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Showing NP-Card for Acetone (NP0000233)

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Record Information
Version2.0
Created at2005-11-20 22:13:15 UTC
Updated at2022-02-22 15:10:17 UTC
NP-MRD IDNP0000233
Secondary Accession NumbersNone
Natural Product Identification
Common NameAcetone
DescriptionAcetone, or propanone, is an organic compound with the formula (CH3)2CO. It is the simplest and smallest ketone. It is a colourless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscible with water and serves as an important organic solvent in its own right, in industry, home, and laboratory. Acetone is produced and disposed of in the human body through normal metabolic processes. It is normally present in blood and urine. People with diabetic ketoacidosis produce it in larger amounts. 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, among others) 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. It is an irritant and inhalation may lead to hepatotoxic effects (causing liver damage). Acetone can be found in Clostridium (PMID: 685531 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000233 (Acetone)


  Mrv1652303252018062D          

  4  3  0  0  0  0            999 V2000
    0.7145   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
M  END
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3D MOL for NP0000233 (Acetone)

HMDB0001659
     RDKit          3D
Acetone
 10  9  0  0  0  0  0  0  0  0999 V2000
    1.2937    0.1215   -0.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0359   -0.2635    0.4921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3064    0.0502   -0.0672 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1173   -0.8546    1.5525 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1331    0.2818    0.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0841    1.0177   -0.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5647   -0.7035   -0.8796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8480    0.6660    0.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8260   -0.9283   -0.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2484    0.6129   -1.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  1  5  1  0
  1  6  1  0
  1  7  1  0
  3  8  1  0
  3  9  1  0
  3 10  1  0
M  END
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3D SDF for NP0000233 (Acetone)


  Mrv1652303252018062D          

  4  3  0  0  0  0            999 V2000
    0.7145   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000233

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C3H6O/c1-3(2)4/h1-2H3

> <INCHI_KEY>
CSCPPACGZOOCGX-UHFFFAOYSA-N

> <FORMULA>
C3H6O

> <MOLECULAR_WEIGHT>
58.0791

> <EXACT_MASS>
58.041864814

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
6.408374755692414

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
propan-2-one

> <ALOGPS_LOGP>
-0.29

> <JCHEM_LOGP>
0.1062798083333333

> <ALOGPS_LOGS>
0.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.511239590750403

> <JCHEM_PKA_STRONGEST_BASIC>
-7.194665505565277

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
16.1948

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.93e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetone

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0000233 (Acetone)

HMDB0001659
     RDKit          3D
Acetone
 10  9  0  0  0  0  0  0  0  0999 V2000
    1.2937    0.1215   -0.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0359   -0.2635    0.4921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3064    0.0502   -0.0672 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1173   -0.8546    1.5525 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1331    0.2818    0.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0841    1.0177   -0.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5647   -0.7035   -0.8796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8480    0.6660    0.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8260   -0.9283   -0.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2484    0.6129   -1.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  1  5  1  0
  1  6  1  0
  1  7  1  0
  3  8  1  0
  3  9  1  0
  3 10  1  0
M  END
Download

PDB for NP0000233 (Acetone)

HEADER    PROTEIN                                 25-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAR-20         0                                  
HETATM    1  C   UNK     0       1.334  -1.155   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -1.155   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000   1.155   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
MASTER        0    0    0    0    0    0    0    0    4    0    6    0
END
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3D PDB for NP0000233 (Acetone)

COMPND    HMDB0001659
HETATM    1  C1  UNL     1       1.294   0.122  -0.202  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.036  -0.264   0.492  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.306   0.050  -0.067  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.117  -0.855   1.552  1.00  0.00           O  
HETATM    5  H1  UNL     1       2.133   0.282   0.481  1.00  0.00           H  
HETATM    6  H2  UNL     1       1.084   1.018  -0.819  1.00  0.00           H  
HETATM    7  H3  UNL     1       1.565  -0.704  -0.880  1.00  0.00           H  
HETATM    8  H4  UNL     1      -1.848   0.666   0.686  1.00  0.00           H  
HETATM    9  H5  UNL     1      -1.826  -0.928  -0.241  1.00  0.00           H  
HETATM   10  H6  UNL     1      -1.248   0.613  -1.002  1.00  0.00           H  
CONECT    1    2    5    6    7
CONECT    2    3    4    4
CONECT    3    8    9   10
END
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SMILES for NP0000233 (Acetone)

CC(C)=O
Download

INCHI for NP0000233 (Acetone)

InChI=1S/C3H6O/c1-3(2)4/h1-2H3
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View in JSmol
Synonyms
ValueSource
2-PropanoneChEBI
AcetonChEBI
AzetonChEBI
beta-KetopropaneChEBI
Dimethyl ketoneChEBI
DimethylcetoneChEBI
DimethylketonChEBI
DimethylketoneChEBI
Methyl ketoneChEBI
PropanonChEBI
PropanoneChEBI
Pyroacetic etherChEBI
b-KetopropaneGenerator
Β-ketopropaneGenerator
DimethylformaldehydeHMDB
Chemical FormulaC3H6O
Average Mass58.0791 Da
Monoisotopic Mass58.04186 Da
IUPAC Namepropan-2-one
Traditional Nameacetone
CAS Registry Number67-64-1
SMILES
CC(C)=O
InChI Identifier
InChI=1S/C3H6O/c1-3(2)4/h1-2H3
InChI KeyCSCPPACGZOOCGX-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-02-22View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Allium cepa L.FooDB
    • J. F. Carson and Francis F. Wong. The Volatile Flavor Components of Onions. J. Agric. Food Chem. ...
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. italicaFooDB
    • Charles F. Forney, James P. Mattheis, and Rodney K. Austin. Volatile Compounds Produced by Brocco...
Bubalus bubalisFooDB
Campylobacter jejuni-
Cannabis sativaCannabisDB
      Not Available
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
Citrus aurantifoliaKNApSAcK Database
Citrus aurantiifoliaPlant
Citrus aurantiumKNApSAcK Database
Citrus grandisKNApSAcK Database
Citrus hystrixKNApSAcK Database
Citrus limonKNApSAcK Database
Citrus maximaPlant
Citrus paradisiKNApSAcK Database
Citrus reticulataKNApSAcK Database
Citrus sinensisKNApSAcK Database
Citrus X sinensis (L.) Osbeck (pro. sp.)Plant
Clostridium difficile-
ColumbaFooDB
ColumbidaeFooDB
Cymbopogon citratusFooDB
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Glycine maxFooDB
Lagopus mutaFooDB
Laurus nobilis L.FooDB
LeporidaeFooDB
Lepus timidusFooDB
Malus pumilaFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mentha aquaticaFooDB
Mentha spicataFooDB
Numida meleagrisFooDB
OdocoileusFooDB
Olea europaeaKNApSAcK Database
OryctolagusFooDB
Oryza sativaFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Pimenta dioicaFooDB
Prunus aviumFooDB
    • Bernalte, M. J., Hernandez, M. T., Vidal-Aragon, M. C. & Sabio, E. (1999) Physical, chemical, fla...
Psidium guajavaFooDB
Pyrus communisFooDB
Ribes nigrumFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum tuberosumFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Vigna radiataFooDB
Zea mays L.FooDB
    • LF. Flora and RC. Wiley. Flora and Wiley., 2007. Sweet corn aroma, chemical components and relati...
Zingiber officinaleFooDB
Species Where Detected
Species NameSourceReference
Homo sapiens (Exhaled breath)KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentKetones
Alternative Parents
Substituents
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-94.8 °CNot Available
Boiling Point56.00 to 57.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000 mg/mL at 25 °CNot Available
LogP-0.24Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility193 g/LALOGPS
logP-0.29ALOGPS
logP0.11ChemAxon
logS0.52ALOGPS
pKa (Strongest Acidic)19.51ChemAxon
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity16.19 m³·mol⁻¹ChemAxon
Polarizability6.41 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001659
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008301
KNApSAcK IDC00048304
Chemspider ID175
KEGG Compound IDC00207
BioCyc IDACETONE
BiGG ID34257
Wikipedia LinkAcetone
METLIN ID3745
PubChem Compound180
PDB IDNot Available
ChEBI ID15347
Good Scents IDrw1001331
References
General References
  1. 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:2587619 ]
  2. 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:15627241 ]
  3. 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:1389018 ]
  4. 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:16223475 ]
  5. 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:10611138 ]
  6. 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:2160776 ]
  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:12895231 ]
  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:11295672 ]
  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:7896568 ]
  10. Benz J: Antidiabetic agents and lactation. J Hum Lact. 1992 Mar;8(1):27-8. [PubMed:1558654 ]
  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:10233334 ]
  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:8668320 ]
  13. 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:2727843 ]
  14. Kalapos MP: Possible physiological roles of acetone metabolism in humans. Med Hypotheses. 1999 Sep;53(3):236-42. [PubMed:10580530 ]
  15. Abou-Zeid AA, Fouad M, Yassein M: Microbiological production of acetone-butanol by Clostridium acetobutylicum. Zentralbl Bakteriol Naturwiss. 1978;133(2):125-34. doi: 10.1016/s0323-6056(78)80023-8. [PubMed:685531 ]
  16. Ganji MD, Rezvani M: Boron nitride nanotube based nanosensor for acetone adsorption: a DFT simulation. J Mol Model. 2013 Mar;19(3):1259-65. doi: 10.1007/s00894-012-1668-9. Epub 2012 Nov 20. [PubMed:23179768 ]