NP-MRD: Showing NP-Card for Uroporphyrinogen III (NP0054937)

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Record Information

Version

2.0

Created at

2022-04-28 01:08:15 UTC

Updated at

2022-04-28 01:08:15 UTC

NP-MRD ID

NP0054937

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Uroporphyrinogen III

Description

Uroporphyrinogen III, also known as uro'gen III, belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure. Uroporphyrinogen III is a weakly acidic compound (based on its pKa). Uroporphyrinogen III exists in all living species, ranging from bacteria to humans. In humans, uroporphyrinogen III is involved in the metabolic disorder called the acute intermittent porphyria pathway. Outside of the human body, Uroporphyrinogen III has been detected, but not quantified in, several different foods, such as rices, gram beans, garden onions, grapes, and natal plums. This could make uroporphyrinogen III a potential biomarker for the consumption of these foods. The molecular structure of uroporphyrinogen III can be described as a hexahydroporphine core, where each pyrrole ring has the hydrogen atoms on its two outermost carbons replaced by an acetic acid group (−CH2−COOH, "A") and a propionic acid group (−CH2−CH2−COOH, "P"). If uroporphyrinogen-III synthase is not present or inactive, the hydroxymethylbilane will spontaneously cyclise into the structural isomer uroporphyrinogen I, which differs from the III isomer in that the acetic acid ("A") and propionic acid ("P") groups are arranged in a rotationally symmetric order, AP-AP-AP-AP. In the biosynthesis of sirohemes, uroporphyrinogen III is converted by two methyl transferases to dihydrosirohydrochlorin, which is subsequently oxidized sirohydrochlorin, a precursor to the siroheme prosthetic group. It is a colorless compound, like other porphyrinogens. The conversion entails a reversal of the last pyrrole unit (thus swapping the acetic and propionic acid groups) and a condensation reaction that closes the macrocycle by eliminating the final hydroxyl −OH with a hydrogen atom of the first ring. Uroporphyrinogen III is a tetrapyrrole, the first macrocyclic intermediate in the biosynthesis of heme, chlorophyll, vitamin B12, and siroheme. The groups are attached in an asymmetric way: Going around the macrocycle, the order is AP-AP-AP-PA.In the general porphyrin biosynthesis pathway, uroporphyrinogen III is derived from the linear tetrapyrrole preuroporphyrinogen (a substituted hydroxymethylbilane) by the action of the enzyme uroporphyrinogen-III cosynthase. Uroporphyrinogen III is found in Apis cerana, Arabidopsis thaliana and Escherichia coli K12. Uroporphyrinogen III was first documented in 2000 (PMID: 11112350). In the biosynthesis of hemes and chlorophylls, uroporphyrinogen III is converted into coproporphyrinogen III by the enzyme uroporphyrinogen III decarboxylase (PMID: 11524417).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231218552D          

 60 64  0  0  0  0            999 V2000
    0.6394   -1.6259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3647   -2.0177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7941   -0.8181    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0963   -1.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9593   -1.4540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4437   -2.8358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6052   -0.7081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8456   -1.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7499   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1965   -3.1728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9387    0.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5778   -2.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9797   -0.8387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3378   -1.8115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2721   -3.9943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6327    0.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0318   -4.3380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9559    1.5778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8146    0.8972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9940   -1.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3030   -3.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6325    1.7015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1865    2.2961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0963    2.0108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2177   -2.1965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5778   -4.5202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1690    1.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9762    0.9212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0556    3.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4549    3.0352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5674    2.9321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4030    2.2584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9905    4.6370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
  8 12  2  0  0  0  0
  8 13  1  0  0  0  0
  9 14  1  0  0  0  0
 10 15  1  0  0  0  0
 11 16  1  0  0  0  0
 12 17  1  0  0  0  0
 12 18  1  0  0  0  0
 13 19  1  0  0  0  0
 14 20  1  0  0  0  0
 14 21  2  0  0  0  0
 15 22  1  0  0  0  0
 15 23  2  0  0  0  0
 16 24  2  0  0  0  0
 16 25  1  0  0  0  0
 17 26  1  0  0  0  0
 18 27  1  0  0  0  0
 19 28  1  0  0  0  0
 24 29  1  0  0  0  0
 24 30  1  0  0  0  0
 25 31  1  0  0  0  0
 26 32  1  0  0  0  0
 27 33  1  0  0  0  0
 28 34  1  0  0  0  0
 29 35  1  0  0  0  0
 30 36  1  0  0  0  0
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  5  7  2  0  0  0  0
 17 19  2  0  0  0  0
 29 31  2  0  0  0  0
 43 46  1  0  0  0  0
 46 47  2  0  0  0  0
M  END

     RDKit          3D

104108  0  0  0  0  0  0  0  0999 V2000
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   -7.5463   -0.4787   -1.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.4783   -0.4465    0.3271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0240   -0.7869    0.3894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9800   -0.1195   -0.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0540   -1.7421    0.8180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4253   -1.8146    1.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1082   -2.8397    1.9622 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.8263   -3.7331    0.5351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2663   -5.2111    1.1971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1030   -2.6830    1.4934 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 02231218552D          

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M  END
> <DATABASE_ID>
NP0054937

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CCC1=C2CC3=C(CCC(O)=O)C(CC(O)=O)=C(CC4=C(CC(O)=O)C(CCC(O)=O)=C(CC5=C(CC(O)=O)C(CCC(O)=O)=C(CC(N2)=C1CC(O)=O)N5)N4)N3

> <INCHI_IDENTIFIER>
InChI=1S/C40H44N4O16/c45-33(46)5-1-17-21(9-37(53)54)29-14-27-19(3-7-35(49)50)22(10-38(55)56)30(43-27)15-28-20(4-8-36(51)52)24(12-40(59)60)32(44-28)16-31-23(11-39(57)58)18(2-6-34(47)48)26(42-31)13-25(17)41-29/h41-44H,1-16H2,(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)(H,59,60)

> <INCHI_KEY>
HUHWZXWWOFSFKF-UHFFFAOYSA-N

> <FORMULA>
C40H44N4O16

> <MOLECULAR_WEIGHT>
836.7946

> <EXACT_MASS>
836.27523138

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
81.5514750357378

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid

> <ALOGPS_LOGP>
0.67

> <JCHEM_LOGP>
1.3885468186666658

> <ALOGPS_LOGS>
-4.28

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-8

> <JCHEM_PKA>
3.5861502444706224

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2116775904243284

> <JCHEM_POLAR_SURFACE_AREA>
361.55999999999995

> <JCHEM_REFRACTIVITY>
206.9264000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
uroporphyrinogen-III

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       1.194  -3.035   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.547  -3.766   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.482  -1.527   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -0.180  -3.613   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.657  -2.714   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.695  -5.293   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.996  -1.322   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.578  -3.086   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.133  -2.303   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.100  -5.923   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.619   0.096   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.945  -3.792   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -1.829  -1.566   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       6.231  -3.381   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.241  -7.456   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.048   1.527   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.049  -2.714   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.958  -5.332   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.349  -1.341   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.713  -2.977   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.845  -4.870   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.977  -8.348   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.659  -8.098   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.651   2.945   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       1.521   1.675   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      -5.589  -2.740   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.299  -6.102   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.081   0.058   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.515   3.952   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.191   2.952   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.181   3.176   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -6.340  -4.081   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.305  -7.642   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.349   1.482   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.509   5.505   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.948   4.286   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.180   3.753   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -7.873  -4.100   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -5.550  -5.396   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -5.640  -8.406   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -2.945  -8.438   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -4.049   2.868   0.000  0.00  0.00           C+0
HETATM   43  N   UNK     0      -1.822   1.720   0.000  0.00  0.00           N+0
HETATM   44  C   UNK     0       3.837   6.275   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       7.533   4.293   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -1.572   3.221   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -2.939   3.940   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -5.589   2.881   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       3.831   7.809   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       5.165   5.512   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0       8.316   5.666   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       8.329   2.932   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      -2.926   5.473   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -6.352   4.216   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -4.248   6.262   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      -7.886   4.222   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      -5.576   5.537   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0      -4.222   7.847   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      -2.836   8.617   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      -5.582   8.656   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9    7                                                  
CONECT    6    2   10                                                       
CONECT    7    3   11    5                                                  
CONECT    8    4   12   13                                                  
CONECT    9    5   14                                                       
CONECT   10    6   15                                                       
CONECT   11    7   16                                                       
CONECT   12    8   17   18                                                  
CONECT   13    8   19                                                       
CONECT   14    9   20   21                                                  
CONECT   15   10   22   23                                                  
CONECT   16   11   24   25                                                  
CONECT   17   12   26   19                                                  
CONECT   18   12   27                                                       
CONECT   19   13   28   17                                                  
CONECT   20   14                                                            
CONECT   21   14                                                            
CONECT   22   15                                                            
CONECT   23   15                                                            
CONECT   24   16   29   30                                                  
CONECT   25   16   31                                                       
CONECT   26   17   32                                                       
CONECT   27   18   33                                                       
CONECT   28   19   34                                                       
CONECT   29   24   35   31                                                  
CONECT   30   24   36                                                       
CONECT   31   25   37   29                                                  
CONECT   32   26   38   39                                                  
CONECT   33   27   40   41                                                  
CONECT   34   28   42   43                                                  
CONECT   35   29   44                                                       
CONECT   36   30   45                                                       
CONECT   37   31   46                                                       
CONECT   38   32                                                            
CONECT   39   32                                                            
CONECT   40   33                                                            
CONECT   41   33                                                            
CONECT   42   34   47   48                                                  
CONECT   43   34   46                                                       
CONECT   44   35   49   50                                                  
CONECT   45   36   51   52                                                  
CONECT   46   37   43   47                                                  
CONECT   47   42   53   46                                                  
CONECT   48   42   54                                                       
CONECT   49   44                                                            
CONECT   50   44                                                            
CONECT   51   45                                                            
CONECT   52   45                                                            
CONECT   53   47   55                                                       
CONECT   54   48   56   57                                                  
CONECT   55   53   58                                                       
CONECT   56   54                                                            
CONECT   57   54                                                            
CONECT   58   55   59   60                                                  
CONECT   59   58                                                            
CONECT   60   58                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  128    0
END

View in JSmol

Synonyms

Value	Source
3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydro-21H,23H-porphine-2,7,12,18-tetrapropanoic acid	ChEBI
3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropionic acid	ChEBI
Uro'gen III	ChEBI
3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydro-21H,23H-porphine-2,7,12,18-tetrapropanoate	Generator
3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropionate	Generator
3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydro-2,7,12,18-porphinetetrapropionate	HMDB
3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydro-2,7,12,18-porphinetetrapropionic acid	HMDB
3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropanoate	HMDB
3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropanoic acid	HMDB
Urogen III	HMDB
Uroporphyrinogen-III	HMDB
Uroporphyrinogens	HMDB

Chemical Formula

C₄₀H₄₄N₄O₁₆

Average Mass

836.7946 Da

Monoisotopic Mass

836.27523 Da

IUPAC Name

3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid

Traditional Name

uroporphyrinogen-III

CAS Registry Number

Not Available

SMILES

OC(=O)CCC1=C2CC3=C(CCC(O)=O)C(CC(O)=O)=C(CC4=C(CC(O)=O)C(CCC(O)=O)=C(CC5=C(CC(O)=O)C(CCC(O)=O)=C(CC(N2)=C1CC(O)=O)N5)N4)N3

InChI Identifier

InChI=1S/C40H44N4O16/c45-33(46)5-1-17-21(9-37(53)54)29-14-27-19(3-7-35(49)50)22(10-38(55)56)30(43-27)15-28-20(4-8-36(51)52)24(12-40(59)60)32(44-28)16-31-23(11-39(57)58)18(2-6-34(47)48)26(42-31)13-25(17)41-29/h41-44H,1-16H2,(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)(H,59,60)

InChI Key

HUHWZXWWOFSFKF-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Apis cerana	LOTUS Database	35616633
Arabidopsis thaliana	Plant	KNApSAcK
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Escherichia coli K12	Bacteria	KNApSAcK
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrapyrroles and derivatives

Sub Class

Porphyrins

Direct Parent

Porphyrins

Alternative Parents

Substituents

Porphyrin
Substituted pyrrole
Pyrrole
Heteroaromatic compound
Carboxylic acid derivative
Carboxylic acid
Azacycle
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

uroporphyrinogen (CHEBI:15437 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	0.67	ALOGPS
logP	1.39	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	3.21	ChemAxon
Physiological Charge	-8	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	361.56 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	206.93 m³·mol⁻¹	ChemAxon
Polarizability	81.55 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0001086

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

1179

PDB ID

Not Available

ChEBI ID

15437

Good Scents ID

Not Available

References

General References

Aizencang G, Solis C, Bishop DF, Warner C, Desnick RJ: Human uroporphyrinogen-III synthase: genomic organization, alternative promoters, and erythroid-specific expression. Genomics. 2000 Dec 1;70(2):223-31. doi: 10.1006/geno.2000.6373. [PubMed:11112350 ]
Martins BM, Grimm B, Mock HP, Huber R, Messerschmidt A: Crystal structure and substrate binding modeling of the uroporphyrinogen-III decarboxylase from Nicotiana tabacum. Implications for the catalytic mechanism. J Biol Chem. 2001 Nov 23;276(47):44108-16. doi: 10.1074/jbc.M104759200. Epub 2001 Aug 27. [PubMed:11524417 ]

Showing NP-Card for Uroporphyrinogen III (NP0054937)

MOL for NP0054937 (Uroporphyrinogen III)

3D MOL for NP0054937 (Uroporphyrinogen III)

3D SDF for NP0054937 (Uroporphyrinogen III)

3D-SDF for NP0054937 (Uroporphyrinogen III)

PDB for NP0054937 (Uroporphyrinogen III)

3D PDB for NP0054937 (Uroporphyrinogen III)

SMILES for NP0054937 (Uroporphyrinogen III)

INCHI for NP0054937 (Uroporphyrinogen III)

Structure for NP0054937 (Uroporphyrinogen III)

3D Structure for NP0054937 (Uroporphyrinogen III)