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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2020-10-09 21:08:42 UTC

HMDB ID

HMDB0000245

Secondary Accession Numbers

HMDB00245

Metabolite Identification

Common Name

Porphobilinogen

Description

Porphobilinogen (PBG) is a pyrrole-containing intermediate in the biosynthesis of porphyrins. It is generated from aminolevulinate (ALA) by the enzyme ALA dehydratase. Porphobilinogen is then converted into hydroxymethylbilane by the enzyme porphobilinogen deaminase (also known as hydroxymethylbilane synthase). Under certain conditions, porphobilinogen can act as a phototoxin, a neurotoxin, and a metabotoxin. A phototoxin leads to cell damage upon exposure to light. A neurotoxin causes damage to nerve cells and nerve tissues. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of porphyrins are associated with porphyrias such as porphyria variegate, acute intermittent porphyria, and hereditary coproporphyria (HCP). There are several types of porphyrias (most are inherited). Hepatic porphyrias are characterized by acute neurological attacks (seizures, psychosis, extreme back and abdominal pain, and an acute polyneuropathy), while the erythropoietic forms present with skin problems (usually a light-sensitive blistering rash and increased hair growth). The neurotoxicity of porphyrins may be due to their selective interactions with tubulin, which disrupt microtubule formation and cause neural malformations (PMID: 3441503 ).

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>
HMDB0000245

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

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

Chemical Formula

C₁₀H₁₄N₂O₄

Average Molecular Weight

226.2292

Monoisotopic Molecular Weight

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 )

Ontology

Physiological effect

Health effect

Genetic disorder

Inborn errors of metabolism

Porphyria (HMDB: HMDB0000245)
Hereditary coproporphyria (HMDB: HMDB0000245)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16497943)

Cell

Erythrocyte (HMDB: HMDB0000245)

Organ

Liver (HMDB: HMDB0000245)

Excreta

Biofluid or Excreta

Urine (PMID: 23908454)

Cellular substructure

Cytoplasm (HMDB: HMDB0000245)
Membrane (HMDB: HMDB0000245)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000245)

Source

Exogenous

Exogenous (HMDB: HMDB0000245)

Food

Food (HMDB: HMDB0000245)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Cabbage

Onion-family vegetable

Allium (FooDB: FOOD00005)
Garden onion (FooDB: FOOD00006)
Leek (FooDB: FOOD00007)
Garden onion (var.) (FooDB: FOOD00226)
Shallot (FooDB: FOOD00243)
Wild leek (FooDB: FOOD00396)
Red onion (FooDB: FOOD00962)
Green onion (FooDB: FOOD00963)
Onion-family vegetables (FooDB: FOOD00855)

Root vegetable

Shoot vegetable

Leaf vegetable

Common beet (FooDB: FOOD00025)
Endive (FooDB: FOOD00048)
Rocket salad (ssp.) (FooDB: FOOD00077)
Swamp cabbage (FooDB: FOOD00091)
Lettuce (FooDB: FOOD00095)
Garden cress (FooDB: FOOD00099)
Spinach (FooDB: FOOD00178)
Swiss chard (FooDB: FOOD00237)
Chicory leaves (FooDB: FOOD00250)
Garland chrysanthemum (FooDB: FOOD00333)
Corn salad (FooDB: FOOD00340)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
Malabar spinach (FooDB: FOOD00404)
New Zealand spinach (FooDB: FOOD00415)
Yautia (FooDB: FOOD00510)
Ostrich fern (FooDB: FOOD00556)
Romaine lettuce (FooDB: FOOD00888)
Iceberg lettuce (FooDB: FOOD00973)
Pea shoots (FooDB: FOOD00975)
Yau choy (FooDB: FOOD00976)
Water spinach (FooDB: FOOD00977)
Rocket salad (FooDB: FOOD00244)
Green vegetables (FooDB: FOOD00872)

Fruit vegetable

Pepper (FooDB: FOOD00040)
Olive (FooDB: FOOD00121)
Avocado (FooDB: FOOD00130)
Garden tomato (FooDB: FOOD00171)
Cherry tomato (FooDB: FOOD00172)
Garden tomato (var.) (FooDB: FOOD00173)
Eggplant (FooDB: FOOD00174)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Groundcherry (FooDB: FOOD00371)
Pepper (C. frutescens) (FooDB: FOOD00428)
Mexican groundcherry (FooDB: FOOD00491)
Pepper (C. pubescens) (FooDB: FOOD00849)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Orange bell pepper (FooDB: FOOD00879)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Jalapeno pepper (FooDB: FOOD00955)
Cubanelle pepper (FooDB: FOOD00971)

Tuber

Stalk vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)
Carob (FooDB: FOOD00321)
Chinese water chestnut (FooDB: FOOD00332)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Nopal (FooDB: FOOD00416)
Okra (FooDB: FOOD00420)
Sesbania flower (FooDB: FOOD00469)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Heart of palm (FooDB: FOOD00718)
Tree fern (FooDB: FOOD00797)

Mushroom

Castanospermum australe (FooDB: FOOD00893)
Gentiana lutea (FooDB: FOOD00894)
Juniperus communis (FooDB: FOOD00895)
Albizia gummifera (FooDB: FOOD00896)

Brassica

Brassicas (FooDB: FOOD00857)

Fruit

Tropical fruit

Citrus

Lime (FooDB: FOOD00053)
Lemon (FooDB: FOOD00054)
Pummelo (FooDB: FOOD00055)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Sweet orange (FooDB: FOOD00057)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Grapefruit (FooDB: FOOD00256)
Persian lime (FooDB: FOOD00543)
Sour orange (FooDB: FOOD00918)
Mikan (FooDB: FOOD00932)
Clementine (FooDB: FOOD00959)
Citrus (FooDB: FOOD00859)

Pome

Berry

Black crowberry (FooDB: FOOD00075)
Strawberry (FooDB: FOOD00083)
Black huckleberry (FooDB: FOOD00084)
Sea-buckthornberry (FooDB: FOOD00087)
Mulberry (FooDB: FOOD00116)
Black mulberry (FooDB: FOOD00117)
Black chokeberry (FooDB: FOOD00136)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Cloudberry (FooDB: FOOD00161)
Red raspberry (FooDB: FOOD00162)
Black raspberry (FooDB: FOOD00163)
Black elderberry (FooDB: FOOD00166)
Rowanberry (FooDB: FOOD00176)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
American cranberry (FooDB: FOOD00192)
Bilberry (FooDB: FOOD00193)
Lingonberry (FooDB: FOOD00194)
Muscadine grape (FooDB: FOOD00203)
Common grape (FooDB: FOOD00204)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Elderberry (FooDB: FOOD00358)
Grape (FooDB: FOOD00369)
Alaska blueberry (FooDB: FOOD00380)
Loganberry (FooDB: FOOD00400)
Ohelo berry (FooDB: FOOD00419)
Salmonberry (FooDB: FOOD00456)
Strawberry guava (FooDB: FOOD00482)
Boysenberry (FooDB: FOOD00542)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)
Rabbiteye blueberry (FooDB: FOOD00898)
Blackberry (FooDB: FOOD00906)
Partridge berry (FooDB: FOOD00931)
Green grape (FooDB: FOOD00964)
Red grape (FooDB: FOOD00965)
Black plum (FooDB: FOOD00966)
Black raisin (FooDB: FOOD00968)
Chinese plum (FooDB: FOOD00978)
Green plum (FooDB: FOOD00979)
Wampee (FooDB: FOOD00980)
Goji (FooDB: FOOD00982)
Monk fruit (FooDB: FOOD00983)
Hawthorn (FooDB: FOOD00985)
Lantern fruit (FooDB: FOOD00986)
Cape gooseberry (FooDB: FOOD00988)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)

Other fruit

Fig (FooDB: FOOD00081)
Date (FooDB: FOOD00135)
Jujube (FooDB: FOOD00388)

Drupe

Prunus (Cherry, Plum) (FooDB: FOOD00143)
Apricot (FooDB: FOOD00144)
Sweet cherry (FooDB: FOOD00145)
Sour cherry (FooDB: FOOD00146)
European plum (FooDB: FOOD00147)
Peach (FooDB: FOOD00149)
Nectarine (FooDB: FOOD00229)
Peach (var.) (FooDB: FOOD00230)
Common chokecherry (FooDB: FOOD00562)

Fruits (FooDB: FOOD00871)

Nut

Cashew nut (FooDB: FOOD00011)
Peanut (FooDB: FOOD00016)
Brazil nut (FooDB: FOOD00024)
Pecan nut (FooDB: FOOD00044)
Chestnut (FooDB: FOOD00045)
Common hazelnut (FooDB: FOOD00062)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Almond (FooDB: FOOD00148)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hazelnut (FooDB: FOOD00376)
Hickory nut (FooDB: FOOD00377)
Japanese chestnut (FooDB: FOOD00385)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Macadamia nut (FooDB: FOOD00525)
Walnut (FooDB: FOOD00608)
Mixed nuts (FooDB: FOOD00771)
Nuts (FooDB: FOOD00869)

Cereal and cereal product

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Leavened bread

Flat bread

Other bread

Potato bread (FooDB: FOOD00811)
Other bread (FooDB: FOOD00269)

Sweet bread

Raisin bread (FooDB: FOOD00817)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Pea

Lentil

Lentils (FooDB: FOOD00098)

Other pulse

Lupine (FooDB: FOOD00104)
White lupine (FooDB: FOOD00403)

Bean

Green lentil (FooDB: FOOD00970)
Pulses (FooDB: FOOD00867)

Gourd

Watermelon (FooDB: FOOD00052)
Muskmelon (FooDB: FOOD00064)
Cucumber (FooDB: FOOD00065)
Cucurbita (FooDB: FOOD00066)
Bitter gourd (FooDB: FOOD00115)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Calabash (FooDB: FOOD00318)
Chayote (FooDB: FOOD00325)
Towel gourd (FooDB: FOOD00492)
Wax gourd (FooDB: FOOD00499)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Acorn squash (FooDB: FOOD00972)
Cantaloupe melon (FooDB: FOOD00984)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Dish

Other dish

Taco shell (FooDB: FOOD00991)
Tostada shell (FooDB: FOOD00992)

Tea

Herbal tea

Hibiscus tea (FooDB: FOOD00723)
Greenthread tea (FooDB: FOOD00820)

Baking good

Wrapper

Wonton wrapper (FooDB: FOOD00818)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Endogenous

Endogenous (HMDB: HMDB0000245)

Plant

Animal

Animal (HMDB: HMDB0000245)

Process

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0000245)

Biomarker

Porphyria (MarkerDB: MDB00013424)

Indirect biological role

Metabotoxin

Metabotoxin (HMDB: HMDB0000245)

Biological role

Metabolite (HMDB: HMDB0000245)
Metabolite (HMDB: HMDB0000245)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	146.217	30932474
[M-H]-	Not Available	146.217	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000423

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	152.121	31661259
DarkChem	[M-H]-	150.032	31661259
AllCCS	[M+H]+	150.33	32859911
AllCCS	[M-H]-	149.521	32859911
DeepCCS	[M+H]+	148.137	30932474
DeepCCS	[M-H]-	145.779	30932474
DeepCCS	[M-2H]-	179.526	30932474
DeepCCS	[M+Na]+	155.146	30932474
AllCCS	[M+H]+	150.3	32859911
AllCCS	[M+H-H2O]+	146.6	32859911
AllCCS	[M+NH4]+	153.8	32859911
AllCCS	[M+Na]+	154.8	32859911
AllCCS	[M-H]-	149.5	32859911
AllCCS	[M+Na-2H]-	150.0	32859911
AllCCS	[M+HCOO]-	150.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.11 minutes	32390414
Predicted by Siyang on May 30, 2022	9.0554 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.67 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	380.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	447.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	237.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	56.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	156.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	52.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	271.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	232.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	836.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	572.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	43.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	653.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	153.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	181.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	677.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	543.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	462.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Porphobilinogen	NCC1=C(CC(O)=O)C(CCC(O)=O)=CN1	3422.0	Standard polar	33892256
Porphobilinogen	NCC1=C(CC(O)=O)C(CCC(O)=O)=CN1	2134.8	Standard non polar	33892256
Porphobilinogen	NCC1=C(CC(O)=O)C(CCC(O)=O)=CN1	2350.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Porphobilinogen,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=C(CN)[NH]C=C1CCC(=O)O	2258.6	Semi standard non polar	33892256
Porphobilinogen,1TMS,isomer #2	C[Si](C)(C)OC(=O)CCC1=C[NH]C(CN)=C1CC(=O)O	2267.2	Semi standard non polar	33892256
Porphobilinogen,1TMS,isomer #3	C[Si](C)(C)NCC1=C(CC(=O)O)C(CCC(=O)O)=C[NH]1	2346.5	Semi standard non polar	33892256
Porphobilinogen,1TMS,isomer #4	C[Si](C)(C)N1C=C(CCC(=O)O)C(CC(=O)O)=C1CN	2321.6	Semi standard non polar	33892256
Porphobilinogen,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCC1=C[NH]C(CN)=C1CC(=O)O[Si](C)(C)C	2247.8	Semi standard non polar	33892256
Porphobilinogen,2TMS,isomer #2	C[Si](C)(C)NCC1=C(CC(=O)O[Si](C)(C)C)C(CCC(=O)O)=C[NH]1	2353.9	Semi standard non polar	33892256
Porphobilinogen,2TMS,isomer #3	C[Si](C)(C)OC(=O)CC1=C(CN)N([Si](C)(C)C)C=C1CCC(=O)O	2330.5	Semi standard non polar	33892256
Porphobilinogen,2TMS,isomer #4	C[Si](C)(C)NCC1=C(CC(=O)O)C(CCC(=O)O[Si](C)(C)C)=C[NH]1	2369.6	Semi standard non polar	33892256
Porphobilinogen,2TMS,isomer #5	C[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C)C(CN)=C1CC(=O)O	2325.1	Semi standard non polar	33892256
Porphobilinogen,2TMS,isomer #6	C[Si](C)(C)N(CC1=C(CC(=O)O)C(CCC(=O)O)=C[NH]1)[Si](C)(C)C	2450.0	Semi standard non polar	33892256
Porphobilinogen,2TMS,isomer #7	C[Si](C)(C)NCC1=C(CC(=O)O)C(CCC(=O)O)=CN1[Si](C)(C)C	2425.1	Semi standard non polar	33892256
Porphobilinogen,3TMS,isomer #1	C[Si](C)(C)NCC1=C(CC(=O)O[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C[NH]1	2315.2	Semi standard non polar	33892256
Porphobilinogen,3TMS,isomer #1	C[Si](C)(C)NCC1=C(CC(=O)O[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C[NH]1	2371.4	Standard non polar	33892256
Porphobilinogen,3TMS,isomer #1	C[Si](C)(C)NCC1=C(CC(=O)O[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C[NH]1	2825.9	Standard polar	33892256
Porphobilinogen,3TMS,isomer #2	C[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C)C(CN)=C1CC(=O)O[Si](C)(C)C	2320.9	Semi standard non polar	33892256
Porphobilinogen,3TMS,isomer #2	C[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C)C(CN)=C1CC(=O)O[Si](C)(C)C	2289.1	Standard non polar	33892256
Porphobilinogen,3TMS,isomer #2	C[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C)C(CN)=C1CC(=O)O[Si](C)(C)C	3012.0	Standard polar	33892256
Porphobilinogen,3TMS,isomer #3	C[Si](C)(C)OC(=O)CC1=C(CN([Si](C)(C)C)[Si](C)(C)C)[NH]C=C1CCC(=O)O	2446.9	Semi standard non polar	33892256
Porphobilinogen,3TMS,isomer #3	C[Si](C)(C)OC(=O)CC1=C(CN([Si](C)(C)C)[Si](C)(C)C)[NH]C=C1CCC(=O)O	2485.5	Standard non polar	33892256
Porphobilinogen,3TMS,isomer #3	C[Si](C)(C)OC(=O)CC1=C(CN([Si](C)(C)C)[Si](C)(C)C)[NH]C=C1CCC(=O)O	2851.3	Standard polar	33892256
Porphobilinogen,3TMS,isomer #4	C[Si](C)(C)NCC1=C(CC(=O)O[Si](C)(C)C)C(CCC(=O)O)=CN1[Si](C)(C)C	2412.7	Semi standard non polar	33892256
Porphobilinogen,3TMS,isomer #4	C[Si](C)(C)NCC1=C(CC(=O)O[Si](C)(C)C)C(CCC(=O)O)=CN1[Si](C)(C)C	2416.7	Standard non polar	33892256
Porphobilinogen,3TMS,isomer #4	C[Si](C)(C)NCC1=C(CC(=O)O[Si](C)(C)C)C(CCC(=O)O)=CN1[Si](C)(C)C	2913.2	Standard polar	33892256
Porphobilinogen,3TMS,isomer #5	C[Si](C)(C)OC(=O)CCC1=C[NH]C(CN([Si](C)(C)C)[Si](C)(C)C)=C1CC(=O)O	2465.6	Semi standard non polar	33892256
Porphobilinogen,3TMS,isomer #5	C[Si](C)(C)OC(=O)CCC1=C[NH]C(CN([Si](C)(C)C)[Si](C)(C)C)=C1CC(=O)O	2490.7	Standard non polar	33892256
Porphobilinogen,3TMS,isomer #5	C[Si](C)(C)OC(=O)CCC1=C[NH]C(CN([Si](C)(C)C)[Si](C)(C)C)=C1CC(=O)O	2817.1	Standard polar	33892256
Porphobilinogen,3TMS,isomer #6	C[Si](C)(C)NCC1=C(CC(=O)O)C(CCC(=O)O[Si](C)(C)C)=CN1[Si](C)(C)C	2428.0	Semi standard non polar	33892256
Porphobilinogen,3TMS,isomer #6	C[Si](C)(C)NCC1=C(CC(=O)O)C(CCC(=O)O[Si](C)(C)C)=CN1[Si](C)(C)C	2425.7	Standard non polar	33892256
Porphobilinogen,3TMS,isomer #6	C[Si](C)(C)NCC1=C(CC(=O)O)C(CCC(=O)O[Si](C)(C)C)=CN1[Si](C)(C)C	2865.1	Standard polar	33892256
Porphobilinogen,3TMS,isomer #7	C[Si](C)(C)N(CC1=C(CC(=O)O)C(CCC(=O)O)=CN1[Si](C)(C)C)[Si](C)(C)C	2561.5	Semi standard non polar	33892256
Porphobilinogen,3TMS,isomer #7	C[Si](C)(C)N(CC1=C(CC(=O)O)C(CCC(=O)O)=CN1[Si](C)(C)C)[Si](C)(C)C	2524.5	Standard non polar	33892256
Porphobilinogen,3TMS,isomer #7	C[Si](C)(C)N(CC1=C(CC(=O)O)C(CCC(=O)O)=CN1[Si](C)(C)C)[Si](C)(C)C	2977.2	Standard polar	33892256
Porphobilinogen,4TMS,isomer #1	C[Si](C)(C)OC(=O)CCC1=C[NH]C(CN([Si](C)(C)C)[Si](C)(C)C)=C1CC(=O)O[Si](C)(C)C	2422.4	Semi standard non polar	33892256
Porphobilinogen,4TMS,isomer #1	C[Si](C)(C)OC(=O)CCC1=C[NH]C(CN([Si](C)(C)C)[Si](C)(C)C)=C1CC(=O)O[Si](C)(C)C	2525.3	Standard non polar	33892256
Porphobilinogen,4TMS,isomer #1	C[Si](C)(C)OC(=O)CCC1=C[NH]C(CN([Si](C)(C)C)[Si](C)(C)C)=C1CC(=O)O[Si](C)(C)C	2573.5	Standard polar	33892256
Porphobilinogen,4TMS,isomer #2	C[Si](C)(C)NCC1=C(CC(=O)O[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=CN1[Si](C)(C)C	2426.5	Semi standard non polar	33892256
Porphobilinogen,4TMS,isomer #2	C[Si](C)(C)NCC1=C(CC(=O)O[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=CN1[Si](C)(C)C	2448.9	Standard non polar	33892256
Porphobilinogen,4TMS,isomer #2	C[Si](C)(C)NCC1=C(CC(=O)O[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=CN1[Si](C)(C)C	2666.0	Standard polar	33892256
Porphobilinogen,4TMS,isomer #3	C[Si](C)(C)OC(=O)CC1=C(CN([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C=C1CCC(=O)O	2567.3	Semi standard non polar	33892256
Porphobilinogen,4TMS,isomer #3	C[Si](C)(C)OC(=O)CC1=C(CN([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C=C1CCC(=O)O	2546.3	Standard non polar	33892256
Porphobilinogen,4TMS,isomer #3	C[Si](C)(C)OC(=O)CC1=C(CN([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C=C1CCC(=O)O	2789.2	Standard polar	33892256
Porphobilinogen,4TMS,isomer #4	C[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C)C(CN([Si](C)(C)C)[Si](C)(C)C)=C1CC(=O)O	2576.1	Semi standard non polar	33892256
Porphobilinogen,4TMS,isomer #4	C[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C)C(CN([Si](C)(C)C)[Si](C)(C)C)=C1CC(=O)O	2554.5	Standard non polar	33892256
Porphobilinogen,4TMS,isomer #4	C[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C)C(CN([Si](C)(C)C)[Si](C)(C)C)=C1CC(=O)O	2749.9	Standard polar	33892256
Porphobilinogen,5TMS,isomer #1	C[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C)C(CN([Si](C)(C)C)[Si](C)(C)C)=C1CC(=O)O[Si](C)(C)C	2563.7	Semi standard non polar	33892256
Porphobilinogen,5TMS,isomer #1	C[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C)C(CN([Si](C)(C)C)[Si](C)(C)C)=C1CC(=O)O[Si](C)(C)C	2564.8	Standard non polar	33892256
Porphobilinogen,5TMS,isomer #1	C[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C)C(CN([Si](C)(C)C)[Si](C)(C)C)=C1CC(=O)O[Si](C)(C)C	2591.1	Standard polar	33892256
Porphobilinogen,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=C(CN)[NH]C=C1CCC(=O)O	2537.0	Semi standard non polar	33892256
Porphobilinogen,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCC1=C[NH]C(CN)=C1CC(=O)O	2561.4	Semi standard non polar	33892256
Porphobilinogen,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NCC1=C(CC(=O)O)C(CCC(=O)O)=C[NH]1	2632.2	Semi standard non polar	33892256
Porphobilinogen,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N1C=C(CCC(=O)O)C(CC(=O)O)=C1CN	2599.3	Semi standard non polar	33892256
Porphobilinogen,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC1=C[NH]C(CN)=C1CC(=O)O[Si](C)(C)C(C)(C)C	2712.5	Semi standard non polar	33892256
Porphobilinogen,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCC1=C(CC(=O)O[Si](C)(C)C(C)(C)C)C(CCC(=O)O)=C[NH]1	2837.3	Semi standard non polar	33892256
Porphobilinogen,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CC1=C(CN)N([Si](C)(C)C(C)(C)C)C=C1CCC(=O)O	2818.9	Semi standard non polar	33892256
Porphobilinogen,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NCC1=C(CC(=O)O)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C[NH]1	2865.2	Semi standard non polar	33892256
Porphobilinogen,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C(CN)=C1CC(=O)O	2840.6	Semi standard non polar	33892256
Porphobilinogen,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N(CC1=C(CC(=O)O)C(CCC(=O)O)=C[NH]1)[Si](C)(C)C(C)(C)C	2912.9	Semi standard non polar	33892256
Porphobilinogen,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)NCC1=C(CC(=O)O)C(CCC(=O)O)=CN1[Si](C)(C)C(C)(C)C	2916.4	Semi standard non polar	33892256
Porphobilinogen,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC1=C(CC(=O)O[Si](C)(C)C(C)(C)C)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C[NH]1	2972.2	Semi standard non polar	33892256
Porphobilinogen,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC1=C(CC(=O)O[Si](C)(C)C(C)(C)C)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C[NH]1	2969.2	Standard non polar	33892256
Porphobilinogen,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC1=C(CC(=O)O[Si](C)(C)C(C)(C)C)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C[NH]1	3031.2	Standard polar	33892256
Porphobilinogen,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C(CN)=C1CC(=O)O[Si](C)(C)C(C)(C)C	2983.8	Semi standard non polar	33892256
Porphobilinogen,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C(CN)=C1CC(=O)O[Si](C)(C)C(C)(C)C	2852.5	Standard non polar	33892256
Porphobilinogen,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C(CN)=C1CC(=O)O[Si](C)(C)C(C)(C)C	3125.6	Standard polar	33892256
Porphobilinogen,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CC1=C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C=C1CCC(=O)O	3114.4	Semi standard non polar	33892256
Porphobilinogen,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CC1=C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C=C1CCC(=O)O	3077.5	Standard non polar	33892256
Porphobilinogen,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CC1=C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C=C1CCC(=O)O	3039.2	Standard polar	33892256
Porphobilinogen,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NCC1=C(CC(=O)O[Si](C)(C)C(C)(C)C)C(CCC(=O)O)=CN1[Si](C)(C)C(C)(C)C	3100.8	Semi standard non polar	33892256
Porphobilinogen,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NCC1=C(CC(=O)O[Si](C)(C)C(C)(C)C)C(CCC(=O)O)=CN1[Si](C)(C)C(C)(C)C	2955.9	Standard non polar	33892256
Porphobilinogen,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NCC1=C(CC(=O)O[Si](C)(C)C(C)(C)C)C(CCC(=O)O)=CN1[Si](C)(C)C(C)(C)C	3091.6	Standard polar	33892256
Porphobilinogen,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)CCC1=C[NH]C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1CC(=O)O	3120.7	Semi standard non polar	33892256
Porphobilinogen,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)CCC1=C[NH]C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1CC(=O)O	3080.1	Standard non polar	33892256
Porphobilinogen,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)CCC1=C[NH]C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1CC(=O)O	3012.9	Standard polar	33892256
Porphobilinogen,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NCC1=C(CC(=O)O)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=CN1[Si](C)(C)C(C)(C)C	3115.9	Semi standard non polar	33892256
Porphobilinogen,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NCC1=C(CC(=O)O)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=CN1[Si](C)(C)C(C)(C)C	2957.0	Standard non polar	33892256
Porphobilinogen,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NCC1=C(CC(=O)O)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=CN1[Si](C)(C)C(C)(C)C	3059.2	Standard polar	33892256
Porphobilinogen,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(CC1=C(CC(=O)O)C(CCC(=O)O)=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3223.8	Semi standard non polar	33892256
Porphobilinogen,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(CC1=C(CC(=O)O)C(CCC(=O)O)=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3027.7	Standard non polar	33892256
Porphobilinogen,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(CC1=C(CC(=O)O)C(CCC(=O)O)=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3131.4	Standard polar	33892256
Porphobilinogen,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC1=C[NH]C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1CC(=O)O[Si](C)(C)C(C)(C)C	3283.5	Semi standard non polar	33892256
Porphobilinogen,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC1=C[NH]C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1CC(=O)O[Si](C)(C)C(C)(C)C	3285.3	Standard non polar	33892256
Porphobilinogen,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC1=C[NH]C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1CC(=O)O[Si](C)(C)C(C)(C)C	2936.9	Standard polar	33892256
Porphobilinogen,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCC1=C(CC(=O)O[Si](C)(C)C(C)(C)C)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=CN1[Si](C)(C)C(C)(C)C	3246.8	Semi standard non polar	33892256
Porphobilinogen,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCC1=C(CC(=O)O[Si](C)(C)C(C)(C)C)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=CN1[Si](C)(C)C(C)(C)C	3136.0	Standard non polar	33892256
Porphobilinogen,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCC1=C(CC(=O)O[Si](C)(C)C(C)(C)C)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=CN1[Si](C)(C)C(C)(C)C	3020.1	Standard polar	33892256
Porphobilinogen,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CC1=C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C=C1CCC(=O)O	3378.1	Semi standard non polar	33892256
Porphobilinogen,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CC1=C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C=C1CCC(=O)O	3217.3	Standard non polar	33892256
Porphobilinogen,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CC1=C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C=C1CCC(=O)O	3067.9	Standard polar	33892256
Porphobilinogen,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1CC(=O)O	3380.6	Semi standard non polar	33892256
Porphobilinogen,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1CC(=O)O	3211.9	Standard non polar	33892256
Porphobilinogen,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1CC(=O)O	3034.0	Standard polar	33892256
Porphobilinogen,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1CC(=O)O[Si](C)(C)C(C)(C)C	3555.6	Semi standard non polar	33892256
Porphobilinogen,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1CC(=O)O[Si](C)(C)C(C)(C)C	3380.8	Standard non polar	33892256
Porphobilinogen,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1CC(=O)O[Si](C)(C)C(C)(C)C	3019.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Porphobilinogen GC-MS (4 TMS)	splash10-001j-1923000000-70c31b91868484322655	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Porphobilinogen GC-MS (Non-derivatized)	splash10-001j-1923000000-70c31b91868484322655	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Porphobilinogen GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-3920000000-d4006159f28f6672d3a5	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Porphobilinogen GC-MS (2 TMS) - 70eV, Positive	splash10-0080-9071000000-ad88926555e7416fedb3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Porphobilinogen GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Porphobilinogen GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Porphobilinogen GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Porphobilinogen GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Porphobilinogen GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Porphobilinogen GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Porphobilinogen GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Porphobilinogen GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Porphobilinogen GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Porphobilinogen GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Porphobilinogen GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Porphobilinogen GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Porphobilinogen GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Porphobilinogen GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Porphobilinogen GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Porphobilinogen GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Porphobilinogen GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Porphobilinogen GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Porphobilinogen GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Porphobilinogen GC-MS (TBDMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Porphobilinogen GC-MS (TBDMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Porphobilinogen Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0a4i-0090000000-912aa953bdd13d6d18ca	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Porphobilinogen Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-00dl-1900000000-8a87960bb63c4915db22	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Porphobilinogen Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-006x-9500000000-c934217374e64d6edee3	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Porphobilinogen LC-ESI-QFT , negative-QTOF	splash10-0udi-1910000000-4a59655d524261d288a0	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Porphobilinogen LC-ESI-QTOF 35V, negative-QTOF	splash10-0a4i-9000000000-5a7fed67c4a8909b6d89	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Porphobilinogen n/a 15V, negative-QTOF	splash10-00xr-0910000000-79d39f97cef0385e0978	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Porphobilinogen Orbitrap 0V, negative-QTOF	splash10-0fb9-0790000000-a3976589df77175b4e7b	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Porphobilinogen Orbitrap 1V, negative-QTOF	splash10-0fb9-0890000000-8659c76eb4cd3bbc050a	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Porphobilinogen Orbitrap 2V, negative-QTOF	splash10-0ui0-0970000000-ace836f5bc7c40d838f3	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Porphobilinogen Orbitrap 4V, negative-QTOF	splash10-0ufr-0970000000-34b54c13783e56f913ed	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Porphobilinogen Orbitrap 6V, negative-QTOF	splash10-0udi-0920000000-ab742bdbcc6ad44ca7ad	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Porphobilinogen Orbitrap 8V, negative-QTOF	splash10-0udi-0900000000-d9086599996dff3ecc2b	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Porphobilinogen Orbitrap 9V, negative-QTOF	splash10-0udi-1900000000-ca027f0ab39ba0260c42	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Porphobilinogen Orbitrap 10V, negative-QTOF	splash10-0zfr-4900000000-c5f999c0aa9c0e985528	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Porphobilinogen Orbitrap 13V, negative-QTOF	splash10-0a4i-9700000000-c39abc4f07f6ba584489	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Porphobilinogen Orbitrap 14V, negative-QTOF	splash10-0a4i-9400000000-6eece2186d7d8e426696	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Porphobilinogen Orbitrap 18V, negative-QTOF	splash10-0a4i-9200000000-4b1d1515941d17b58cd8	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Porphobilinogen n/a 15V, negative-QTOF	splash10-0udi-0900000000-4211fc4d53d78720f632	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Porphobilinogen n/a 15V, negative-QTOF	splash10-0a4i-0900000000-3b3b751b5b26d5ba4273	2020-07-22	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Porphobilinogen 10V, Positive-QTOF	splash10-0a4l-0980000000-423d28b762ba4c07586b	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Porphobilinogen 20V, Positive-QTOF	splash10-03dl-0910000000-31575764ba8bd8d50279	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Porphobilinogen 40V, Positive-QTOF	splash10-074r-0900000000-9d96bd59f1a4371a8df4	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Porphobilinogen 10V, Negative-QTOF	splash10-0059-0790000000-2cc911a67c1aa8e35d99	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Porphobilinogen 20V, Negative-QTOF	splash10-06ur-0940000000-2c3da60da6ab9523fbf3	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Porphobilinogen 40V, Negative-QTOF	splash10-0bt9-4900000000-cf52dffb4284f9eeaa5d	2015-05-27	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Erythrocyte
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Porphyrin Metabolism
Acute Intermittent Porphyria		Not Available
Porphyria Variegata (PV)		Not Available
Congenital Erythropoietic Porphyria (CEP) or Gunther Disease		Not Available
Hereditary Coproporphyria (HCP)		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.06 (0.00-0.12) uM	Adult (>18 years old)	Both	Normal	16497943	details
Urine	Detected and Quantified	<=0.579 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	978-0-911910-19-3	details
Urine	Detected and Quantified	0.31 +/- 0.13 umol/mmol creatinine	Children (1-13 years old)	Both	Normal	Geigy Scientific ... West Cadwell, N.J... Basel, Switzerlan...	details
Urine	Detected and Quantified	0.29 +/- 0.14 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ... West Cadwell, N.J... Basel, Switzerlan...	details
Urine	Detected and Quantified	0-1.5 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	23908454	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	3.1 +/- 1.0 uM	Adult (>18 years old)	Both	Porphyria	16497943	details
Urine	Detected and Quantified	57.1 (19.6-132.7) umol/mmol creatinine	Adult (>18 years old)	Both	Acute intermittent porphyria	23908454	details
Urine	Detected and Quantified	17.2 (74.9-41.6) umol/mmol creatinine	Adult (>18 years old)	Both	Acute intermittent porphyria	23908454	details
Urine	Detected and Quantified	9.7 (21.8-10.5) umol/mmol creatinine	Adult (>18 years old)	Both	Acute intermittent porphyria	23908454	details
Urine	Detected and Quantified	2.3 (5.1-2.9) umol/mmol creatinine	Adult (>18 years old)	Both	Asymptomatic acute intermittent porphyria	23908454	details
Urine	Detected and Quantified	0.589-0.654 umol/mmol creatinine	Adult (>18 years old)	Male	Protoporphyria, Erythropoietic	13765301	details

Associated Disorders and Diseases

Disease References

Porphyria
Floderus Y, Sardh E, Moller C, Andersson C, Rejkjaer L, Andersson DE, Harper P: Variations in porphobilinogen and 5-aminolevulinic acid concentrations in plasma and urine from asymptomatic carriers of the acute intermittent porphyria gene with increased porphyrin precursor excretion. Clin Chem. 2006 Apr;52(4):701-7. Epub 2006 Feb 23. [PubMed:16497943 ]
Acute intermittent porphyria
Marsden JT, Rees DC: Urinary excretion of porphyrins, porphobilinogen and delta-aminolaevulinic acid following an attack of acute intermittent porphyria. J Clin Pathol. 2014 Jan;67(1):60-5. doi: 10.1136/jclinpath-2012-201367. Epub 2013 Aug 1. [PubMed:23908454 ]
Protoporphyria, Erythropoietic
MAGNUS IA, JARRETT A, PRANKERD TA, RIMINGTON C: Erythropoietic protoporphyria. A new porphyria syndrome with solar urticaria due to protoporphyrinaemia. Lancet. 1961 Aug 26;2(7200):448-51. [PubMed:13765301 ]

Associated OMIM IDs

176000 (Acute intermittent porphyria)
177000 (Protoporphyria, Erythropoietic)

External Links

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

VMH ID

PPBNG

MarkerDB ID

MDB00013424

Good Scents ID

Not Available

References

Synthesis Reference

Frydman, Benjamin; Despuy, Maria E.; Rapoport, Henry. Pyrroles from azaindoles. A synthesis of porphobilinogen. Journal of the American Chemical Society (1965), 87(15), 3530-1.

Material Safety Data Sheet (MSDS)

Download (PDF)

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. [PubMed:1147435 ]
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 ]
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 ]
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. [PubMed:3658064 ]
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. [PubMed:4073306 ]
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. [PubMed:3677422 ]
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 ]
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. [PubMed:1165472 ]
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 ]
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 ]
Mustajoki P: Normal erythrocyte uroporphyrinogen I synthase in a kindred with acute intermittent porphyria. Ann Intern Med. 1981 Aug;95(2):162-6. [PubMed:7258864 ]
Winkelman JW, Collins GH: Neurotoxicity of tetraphenylporphinesulfonate TPPS4 and its relation to photodynamic therapy. Photochem Photobiol. 1987 Nov;46(5):801-7. [PubMed:3441503 ]

Enzymes

Enzyme Details

1. Porphobilinogen deaminase

General function:: Involved in hydroxymethylbilane synthase activity
Specific function:: Tetrapolymerization of the monopyrrole PBG into the hydroxymethylbilane pre-uroporphyrinogen in several discrete steps.
Gene Name:: HMBS
Uniprot ID:: P08397
Molecular weight:: 39329.74

Reactions

Porphobilinogen + Water → Hydroxymethylbilane + Ammonia	details

Enzyme Details

2. Delta-aminolevulinic acid dehydratase

General function:: Involved in porphobilinogen synthase activity
Specific function:: Catalyzes an early step in the biosynthesis of tetrapyrroles. Binds two molecules of 5-aminolevulinate per subunit, each at a distinct site, and catalyzes their condensation to form porphobilinogen.
Gene Name:: ALAD
Uniprot ID:: P13716
Molecular weight:: 36294.485

Reactions

5-Aminolevulinic acid → Porphobilinogen + Water	details

Showing metabocard for Porphobilinogen (HMDB0000245)

MOL for HMDB0000245 (Porphobilinogen)

3D MOL for HMDB0000245 (Porphobilinogen)

3D SDF for HMDB0000245 (Porphobilinogen)

3D-SDF for HMDB0000245 (Porphobilinogen)

PDB for HMDB0000245 (Porphobilinogen)

3D PDB for HMDB0000245 (Porphobilinogen)

SMILES for HMDB0000245 (Porphobilinogen)

INCHI for HMDB0000245 (Porphobilinogen)

Structure for HMDB0000245 (Porphobilinogen)

3D Structure for HMDB0000245 (Porphobilinogen)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions