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Human Metabolome Database Version 2.5

 

Showing metabocard for Acetone (HMDB01659)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2005-11-20 22:13:15
Update Date 2010-04-12 14:55:32
Accession Number HMDB01659
Secondary Accession Numbers Not Available
Common Name Acetone
Description Acetone is one of the ketone bodies produced during ketoacidosis. Acetone is not regarded as a waste product of metabolism. However, its physiological role in biochemical machinery is not clear. A model for the role of acetone metabolism is presented that orders the events occurring in acetonemia in sequence: in diabetic ketosis or starvation, ketone body production (b-hydroxy-butyrate, acetoacetate) provides fuel for vital organs (heart, brain . . .) raising the chance of survival of the metabolic catastrophe. However, when ketone body production exceeds the degrading capacity, the accumulating acetoacetic acid presents a new challenge to the pH regulatory system. Acetone production and its further degradation to C3 fragments fulfill two purposes: the maintenance of pH buffering capacity and provision of fuel for peripheral tissues. Since ketosis develops under serious metabolic circumstances, all the mechanisms that balance or moderate the effects of ketosis enhance the chance for survival. From this point of view, the theory that transportable C3 fragments can serve as additional nutrients is a novel view of acetone metabolism which introduces a new approach to the study of acetone degradation, especially in understanding its physiological function and the interrelationship between liver and peripheral tissues. (PMID 10580530). Acetone is typically derived from acetoacetate through the action of microbial acetoacetate decarboxylases found in gut microflora. In chemistry, acetone is the simplest representative of the ketones. Acetone is a colorless, mobile, flammable liquid readily soluble in water, ethanol, ether, etc., and itself serves as an important solvent. Acetone is an irritant and inhalation may lead to hepatotoxic effects (causing liver damage).
Synonyms
  1. Acetone
  2. Dimethyl ketone
  3. Dimethylformaldehyde
  4. Methyl ketone
  5. Propanone
  6. Pyroacetic ether
  7. b-Ketopropane
  8. beta-Ketopropane
Chemical IUPAC Name Acetone
Chemical Formula C3H6O
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Ketones and aldehydes
Class
  • Ketones
Sub Class
  • Short chain ketones
Family
  • Microbial Metabolite
Species
  • ketone
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 58.079
Monoisotopic Molecular Weight 58.041866
Isomeric SMILES CC(C)=O
Canonical SMILES CC(C)=O
KEGG Compound ID C00207 Link Image
BioCyc ID Not Available
BiGG ID 34257 Link Image
Wikipedia Link Acetone Link Image
NuGOwiki Link HMDB01659 Link Image
Metagene Link HMDB01659 Link Image
METLIN ID 3745 Link Image
PubChem Compound 180 Link Image
PubChem Substance 3507 Link Image
ChEBI ID 15347 Link Image
CAS Registry Number 67-64-1
InChI Identifier InChI=1/C3H6O/c1-3(2)4/h1-2H3
Synthesis Reference Ishizaki, Fumiaki. Acetone and butanol fermentation. Baiomasu Handobukku (2002), 166-175.
Melting Point (Experimental) -94.8 oC
Experimental Water Solubility 1000 mg/mL at 25 oC [RIDDICK,JA et al. (1986)] Source: PhysProp
Predicted Water Solubility 193.0 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Liquid
Experimental LogP/Hydrophobicity -0.24 [HANSCH,C ET AL. (1995)] Source: PhysProp
Predicted LogP/Hydrophobicity -0.29 [Predicted by ALOGPS]; 0.2 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
Download FID (Varian)
Show Experimental Conditions Link Image
Experimental 13C NMR Spectrum Download Spectrum
Download FID (Bruker)
Show Experimental Conditions Link Image
Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
Show Experimental Conditions Link Image
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum
Low Energy
Download File
Show Experimental Conditions Link Image
Medium Energy
Download File
Show Experimental Conditions Link Image
High Energy
Download File
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
  • Extracellular
  • mitochondria
Biofluid Location
  • Blood
  • Cerebrospinal Fluid
  • Urine
Tissue Location
Tissue References
Adipose Tissue —
Adrenal Gland —
Bladder —
Brain —
Fibroblasts —
Kidney —
Liver —
Myelin —
Pancreas —
Placenta —
Skin —
Stratum Corneum —
Testes —
Thyroid Gland —
Concentrations (Normal)
Biofluid Blood
Value 50.0 +/- 5.0 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal (fasting)
Comments Not Available
References
  • Geigy Scientific Tables, 8th Rev edition, pp. 165-177. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.
Biofluid Blood
Value 30.0 +/- 20.0 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Geigy Scientific Tables, 8th Rev edition, pp. 165-177. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.
Biofluid Blood
Value 1270.0 +/- 520.0 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Following chlorzoxazone and acetone exposure
References
  • Ernstgard L, Gullstrand E, Johanson G, Lof A: Toxicokinetic interactions between orally ingested chlorzoxazone and inhaled acetone or toluene in male volunteers. Toxicol Sci. 1999 Apr;48(2):189-96. [PubMed Link Image]
Biofluid Blood
Value 106.0 (35.0-170.0) uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Brega A, Villa P, Quadrini G, Quadri A, Lucarelli C: High-performance liquid chromatographic determination of acetone in blood and urine in the clinical diagnostic laboratory. J Chromatogr. 1991 Aug 16;553(1-2):249-54. [PubMed Link Image]
Biofluid Blood
Value 47.3 (40.4 - 54.2) uM
Age Adult:>18 yrs old
Sex Male
Patient information Normal
Comments Not Available
References
  • Ernstgard L, Gullstrand E, Johanson G, Lof A: Toxicokinetic interactions between orally ingested chlorzoxazone and inhaled acetone or toluene in male volunteers. Toxicol Sci. 1999 Apr;48(2):189-96. [PubMed Link Image]
Biofluid CSF
Value 117.0 +/- 65.0 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Geigy Scientific Tables, 8th Rev edition, pp. 165-177. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.
Biofluid CSF
Value 67.1 (43.0-91.2) uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Subramanian A, Gupta A, Saxena S, Gupta A, Kumar R, Nigam A, Kumar R, Mandal SK, Roy R: Proton MR CSF analysis and a new software as predictors for the differentiation of meningitis in children. NMR Biomed. 2005 Jun;18(4):213-25. [PubMed Link Image]
Biofluid CSF
Value 20 +/- 21 uM
Age N/A
Sex Both
Patient information Normal
Comments Not Available
References
  • Wishart DS, Lewis MJ, Morrissey JA, Flegel MD, Jeroncic K, Xiong Y, Cheng D, Eisner R, Gautam B, Tzur D, Sawhney S, Bamforth F, Greiner R, Li L: The human cerebrospinal fluid metabolome. J Chromatogr B Analyt Technol Biomed Life Sci. 2008 Aug 15;871(2):164-173. Epub 2008 May 8. [PubMed Link Image]
Biofluid Urine
Value <6.6 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Bairaktari E, Katopodis K, Siamopoulos KC, Tsolas O: Paraquat-induced renal injury studied by 1H nuclear magnetic resonance spectroscopy of urine. Clin Chem. 1998 Jun;44(6 Pt 1):1256-61. [PubMed Link Image]
Biofluid Urine
Value 320.0 (103.0-1290.0) umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Brega A, Villa P, Quadrini G, Quadri A, Lucarelli C: High-performance liquid chromatographic determination of acetone in blood and urine in the clinical diagnostic laboratory. J Chromatogr. 1991 Aug 16;553(1-2):249-54. [PubMed Link Image]
Biofluid Urine
Value 4.2 (0.98-15.3) umol/mmol creatinine
Age Infant:0-1 yr old
Sex Both
Patient information Normal
Comments Not Available
References
  • Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Biofluid Urine
Value 0.92 (0.20-2.8) umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Concentrations (Abnormal)
Biofluid Blood
Value 25.0 +/- 85.0 uM
Age Adult:>18 yrs old
Sex Both
Condition Kidney disease
Comments Chronic renal insufficiency
References
  • Liebich HM, Woll J: Volatile substances in blood serum: profile analysis and quantitative determination. J Chromatogr. 1977 Nov 11;142:505-16. [PubMed Link Image]
Biofluid Blood
Value 1520.0 (206.6-5285.0) uM
Age Adult:>18 yrs old
Sex Both
Condition Alcoholism
Comments Not Available
References
  • Jones AW, Lund M, Andersson E: Drinking drivers in Sweden who consume denatured alcohol preparations: an analytical-toxicological study. J Anal Toxicol. 1989 Jul-Aug;13(4):199-203. [PubMed Link Image]
Biofluid CSF
Value 2700 uM
Age Adult:>18 yrs old
Sex N/A
Condition Hepatic encephalopathy
Comments Not Available
References
  • Goldberg EM, Blendis LM, Sandler S: A gas chromatographic--mass spectrometric study of profiles of volatile metabolites in hepatic encephalopathy. J Chromatogr. 1981 Dec 11;226(2):291-9. [PubMed Link Image]
Biofluid Urine
Value 11.2 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Condition Paraquat poisoning
Comments Not Available
References
  • Bairaktari E, Katopodis K, Siamopoulos KC, Tsolas O: Paraquat-induced renal injury studied by 1H nuclear magnetic resonance spectroscopy of urine. Clin Chem. 1998 Jun;44(6 Pt 1):1256-61. [PubMed Link Image]
Biofluid Urine
Value 13.2 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Condition Diabetes mellitus type 2
Comments Not Available
References
  • Bales JR, Higham DP, Howe I, Nicholson JK, Sadler PJ: Use of high-resolution proton nuclear magnetic resonance spectroscopy for rapid multi-component analysis of urine. Clin Chem. 1984 Mar;30(3):426-32. [PubMed Link Image]
Biofluid Urine
Value 5.0 +/- 5.0 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Condition Lung Cancer
Comments Not Available
References
  • HMP experimental
Associated Disorders
Condition References
Alcoholism
  • Jones AW, Lund M, Andersson E: Drinking drivers in Sweden who consume denatured alcohol preparations: an analytical-toxicological study. J Anal Toxicol. 1989 Jul-Aug;13(4):199-203. [PubMed Link Image]
Diabetes mellitus type 2
  • Bales JR, Higham DP, Howe I, Nicholson JK, Sadler PJ: Use of high-resolution proton nuclear magnetic resonance spectroscopy for rapid multi-component analysis of urine. Clin Chem. 1984 Mar;30(3):426-32. [PubMed Link Image]
Hepatic encephalopathy
  • Goldberg EM, Blendis LM, Sandler S: A gas chromatographic--mass spectrometric study of profiles of volatile metabolites in hepatic encephalopathy. J Chromatogr. 1981 Dec 11;226(2):291-9. [PubMed Link Image]
Kidney disease
  • Liebich HM, Woll J: Volatile substances in blood serum: profile analysis and quantitative determination. J Chromatogr. 1977 Nov 11;142:505-16. [PubMed Link Image]
Lung Cancer
  • HMP experimental
Paraquat poisoning
  • Bairaktari E, Katopodis K, Siamopoulos KC, Tsolas O: Paraquat-induced renal injury studied by 1H nuclear magnetic resonance spectroscopy of urine. Clin Chem. 1998 Jun;44(6 Pt 1):1256-61. [PubMed Link Image]
OMIM ID
Pathways
Name SMPDB Link KEGG Link
Ketone Body Metabolism SMP00071 Link Image map00072 Link Image
General References
  1. Subramanian A, Gupta A, Saxena S, Gupta A, Kumar R, Nigam A, Kumar R, Mandal SK, Roy R: Proton MR CSF analysis and a new software as predictors for the differentiation of meningitis in children. NMR Biomed. 2005 Jun;18(4):213-25. [PubMed Link Image]
  2. Robinson RC, Shorr RG, Varrichio A, Park SS, Gelboin HV, Miller H, Friedman FK: Human liver cytochrome P-450 related to a rat acetone-inducible, nitrosamine-metabolizing cytochrome P-450: identification and isolation. Pharmacology. 1989;39(3):137-44. [PubMed Link Image]
  3. Yamane N, Tsuda T, Nose K, Yamamoto A, Ishiguro H, Kondo T: Relationship between skin acetone and blood beta-hydroxybutyrate concentrations in diabetes. Clin Chim Acta. 2006 Mar;365(1-2):325-9. Epub 2005 Oct 11. [PubMed Link Image]
  4. Palamanda J, Feng WW, Lin CC, Nomeir AA: Stimulation of tolbutamide hydroxylation by acetone and acetonitrile in human liver microsomes and in a cytochrome P-450 2C9-reconstituted system. Drug Metab Dispos. 2000 Jan;28(1):38-43. [PubMed Link Image]
  5. Crawley SC, Hindsgaul O, Alton G, Pierce M, Palcic MM: An enzyme-linked immunosorbent assay for N-acetylglucosaminyltransferase-V. Anal Biochem. 1990 Feb 15;185(1):112-7. [PubMed Link Image]
  6. Bairaktari E, Katopodis K, Siamopoulos KC, Tsolas O: Paraquat-induced renal injury studied by 1H nuclear magnetic resonance spectroscopy of urine. Clin Chem. 1998 Jun;44(6 Pt 1):1256-61. [PubMed Link Image]
  7. Inoue S, Sato Y, Hasegawa H, Noguchi A, Yamada A, Kurata T, Iwasaki T: Cross-reactive antigenicity of nucleoproteins of lyssaviruses recognized by a monospecific antirabies virus nucleoprotein antiserum on paraffin sections of formalin-fixed tissues. Pathol Int. 2003 Aug;53(8):525-33. [PubMed Link Image]
  8. Meiser JB, Nelson HS: Comparing conventional and acetone-precipitated dog allergen extract skin testing. J Allergy Clin Immunol. 2001 Apr;107(4):744-5. [PubMed Link Image]
  9. Baum HP, Reichrath J, Theobald A, Schock G: Fixation requirements for the immunohistochemical reactivity of PCNA antibody PC10 on cryostat sections. Histochem J. 1994 Dec;26(12):929-33. [PubMed Link Image]
  10. Benz J: Antidiabetic agents and lactation. J Hum Lact. 1992 Mar;8(1):27-8. [PubMed Link Image]
  11. Benfeldt E, Serup J, Menne T: Effect of barrier perturbation on cutaneous salicylic acid penetration in human skin: in vivo pharmacokinetics using microdialysis and non-invasive quantification of barrier function. Br J Dermatol. 1999 Apr;140(4):739-48. [PubMed Link Image]
  12. Paweska JT, Barnard BJ, Williams R: The use of sucrose-acetone-extracted Rift Valley fever virus antigen derived from cell culture in an indirect enzyme-linked immunosorbent assay and haemagglutination-inhibition test. Onderstepoort J Vet Res. 1995 Dec;62(4):227-33. [PubMed Link Image]
  13. Wittmann S, Gilg T, Dietz HG, Grantzow R, Peschel O, von Meyer L: [Isopropanol and acetone level in serum after preoperative surface disinfection with antiseptics containing isopropanol] Blutalkohol. 1992 Sep;29(5):326-35. [PubMed Link Image]
  14. Bales JR, Higham DP, Howe I, Nicholson JK, Sadler PJ: Use of high-resolution proton nuclear magnetic resonance spectroscopy for rapid multi-component analysis of urine. Clin Chem. 1984 Mar;30(3):426-32. [PubMed Link Image]
  15. Bird AR, Kossew B, Mulligan TP, Jacobs P: Regional thromboplastin standardisation using a human brain extract. S Afr Med J. 1989 Jun 3;75(11):538-40. [PubMed Link Image]
  16. Wikipedia Link Image
Metabolic Enzymes
  1. 2-nitropropane dioxygenase (EC 1.13.11.32)
Enzyme 1 [top]
Enzyme 1 ID 16055
Enzyme 1 Name 2-nitropropane dioxygenase (EC 1.13.11.32)
Enzyme 1 Synonyms Not Available
Enzyme 1 Gene Name Not Available
Enzyme 1 Protein Sequence >2-nitropropane dioxygenase (EC 1.13.11.32) 
MSITEMLGIQYPIFSGAMMRIATHELVGAVSEAGGLGVLGSAGLSAEQLRAEIQATRKLT
DKPFGVNLMLQMKNCPELAQVIIDEGVKVVTTGAGNPTSYIPPLHAAGIKVIPVIASVHH
AHKMVAAGADAVVAEGQESGGHIGQTSTMALLPQVVDAVDIPVIGAGGVGDGRSIAAMFA
LGAQGVQCGTIFLTAEECPVPASYKQRVLAASDTDTIVTGRSQRDPVRALVNPMLAQYLQ
LEQTNAPVAELHALADGSFAKAVEDGDMEHGTPMAGEVAGMMTTIRPVKEIIMTLFGQAR
EVAAQLKIE
Enzyme 1 Number of Residues 309
Enzyme 1 Molecular Weight 32055
Enzyme 1 Theoretical pI 4.97
Enzyme 1 GO Classification
Function
  • catalytic activity
  • oxidoreductase activity
Process
  • cellular metabolism
  • electron transport
  • generation of precursor metabolites and energy
  • metabolism
  • physiological process
Component
—
Enzyme 1 General Function Not Available
Enzyme 1 Specific Function Not Available
Enzyme 1 Pathways Not Available
Enzyme 1 Reactions
  • 2 2-nitropropane + O2 = 2 acetone + 2 nitrite [RN:R00025] ALL_REAC R00025
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein Not Available
Enzyme 1 UniProtKB/Swiss-Prot ID Q88Y76 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name Q88Y76_LACPL Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence Not Available
Enzyme 1 GenBank Gene ID AL935254 Link Image
Enzyme 1 GeneCard ID Not Available
Enzyme 1 GenAtlas ID Not Available
Enzyme 1 HGNC ID Not Available
Enzyme 1 Chromosome Location Not Available
Enzyme 1 Locus Not Available
Enzyme 1 SNPs Not Available
Enzyme 1 General References
  1. Kleerebezem M, Boekhorst J, van Kranenburg R, Molenaar D, Kuipers OP, Leer R, Tarchini R, Peters SA, Sandbrink HM, Fiers MW, Stiekema W, Lankhorst RM, Bron PA, Hoffer SM, Groot MN, Kerkhoven R, de Vries M, Ursing B, de Vos WM, Siezen RJ: Complete genome sequence of Lactobacillus plantarum WCFS1. Proc Natl Acad Sci U S A. 2003 Feb 18;100(4):1990-5. Epub 2003 Feb 3. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available