MiMeDB: Showing metabocard for Siroheme (MMDBc0030097)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:53:48 UTC

Update Date

2022-08-31 17:39:42 UTC

Metabolite ID

MMDBc0030097

Metabolite Identification

Common Name

Siroheme

Description

Siroheme belongs to the class of Precorrins. These are intermediates formed by methylation at one or more of the four rings prior to the formation of the macrocyclic corrin ring. (inferred from compound structure)Siroheme (or sirohaem) is a heme-like prosthetic group used by some enzymes to accomplish the six-electron reduction of sulfur and nitrogen. Siroheme is synthesized from uroporphyrinogen III, a heme and vitamin B12 precursor. It plays a major role in the sulfur assimilation pathway: converting sulfite to a biologically useful sulfide, which can be incorporated into the organic compound homocysteine. (WikiPedia)

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241222482D          

 63 70  0  0  0  0            999 V2000
   -1.6487    0.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7096    1.6696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.0870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7305    1.6696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6696    0.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0871    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6696   -0.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7305   -1.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7096   -1.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6487   -0.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0661    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8557    0.8557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8557   -0.8557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8348   -0.8557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4400   -2.0453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6535   -2.8422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4504   -3.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4610   -2.0453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4608   -4.0661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6639   -3.8526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0806   -4.4360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8348    0.8557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0244   -1.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8213   -1.6744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1911   -0.2941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4045   -1.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2014   -1.3044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0244    1.4609    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8213    1.6744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0348    2.4713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4151    2.1015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8317    2.6847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0452    3.4816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6745    2.8422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4610    2.0453    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4714    3.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1016    4.4360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6848    3.8526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4817    4.0661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4400    2.8702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0109    2.8703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7254    3.2827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7254    4.1078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4400    2.0453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0234    2.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8910    1.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8911    0.0319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3035    0.7463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1286    0.7463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0662    1.4609    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6496    2.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0662   -1.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8630   -1.6744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4933   -3.0548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0765   -2.4713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8734   -2.6849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6745   -2.8422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1016   -4.4360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0911   -3.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7215   -4.8059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3047   -4.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 Fe  0  0  0  0  0  0  0  0  0  0  0  0
  1 23  1  0  0  0  0
 29  1  1  0  0  0  0
 12  1  2  0  0  0  0
  2  3  1  0  0  0  0
 23  2  2  0  0  0  0
 45  2  1  0  0  0  0
  3  4  2  0  0  0  0
  4 13  1  0  0  0  0
 36  4  1  0  0  0  0
  5  6  2  0  0  0  0
 13  5  1  0  0  0  0
 51  5  1  0  0  0  0
  6  7  1  0  0  0  0
  7 14  2  0  0  0  0
  7 53  1  0  0  0  0
  8  9  2  0  0  0  0
 19  8  1  0  0  0  0
 14  8  1  0  0  0  0
 10  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16 10  2  0  0  0  0
 11 12  1  0  0  0  0
 15 11  1  0  0  0  0
 24 11  2  0  0  0  0
 45 29  1  0  0  0  0
 36 51  1  0  0  0  0
 53 19  2  0  0  0  0
 24 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 21  1  0  0  0  0
 19 58  1  0  0  0  0
 21 20  1  0  0  0  0
 21 22  2  0  0  0  0
 25 27  1  0  0  0  0
 27 26  2  0  0  0  0
 27 28  1  0  0  0  0
 24 25  1  0  0  0  0
 30 31  1  0  0  0  0
 31 33  1  0  0  0  0
 33 32  1  0  0  0  0
 33 34  2  0  0  0  0
 35 37  1  0  0  0  0
 36 35  1  1  0  0  0
 37 39  1  0  0  0  0
 39 38  1  0  0  0  0
 39 40  2  0  0  0  0
 29 30  1  1  0  0  0
 45 41  1  6  0  0  0
 41 43  1  0  0  0  0
 43 42  1  0  0  0  0
 43 44  2  0  0  0  0
 45 46  1  0  0  0  0
 51 47  1  6  0  0  0
 47 49  1  0  0  0  0
 49 48  1  0  0  0  0
 49 50  2  0  0  0  0
 51 52  1  0  0  0  0
 54 56  1  0  0  0  0
 56 55  1  0  0  0  0
 56 57  2  0  0  0  0
 58 60  1  0  0  0  0
 62 59  2  0  0  0  0
 60 62  1  0  0  0  0
 62 61  1  0  0  0  0
 53 54  1  0  0  0  0
 15 63  1  0  0  0  0
 13 63  1  0  0  0  0
 23 63  8  0  0  0  0
 14 63  8  0  0  0  0
M  STY  2   1 DAT   2 DAT
M  SAL   1  2  23  63
M  SDT   1 MRV_COORDINATE_BOND_TYPE                              
M  SDD   1     0.0000    0.0000    DR    ALL  0       0  
M  SED   1 69
M  SAL   2  2  14  63
M  SDT   2 MRV_COORDINATE_BOND_TYPE                              
M  SDD   2     0.0000    0.0000    DR    ALL  0       0  
M  SED   2 70
M  END


  Mrv0541 02241222482D          

 63 70  0  0  0  0            999 V2000
   -1.6487    0.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7096    1.6696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.0870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7305    1.6696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6696    0.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0871    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6696   -0.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7305   -1.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7096   -1.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6487   -0.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0661    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8557    0.8557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8557   -0.8557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8348   -0.8557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4400   -2.0453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6535   -2.8422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4504   -3.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4610   -2.0453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4608   -4.0661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6639   -3.8526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0806   -4.4360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8348    0.8557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0244   -1.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8213   -1.6744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1911   -0.2941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4045   -1.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2014   -1.3044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0244    1.4609    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8213    1.6744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0348    2.4713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4151    2.1015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8317    2.6847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0452    3.4816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6745    2.8422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4610    2.0453    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4714    3.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1016    4.4360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6848    3.8526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4817    4.0661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4400    2.8702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0109    2.8703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7254    3.2827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7254    4.1078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4400    2.0453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0234    2.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8910    1.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8911    0.0319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3035    0.7463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1286    0.7463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0662    1.4609    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6496    2.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0662   -1.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8630   -1.6744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4933   -3.0548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0765   -2.4713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8734   -2.6849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6745   -2.8422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1016   -4.4360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0911   -3.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7215   -4.8059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3047   -4.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 Fe  0  0  0  0  0  0  0  0  0  0  0  0
  1 23  1  0  0  0  0
 29  1  1  0  0  0  0
 12  1  2  0  0  0  0
  2  3  1  0  0  0  0
 23  2  2  0  0  0  0
 45  2  1  0  0  0  0
  3  4  2  0  0  0  0
  4 13  1  0  0  0  0
 36  4  1  0  0  0  0
  5  6  2  0  0  0  0
 13  5  1  0  0  0  0
 51  5  1  0  0  0  0
  6  7  1  0  0  0  0
  7 14  2  0  0  0  0
  7 53  1  0  0  0  0
  8  9  2  0  0  0  0
 19  8  1  0  0  0  0
 14  8  1  0  0  0  0
 10  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16 10  2  0  0  0  0
 11 12  1  0  0  0  0
 15 11  1  0  0  0  0
 24 11  2  0  0  0  0
 45 29  1  0  0  0  0
 36 51  1  0  0  0  0
 53 19  2  0  0  0  0
 24 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 21  1  0  0  0  0
 19 58  1  0  0  0  0
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 30 31  1  0  0  0  0
 31 33  1  0  0  0  0
 33 32  1  0  0  0  0
 33 34  2  0  0  0  0
 35 37  1  0  0  0  0
 36 35  1  1  0  0  0
 37 39  1  0  0  0  0
 39 38  1  0  0  0  0
 39 40  2  0  0  0  0
 29 30  1  1  0  0  0
 45 41  1  6  0  0  0
 41 43  1  0  0  0  0
 43 42  1  0  0  0  0
 43 44  2  0  0  0  0
 45 46  1  0  0  0  0
 51 47  1  6  0  0  0
 47 49  1  0  0  0  0
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 49 50  2  0  0  0  0
 51 52  1  0  0  0  0
 54 56  1  0  0  0  0
 56 55  1  0  0  0  0
 56 57  2  0  0  0  0
 58 60  1  0  0  0  0
 62 59  2  0  0  0  0
 60 62  1  0  0  0  0
 62 61  1  0  0  0  0
 53 54  1  0  0  0  0
 15 63  1  0  0  0  0
 13 63  1  0  0  0  0
 23 63  8  0  0  0  0
 14 63  8  0  0  0  0
M  STY  2   1 DAT   2 DAT
M  SAL   1  2  23  63
M  SDT   1 MRV_COORDINATE_BOND_TYPE                              
M  SDD   1     0.0000    0.0000    DR    ALL  0       0  
M  SED   1 69
M  SAL   2  2  14  63
M  SDT   2 MRV_COORDINATE_BOND_TYPE                              
M  SDD   2     0.0000    0.0000    DR    ALL  0       0  
M  SED   2 70
M  END
> <DATABASE_ID>
MMDBc0030097

> <DATABASE_NAME>
MIME

> <SMILES>
C[C@]1(CC(O)=O)[C@H](CCC(O)=O)\C2=C\C3=C(CC(O)=O)C(CCC(O)=O)=C4\C=C5/N=C(/C=C6\N([Fe]N34)\C(=C/C1=N2)[C@@H](CCC(O)=O)[C@]6(C)CC(O)=O)C(CC(O)=O)=C5CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C42H46N4O16.Fe/c1-41(17-39(59)60)23(5-9-35(51)52)29-14-27-21(11-37(55)56)19(3-7-33(47)48)25(43-27)13-26-20(4-8-34(49)50)22(12-38(57)58)28(44-26)15-31-42(2,18-40(61)62)24(6-10-36(53)54)30(46-31)16-32(41)45-29;/h13-16,23-24H,3-12,17-18H2,1-2H3,(H10,43,44,45,46,47,48,49,50,51,52,53,54,55,56,57,58,59,60,61,62);/q;+2/p-2/t23-,24-,41+,42+;/m1./s1

> <INCHI_KEY>
DLKSSIHHLYNIKN-QIISWYHFSA-L

> <FORMULA>
C42H44FeN4O16

> <MOLECULAR_WEIGHT>
916.661

> <EXACT_MASS>
916.210173513

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(4S,5S,9S,10S,11Z,16Z)-9,15,19-tris(2-carboxyethyl)-5,10,14,20-tetrakis(carboxymethyl)-5,10-dimethyl-21,23,24,25-tetraaza-22-ferrahexacyclo[9.9.3.1³,⁶.1¹³,¹⁶.0⁸,²³.0¹⁸,²¹]pentacosa-1(20),2,6(25),7,11,13(24),14,16,18-nonaen-4-yl]propanoic acid

> <ALOGPS_LOGP>
1.07

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-8

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7940590963612455

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.28e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(4S,5S,9S,10S,11Z,16Z)-9,15,19-tris(2-carboxyethyl)-5,10,14,20-tetrakis(carboxymethyl)-5,10-dimethyl-21,23,24,25-tetraaza-22-ferrahexacyclo[9.9.3.1³,⁶.1¹³,¹⁶.0⁸,²³.0¹⁸,²¹]pentacosa-1(20),2,6(25),7,11,13(24),14,16,18-nonaen-4-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.078   1.325   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.325   3.117   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   3.896   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.364   3.117   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.117   1.325   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.896   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.117  -1.325   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.364  -3.117   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -3.896   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.325  -3.117   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.078  -1.325   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.857   0.000   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       1.597   1.597   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       1.597  -1.597   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0      -1.558  -1.597   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      -2.688  -3.818   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.087  -5.305   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.574  -5.704   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.727  -3.818   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -6.460  -7.590   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -4.973  -7.192   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.884  -8.281   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0      -1.558   1.597   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      -3.779  -2.727   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.266  -3.126   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -5.957  -0.549   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -6.355  -2.036   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -7.843  -2.435   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -3.779   2.727   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.266   3.126   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.665   4.613   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -8.242   3.923   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -7.153   5.011   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -7.551   6.499   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       3.126   5.305   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.727   3.818   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.613   5.704   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       3.923   8.281   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       5.012   7.192   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       6.499   7.590   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -2.688   5.358   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -0.020   5.358   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -1.354   6.128   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -1.354   7.668   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -2.688   3.818   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -3.777   4.907   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       5.397   2.727   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       5.397   0.060   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       6.167   1.393   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       7.707   1.393   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       3.857   2.727   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       4.946   3.816   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       3.857  -2.727   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       5.344  -3.126   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0       4.654  -5.702   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0       5.743  -4.613   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0       7.230  -5.012   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0       3.126  -5.305   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0       3.923  -8.281   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0       2.037  -6.394   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0       1.347  -8.971   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0       2.435  -7.882   0.000  0.00  0.00           C+0
HETATM   63 Fe   UNK     0       0.000   0.000   0.000  0.00  0.00          Fe+0
CONECT    1   23   29   12                                                  
CONECT    2    3   23   45                                                  
CONECT    3    2    4                                                       
CONECT    4    3   13   36                                                  
CONECT    5    6   13   51                                                  
CONECT    6    5    7                                                       
CONECT    7    6   14   53                                                  
CONECT    8    9   19   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   15   16                                                  
CONECT   11   12   15   24                                                  
CONECT   12    1   11                                                       
CONECT   13    4    5   63                                                  
CONECT   14    7    8   63                                                  
CONECT   15   10   11   63                                                  
CONECT   16   10   24   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   21                                                       
CONECT   19    8   53   58                                                  
CONECT   20   21                                                            
CONECT   21   18   20   22                                                  
CONECT   22   21                                                            
CONECT   23    1    2   63                                                  
CONECT   24   11   16   25                                                  
CONECT   25   27   24                                                       
CONECT   26   27                                                            
CONECT   27   25   26   28                                                  
CONECT   28   27                                                            
CONECT   29    1   45   30                                                  
CONECT   30   31   29                                                       
CONECT   31   30   33                                                       
CONECT   32   33                                                            
CONECT   33   31   32   34                                                  
CONECT   34   33                                                            
CONECT   35   37   36                                                       
CONECT   36    4   51   35                                                  
CONECT   37   35   39                                                       
CONECT   38   39                                                            
CONECT   39   37   38   40                                                  
CONECT   40   39                                                            
CONECT   41   45   43                                                       
CONECT   42   43                                                            
CONECT   43   41   42   44                                                  
CONECT   44   43                                                            
CONECT   45    2   29   41   46                                             
CONECT   46   45                                                            
CONECT   47   51   49                                                       
CONECT   48   49                                                            
CONECT   49   47   48   50                                                  
CONECT   50   49                                                            
CONECT   51    5   36   47   52                                             
CONECT   52   51                                                            
CONECT   53    7   19   54                                                  
CONECT   54   56   53                                                       
CONECT   55   56                                                            
CONECT   56   54   55   57                                                  
CONECT   57   56                                                            
CONECT   58   19   60                                                       
CONECT   59   62                                                            
CONECT   60   58   62                                                       
CONECT   61   62                                                            
CONECT   62   59   60   61                                                  
CONECT   63   15   13   23   14                                             
MASTER        0    0    0    0    0    0    0    0   63    0  140    0
END

Synonyms

Value	Source
Sirohaem	ChEBI
Octacarboxylate iron-tetrahydroporphyrin	MeSH

Molecular Formula

C₄₂H₄₄FeN₄O₁₆

Average Mass

916.661

Monoisotopic Mass

916.210173513

IUPAC Name

3-[(4S,5S,9S,10S,11Z,16Z)-9,15,19-tris(2-carboxyethyl)-5,10,14,20-tetrakis(carboxymethyl)-5,10-dimethyl-21,23,24,25-tetraaza-22-ferrahexacyclo[9.9.3.1³,⁶.1¹³,¹⁶.0⁸,²³.0¹⁸,²¹]pentacosa-1(20),2,6(25),7,11,13(24),14,16,18-nonaen-4-yl]propanoic acid

Traditional Name

CAS Registry Number

52553-42-1

SMILES

C[C@]1(CC(O)=O)[C@H](CCC(O)=O)\C2=C\C3=C(CC(O)=O)C(CCC(O)=O)=C4\C=C5/N=C(/C=C6\N([Fe]N34)\C(=C/C1=N2)[C@@H](CCC(O)=O)[C@]6(C)CC(O)=O)C(CC(O)=O)=C5CCC(O)=O

InChI Identifier

InChI=1S/C42H46N4O16.Fe/c1-41(17-39(59)60)23(5-9-35(51)52)29-14-27-21(11-37(55)56)19(3-7-33(47)48)25(43-27)13-26-20(4-8-34(49)50)22(12-38(57)58)28(44-26)15-31-42(2,18-40(61)62)24(6-10-36(53)54)30(46-31)16-32(41)45-29;/h13-16,23-24H,3-12,17-18H2,1-2H3,(H10,43,44,45,46,47,48,49,50,51,52,53,54,55,56,57,58,59,60,61,62);/q;+2/p-2/t23-,24-,41+,42+;/m1./s1

InChI Key

DLKSSIHHLYNIKN-QIISWYHFSA-L

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as metallotetrapyrroles. These are polycyclic compounds containing a tetrapyrrole skeleton combined with a metal atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrapyrroles and derivatives

Sub Class

Metallotetrapyrroles

Direct Parent

Metallotetrapyrroles

Alternative Parents

Substituents

Metallotetrapyrrole skeleton
Substituted pyrrole
Pyrrole
Heteroaromatic compound
Azacycle
Organic transition metal salt
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Carbonyl group
Organic salt
Organic zwitterion
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

heme (CHEBI:28599 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.13 g/L	ALOGPS
logP	1.07	ALOGPS
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	2.79	ChemAxon
Physiological Charge	-8	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05i1-0000000090-f46f6449060cf2ca1980	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00b9-0000000090-84962b34725f7a689488	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01t9-0000000090-00a96804df0e7027208c	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00xr-0000000092-0b4a42172e52e76b6f63	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ufr-0000000090-e9c0f647cacbe1d93a40	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0000000090-191e040b23bfd9ce6a65	2015-09-15	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0006975	Sirohydrochlorin	Siroheme	Not Available		VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	283	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; Human stool; Sheep ; Cattle ; Turkey ; River trout	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	276	Human feces; Human ; Human subgingival plaque; Cattle ; Human pleural fluid plaque; Pig ; Human stool; Human saliva	Metabolic reconstruction
Bacteria	Actinobacteria	104	Human feces; Human pleural fluid plaque; Human dental plaque; Human sputum; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva; Human nasopharyngeal swab	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	77	Human feces; Human ; Human gastric fluid; Human saliva; Human subgingival plaque; Human appendix biopsy; Human supragingival plaque; Human stool	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	15	Human feces; Human	Metabolic reconstruction
Bacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Bacteria	Tenericutes	4	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Archaea/Archaea	Euryarchaeota	1		Metabolic reconstruction
Bacteria	Aquificae	1
Eukaryota/Fungi	Ascomycota	3	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00007626

Chemspider ID

Not Available

KEGG Compound ID

C00748

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Siroheme

METLIN ID

Not Available

PubChem Compound

439303

PDB ID

Not Available

ChEBI ID

28599

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]
Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for Siroheme (MMDBc0030097)

MOL for #<Metabolite:0x00007fecfcfc0698>

3D MOL for #<Metabolite:0x00007fecfcfc0698>

3D SDF for #<Metabolite:0x00007fecfcfc0698>

3D-SDF for #<Metabolite:0x00007fecfcfc0698>

PDB for #<Metabolite:0x00007fecfcfc0698>

3D PDB for #<Metabolite:0x00007fecfcfc0698>

SMILES for #<Metabolite:0x00007fecfcfc0698>

INCHI for #<Metabolite:0x00007fecfcfc0698>

Structure for #<Metabolite:0x00007fecfcfc0698>

3D Structure for #<Metabolite:0x00007fecfcfc0698>