MiMeDB: Showing metabocard for Sirohydrochlorin (MMDBc0030098)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:53:50 UTC

Update Date

2022-08-31 17:39:42 UTC

Metabolite ID

MMDBc0030098

Metabolite Identification

Common Name

Sirohydrochlorin

Description

Sirohydrochlorin is a member of the chemical class known as Precorrins. These are intermediates formed by methylation at one or more of the four rings prior to the formation of the macrocyclic corrin ring. typhimurium, precorrin-2 is a precursor of both siroheme and B12. (PMID 8955319 )

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241222112D          

 62 66  0  0  0  0            999 V2000
   13.0993    1.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3684    1.6396    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.8509    1.5297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9654    0.4386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7712    1.0597    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.3787    2.4633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5851    1.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1487    0.3116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9442    1.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4625    1.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6683    2.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2955    1.6430    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.7602    0.4145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7541   -0.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5393    1.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6786    3.7055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9132    1.0940    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.2921    2.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5028    1.8490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5803    0.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1487   -1.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7157    1.7872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9544    2.4941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9717    4.1241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3958    4.1103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7368    1.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0058    2.8887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8892   -0.4262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7712   -1.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9621   -1.3219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1417    1.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0058    3.7124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7231    2.4803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5597   -1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3649   -2.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9613   -2.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0959   -2.1386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9687    1.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9167   -1.9395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7429   -1.3013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3581   -3.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6731   -2.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8509   -2.4199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3771    2.5386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3874    1.1078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3161   -2.4989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7127   -1.7199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5920   -2.1112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6340   -3.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8633   -2.9828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1948   -3.4803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3950   -3.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2962   -2.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6306   -4.5853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1500   -3.6621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0923   -2.0803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0903   -3.0961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9203   -4.9902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3409   -4.9971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2255   -4.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5494   -4.9594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9839   -4.8255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  6  0  0  0
  3  7  2  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  1  0  0  0
  5 10  1  6  0  0  0
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
  7 13  1  0  0  0  0
  8 14  2  0  0  0  0
  9 15  1  0  0  0  0
 11 16  1  0  0  0  0
 12 17  1  0  0  0  0
 12 18  1  1  0  0  0
 12 19  1  6  0  0  0
 13 20  1  0  0  0  0
 14 21  1  0  0  0  0
 15 22  1  0  0  0  0
 15 23  2  0  0  0  0
 16 24  1  0  0  0  0
 16 25  2  0  0  0  0
 17 26  1  6  0  0  0
 18 27  1  0  0  0  0
 20 28  2  0  0  0  0
 21 29  2  0  0  0  0
 21 30  1  0  0  0  0
 26 31  1  0  0  0  0
 27 32  1  0  0  0  0
 27 33  2  0  0  0  0
 28 34  1  0  0  0  0
 29 35  1  0  0  0  0
 29 36  1  0  0  0  0
 30 37  1  0  0  0  0
 31 38  1  0  0  0  0
 34 39  1  0  0  0  0
 34 40  2  0  0  0  0
 35 41  1  0  0  0  0
 36 42  1  0  0  0  0
 37 43  1  0  0  0  0
 38 44  1  0  0  0  0
 38 45  2  0  0  0  0
 39 46  2  0  0  0  0
 39 47  1  0  0  0  0
 40 48  1  0  0  0  0
 41 49  1  0  0  0  0
 42 50  1  0  0  0  0
 42 51  2  0  0  0  0
 46 52  1  0  0  0  0
 47 53  1  0  0  0  0
 49 54  1  0  0  0  0
 52 55  1  0  0  0  0
 53 56  1  0  0  0  0
 53 57  2  0  0  0  0
 54 58  1  0  0  0  0
 54 59  2  0  0  0  0
 55 60  1  0  0  0  0
 60 61  1  0  0  0  0
 60 62  2  0  0  0  0
  5  8  1  0  0  0  0
 17 20  1  0  0  0  0
 35 37  2  0  0  0  0
 43 48  2  0  0  0  0
 46 48  1  0  0  0  0
M  END


  Mrv0541 02241222112D          

 62 66  0  0  0  0            999 V2000
   13.0993    1.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3684    1.6396    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.8509    1.5297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9654    0.4386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7712    1.0597    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.3787    2.4633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5851    1.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1487    0.3116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9442    1.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4625    1.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6683    2.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2955    1.6430    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.7602    0.4145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7541   -0.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5393    1.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6786    3.7055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9132    1.0940    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.2921    2.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5028    1.8490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5803    0.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1487   -1.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7157    1.7872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9544    2.4941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9717    4.1241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3958    4.1103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7368    1.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0058    2.8887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8892   -0.4262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7712   -1.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9621   -1.3219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1417    1.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0058    3.7124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7231    2.4803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5597   -1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3649   -2.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9613   -2.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0959   -2.1386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9687    1.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9167   -1.9395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7429   -1.3013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3581   -3.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6731   -2.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8509   -2.4199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3771    2.5386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3874    1.1078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3161   -2.4989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7127   -1.7199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5920   -2.1112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6340   -3.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8633   -2.9828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1948   -3.4803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3950   -3.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2962   -2.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6306   -4.5853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1500   -3.6621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0923   -2.0803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0903   -3.0961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9203   -4.9902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3409   -4.9971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2255   -4.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5494   -4.9594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9839   -4.8255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  6  0  0  0
  3  7  2  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  1  0  0  0
  5 10  1  6  0  0  0
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
  7 13  1  0  0  0  0
  8 14  2  0  0  0  0
  9 15  1  0  0  0  0
 11 16  1  0  0  0  0
 12 17  1  0  0  0  0
 12 18  1  1  0  0  0
 12 19  1  6  0  0  0
 13 20  1  0  0  0  0
 14 21  1  0  0  0  0
 15 22  1  0  0  0  0
 15 23  2  0  0  0  0
 16 24  1  0  0  0  0
 16 25  2  0  0  0  0
 17 26  1  6  0  0  0
 18 27  1  0  0  0  0
 20 28  2  0  0  0  0
 21 29  2  0  0  0  0
 21 30  1  0  0  0  0
 26 31  1  0  0  0  0
 27 32  1  0  0  0  0
 27 33  2  0  0  0  0
 28 34  1  0  0  0  0
 29 35  1  0  0  0  0
 29 36  1  0  0  0  0
 30 37  1  0  0  0  0
 31 38  1  0  0  0  0
 34 39  1  0  0  0  0
 34 40  2  0  0  0  0
 35 41  1  0  0  0  0
 36 42  1  0  0  0  0
 37 43  1  0  0  0  0
 38 44  1  0  0  0  0
 38 45  2  0  0  0  0
 39 46  2  0  0  0  0
 39 47  1  0  0  0  0
 40 48  1  0  0  0  0
 41 49  1  0  0  0  0
 42 50  1  0  0  0  0
 42 51  2  0  0  0  0
 46 52  1  0  0  0  0
 47 53  1  0  0  0  0
 49 54  1  0  0  0  0
 52 55  1  0  0  0  0
 53 56  1  0  0  0  0
 53 57  2  0  0  0  0
 54 58  1  0  0  0  0
 54 59  2  0  0  0  0
 55 60  1  0  0  0  0
 60 61  1  0  0  0  0
 60 62  2  0  0  0  0
  5  8  1  0  0  0  0
 17 20  1  0  0  0  0
 35 37  2  0  0  0  0
 43 48  2  0  0  0  0
 46 48  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0030098

> <DATABASE_NAME>
MIME

> <SMILES>
C[C@]1(CC(O)=O)[C@H](CCC(O)=O)\C2=C\C3=N\C(=C/C4=C(CCC(O)=O)C(CC(O)=O)=C(N4)\C=C4/N=C(/C=C1\N2)[C@@H](CCC(O)=O)[C@]4(C)CC(O)=O)\C(CCC(O)=O)=C3CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C42H46N4O16/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/h13-16,23-24,44-45H,3-12,17-18H2,1-2H3,(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)(H,59,60)(H,61,62)/b25-13-,29-14-,31-15-,32-16-/t23-,24-,41+,42+/m1/s1

> <INCHI_KEY>
KWIZRXMMFRBUML-AHGFGAHVSA-N

> <FORMULA>
C42H46N4O16

> <MOLECULAR_WEIGHT>
862.8318

> <EXACT_MASS>
862.290881444

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
89.44342006533834

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(4S,5S,9S,10S)-9,15,19-tris(2-carboxyethyl)-5,10,14,20-tetrakis(carboxymethyl)-5,10-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,6,8(23),11,13,15,17,19-nonaen-4-yl]propanoic acid

> <ALOGPS_LOGP>
1.04

> <JCHEM_LOGP>
3.116881802

> <ALOGPS_LOGS>
-4.54

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-8

> <JCHEM_PKA>
3.4318325811550707

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.05614721406891

> <JCHEM_POLAR_SURFACE_AREA>
355.76

> <JCHEM_REFRACTIVITY>
209.3843000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.52e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sirohydrochlorin

> <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      24.452   2.331   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      23.088   3.061   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.855   2.855   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      24.202   0.819   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      21.973   1.978   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.107   4.598   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.226   2.279   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.678   0.582   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.429   1.985   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.397   3.400   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.781   5.373   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      28.552   3.067   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      27.552   0.774   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      21.941  -0.834   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      19.673   3.323   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.800   6.917   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.705   2.042   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.545   4.624   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      27.072   3.451   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      29.083   0.633   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      22.678  -2.243   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      18.136   3.336   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      20.448   4.656   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      20.481   7.698   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      23.139   7.673   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      31.242   2.048   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      29.877   5.392   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      29.660  -0.796   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      21.973  -3.627   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0      24.196  -2.468   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0      31.998   3.387   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      29.877   6.930   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      31.216   4.630   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      29.045  -2.218   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      23.081  -4.690   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      20.461  -3.877   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      24.446  -3.992   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      33.542   3.400   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      29.711  -3.620   0.000  0.00  0.00           C+0
HETATM   40  N   UNK     0      27.520  -2.429   0.000  0.00  0.00           N+0
HETATM   41  C   UNK     0      23.068  -6.234   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      19.923  -5.311   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      25.855  -4.517   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      34.304   4.739   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      34.323   2.068   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      28.590  -4.665   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      31.197  -3.210   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      27.238  -3.941   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      21.717  -7.009   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      18.411  -5.568   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      20.897  -6.497   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      28.737  -6.195   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      32.286  -4.287   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      21.710  -8.559   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      30.147  -6.836   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      33.772  -3.883   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      31.902  -5.779   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      20.385  -9.315   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      23.036  -9.328   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      30.288  -8.373   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      29.026  -9.258   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0      31.703  -9.008   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   10    8                                             
CONECT    6    2   11                                                       
CONECT    7    3   12   13                                                  
CONECT    8    4   14    5                                                  
CONECT    9    5   15                                                       
CONECT   10    5                                                            
CONECT   11    6   16                                                       
CONECT   12    7   17   18   19                                             
CONECT   13    7   20                                                       
CONECT   14    8   21                                                       
CONECT   15    9   22   23                                                  
CONECT   16   11   24   25                                                  
CONECT   17   12   26   20                                                  
CONECT   18   12   27                                                       
CONECT   19   12                                                            
CONECT   20   13   28   17                                                  
CONECT   21   14   29   30                                                  
CONECT   22   15                                                            
CONECT   23   15                                                            
CONECT   24   16                                                            
CONECT   25   16                                                            
CONECT   26   17   31                                                       
CONECT   27   18   32   33                                                  
CONECT   28   20   34                                                       
CONECT   29   21   35   36                                                  
CONECT   30   21   37                                                       
CONECT   31   26   38                                                       
CONECT   32   27                                                            
CONECT   33   27                                                            
CONECT   34   28   39   40                                                  
CONECT   35   29   41   37                                                  
CONECT   36   29   42                                                       
CONECT   37   30   43   35                                                  
CONECT   38   31   44   45                                                  
CONECT   39   34   46   47                                                  
CONECT   40   34   48                                                       
CONECT   41   35   49                                                       
CONECT   42   36   50   51                                                  
CONECT   43   37   48                                                       
CONECT   44   38                                                            
CONECT   45   38                                                            
CONECT   46   39   52   48                                                  
CONECT   47   39   53                                                       
CONECT   48   40   43   46                                                  
CONECT   49   41   54                                                       
CONECT   50   42                                                            
CONECT   51   42                                                            
CONECT   52   46   55                                                       
CONECT   53   47   56   57                                                  
CONECT   54   49   58   59                                                  
CONECT   55   52   60                                                       
CONECT   56   53                                                            
CONECT   57   53                                                            
CONECT   58   54                                                            
CONECT   59   54                                                            
CONECT   60   55   61   62                                                  
CONECT   61   60                                                            
CONECT   62   60                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  132    0
END

Synonyms

Value	Source
(7S,8S,12S,13S)-3,8,13,17-Tetrakis(carboxymethyl)-8,13-dimethyl-7,8,12,13-tetrahydroporphyrin-2,7,12,18-tetrapropionic acid	ChEBI
(7S,8S,12S,13S)-3,8,13,17-Tetrakis(carboxymethyl)-8,13-dimethyl-7,8,12,13-tetrahydroporphyrin-2,7,12,18-tetrapropionate	Generator

Molecular Formula

C₄₂H₄₆N₄O₁₆

Average Mass

862.8318

Monoisotopic Mass

862.290881444

IUPAC Name

3-[(4S,5S,9S,10S)-9,15,19-tris(2-carboxyethyl)-5,10,14,20-tetrakis(carboxymethyl)-5,10-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,6,8(23),11,13,15,17,19-nonaen-4-yl]propanoic acid

Traditional Name

sirohydrochlorin

CAS Registry Number

65207-12-7

SMILES

C[C@]1(CC(O)=O)[C@H](CCC(O)=O)\C2=C\C3=N\C(=C/C4=C(CCC(O)=O)C(CC(O)=O)=C(N4)\C=C4/N=C(/C=C1\N2)[C@@H](CCC(O)=O)[C@]4(C)CC(O)=O)\C(CCC(O)=O)=C3CC(O)=O

InChI Identifier

InChI=1S/C42H46N4O16/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/h13-16,23-24,44-45H,3-12,17-18H2,1-2H3,(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)(H,59,60)(H,61,62)/b25-13-,29-14-,31-15-,32-16-/t23-,24-,41+,42+/m1/s1

InChI Key

KWIZRXMMFRBUML-AHGFGAHVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrapyrroles and derivatives. These are polycyclic aromatic compounds containing four pyrrole rings joined by one-carbon units linking position 2 of one pyrrole ring to position 5 of the next.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrapyrroles and derivatives

Sub Class

Not Available

Direct Parent

Tetrapyrroles and derivatives

Alternative Parents

Substituents

Tetrapyrrole skeleton
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

isobacteriochlorins (CHEBI:18023 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.025 g/L	ALOGPS
logP	1.04	ALOGPS
logP	3.12	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	3.06	ChemAxon
Physiological Charge	-8	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	355.76 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	209.38 m³·mol⁻¹	ChemAxon
Polarizability	89.44 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-0000000590-ed03bd2dfabb11dffa05	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006t-0000000940-5b3a240ffe55a81be5b8	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0avi-0000000920-e98aa012967f148e1d86	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0301-0000000790-d2080d5c77f3c757c10e	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00r2-0000000950-fad195608adfddb030b6	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052b-2000000930-856c98525e7bd6b9a47c	2016-09-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	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
MMDBr0006974	Cobalt	Cobalt-precorrin 2	Not Available		VMH	30371894
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	265	Human feces; Human ; Human sputum; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; Human stool; Cattle ; Turkey ; River trout	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	230	Human feces; Human ; Human stool; Human saliva; Human subgingival plaque; Cattle	Metabolic reconstruction
Bacteria	Bacteroidetes	57	Human feces; Human ; Human gastric fluid; Human saliva; Human subgingival plaque	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	19	Human feces; Human	Metabolic reconstruction
Bacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Bacteria	Actinobacteria	63	Human feces; Human ; Human pleural fluid plaque; Human dental plaque; Human sputum; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	3	Human feces; Human saliva	Unknown
Archaea/Archaea	Euryarchaeota	11		Metabolic reconstruction
Archaea	Crenarchaeota	1
Archaea/Archaea	Crenarchaeota	8
Bacteria	nah	1

Exposure Sources

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

C00007315

Chemspider ID

Not Available

KEGG Compound ID

C05778

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sirohydrochlorin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

18023

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 Sirohydrochlorin (MMDBc0030098)

MOL for #<Metabolite:0x00007fdaf1b56228>

3D MOL for #<Metabolite:0x00007fdaf1b56228>

3D SDF for #<Metabolite:0x00007fdaf1b56228>

3D-SDF for #<Metabolite:0x00007fdaf1b56228>

PDB for #<Metabolite:0x00007fdaf1b56228>

3D PDB for #<Metabolite:0x00007fdaf1b56228>

SMILES for #<Metabolite:0x00007fdaf1b56228>

INCHI for #<Metabolite:0x00007fdaf1b56228>

Structure for #<Metabolite:0x00007fdaf1b56228>

3D Structure for #<Metabolite:0x00007fdaf1b56228>