NP-MRD: Showing NP-Card for Coproporphyrinogen III (NP0054908)

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Record Information

Version

2.0

Created at

2022-04-28 01:06:39 UTC

Updated at

2022-04-28 01:06:40 UTC

NP-MRD ID

NP0054908

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Coproporphyrinogen III

Description

Coproporphyrinogen III, also known as coproporphyrin 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. Coproporphyrinogen III is a weakly acidic compound (based on its pKa). The compound is a porphyrinogen, a class of compounds characterized by a hexahydroporphine core with various side chains. The coproporphyrinogens have the outermost hydrogen atoms of the core replaced by four methyl groups −CH3 (M) and four propionic acid groups −CH2−CH2−COOH (P). In the main porphyrin biosynthesis pathway, coproporphyrinogen III is derived from uroporphyrinogen III by the action of the enzyme uroporphyrinogen III decarboxylase:The conversion entails four decarboxylations, which turn the four acetic acid groups −CH2−COOH into methyl groups −CH3, with release of four carbon dioxide molecules. Coproporphyrinogen III exists in all living species, ranging from bacteria to humans. In humans, coproporphyrinogen III is involved in the metabolic disorder called the acute intermittent porphyria pathway. Coproporphyrinogen III is a metabolic intermediate in the biosynthesis of many compounds that are critical for living organisms, such as hemoglobin and chlorophyll. Outside of the human body, Coproporphyrinogen III has been detected, but not quantified in, several different foods, such as apples, mixed nuts, dates, nances, and sweet potato. This could make coproporphyrinogen III a potential biomarker for the consumption of these foods. Coproporphyrinogen III is a potentially toxic compound. Coproporphyrinogen III is further used as a substrate for the enzyme coproporphyrinogen III oxidase which oxidizes and further decarboxylates it to protoporphyrinogen IX. For comparison, coproporphyrinogen I has them in the sequence MP-MP-MP-MP. In coproporphyrogen III, the order around the outer ring is MP-MP-MP-PM. Coproporphyrinogen III is found in Apis cerana, Arabidopsis thaliana, Paraburkholderia phymatum and Rhodobacter sphaeroides. It is a colorless solid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652303021818582D          

 48 52  0  0  0  0            999 V2000
    2.2341    0.1551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7898   -2.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8585    0.8606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5591   -3.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2448    1.6483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0691    1.0125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1996   -1.8798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6854   -3.8188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6923    2.2085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0591    1.7809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8992    1.8335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0426   -4.3359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4547   -4.1171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8362    3.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1993    2.2190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2046    3.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5354    1.8144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3487    4.3640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2938    2.2296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8191   -0.5738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4889   -0.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8454   -1.2505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6996   -0.7023    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2639   -1.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5588   -1.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  2  0  0  0  0
  3  6  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6 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
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 14 16  1  0  0  0  0
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  9 11  2  0  0  0  0
 24 29  1  0  0  0  0
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  2 40  1  0  0  0  0
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 41 39  1  0  0  0  0
 39  7  1  0  0  0  0
 43 41  1  0  0  0  0
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 43 42  2  0  0  0  0
 45 44  2  0  0  0  0
 47 45  1  0  0  0  0
 45 22  1  0  0  0  0
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 47 18  1  0  0  0  0
 48 46  1  0  0  0  0
 48 47  2  0  0  0  0
  7 48  1  0  0  0  0
M  END

     RDKit          3D

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   -4.7601   -2.3105    1.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4268    2.5992   -1.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
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 17 62  1  0
 18 63  1  0
 18 64  1  0
 21 65  1  0
 23 66  1  0
 23 67  1  0
 23 68  1  0
 12 58  1  0
 12 59  1  0
  4 52  1  0
  7 53  1  0
  7 54  1  0
  8 55  1  0
  8 56  1  0
 11 57  1  0
 14 60  1  0
 26 71  1  0
 38 82  1  0
M  END


  Mrv1652303021818582D          

 48 52  0  0  0  0            999 V2000
    2.2341    0.1551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7898   -2.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8585    0.8606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5591   -3.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2448    1.6483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0691    1.0125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1996   -1.8798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6854   -3.8188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6923    2.2085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0591    1.7809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8992    1.8335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0426   -4.3359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4547   -4.1171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8362    3.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1993    2.2190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2046    3.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5354    1.8144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4018   -2.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3487    4.3640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2938    2.2296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6579    1.0540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6596   -1.3834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7664   -3.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8643    0.2134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7171    4.8949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1241    4.6456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8539    1.6772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4078    3.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4788    0.9133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9041   -3.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6673    1.8153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6776   -4.2804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2686   -4.5192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1935    1.1798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0069    1.3176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5330    0.6822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2941    2.0911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0390   -1.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9050   -1.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6635   -1.8902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0571   -0.6855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2236   -1.3378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8191   -0.5738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4889   -0.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8454   -1.2505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6996   -0.7023    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2639   -1.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5588   -1.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  2  0  0  0  0
  3  6  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6 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
 11 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 19  1  0  0  0  0
 17 20  2  0  0  0  0
 17 21  1  0  0  0  0
 18 23  1  0  0  0  0
 19 25  1  0  0  0  0
 19 26  2  0  0  0  0
 20 27  1  0  0  0  0
 20 28  1  0  0  0  0
 21 29  1  0  0  0  0
 23 30  1  0  0  0  0
 27 31  1  0  0  0  0
 30 32  2  0  0  0  0
 30 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
  9 11  2  0  0  0  0
 24 29  1  0  0  0  0
 27 29  2  0  0  0  0
 42 38  1  0  0  0  0
  2 40  1  0  0  0  0
 40 39  2  0  0  0  0
 42 40  1  0  0  0  0
 41 39  1  0  0  0  0
 39  7  1  0  0  0  0
 43 41  1  0  0  0  0
 43  1  1  0  0  0  0
 43 42  2  0  0  0  0
 45 44  2  0  0  0  0
 47 45  1  0  0  0  0
 45 22  1  0  0  0  0
 46 44  1  0  0  0  0
 44 24  1  0  0  0  0
 47 18  1  0  0  0  0
 48 46  1  0  0  0  0
 48 47  2  0  0  0  0
  7 48  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054908

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2CC3=C(C)C(CCC(O)=O)=C(CC4=C(CCC(O)=O)C(C)=C(CC5=C(CCC(O)=O)C(C)=C(CC(N2)=C1CCC(O)=O)N5)N4)N3

> <INCHI_IDENTIFIER>
InChI=1S/C36H44N4O8/c1-17-21(5-9-33(41)42)29-14-27-19(3)22(6-10-34(43)44)30(39-27)15-28-20(4)24(8-12-36(47)48)32(40-28)16-31-23(7-11-35(45)46)18(2)26(38-31)13-25(17)37-29/h37-40H,5-16H2,1-4H3,(H,41,42)(H,43,44)(H,45,46)(H,47,48)

> <INCHI_KEY>
NIUVHXTXUXOFEB-UHFFFAOYSA-N

> <FORMULA>
C36H44N4O8

> <MOLECULAR_WEIGHT>
660.7566

> <EXACT_MASS>
660.315914404

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
92

> <JCHEM_AVERAGE_POLARIZABILITY>
72.85338000201646

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid

> <ALOGPS_LOGP>
1.96

> <JCHEM_LOGP>
4.891239218666666

> <ALOGPS_LOGS>
-4.77

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
4.229360781234833

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8015317067975603

> <JCHEM_POLAR_SURFACE_AREA>
212.35999999999996

> <JCHEM_REFRACTIVITY>
181.86080000000013

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-MAR-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-MAR-18         0                                  
HETATM    1  C   UNK     0       4.170   0.290   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.341  -5.050   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.469   1.606   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.777  -5.607   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.190   3.077   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       1.996   1.890   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       0.373  -3.509   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.013  -7.128   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.159   4.123   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.710   3.324   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.679   3.423   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.813  -8.094   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       6.449  -7.685   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.428   5.639   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.372   4.142   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.249   6.630   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.999   3.387   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.617  -4.953   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.518   8.146   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.415   4.162   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      -1.228   1.968   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      -4.965  -2.582   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.431  -5.935   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.480   0.398   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.339   9.137   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       3.965   8.672   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -3.461   3.131   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.628   5.687   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.760   1.705   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.688  -7.454   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.979   3.388   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -3.131  -7.990   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -0.501  -8.436   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -5.961   2.202   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -7.480   2.459   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -8.462   1.273   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -8.016   3.903   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       5.673  -2.732   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.689  -2.808   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       3.105  -3.528   0.000  0.00  0.00           C+0
HETATM   41  N   UNK     0       1.973  -1.280   0.000  0.00  0.00           N+0
HETATM   42  C   UNK     0       4.151  -2.497   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       3.396  -1.071   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -2.779  -0.973   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -3.445  -2.334   0.000  0.00  0.00           C+0
HETATM   46  N   UNK     0      -1.306  -1.311   0.000  0.00  0.00           N+0
HETATM   47  C   UNK     0      -2.359  -3.435   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -1.043  -2.789   0.000  0.00  0.00           C+0
CONECT    1    3   43                                                       
CONECT    2    4   40                                                       
CONECT    3    1    5    6                                                  
CONECT    4    2    8                                                       
CONECT    5    3    9   10                                                  
CONECT    6    3   11                                                       
CONECT    7   39   48                                                       
CONECT    8    4   12   13                                                  
CONECT    9    5   14   11                                                  
CONECT   10    5                                                            
CONECT   11    6   15    9                                                  
CONECT   12    8                                                            
CONECT   13    8                                                            
CONECT   14    9   16                                                       
CONECT   15   11   17                                                       
CONECT   16   14   19                                                       
CONECT   17   15   20   21                                                  
CONECT   18   23   47                                                       
CONECT   19   16   25   26                                                  
CONECT   20   17   27   28                                                  
CONECT   21   17   29                                                       
CONECT   22   45                                                            
CONECT   23   18   30                                                       
CONECT   24   29   44                                                       
CONECT   25   19                                                            
CONECT   26   19                                                            
CONECT   27   20   31   29                                                  
CONECT   28   20                                                            
CONECT   29   21   24   27                                                  
CONECT   30   23   32   33                                                  
CONECT   31   27   34                                                       
CONECT   32   30                                                            
CONECT   33   30                                                            
CONECT   34   31   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   42                                                            
CONECT   39   40   41    7                                                  
CONECT   40    2   39   42                                                  
CONECT   41   39   43                                                       
CONECT   42   38   40   43                                                  
CONECT   43   41    1   42                                                  
CONECT   44   45   46   24                                                  
CONECT   45   44   47   22                                                  
CONECT   46   44   48                                                       
CONECT   47   45   18   48                                                  
CONECT   48   46   47    7                                                  
MASTER        0    0    0    0    0    0    0    0   48    0  104    0
END

View in JSmol

Synonyms

Value	Source
3,8,13,17-Tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropionic acid	ChEBI
5,10,15,20,22,24-Hexahydro-3,8,13,17-tetramethyl-21H,23H-porphine-2,7,12,18-tetrapropanoic acid	ChEBI
COPROPORPHYRIN III	ChEBI
3,8,13,17-Tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropionate	Generator
5,10,15,20,22,24-Hexahydro-3,8,13,17-tetramethyl-21H,23H-porphine-2,7,12,18-tetrapropanoate	Generator
3,8,13,17-Tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropanoate	HMDB
3,8,13,17-Tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropanoic acid	HMDB
5,10,15,20,22,24-Hexahydro-3,8,13,17-tetramethyl-2,7,12,18-porphinetetrapropionate	HMDB
5,10,15,20,22,24-Hexahydro-3,8,13,17-tetramethyl-2,7,12,18-porphinetetrapropionic acid	HMDB
Coproporphyrinogen	HMDB
Coproporphyrinogen-III	HMDB

Chemical Formula

C₃₆H₄₄N₄O₈

Average Mass

660.7566 Da

Monoisotopic Mass

660.31591 Da

IUPAC Name

3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid

Traditional Name

3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid

CAS Registry Number

Not Available

SMILES

CC1=C2CC3=C(C)C(CCC(O)=O)=C(CC4=C(CCC(O)=O)C(C)=C(CC5=C(CCC(O)=O)C(C)=C(CC(N2)=C1CCC(O)=O)N5)N4)N3

InChI Identifier

InChI=1S/C36H44N4O8/c1-17-21(5-9-33(41)42)29-14-27-19(3)22(6-10-34(43)44)30(39-27)15-28-20(4)24(8-12-36(47)48)32(40-28)16-31-23(7-11-35(45)46)18(2)26(38-31)13-25(17)37-29/h37-40H,5-16H2,1-4H3,(H,41,42)(H,43,44)(H,45,46)(H,47,48)

InChI Key

NIUVHXTXUXOFEB-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
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
Paraburkholderia phymatum	-	KNApSAcK
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Rhodobacter sphaeroides	--	KNApSAcK
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
Tetracarboxylic acid or derivatives
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

coproporphyrinogen (CHEBI:15439 )

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	1.96	ALOGPS
logP	4.89	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	3.8	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	212.36 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	181.86 m³·mol⁻¹	ChemAxon
Polarizability	72.85 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