Showing metabocard for N-Acetylcadaverine (MMDBc0000821)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 22:03:46 UTC
Update Date2024-04-30 19:33:46 UTC
Metabolite IDMMDBc0000821
Metabolite Identification
Common NameN-Acetylcadaverine
DescriptionN-Acetylcadaverine is the acetylated form of the polyamine cadaverine. Cadaverine is produced by the breakdown of amino acids in living and dead organisms and is toxic in large doses. Cadaverine is largely responsible for the foul odor of putrefying flesh, but also contributes to the odor of such processes as bad breath and bacterial vaginosis. Cadaverine is also found in semen. Polyamines (and their acetylated forms) are known to be closely related with cell growth, cell proliferation, and synthesis of proteins and nucleic acids. Their concentrations are adjusted either by regulating the activity levels of the biosynthetic and catabolic reactions or by controlling the net direction of polyamine acetylation-deacetylation. In Alzheimer's disease (AD), the neurotoxic amyloid β-peptide is known to up-regulate polyamine metabolism by increasing ornithine decarboxylase activity and polyamine uptake by initiating free radical damage. Because of these findings, polyamines have been considered to play an important role in response to neurodegenerative conditions. Altered levels of polyamines have been found in tissue, hair and body fluids of patients with neuromuscular diseases and neurodegenerative conditions. (PMID: 17723614 ). N-Acetylcadaverine has been found to be a metabolite of several bacteria species (https://www.sciencedirect.com/science/article/pii/S209580991730423X).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f923803ba20>

R-Methylmalonyl-CoA.mol
  Mrv0541 02231219282D          

 10  9  0  0  0  0            999 V2000
    1.7862   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    0.8250    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  1  8  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007f923803ba20>

HMDB0002284
     RDKit          3D
N-Acetylcadaverine
 26 25  0  0  0  0  0  0  0  0999 V2000
    3.6482    1.7301   -0.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0779    0.3573   -0.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8945   -0.5985   -0.2333 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6893    0.1533    0.0410 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2251   -1.2105    0.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2747   -1.2733    0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9813   -0.6735   -0.7518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4725   -0.7001   -0.6081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9538    0.0547    0.5800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5803    1.4118    0.5240 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224    2.5213   -0.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5524    1.7757    0.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0091    1.8274   -1.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0751    0.9888    0.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7448   -1.6296    1.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4553   -1.7459   -0.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5286   -2.3697    0.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5729   -0.8759    1.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7261   -1.2737   -1.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6004    0.3625   -0.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0001   -0.4110   -1.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7696   -1.7798   -0.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0702   -0.0391    0.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5462   -0.4250    1.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2099    2.0948    0.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0074    1.7278   -0.2533 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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  0
  7 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f923803ba20>

R-Methylmalonyl-CoA.mol
  Mrv0541 02231219282D          

 10  9  0  0  0  0            999 V2000
    1.7862   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    0.8250    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  1  8  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000821

> <DATABASE_NAME>
MIME

> <SMILES>
CC(=O)NCCCCCN

> <INCHI_IDENTIFIER>
InChI=1S/C7H16N2O/c1-7(10)9-6-4-2-3-5-8/h2-6,8H2,1H3,(H,9,10)

> <INCHI_KEY>
RMOIHHAKNOFHOE-UHFFFAOYSA-N

> <FORMULA>
C7H16N2O

> <MOLECULAR_WEIGHT>
144.2147

> <EXACT_MASS>
144.126263144

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
17.35863562225048

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-(5-aminopentyl)acetamide

> <ALOGPS_LOGP>
-0.40

> <JCHEM_LOGP>
-0.5817049959999998

> <ALOGPS_LOGS>
-0.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.52551523406192

> <JCHEM_PKA_STRONGEST_BASIC>
10.205472849805181

> <JCHEM_POLAR_SURFACE_AREA>
55.12

> <JCHEM_REFRACTIVITY>
41.4234

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.37e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-acetylcadaverine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f923803ba20>

HMDB0002284
     RDKit          3D
N-Acetylcadaverine
 26 25  0  0  0  0  0  0  0  0999 V2000
    3.6482    1.7301   -0.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0779    0.3573   -0.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8945   -0.5985   -0.2333 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6893    0.1533    0.0410 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2251   -1.2105    0.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2747   -1.2733    0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9813   -0.6735   -0.7518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4725   -0.7001   -0.6081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9538    0.0547    0.5800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5803    1.4118    0.5240 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224    2.5213   -0.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5524    1.7757    0.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0091    1.8274   -1.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0751    0.9888    0.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7448   -1.6296    1.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4553   -1.7459   -0.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5286   -2.3697    0.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5729   -0.8759    1.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7261   -1.2737   -1.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6004    0.3625   -0.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0001   -0.4110   -1.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7696   -1.7798   -0.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0702   -0.0391    0.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5462   -0.4250    1.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2099    2.0948    0.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0074    1.7278   -0.2533 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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  0
  7 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
M  END
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PDB for #<Metabolite:0x00007f923803ba20>

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: R-Methylmalonyl-CoA.mol                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       3.334  -0.770   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.001  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.667  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.667  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.334  -1.540   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -4.668  -0.770   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       3.334   0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.001   1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.668   1.540   0.000  0.00  0.00           C+0
CONECT    1    2    8                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    9   10    1                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for #<Metabolite:0x00007f923803ba20>

COMPND    HMDB0002284
HETATM    1  C1  UNL     1       3.648   1.730  -0.355  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.078   0.357  -0.178  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.895  -0.598  -0.233  1.00  0.00           O  
HETATM    4  N1  UNL     1       1.689   0.153   0.041  1.00  0.00           N  
HETATM    5  C3  UNL     1       1.225  -1.210   0.202  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.275  -1.273   0.427  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.981  -0.674  -0.752  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.473  -0.700  -0.608  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.954   0.055   0.580  1.00  0.00           C  
HETATM   10  N2  UNL     1      -2.580   1.412   0.524  1.00  0.00           N  
HETATM   11  H1  UNL     1       2.922   2.521  -0.121  1.00  0.00           H  
HETATM   12  H2  UNL     1       4.552   1.776   0.308  1.00  0.00           H  
HETATM   13  H3  UNL     1       4.009   1.827  -1.409  1.00  0.00           H  
HETATM   14  H4  UNL     1       1.075   0.989   0.075  1.00  0.00           H  
HETATM   15  H5  UNL     1       1.745  -1.630   1.080  1.00  0.00           H  
HETATM   16  H6  UNL     1       1.455  -1.746  -0.736  1.00  0.00           H  
HETATM   17  H7  UNL     1      -0.529  -2.370   0.430  1.00  0.00           H  
HETATM   18  H8  UNL     1      -0.573  -0.876   1.395  1.00  0.00           H  
HETATM   19  H9  UNL     1      -0.726  -1.274  -1.664  1.00  0.00           H  
HETATM   20  H10 UNL     1      -0.600   0.363  -0.897  1.00  0.00           H  
HETATM   21  H11 UNL     1      -3.000  -0.411  -1.541  1.00  0.00           H  
HETATM   22  H12 UNL     1      -2.770  -1.780  -0.451  1.00  0.00           H  
HETATM   23  H13 UNL     1      -4.070  -0.039   0.616  1.00  0.00           H  
HETATM   24  H14 UNL     1      -2.546  -0.425   1.492  1.00  0.00           H  
HETATM   25  H15 UNL     1      -3.210   2.095   0.958  1.00  0.00           H  
HETATM   26  H16 UNL     1      -2.007   1.728  -0.253  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    3    4
CONECT    4    5   14
CONECT    5    6   15   16
CONECT    6    7   17   18
CONECT    7    8   19   20
CONECT    8    9   21   22
CONECT    9   10   23   24
CONECT   10   25   26
END
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SMILES for #<Metabolite:0x00007f923803ba20>

CC(=O)NCCCCCN
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INCHI for #<Metabolite:0x00007f923803ba20>

InChI=1S/C7H16N2O/c1-7(10)9-6-4-2-3-5-8/h2-6,8H2,1H3,(H,9,10)
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Synonyms
ValueSource
Monoacetyl cadaverineChEBI
MonoacetylcadaverineChEBI
AcetylcadaverineHMDB
N-(5-Aminopentyl)acetamideHMDB
Molecular FormulaC7H16N2O
Average Mass144.2147
Monoisotopic Mass144.126263144
IUPAC NameN-(5-aminopentyl)acetamide
Traditional NameN-acetylcadaverine
CAS Registry NumberNot Available
SMILES
CC(=O)NCCCCCN
InChI Identifier
InChI=1S/C7H16N2O/c1-7(10)9-6-4-2-3-5-8/h2-6,8H2,1H3,(H,9,10)
InChI KeyRMOIHHAKNOFHOE-UHFFFAOYSA-N