Showing metabocard for Acetone (MMDBc0000201)

Not Available
Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:39:33 UTC
Update Date2024-09-27 17:17:39 UTC
Metabolite IDMMDBc0000201
Metabolite Identification
Common NameAcetone
DescriptionAcetone 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. It is an irritant and inhalation may lead to hepatotoxic effects (causing liver damage). Acetone can be found in Clostridium (PMID: 685531 ) (https://www.sciencedirect.com/science/article/pii/S0079635206800470).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fdb4d1cda88>


  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 #<Metabolite:0x00007fdb4d1cda88>

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 #<Metabolite:0x00007fdb4d1cda88>


  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>
MMDBc0000201

> <DATABASE_NAME>
MIME

> <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

$$$$
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3D-SDF for #<Metabolite:0x00007fdb4d1cda88>

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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PDB for #<Metabolite:0x00007fdb4d1cda88>

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 #<Metabolite:0x00007fdb4d1cda88>

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 #<Metabolite:0x00007fdb4d1cda88>

CC(C)=O
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INCHI for #<Metabolite:0x00007fdb4d1cda88>

InChI=1S/C3H6O/c1-3(2)4/h1-2H3
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Synonyms
ValueSource
2-PropanoneChEBI
AcetonChEBI
AzetonChEBI
beta-KetopropaneChEBI
Dimethyl ketoneChEBI
DimethylcetoneChEBI
DimethylketonChEBI
DimethylketoneChEBI
Methyl ketoneChEBI
PropanonChEBI
PropanoneChEBI
Pyroacetic etherChEBI
b-KetopropaneGenerator
Β-ketopropaneGenerator
DimethylformaldehydeHMDB
Molecular FormulaC3H6O
Average Mass58.0791
Monoisotopic Mass58.041864814
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