Showing metabocard for Acetamidopropanal (MMDBc0032084)

Plant
Animal
Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-11-18 02:01:33 UTC
Update Date2025-11-05 17:13:03 UTC
Metabolite IDMMDBc0032084
Metabolite Identification
Common NameAcetamidopropanal
DescriptionAcetamidopropanal is a member of the aldehyde chemical class, specifically categorized as an acetoamidoaldehyde. It is produced during the oxidative degradation of polyamines, such as spermine and N(1)-acetylspermine, through the action of polyamine oxidase (PAO). The metabolic pathways involving acetamidopropanal are significant, as they contribute to various biological processes, including isoprenoid biosynthesis and carbohydrate metabolism, which are essential for flowering (PMID:39365353 ). Additionally, acetamidopropanal is implicated in neurodegenerative mechanisms due to its cytotoxic effects alongside other aldehydes, such as hydrogen peroxide and 3-aminopropanal, in retinal ganglion cells (PMID:17362887 ). The enzymatic activity of PAO not only generates acetamidopropanal but also produces hydrogen peroxide, which is known for its cytotoxic properties (PMID:12095537 ). Furthermore, research has shown that acetamidopropanal can influence cellular apoptosis and proliferation, highlighting its role in cellular stress responses (PMID:168 ...). Overall, acetamidopropanal serves as a crucial metabolite in polyamine metabolism with implications for both plant biology and neurobiology.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x000056431ffb1860>


  Mrv1652303102016462D          

  8  7  0  0  0  0            999 V2000
   10.2910   -9.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7660   -8.4831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3535   -9.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5909   -8.4831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1160   -9.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5285   -9.1977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0034   -7.7692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5285  -10.6268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  2  0  0  0  0
  5  8  2  0  0  0  0
  5  6  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x000056431ffb1860>

HMDB0012880
     RDKit          3D
Acetamidopropanal
 17 16  0  0  0  0  0  0  0  0999 V2000
    2.8357    0.0318    0.7410 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6629    0.4986   -0.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8529    1.4959   -0.7937 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3961   -0.1202    0.0203 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6922    0.3817   -0.7660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9653   -0.3755   -0.5890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4563   -0.3627    0.8076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4870   -0.9501    1.0618 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4953   -0.2664    1.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3244   -0.8490    0.2976 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5666    0.8525    0.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2397   -0.9352    0.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8349    1.4530   -0.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4011    0.2987   -1.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8521   -1.4247   -0.9370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7452    0.1299   -1.2062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9395    0.1418    1.5950 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  2  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  4 12  1  0
  5 13  1  0
  5 14  1  0
  6 15  1  0
  6 16  1  0
  7 17  1  0
M  END
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3D SDF for #<Metabolite:0x000056431ffb1860>


  Mrv1652303102016462D          

  8  7  0  0  0  0            999 V2000
   10.2910   -9.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7660   -8.4831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3535   -9.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5909   -8.4831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1160   -9.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5285   -9.1977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0034   -7.7692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5285  -10.6268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  2  0  0  0  0
  5  8  2  0  0  0  0
  5  6  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032084

> <DATABASE_NAME>
MIME

> <SMILES>
CC(=O)NCCC=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H9NO2/c1-5(8)6-3-2-4-7/h4H,2-3H2,1H3,(H,6,8)

> <INCHI_KEY>
ARJPPNFIEQKVBB-UHFFFAOYSA-N

> <FORMULA>
C5H9NO2

> <MOLECULAR_WEIGHT>
115.1305

> <EXACT_MASS>
115.063328537

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
11.83593905076419

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-(3-oxopropyl)acetamide

> <ALOGPS_LOGP>
-0.72

> <JCHEM_LOGP>
-1.2502324700000003

> <ALOGPS_LOGS>
-0.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.100719410678707

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.664120946997095

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5718537368583139

> <JCHEM_POLAR_SURFACE_AREA>
46.17

> <JCHEM_REFRACTIVITY>
29.221200000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.02e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-acetamidopropanal

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x000056431ffb1860>

HMDB0012880
     RDKit          3D
Acetamidopropanal
 17 16  0  0  0  0  0  0  0  0999 V2000
    2.8357    0.0318    0.7410 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6629    0.4986   -0.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8529    1.4959   -0.7937 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3961   -0.1202    0.0203 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6922    0.3817   -0.7660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9653   -0.3755   -0.5890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4563   -0.3627    0.8076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4870   -0.9501    1.0618 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4953   -0.2664    1.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3244   -0.8490    0.2976 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5666    0.8525    0.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2397   -0.9352    0.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8349    1.4530   -0.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4011    0.2987   -1.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8521   -1.4247   -0.9370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7452    0.1299   -1.2062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9395    0.1418    1.5950 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  2  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  4 12  1  0
  5 13  1  0
  5 14  1  0
  6 15  1  0
  6 16  1  0
  7 17  1  0
M  END
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PDB for #<Metabolite:0x000056431ffb1860>

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0      19.210 -18.503   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      23.830 -15.835   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.060 -17.169   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.370 -15.835   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.750 -18.503   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      21.520 -17.169   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0      26.140 -14.503   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      21.520 -19.837   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    3    4                                                       
CONECT    3    2    6                                                       
CONECT    4    2    7                                                       
CONECT    5    1    8    6                                                  
CONECT    6    3    5                                                       
CONECT    7    4                                                            
CONECT    8    5                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for #<Metabolite:0x000056431ffb1860>

COMPND    HMDB0012880
HETATM    1  C1  UNL     1       2.836   0.032   0.741  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.663   0.499  -0.046  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.853   1.496  -0.794  1.00  0.00           O  
HETATM    4  N1  UNL     1       0.396  -0.120   0.020  1.00  0.00           N  
HETATM    5  C3  UNL     1      -0.692   0.382  -0.766  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.965  -0.376  -0.589  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.456  -0.363   0.808  1.00  0.00           C  
HETATM    8  O2  UNL     1      -3.487  -0.950   1.062  1.00  0.00           O  
HETATM    9  H1  UNL     1       2.495  -0.266   1.772  1.00  0.00           H  
HETATM   10  H2  UNL     1       3.324  -0.849   0.298  1.00  0.00           H  
HETATM   11  H3  UNL     1       3.567   0.853   0.894  1.00  0.00           H  
HETATM   12  H4  UNL     1       0.240  -0.935   0.631  1.00  0.00           H  
HETATM   13  H5  UNL     1      -0.835   1.453  -0.556  1.00  0.00           H  
HETATM   14  H6  UNL     1      -0.401   0.299  -1.841  1.00  0.00           H  
HETATM   15  H7  UNL     1      -1.852  -1.425  -0.937  1.00  0.00           H  
HETATM   16  H8  UNL     1      -2.745   0.130  -1.206  1.00  0.00           H  
HETATM   17  H9  UNL     1      -1.939   0.142   1.595  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    3    4
CONECT    4    5   12
CONECT    5    6   13   14
CONECT    6    7   15   16
CONECT    7    8    8   17
END
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SMILES for #<Metabolite:0x000056431ffb1860>

CC(=O)NCCC=O
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INCHI for #<Metabolite:0x000056431ffb1860>

InChI=1S/C5H9NO2/c1-5(8)6-3-2-4-7/h4H,2-3H2,1H3,(H,6,8)
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Synonyms
ValueSource
N-(3-Oxopropyl)acetamideHMDB
3-AcetamidopropanalHMDB
3AAPHMDB
Molecular FormulaC5H9NO2
Average Mass115.1305
Monoisotopic Mass115.063328537
IUPAC NameN-(3-oxopropyl)acetamide
Traditional Name3-acetamidopropanal
CAS Registry NumberNot Available
SMILES
CC(=O)NCCC=O
InChI Identifier
InChI=1S/C5H9NO2/c1-5(8)6-3-2-4-7/h4H,2-3H2,1H3,(H,6,8)
InChI KeyARJPPNFIEQKVBB-UHFFFAOYSA-N