MiMeDB: Showing metabocard for Heme (MMDBc0029705)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:38:18 UTC

Update Date

2024-04-30 19:40:56 UTC

Metabolite ID

MMDBc0029705

Metabolite Identification

Common Name

Heme

Description

Heme B or haem B (also known as protoheme IX) is the most abundant heme in nature. E. coli is known to produce 4 different hemes: protoheme IX (heme B), heme C, heme D, and siroheme. A heme or haem is a prosthetic group that consists of an iron atom contained in the center of a large heterocyclic organic ring called a porphyrin. Not all porphyrins contain iron, but a substantial fraction of porphyrin-containing metalloproteins have heme as their prosthetic subunit; these are known as hemoproteins. Generally, heme B is attached to the surrounding protein matrix (known as the apoprotein) through a single coordination bond between the heme iron and an amino-acid side-chain. When oxygen is bound the iron becomes hexacoordinated. Since the iron in heme B containing proteins is bound to the four nitrogens of the porphyrin (forming a plane) and a single electron donating atom of the protein, the iron is often in a pentacoordinate state.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02231216182D          

 43 50  0  0  1  0            999 V2000
    0.8839   -0.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5815   -0.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6353    0.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0008    0.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2269    0.6903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4075    1.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1815    0.9319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2680    2.0308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4348    0.6519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9554    1.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6697    2.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3042    1.4746    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    5.0018    1.9151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9392    1.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3519    0.6802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1183    0.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8159    0.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7833    1.6394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0645   -0.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6989   -0.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2649   -0.6519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7444   -1.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0300   -2.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7245   -2.7684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1649   -3.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7810   -4.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9013   -2.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3739   -3.3490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6980   -1.9151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3956   -1.4746    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.3499    0.0000    0.0000 Fe  0  0  1  0  0  0  0  0  0  0  0  0
    2.8752   -0.0457    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3479   -0.6802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7605   -1.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8245    0.0457    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7985    2.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3259    3.3490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9753    2.7684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5348    3.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7105    3.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    2.7032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7669    2.0056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5022    2.6706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 24 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 23 30  1  0  0  0  0
 31 30  1  1  0  0  0
 12 31  1  0  0  0  0
 31 32  1  0  0  0  0
  9 32  1  0  0  0  0
 32 33  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
 31 35  1  0  0  0  0
 15 35  1  0  0  0  0
 21 35  1  0  0  0  0
 13 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 11 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
M  CHG  2  12   1  30   1
M  END


  Mrv0541 02231216182D          

 43 50  0  0  1  0            999 V2000
    0.8839   -0.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5815   -0.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6353    0.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0008    0.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2269    0.6903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4075    1.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1815    0.9319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2680    2.0308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4348    0.6519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9554    1.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6697    2.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3042    1.4746    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    5.0018    1.9151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9392    1.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3519    0.6802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1183    0.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8159    0.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7833    1.6394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0645   -0.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6989   -0.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2649   -0.6519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7444   -1.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0300   -2.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7245   -2.7684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1649   -3.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7810   -4.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9013   -2.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3739   -3.3490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6980   -1.9151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3956   -1.4746    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.3499    0.0000    0.0000 Fe  0  0  1  0  0  0  0  0  0  0  0  0
    2.8752   -0.0457    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3479   -0.6802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7605   -1.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8245    0.0457    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7985    2.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3259    3.3490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9753    2.7684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5348    3.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7105    3.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    2.7032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7669    2.0056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5022    2.6706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 24 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 23 30  1  0  0  0  0
 31 30  1  1  0  0  0
 12 31  1  0  0  0  0
 31 32  1  0  0  0  0
  9 32  1  0  0  0  0
 32 33  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
 31 35  1  0  0  0  0
 15 35  1  0  0  0  0
 21 35  1  0  0  0  0
 13 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 11 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
M  CHG  2  12   1  30   1
M  END
> <DATABASE_ID>
MMDBc0029705

> <DATABASE_NAME>
MIME

> <SMILES>
CC1=C(CCC(O)=O)C2=CC3=[N+]4C(=CC5=C(C=C)C(C)=C6C=C7C(C=C)=C(C)C8=[N+]7[Fe@]4(N2C1=C8)N56)C(C)=C3CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C34H34N4O4.Fe/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25;/h7-8,13-16H,1-2,9-12H2,3-6H3,(H4,35,36,37,38,39,40,41,42);/q;+4/p-2/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;

> <INCHI_KEY>
YHLKGEDAGPGZPN-RGGAHWMASA-L

> <FORMULA>
C34H32FeN4O4

> <MOLECULAR_WEIGHT>
616.487

> <EXACT_MASS>
616.177297665

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
69.61434483380572

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R)-15,19-bis(2-carboxyethyl)-5,10-diethenyl-4,9,14,20-tetramethyl-2λ⁵,22,23λ⁵,25-tetraaza-1-ferraoctacyclo[11.9.1.1¹,⁸.1³,²¹.0²,⁶.0¹⁶,²³.0¹⁸,²².0¹¹,²⁵]pentacosa-2,4,6,8,10,12,14,16(23),17,19,21(24)-undecaene-2,23-bis(ylium)

> <ALOGPS_LOGP>
0.29

> <JCHEM_LOGP>
2.1870516170565084

> <ALOGPS_LOGS>
-5.63

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.8841271167751907

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2814512214505407

> <JCHEM_POLAR_SURFACE_AREA>
92.22

> <JCHEM_REFRACTIVITY>
169.76940000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.61e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
Heme

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       1.650  -1.521   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.952  -0.699   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.053   0.837   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.868   1.822   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.424   1.289   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.761   2.273   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.205   1.740   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -0.500   3.791   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.545   1.217   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.517   2.967   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.850   3.737   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       8.035   2.753   0.000  0.00  0.00           N+1
HETATM   13  C   UNK     0       9.337   3.575   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.087   2.603   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.857   1.270   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.287   0.699   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.590   1.521   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.529   3.060   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.187  -0.837   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.371  -1.822   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.694  -1.217   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.723  -2.967   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.389  -3.737   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.819  -5.168   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.641  -6.470   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.925  -7.833   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.282  -5.067   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.298  -6.251   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.903  -3.575   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       8.205  -2.753   0.000  0.00  0.00           N+1
HETATM   31 Fe   UNK     0       8.120   0.000   0.000  0.00  0.00          Fe+0
HETATM   32  N   UNK     0       5.367  -0.085   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0       4.383  -1.270   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.153  -2.603   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0      10.872   0.085   0.000  0.00  0.00           N+0
HETATM   36  C   UNK     0       8.957   5.067   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.942   6.251   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       7.421   5.168   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.598   6.470   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       5.060   6.409   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       4.343   5.046   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       5.165   3.744   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       2.804   4.985   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    3   10   32                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   38                                                  
CONECT   12   11   13   31                                                  
CONECT   13   12   14   36                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   35                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   35                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   30                                                  
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   34                                                  
CONECT   30   29   23   31                                                  
CONECT   31   30   12   32   35                                             
CONECT   32   31    9   33                                                  
CONECT   33   32    2   34                                                  
CONECT   34   33   29                                                       
CONECT   35   31   15   21                                                  
CONECT   36   13   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   11   39                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
MASTER        0    0    0    0    0    0    0    0   43    0  100    0
END

Synonyms

Value	Source
(protoporphyrinato)Iron	HMDB
Ferroheme	HMDB
Ferroheme b	HMDB
Ferroprotoheme	HMDB
Ferroprotoporphyrin	HMDB
Ferroprotoporphyrin IX	HMDB
Ferrous protoheme	HMDB
Ferrous protoheme IX	HMDB
Haem	HMDB
Hem	HMDB
Iron protoporphyrin	HMDB
Iron protoporphyrin IX	HMDB
Iron(II) protoporphyrin IX	HMDB
Protoferroheme	HMDB
Protohaem	HMDB
Protoheme	HMDB
Protoheme IX	HMDB
Reduced hematin	HMDB

Molecular Formula

C₃₄H₃₂FeN₄O₄

Average Mass

616.487

Monoisotopic Mass

616.177297665

IUPAC Name

(1R)-15,19-bis(2-carboxyethyl)-5,10-diethenyl-4,9,14,20-tetramethyl-2λ⁵,22,23λ⁵,25-tetraaza-1-ferraoctacyclo[11.9.1.1¹,⁸.1³,²¹.0²,⁶.0¹⁶,²³.0¹⁸,²².0¹¹,²⁵]pentacosa-2,4,6,8,10,12,14,16(23),17,19,21(24)-undecaene-2,23-bis(ylium)

Traditional Name

Heme

CAS Registry Number

14875-96-8

SMILES

CC1=C(CCC(O)=O)C2=CC3=[N+]4C(=CC5=C(C=C)C(C)=C6C=C7C(C=C)=C(C)C8=[N+]7[Fe@]4(N2C1=C8)N56)C(C)=C3CCC(O)=O

InChI Identifier

InChI=1S/C34H34N4O4.Fe/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25;/h7-8,13-16H,1-2,9-12H2,3-6H3,(H4,35,36,37,38,39,40,41,42);/q;+4/p-2/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;

InChI Key

YHLKGEDAGPGZPN-RGGAHWMASA-L

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0016 g/L	ALOGPS
logP	0.29	ALOGPS
logP	2.19	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	3.28	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	92.22 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	169.77 m³·mol⁻¹	ChemAxon
Polarizability	69.61 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	Yes	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	splash10-014i-0000009000-08e94d7c2cff81987ae6	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00or-0000039000-150b04b26bd0fad6c95e	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-4000091000-4c81932d5d5b64f74979	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000009000-77439249aa1341eca15b	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-4000019000-d5852f40e204e6105174	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000074000-cdc39a1b5fe31aa6657e	2015-09-15	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

Cytoplasm
Extracellular
Mitochondria

Biospecimen Locations

Epidermis
Feces
Placenta

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	Data Source	Reference
MMDBr0001209	Protoporphyrin IX	Heme	ferrochelatase	VMH; KEGG	7983009
MMDBr0001454	Heme	Biliverdin	heme oxygenase (decycling) 1	VMH	16356137
MMDBr0007400	Protoporphyrin IX	Heme	Not Available	VMH	30371894
MMDBr0007863	Farnesyl pyrophosphate	Heme O	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	268	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	533	Human feces; Human pleural fluid plaque; Pig ; Human ; Human sputum; Human saliva; Human urine; Human supragingival plaque; Cattle ; Human stool; Human subgingival plaque	Metabolic reconstruction
Bacteria	Actinobacteria	204	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Verrucomicrobia	2	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	234	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria	Spirochaetes	2	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	2		Metabolic reconstruction
Bacteria	Fusobacteria	17	Human feces; Human	Metabolic reconstruction
Bacteria	Synergistetes	4	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	8		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	2	Human feces	Metabolic reconstruction
Bacteria	Tenericutes	8	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	2		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified				HMDB
Human Epidermis	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Zhang JP, Normark S: Induction of gene expression in Escherichia coli after pilus-mediated adherence. Science. 1996 Aug 30;273(5279):1234-6. doi: 10.1126/science.273.5279.1234. [PubMed:8703059 ]
Taylor TD, Litt M, Kramer P, Pandolfo M, Angelini L, Nardocci N, Davis S, Pineda M, Hattori H, Flett PJ, Cilio MR, Bertini E, Hayflick SJ: Homozygosity mapping of Hallervorden-Spatz syndrome to chromosome 20p12.3-p13. Nat Genet. 1996 Dec;14(4):479-81. doi: 10.1038/ng1296-479. [PubMed:8944032 ]
Kuhnel A, Gross U, Doss MO: Hereditary coproporphyria in Germany: clinical-biochemical studies in 53 patients. Clin Biochem. 2000 Aug;33(6):465-73. doi: 10.1016/s0009-9120(00)00159-4. [PubMed:11074238 ]
Walczyk T, von Blanckenburg F: Natural iron isotope variations in human blood. Science. 2002 Mar 15;295(5562):2065-6. doi: 10.1126/science.1069389. [PubMed:11896276 ]
Allhorn M, Lundqvist K, Schmidtchen A, Akerstrom B: Heme-scavenging role of alpha1-microglobulin in chronic ulcers. J Invest Dermatol. 2003 Sep;121(3):640-6. doi: 10.1046/j.1523-1747.2003.12409.x. [PubMed:12925227 ]
Park KK, Park JH, Jung YJ, Chung WY: Inhibitory effects of chlorophyllin, hemin and tetrakis(4-benzoic acid)porphyrin on oxidative DNA damage and mouse skin inflammation induced by 12-O-tetradecanoylphorbol-13-acetate as a possible anti-tumor promoting mechanism. Mutat Res. 2003 Dec 9;542(1-2):89-97. doi: 10.1016/j.mrgentox.2003.09.001. [PubMed:14644357 ]
Ono F, Sharma BK, Smith CC, Burnett JW, Aurelian L: CD34+ cells in the peripheral blood transport herpes simplex virus DNA fragments to the skin of patients with erythema multiforme (HAEM). J Invest Dermatol. 2005 Jun;124(6):1215-24. doi: 10.1111/j.0022-202X.2005.23712.x. [PubMed:15955097 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Heme (MMDBc0029705)

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