MiMeDB: Showing metabocard for Porphobilinogen (MMDBc0029486)

Plant

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:24:15 UTC

Update Date

2022-08-31 10:31:41 UTC

Metabolite ID

MMDBc0029486

Metabolite Identification

Common Name

Porphobilinogen

Description

Porphobilinogen is a pyrrole involved in porphyrin metabolism. -- Wikipedia ; It consists of a pyrrole ring with acetyl, propionyl, and aminomethyl side chains; It is a key monopyrrolic intermediate in porphyrin, chlorophyll and vitamin B12 biosynthesis. Porphobilinogen is generated by the enzyme ALA dehydratase by combining two molecules of dALA together, and converted into hydroxymethyl bilane by the enzyme porphobilinogen deaminase. 4 molecules of porphobilinogen are condensed to form one molecule of uroporphyrinogen I, which is then converted successively to coproporphyrinogen I, protoporphyrin IX, and heme.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0000245
     RDKit          3D
Porphobilinogen
 30 30  0  0  0  0  0  0  0  0999 V2000
   -3.9164   -1.4425    0.2449 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7954   -1.2230   -0.5285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4073   -1.2023    0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6947   -2.1037    0.6901 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5998   -1.6640    0.8588 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6882   -0.4106    0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8620    0.4735    0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1795   -0.1118    0.4234 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2164    0.6146   -0.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7950    1.0909   -1.5364 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4958    0.7384   -0.0777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5522   -0.0986   -0.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0848    1.1685   -0.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0802    1.6673    0.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3393    1.0868    1.5125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7176    2.8498    0.2446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5330   -2.2451    0.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6182   -0.5724    0.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8219   -0.6435   -1.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6559   -2.3337   -1.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9634   -3.0782    1.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4498   -2.1771    1.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6476    1.4210    0.6265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8299    0.7737   -1.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4514    0.0627    1.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2413   -1.1635    0.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9860    1.6289    0.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2550    1.9669   -0.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5215    1.2510   -1.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4858    3.6757   -0.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  6 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 12  3  2  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
 11 27  1  0
 13 28  1  0
 13 29  1  0
 16 30  1  0
M  END


  Mrv1652309032023582D          

 16 16  0  0  0  0            999 V2000
 9998.5088 9999.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.7953 9999.6341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.0801 9999.2200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.795310000.4597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.7728 9999.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4898 9999.6341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.2048 9999.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.9198 9999.6341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.2048 9998.3941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.273010000.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.273010001.6458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.653110000.9003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.985710000.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2406 9999.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0656 9999.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.320510000.4153    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
  2  4  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
 10 11  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 12 13  1  0  0  0  0
 12 16  1  0  0  0  0
  1 14  1  0  0  0  0
 15  5  1  0  0  0  0
 13 10  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029486

> <DATABASE_NAME>
MIME

> <SMILES>
NCC1=C(CC(O)=O)C(CCC(O)=O)=CN1

> <INCHI_IDENTIFIER>
InChI=1S/C10H14N2O4/c11-4-8-7(3-10(15)16)6(5-12-8)1-2-9(13)14/h5,12H,1-4,11H2,(H,13,14)(H,15,16)

> <INCHI_KEY>
QSHWIQZFGQKFMA-UHFFFAOYSA-N

> <FORMULA>
C10H14N2O4

> <MOLECULAR_WEIGHT>
226.2292

> <EXACT_MASS>
226.095356946

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
22.557878019255046

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[5-(aminomethyl)-4-(carboxymethyl)-1H-pyrrol-3-yl]propanoic acid

> <ALOGPS_LOGP>
-2.40

> <JCHEM_LOGP>
-2.6797758986088773

> <ALOGPS_LOGS>
-1.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.3999884503565605

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6647253376201103

> <JCHEM_PKA_STRONGEST_BASIC>
8.782950994059014

> <JCHEM_POLAR_SURFACE_AREA>
116.41

> <JCHEM_REFRACTIVITY>
56.3839

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.72e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
porphobilinogen

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000245
     RDKit          3D
Porphobilinogen
 30 30  0  0  0  0  0  0  0  0999 V2000
   -3.9164   -1.4425    0.2449 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7954   -1.2230   -0.5285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4073   -1.2023    0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6947   -2.1037    0.6901 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5998   -1.6640    0.8588 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6882   -0.4106    0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8620    0.4735    0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1795   -0.1118    0.4234 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2164    0.6146   -0.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7950    1.0909   -1.5364 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4958    0.7384   -0.0777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5522   -0.0986   -0.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0848    1.1685   -0.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0802    1.6673    0.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3393    1.0868    1.5125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7176    2.8498    0.2446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5330   -2.2451    0.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6182   -0.5724    0.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8219   -0.6435   -1.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6559   -2.3337   -1.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9634   -3.0782    1.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4498   -2.1771    1.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6476    1.4210    0.6265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8299    0.7737   -1.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4514    0.0627    1.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2413   -1.1635    0.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9860    1.6289    0.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2550    1.9669   -0.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5215    1.2510   -1.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4858    3.6757   -0.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  6 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 12  3  2  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
 11 27  1  0
 13 28  1  0
 13 29  1  0
 16 30  1  0
M  END

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  C   UNK     0    8663.8838665.211   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8662.5518665.984   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8661.2168665.211   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8662.5518667.525   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8668.1098665.211   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8669.4488665.984   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8670.7828665.211   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8672.1178665.984   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8670.7828663.669   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8663.4438668.196   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0    8663.4438669.739   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0    8666.0198668.347   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0    8664.7738667.442   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8665.2498665.977   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8666.7898665.977   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8667.2658667.442   0.000  0.00  0.00           C+0
CONECT    1    2   14                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    6   15                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10   11   13                                                       
CONECT   11   10                                                            
CONECT   12   13   16                                                       
CONECT   13   14   12   10                                                  
CONECT   14   13   15    1                                                  
CONECT   15   14   16    5                                                  
CONECT   16   15   12                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0000245
HETATM    1  N1  UNL     1      -3.916  -1.443   0.245  1.00  0.00           N  
HETATM    2  C1  UNL     1      -2.795  -1.223  -0.529  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.407  -1.202   0.117  1.00  0.00           C  
HETATM    4  N2  UNL     1      -0.695  -2.104   0.690  1.00  0.00           N  
HETATM    5  C3  UNL     1       0.600  -1.664   0.859  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.688  -0.411   0.350  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.862   0.474   0.034  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.179  -0.112   0.423  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.216   0.615  -0.432  1.00  0.00           C  
HETATM   10  O1  UNL     1       3.795   1.091  -1.536  1.00  0.00           O  
HETATM   11  O2  UNL     1       5.496   0.738  -0.078  1.00  0.00           O  
HETATM   12  C8  UNL     1      -0.552  -0.099  -0.104  1.00  0.00           C  
HETATM   13  C9  UNL     1      -1.085   1.169  -0.604  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.080   1.667   0.454  1.00  0.00           C  
HETATM   15  O3  UNL     1      -2.339   1.087   1.513  1.00  0.00           O  
HETATM   16  O4  UNL     1      -2.718   2.850   0.245  1.00  0.00           O  
HETATM   17  H1  UNL     1      -4.533  -2.245   0.142  1.00  0.00           H  
HETATM   18  H2  UNL     1      -4.618  -0.572   0.020  1.00  0.00           H  
HETATM   19  H3  UNL     1      -2.822  -0.643  -1.469  1.00  0.00           H  
HETATM   20  H4  UNL     1      -2.656  -2.334  -1.094  1.00  0.00           H  
HETATM   21  H5  UNL     1      -0.963  -3.078   1.003  1.00  0.00           H  
HETATM   22  H6  UNL     1       1.450  -2.177   1.328  1.00  0.00           H  
HETATM   23  H7  UNL     1       1.648   1.421   0.627  1.00  0.00           H  
HETATM   24  H8  UNL     1       1.830   0.774  -1.020  1.00  0.00           H  
HETATM   25  H9  UNL     1       3.451   0.063   1.522  1.00  0.00           H  
HETATM   26  H10 UNL     1       3.241  -1.163   0.219  1.00  0.00           H  
HETATM   27  H11 UNL     1       5.986   1.629   0.117  1.00  0.00           H  
HETATM   28  H12 UNL     1      -0.255   1.967  -0.559  1.00  0.00           H  
HETATM   29  H13 UNL     1      -1.522   1.251  -1.572  1.00  0.00           H  
HETATM   30  H14 UNL     1      -2.486   3.676  -0.178  1.00  0.00           H  
CONECT    1    2   17   18
CONECT    2    3   19   20
CONECT    3    4   12   12
CONECT    4    5   21
CONECT    5    6    6   22
CONECT    6    7   12
CONECT    7    8   23   24
CONECT    8    9   25   26
CONECT    9   10   10   11
CONECT   11   27
CONECT   12   13
CONECT   13   14   28   29
CONECT   14   15   15   16
CONECT   16   30
END

HMDB0000245
     RDKit          3D
Porphobilinogen
 30 30  0  0  0  0  0  0  0  0999 V2000
   -3.9164   -1.4425    0.2449 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7954   -1.2230   -0.5285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4073   -1.2023    0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6947   -2.1037    0.6901 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5998   -1.6640    0.8588 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6882   -0.4106    0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8620    0.4735    0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1795   -0.1118    0.4234 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2164    0.6146   -0.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7950    1.0909   -1.5364 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4958    0.7384   -0.0777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5522   -0.0986   -0.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0848    1.1685   -0.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0802    1.6673    0.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3393    1.0868    1.5125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7176    2.8498    0.2446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5330   -2.2451    0.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6182   -0.5724    0.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8219   -0.6435   -1.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6559   -2.3337   -1.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9634   -3.0782    1.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4498   -2.1771    1.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6476    1.4210    0.6265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8299    0.7737   -1.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4514    0.0627    1.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2413   -1.1635    0.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9860    1.6289    0.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2550    1.9669   -0.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5215    1.2510   -1.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4858    3.6757   -0.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  6 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 12  3  2  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
 11 27  1  0
 13 28  1  0
 13 29  1  0
 16 30  1  0
M  END

Synonyms

Value	Source
5-(Aminomethyl)-4-(carboxymethyl)-pyrrole-3-propionate	HMDB
5-(Aminomethyl)-4-(carboxymethyl)-pyrrole-3-propionic acid	HMDB
PBG	HMDB
Porphobilinogen	HMDB

Molecular Formula

C₁₀H₁₄N₂O₄

Average Mass

226.2292

Monoisotopic Mass

226.095356946

IUPAC Name

3-[5-(aminomethyl)-4-(carboxymethyl)-1H-pyrrol-3-yl]propanoic acid

Traditional Name

porphobilinogen

CAS Registry Number

487-90-1

SMILES

NCC1=C(CC(O)=O)C(CCC(O)=O)=CN1

InChI Identifier

InChI=1S/C10H14N2O4/c11-4-8-7(3-10(15)16)6(5-12-8)1-2-9(13)14/h5,12H,1-4,11H2,(H,13,14)(H,15,16)

InChI Key

QSHWIQZFGQKFMA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Aralkylamines

Alternative Parents

Substituents

Aralkylamine
Dicarboxylic acid or derivatives
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Amino acid
Amino acid or derivatives
Carboxylic acid derivative
Azacycle
Carboxylic acid
Organoheterocyclic compound
Organopnictogen compound
Primary amine
Organooxygen compound
Primary aliphatic amine
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dicarboxylic acid (CHEBI:17381 )
pyrroles (CHEBI:17381 )
aralkylamino compound (CHEBI:17381 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	2.72 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-2.7	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	3.66	ChemAxon
pKa (Strongest Basic)	8.78	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.41 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	56.38 m³·mol⁻¹	ChemAxon
Polarizability	22.56 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Erythrocyte
Feces
Liver
Urine

Tissue Locations

Erythrocyte
Liver

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192026	Porphobilinogen deaminase	Unknown	P08397	Homo_sapiens
MMDBp0192669	Delta-aminolevulinic acid dehydratase	Unknown	P13716	Homo_sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Acute intermittent porphyria	Increased	Association	Human Urine	HMDB	23908454
Porphyria	Increased	Association	Human Blood	HMDB	16497943

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	408	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; Cattle ; Sheep ; Dog ; Lion ; Chicken ; American dog tick	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	330	Pig ; Human feces; Human ; Cattle ; Catfish	Metabolic reconstruction
Bacteria	Actinobacteria	109	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Cattle	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	49	Human feces; Human	Metabolic reconstruction
Archaea	Thaumarchaeota	1	Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Bacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	5	Human feces; Cattle ; Human	Metabolic reconstruction
Bacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1	Human feces	Metabolic reconstruction
Archaea/Archaea	Crenarchaeota	17	Human feces	Metabolic reconstruction
Bacteria	Aquificae	1
Archaea/Archaea	Euryarchaeota	13	Human feces; Cattle ; Human	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	10	Human feces	Unknown
Bacteria	Chlorobi	11
Bacteria	Chlamydiae	3	Human
Bacteria	Deinococcus-Thermus	5
Bacteria	Cyanobacteria	21
Bacteria	Acidobacteria	1
Archaea/Archaea	Thaumarchaeota	1	Human feces	Metabolic reconstruction
Bacteria	Chloroflexi	2
Bacteria	nah	1
Bacteria/NULL	Proteobacteria	1	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; Cattle ; Sheep ; Dog ; Lion ; Chicken ; American dog tick	Unknown; Metabolic reconstruction
Archaea	nah	1

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified								HMDB
Human	Detected and Quantified	17.2		74.9	41.6	Adult (>18 years old)	Both	Acute intermittent porphyria	HMDB	23908454
Human	Detected and Quantified	2.3		5.1	2.9	Adult (>18 years old)	Both	Asymptomatic acute intermittent porphyria	HMDB	23908454
Human	Detected and Quantified	57.1		19.6	132.7	Adult (>18 years old)	Both	Acute intermittent porphyria	HMDB	23908454
Human	Detected and Quantified	9.7		21.8	10.5	Adult (>18 years old)	Both	Acute intermittent porphyria	HMDB	23908454
Human	Detected and Quantified	3.1	1.0			Adult (>18 years old)	Both	Porphyria	HMDB	16497943
Human	Detected and Quantified			0.589	0.654	Adult (>18 years old)	Male	Protoporphyria, Erythropoietic	HMDB	13765301
Human	Detected and Quantified			0	1.5	Adult (>18 years old)	Both	Normal	HMDB	23908454
Human	Detected and Quantified	0.06		0.00	0.12	Adult (>18 years old)	Both	Normal	HMDB	16497943
Human	Detected and Quantified	0.29	0.14			Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human	Detected and Quantified	0.31	0.13			Children (1-13 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human	Detected and Quantified	<=0.579				Adult (>18 years old)	Both	Normal	HMDB	Merck Manual of Diagnosis and Therapy.
Human Erythrocyte	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0000245

DrugBank ID

DB02272

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Porphobilinogen

METLIN ID

Not Available

PubChem Compound

1021

PDB ID

Not Available

ChEBI ID

17381

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Dhar GJ, Bossenmaier I, Petryka ZJ, Cardinal R, Watson CJ: Effects of hematin in hepatic porphyria. Further studies. Ann Intern Med. 1975 Jul;83(1):20-30. doi: 10.7326/0003-4819-83-1-20. [PubMed:1147435 ]
Sassa S, Solish G, Levere RD, Kappas A: Studies in porphyria. IV. Expression of the gene defect of acute intermittent porphyria in cultured human skin fibroblasts and amniotic cells: prenatal diagnosis of the porphyric trait. J Exp Med. 1975 Sep 1;142(3):722-31. doi: 10.1084/jem.142.3.722. [PubMed:1165472 ]
Shiue JW, Lee FY, Hsiao KJ, Tsai YT, Lee SD, Wu SJ: Abnormal thyroid function and hypercholesterolemia in a case of acute intermittent porphyria. Taiwan Yi Xue Hui Za Zhi. 1989 Jul;88(7):729-31. [PubMed:2809566 ]
Winkelman JW, Collins GH: Neurotoxicity of tetraphenylporphinesulfonate TPPS4 and its relation to photodynamic therapy. Photochem Photobiol. 1987 Nov;46(5):801-7. doi: 10.1111/j.1751-1097.1987.tb04851.x. [PubMed:3441503 ]
Buchet JP, Lauwerys R, Hassoun A, Dratwa M, Wens R, Collart F, Tielemans C: Effect of aluminum on porphyrin metabolism in hemodialyzed patients. Nephron. 1987;46(4):360-3. doi: 10.1159/000184390. [PubMed:3658064 ]
Hsiao KJ, Lee FY, Wu SJ, Chang WJ: Determination of erythrocyte porphobilinogen deaminase activity using porphobilinogen as substrate. Clin Chim Acta. 1987 Sep 30;168(2):257-8. doi: 10.1016/0009-8981(87)90296-8. [PubMed:3677422 ]
Tishler PV, Woodward B, O'Connor J, Holbrook DA, Seidman LJ, Hallett M, Knighton DJ: High prevalence of intermittent acute porphyria in a psychiatric patient population. Am J Psychiatry. 1985 Dec;142(12):1430-6. doi: 10.1176/ajp.142.12.1430. [PubMed:4073306 ]
Ivanov E, Pisanets M: Studies on the biosynthesis of porphyrins in erythrocytes after incubation with delta-aminolevulinic acid: an attempt to investigate the pathogenesis of nephrogenic anemia. Acta Biol Med Ger. 1982;41(4):307-13. [PubMed:7124248 ]
Mustajoki P: Normal erythrocyte uroporphyrinogen I synthase in a kindred with acute intermittent porphyria. Ann Intern Med. 1981 Aug;95(2):162-6. doi: 10.7326/0003-4819-95-2-162. [PubMed:7258864 ]
Evans J, Lefkowitch J, Lim CK, Billing B: Fecal porphyrin abnormalities in a patient with features of Rotor's syndrome. Gastroenterology. 1981 Dec;81(6):1125-30. [PubMed:7286590 ]
Ford RE, Ou CN, Ellefson RD: Assay for erythrocyte uroporphyrinogen I synthase activity, with porphobilinogen as substrate. Clin Chem. 1980 Jul;26(8):1182-5. [PubMed:7389090 ]
Ellencweig N, Schoenfeld N, Zemishlany Z: Acute intermittent porphyria: psychosis as the only clinical manifestation. Isr J Psychiatry Relat Sci. 2006;43(1):52-6. [PubMed:16910386 ]

Showing metabocard for Porphobilinogen (MMDBc0029486)

MOL for #<Metabolite:0x00007f1240940148>

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Structure for #<Metabolite:0x00007f1240940148>

3D Structure for #<Metabolite:0x00007f1240940148>