Showing metabocard for 2-Aminomuconic acid semialdehyde (MMDBc0048258)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-04-29 21:54:55 UTC
Update Date2024-04-30 20:36:07 UTC
Metabolite IDMMDBc0048258
Metabolite Identification
Common Name2-Aminomuconic acid semialdehyde
Description2-aminomuconic semialdehyde is an intermediate in the oxidative metabolism of tryptophan in mammals, and takes place via the kynurenine pathway, which is also used for NAD biosynthesis in all eukaryotic organisms. 2-Aminomuconic semialdehyde is reported to be unstable and spontaneously converted to picolinic acid (regarded as metabolically inert and is excreted in the urine as a glycine conjugate), and enzymatically converted to 2-aminomuconic acid through the action of 2-aminomuconic semialdehyde dehydrogenase. (PMID: 10510494 , 16267312 , 14275129 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fecf4054748>


  Mrv0541 02231219022D          

 10  9  0  0  0  0            999 V2000
    0.4715    0.7921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2602    1.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4715    0.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1882    1.0863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0863    0.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0830   -0.1320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0939   -0.1659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0826   -0.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3621   -1.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3545   -1.8747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  2  0  0  0  0
  5  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fecf4054748>

HMDB0001280
     RDKit          3D
2-Aminomuconic acid semialdehyde
 17 16  0  0  0  0  0  0  0  0999 V2000
    2.1725   -0.9329   -0.4176 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1562    0.0340    0.0098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1010   -0.2824   -0.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1857    0.5713    0.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4640    0.2370    0.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8567   -1.0083   -0.5993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0995   -1.2202   -0.7356 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5934    1.2539    0.5991 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8753    2.1595    1.0062 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9738    1.4511    0.7324 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9955   -0.5156   -0.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0975   -1.9333   -0.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2910   -1.2808   -0.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0151    1.5253    0.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2006    0.9886    0.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1378   -1.7350   -0.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4871    0.6876    1.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  2  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  6 16  1  0
 10 17  1  0
M  END
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3D SDF for #<Metabolite:0x00007fecf4054748>


  Mrv0541 02231219022D          

 10  9  0  0  0  0            999 V2000
    0.4715    0.7921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2602    1.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4715    0.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1882    1.0863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0863    0.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0830   -0.1320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0939   -0.1659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0826   -0.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3621   -1.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3545   -1.8747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  2  0  0  0  0
  5  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0048258

> <DATABASE_NAME>
MIME

> <SMILES>
N\C(=C\C=C/C=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H7NO3/c7-5(6(9)10)3-1-2-4-8/h1-4H,7H2,(H,9,10)/b2-1-,5-3+

> <INCHI_KEY>
QCGTZPZKJPTAEP-REDYYMJGSA-N

> <FORMULA>
C6H7NO3

> <MOLECULAR_WEIGHT>
141.1247

> <EXACT_MASS>
141.042593095

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
12.955028553813651

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,4Z)-2-amino-6-oxohexa-2,4-dienoic acid

> <ALOGPS_LOGP>
-0.14

> <JCHEM_LOGP>
-3.074032307631351

> <ALOGPS_LOGS>
-1.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.759990591792232

> <JCHEM_PKA_STRONGEST_BASIC>
7.719389495707983

> <JCHEM_POLAR_SURFACE_AREA>
80.39

> <JCHEM_REFRACTIVITY>
37.6251

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.90e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-aminomuconic semialdehyde

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007fecf4054748>

HMDB0001280
     RDKit          3D
2-Aminomuconic acid semialdehyde
 17 16  0  0  0  0  0  0  0  0999 V2000
    2.1725   -0.9329   -0.4176 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1562    0.0340    0.0098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1010   -0.2824   -0.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1857    0.5713    0.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4640    0.2370    0.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8567   -1.0083   -0.5993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0995   -1.2202   -0.7356 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5934    1.2539    0.5991 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8753    2.1595    1.0062 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9738    1.4511    0.7324 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9955   -0.5156   -0.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0975   -1.9333   -0.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2910   -1.2808   -0.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0151    1.5253    0.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2006    0.9886    0.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1378   -1.7350   -0.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4871    0.6876    1.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  2  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  6 16  1  0
 10 17  1  0
M  END
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PDB for #<Metabolite:0x00007fecf4054748>

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       0.880   1.479   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.486   2.119   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.880   0.310   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       2.218   2.028   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -2.028   1.288   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.155  -0.246   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.042  -0.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.021  -1.204   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.676  -1.964   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.662  -3.499   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6    7                                                  
CONECT    4    1                                                            
CONECT    5    2    8                                                       
CONECT    6    3                                                            
CONECT    7    3                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for #<Metabolite:0x00007fecf4054748>

COMPND    HMDB0001280
HETATM    1  N1  UNL     1       2.172  -0.933  -0.418  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.156   0.034   0.010  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.101  -0.282  -0.176  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.186   0.571   0.196  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.464   0.237   0.001  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.857  -1.008  -0.599  1.00  0.00           C  
HETATM    7  O1  UNL     1      -4.100  -1.220  -0.736  1.00  0.00           O  
HETATM    8  C6  UNL     1       1.593   1.254   0.599  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.875   2.159   1.006  1.00  0.00           O  
HETATM   10  O3  UNL     1       2.974   1.451   0.732  1.00  0.00           O  
HETATM   11  H1  UNL     1       2.996  -0.516  -0.878  1.00  0.00           H  
HETATM   12  H2  UNL     1       2.098  -1.933  -0.284  1.00  0.00           H  
HETATM   13  H3  UNL     1      -0.291  -1.281  -0.654  1.00  0.00           H  
HETATM   14  H4  UNL     1      -1.015   1.525   0.652  1.00  0.00           H  
HETATM   15  H5  UNL     1      -3.201   0.989   0.334  1.00  0.00           H  
HETATM   16  H6  UNL     1      -2.138  -1.735  -0.922  1.00  0.00           H  
HETATM   17  H7  UNL     1       3.487   0.688   1.136  1.00  0.00           H  
CONECT    1    2   11   12
CONECT    2    3    3    8
CONECT    3    4   13
CONECT    4    5    5   14
CONECT    5    6   15
CONECT    6    7    7   16
CONECT    8    9    9   10
CONECT   10   17
END
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SMILES for #<Metabolite:0x00007fecf4054748>

N\C(=C\C=C/C=O)C(O)=O
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INCHI for #<Metabolite:0x00007fecf4054748>

InChI=1S/C6H7NO3/c7-5(6(9)10)3-1-2-4-8/h1-4H,7H2,(H,9,10)/b2-1-,5-3+
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Synonyms
ValueSource
2-Aminomuconate 6-semialdehydeChEBI
2-Aminomuconate semialdehydeChEBI
2-Aminomuconic semialdehydeChEBI
2-Aminomuconic acid 6-semialdehydeGenerator
Molecular FormulaC6H7NO3
Average Mass141.1247
Monoisotopic Mass141.042593095
IUPAC Name(2E,4Z)-2-amino-6-oxohexa-2,4-dienoic acid
Traditional Name2-aminomuconic semialdehyde
CAS Registry Number245128-91-0
SMILES
N\C(=C\C=C/C=O)C(O)=O
InChI Identifier
InChI=1S/C6H7NO3/c7-5(6(9)10)3-1-2-4-8/h1-4H,7H2,(H,9,10)/b2-1-,5-3+
InChI KeyQCGTZPZKJPTAEP-REDYYMJGSA-N