IDNot Available
Wikipedia LinkHydroxyacetone
METLIN IDNot Available
PubChem Compound8299
PDB IDNot Available
ChEBI ID27957
Food Biomarker OntologyNot Available
VMH IDACETOL
MarkerDB IDNot Available
Good Scents IDrw1132561
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Casazza JP, Felver ME, Veech RL: The metabolism of acetone in rat. J Biol Chem. 1984 Jan 10;259(1):231-6. [PubMed:6706932 ]
  2. Kelley JJ, Dekker EE: D-1-amino-2-propanol:NAD+ oxidoreductase. Purification and general properties of the large molecular form of the enzyme from Escherichia coli K12. J Biol Chem. 1984 Feb 25;259(4):2124-9. [PubMed:6365902 ]
  3. WERLE E, STIESS P: [Quantitative determination of acetol, with special reference to its formation in alkaline sugar decomposition]. Biochem Z. 1951;321(6):485-91. [PubMed:14858384 ]
  4. Kasai H, Nishimura S: Hydroxylation of deoxyguanosine at the C-8 position by ascorbic acid and other reducing agents. Nucleic Acids Res. 1984 Feb 24;12(4):2137-45. [PubMed:6701097 ]
  5. Yamada-Onodera K, Ono K, Tani Y: Purification and characterization of an enzyme that has dihydroxyacetone-reducing activity from methanol-grown Hansenula ofunaensis. J Biosci Bioeng. 1999;88(2):148-52. [PubMed:16232589 ]
  6. Hatanaka Y, Kudo T, Miyataka M, Kobayashi O, Higashihara M, Hiyama K: Asymmetric reduction of hydroxyacetone to propanediol in immobilized halotolerant microalga Dunaliella parva. J Biosci Bioeng. 1999;88(3):281-6. [PubMed:16232612 ]
  7. HUGGINS CG, MILLER ON: The quantitative determination of acetol. J Biol Chem. 1956 Aug;221(2):711-8. [PubMed:13357464 ]
  8. SELLINGER OZ, MILLER ON: The phosphorylation of acetol. Biochim Biophys Acta. 1959 Nov;36:266-8. [PubMed:14444756 ]
  9. Ishikawa T, Aikawa T, Ohata E, Iseki T, Maeda S, Matsuo T, Fujino T, Saito S: Two-directional elaboration of hydroxyacetone under thermodynamically controlled conditions: allylation or 2-propynylation and aldol reaction. J Org Chem. 2007 Jan 19;72(2):435-41. [PubMed:17221959 ]
  10. Yaylayan VA, Keyhani A: Origin of carbohydrate degradation products in L-Alanine/D-[(13)C]glucose model systems. J Agric Food Chem. 2000 Jun;48(6):2415-9. [PubMed:10888560 ]

Enzymes

Enzyme Details
1. Retinol dehydrogenase 13
General function:
Involved in oxidoreductase activity
Specific function:
Does not exhibit retinol dehydrogenase (RDH) activity in vitro
Gene Name:
RDH13
Uniprot ID:
Q8NBN7
Molecular weight:
35931.8