NP-MRD: Showing NP-Card for Hemin (NP0046748)

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Record Information

Version

2.0

Created at

2022-03-17 20:28:55 UTC

Updated at

2022-03-17 20:28:55 UTC

NP-MRD ID

NP0046748

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hemin

Description

Hemin, also known as protohemin or ferriheme, belongs to the class of organic compounds known as metalloporphyrins. These are polycyclic compounds containing a porphyrin moiety and a metal atom. Hemin (trade name Panhematin) is an iron-containing porphyrin. Hemin is a drug which is used in the management of porphyria attacks, particularly in acute intermittent porphyria. Hemin is possibly neutral. Outside of the human body, Hemin is found, on average, in the highest concentration within sea-buckthornberries. Hemin was first documented in 1968 (PMID: 4297976). This could make hemin a potential biomarker for the consumption of these foods (PMID: 3708575) (PMID: 2537104) (PMID: 12545852) (PMID: 2486293) (PMID: 1895756) (PMID: 1998709).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305171801582D          

 44 51  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
   -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
    1.4610    2.0453    0.0000 C   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
    2.0662   -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
   -2.0244   -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
   -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
    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
    3.0765    2.4713    0.0000 C   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
    1.6745   -2.8422    0.0000 C   0  0  0  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
   -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
    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
   -0.8348    0.8557    0.0000 N   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
    0.0000    0.8250    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1 42  1  0  0  0  0
 16  1  2  0  0  0  0
  1 12  1  0  0  0  0
  2  3  1  0  0  0  0
 42  2  1  0  0  0  0
 24  2  2  0  0  0  0
  3  4  2  0  0  0  0
  4 13  1  0  0  0  0
 18  4  1  0  0  0  0
  5  6  1  0  0  0  0
 13  5  2  0  0  0  0
 27  5  1  0  0  0  0
  6  7  2  0  0  0  0
  7 14  1  0  0  0  0
  7 20  1  0  0  0  0
  8  9  2  0  0  0  0
 33  8  1  0  0  0  0
 14  8  1  0  0  0  0
 10  9  1  0  0  0  0
 15 10  2  0  0  0  0
 30 10  1  0  0  0  0
 11 12  2  0  0  0  0
 15 11  1  0  0  0  0
 22 11  1  0  0  0  0
 13 43  1  0  0  0  0
 43 14  1  0  0  0  0
 43 15  1  0  0  0  0
 24 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 27  2  0  0  0  0
 18 19  1  0  0  0  0
 20 33  2  0  0  0  0
 20 21  1  0  0  0  0
 22 30  2  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 37  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 40  1  0  0  0  0
 37 36  1  0  0  0  0
 37 38  2  0  0  0  0
 40 39  1  0  0  0  0
 40 41  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
M  END


  Mrv1652305171801582D          

 44 51  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
   -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
    1.4610    2.0453    0.0000 C   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
    2.0662   -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
   -2.0244   -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
   -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
    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
    3.0765    2.4713    0.0000 C   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
    1.6745   -2.8422    0.0000 C   0  0  0  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
   -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
    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
   -0.8348    0.8557    0.0000 N   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
    0.0000    0.8250    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1 42  1  0  0  0  0
 16  1  2  0  0  0  0
  1 12  1  0  0  0  0
  2  3  1  0  0  0  0
 42  2  1  0  0  0  0
 24  2  2  0  0  0  0
  3  4  2  0  0  0  0
  4 13  1  0  0  0  0
 18  4  1  0  0  0  0
  5  6  1  0  0  0  0
 13  5  2  0  0  0  0
 27  5  1  0  0  0  0
  6  7  2  0  0  0  0
  7 14  1  0  0  0  0
  7 20  1  0  0  0  0
  8  9  2  0  0  0  0
 33  8  1  0  0  0  0
 14  8  1  0  0  0  0
 10  9  1  0  0  0  0
 15 10  2  0  0  0  0
 30 10  1  0  0  0  0
 11 12  2  0  0  0  0
 15 11  1  0  0  0  0
 22 11  1  0  0  0  0
 13 43  1  0  0  0  0
 43 14  1  0  0  0  0
 43 15  1  0  0  0  0
 24 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 27  2  0  0  0  0
 18 19  1  0  0  0  0
 20 33  2  0  0  0  0
 20 21  1  0  0  0  0
 22 30  2  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 37  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 40  1  0  0  0  0
 37 36  1  0  0  0  0
 37 38  2  0  0  0  0
 40 39  1  0  0  0  0
 40 41  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046748

> <DATABASE_NAME>
NP-MRD

> <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(Cl)(N2C1=C8)N56)C(C)=C3CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C34H34N4O4.ClH.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);1H;/q;;+3/p-3/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;;

> <INCHI_KEY>
BTIJJDXEELBZFS-HXFTUNQESA-K

> <FORMULA>
C34H32ClFeN4O4

> <MOLECULAR_WEIGHT>
651.94

> <EXACT_MASS>
651.146150372

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
71.81071063327929

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[5-(2-carboxyethyl)-1-chloro-14,19-diethenyl-4,10,15,20-tetramethyl-2lambda4,22,23lambda4,25-tetraaza-1-ferraoctacyclo[11.9.1.1^{1,8}.1^{3,21}.0^{2,6}.0^{16,23}.0^{18,22}.0^{11,25}]pentacosa-2(6),3(24),4,7,9,11,13(23),14,16,18,20-undecaen-9-yl]propanoic acid

> <ALOGPS_LOGP>
1.58

> <ALOGPS_LOGS>
-5.08

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_POLAR_SURFACE_AREA>
121.19000000000003

> <JCHEM_REFRACTIVITY>
182.32180000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.43e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[5-(2-carboxyethyl)-1-chloro-14,19-diethenyl-4,10,15,20-tetramethyl-2lambda4,22,23lambda4,25-tetraaza-1-ferraoctacyclo[11.9.1.1^{1,8}.1^{3,21}.0^{2,6}.0^{16,23}.0^{18,22}.0^{11,25}]pentacosa-2(6),3(24),4,7,9,11,13(23),14,16,18,20-undecaen-9-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-MAY-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-MAY-18         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      -3.779   2.727   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.266   3.126   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.727   3.818   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.126   5.305   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.857  -2.727   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.344  -3.126   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.779  -2.727   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.266  -3.126   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.688   3.818   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.087   5.305   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.574   5.704   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.857   2.727   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.344   3.126   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.743   4.613   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.688  -3.818   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.087  -5.305   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.574  -5.704   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.727  -3.818   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.126  -5.305   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.613  -5.704   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -6.460  -7.590   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -4.973  -7.192   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -3.884  -8.281   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       3.923  -8.281   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       5.012  -7.192   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       6.499  -7.590   0.000  0.00  0.00           O+0
HETATM   42  N   UNK     0      -1.558   1.597   0.000  0.00  0.00           N+0
HETATM   43 Fe   UNK     0       0.000   0.000   0.000  0.00  0.00          Fe+0
HETATM   44 Cl   UNK     0       0.000   1.540   0.000  0.00  0.00          Cl+0
CONECT    1   42   16   12                                                  
CONECT    2    3   42   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3   13   18                                                  
CONECT    5    6   13   27                                                  
CONECT    6    5    7                                                       
CONECT    7    6   14   20                                                  
CONECT    8    9   33   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   15   30                                                  
CONECT   11   12   15   22                                                  
CONECT   12    1   11                                                       
CONECT   13    4    5   43                                                  
CONECT   14    7    8   43                                                  
CONECT   15   10   11   43                                                  
CONECT   16    1   24   17                                                  
CONECT   17   16                                                            
CONECT   18    4   27   19                                                  
CONECT   19   18                                                            
CONECT   20    7   33   21                                                  
CONECT   21   20                                                            
CONECT   22   11   30   23                                                  
CONECT   23   22                                                            
CONECT   24    2   16   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27    5   18   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   10   22   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   37                                                       
CONECT   33    8   20   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   40                                                       
CONECT   36   37                                                            
CONECT   37   32   36   38                                                  
CONECT   38   37                                                            
CONECT   39   40                                                            
CONECT   40   35   39   41                                                  
CONECT   41   40                                                            
CONECT   42    1    2   43                                                  
CONECT   43   13   14   15   42                                             
CONECT   43   44                                        
CONECT   44   43                                                            
MASTER        0    0    0    0    0    0    0    0   44    0  102    0
END

View in JSmol

Synonyms

Value	Source
Chloro(protoporphyrinato)iron(III)	ChEBI
Chloro[3,7,12,17-tetramethyl-8,13-divinylporphyrin-2,18-dipropanoato(2-)]iron(III)	ChEBI
Haemin	ChEBI
Hemine	ChEBI
Protohemin	ChEBI
Normosang	Kegg
Chloro(protoporphyrinato)iron	HMDB
Chloroprotoferriheme	HMDB
Chloroprotohemin	HMDB
Chloroprotoporphyrin IX iron	HMDB
Ferric hemin	HMDB
Ferriheme	HMDB
Ferriporphyrin chloride	HMDB
Ferriprotoporphyrin	HMDB
Ferriprotoporphyrin IX	HMDB
Ferriprotoporphyrin IX chloride	HMDB
Hamin	HMDB
Hemin chloride	HMDB
Hemin IX	HMDB
Hemin porcine	HMDB
Hemin ultra-pure	HMDB
Iron(III) protoporphyrin chloride	HMDB
Panhematin	HMDB
Protoferriheme	HMDB
Protohemin chloride	HMDB
Protohemin IX	HMDB
Teichmann'S crystals	HMDB

Chemical Formula

C₃₄H₃₂ClFeN₄O₄

Average Mass

651.9400 Da

Monoisotopic Mass

651.14615 Da

IUPAC Name

3-[5-(2-carboxyethyl)-1-chloro-14,19-diethenyl-4,10,15,20-tetramethyl-2lambda4,22,23lambda4,25-tetraaza-1-ferraoctacyclo[11.9.1.1^{1,8}.1^{3,21}.0^{2,6}.0^{16,23}.0^{18,22}.0^{11,25}]pentacosa-2(6),3(24),4,7,9,11,13(23),14,16,18,20-undecaen-9-yl]propanoic acid

Traditional Name

CAS Registry Number

16009-13-5

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(Cl)(N2C1=C8)N56)C(C)=C3CCC(O)=O

InChI Identifier

InChI=1S/C34H34N4O4.ClH.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);1H;/q;;+3/p-3/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;;

InChI Key

BTIJJDXEELBZFS-HXFTUNQESA-K

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Hippophae rhamnoides	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as metalloporphyrins. These are polycyclic compounds containing a porphyrin moiety and a metal atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrapyrroles and derivatives

Sub Class

Metallotetrapyrroles

Direct Parent

Metalloporphyrins

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Not Available

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.58	ALOGPS
logS	-5.1	ALOGPS
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	121.19 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	182.32 m³·mol⁻¹	ChemAxon
Polarizability	71.81 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0000887

DrugBank ID

DB03404

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB005746

KNApSAcK ID

Not Available

Chemspider ID

401223

KEGG Compound ID

C06767

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hemin

METLIN ID

5845

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

50385

Good Scents ID

Not Available

References

General References

Tsiftsoglou AS, Wong W, Wheeler C, Steinberg HN, Robinson SH: Prevention of anthracycline-induced cytotoxicity in hemopoietic cells by hemin. Cancer Res. 1986 Jul;46(7):3436-40. [PubMed:3708575 ]
Wyse JW, Butterfield DA: Interaction of hemin with erythrocyte membranes: alterations in the physical state of the major sialoglycoprotein. Biochim Biophys Acta. 1989 Feb 13;979(1):121-6. doi: 10.1016/0005-2736(89)90531-2. [PubMed:2537104 ]
Wu L, Zhang W, Yang H, Xu Q, Yang X: [Determination of blood glucose by chemiluminescent flow-injection analysis with immobilized glucoxidase column]. Hua Xi Yi Ke Da Xue Xue Bao. 2000 Sep;31(3):422-4. [PubMed:12545852 ]
Alter BP, Schofield JM, He LY, Weinberg RS: Effects of hemin on erythropoiesis. Adv Exp Med Biol. 1989;271:95-102. doi: 10.1007/978-1-4613-0623-8_11. [PubMed:2486293 ]
Hooper WC, Pruckler J, Jackson D, Evatt BL: The synergistic effect of hemin and transforming growth factor-beta on hemoglobin accumulation in HEL erythroleukemia cells. Leuk Res. 1991;15(8):753-8. doi: 10.1016/0145-2126(91)90079-9. [PubMed:1895756 ]
Solar I, Muller-Eberhard U, Shviro Y, Shaklai N: Long-term intercalation of residual hemin in erythrocyte membranes distorts the cell. Biochim Biophys Acta. 1991 Feb 11;1062(1):51-8. doi: 10.1016/0005-2736(91)90334-5. [PubMed:1998709 ]
Malik Z, Agam G, Djaldetti M: Effect of hemin and Protoporphyrin IX on the protein-synthesizing activity of human granulocytes, lymphocytes and platelets. Acta Haematol. 1979;61(3):138-43. doi: 10.1159/000207646. [PubMed:108889 ]
Lu L, Broxmeyer HE: The selective enhancing influence of hemin and products of human erythrocytes on colony formation by human multipotential (CFUGEMM) and erythroid (BFUE) progenitor cells in vitro. Exp Hematol. 1983 Sep;11(8):721-9. [PubMed:6628580 ]
Lakshmi VM, Hsu FF, Zenser TV: Nitric oxide-mediated nitrosation of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline potentiated by hemin and myeloperoxidase. Chem Res Toxicol. 2005 Jun;18(6):1038-47. doi: 10.1021/tx0500070. [PubMed:15962939 ]
Zunszain PA, Ghuman J, Komatsu T, Tsuchida E, Curry S: Crystal structural analysis of human serum albumin complexed with hemin and fatty acid. BMC Struct Biol. 2003 Jul 7;3:6. doi: 10.1186/1472-6807-3-6. Epub 2003 Jul 7. [PubMed:12846933 ]
Doss M, Bode U: [Thin layer chromatographic separation of porphyrins, hemin and lipids on Silica Gel H plates for the determination of the erythrocyte porphyrins as their methyl esters]. J Chromatogr. 1968 Jun 4;35(2):248-56. doi: 10.1016/s0021-9673(01)82381-5. [PubMed:4297976 ]
Palma JF, Gao X, Lin CH, Wu S, Solomon WB: Iron protoporphyrin IX (hemin) but not tin or zinc protoporphyrin IX can stimulate gene expression in K562 cells from enhancer elements containing binding sites for NF-E2. Blood. 1994 Aug 15;84(4):1288-97. [PubMed:8049443 ]
Shaklai N, Shviro Y, Rabizadeh E, Kirschner-Zilber I: Accumulation and drainage of hemin in the red cell membrane. Biochim Biophys Acta. 1985 Dec 5;821(2):355-66. doi: 10.1016/0005-2736(85)90106-3. [PubMed:4063370 ]

Showing NP-Card for Hemin (NP0046748)

MOL for NP0046748 (Hemin)

3D MOL for NP0046748 (Hemin)

3D SDF for NP0046748 (Hemin)

3D-SDF for NP0046748 (Hemin)

PDB for NP0046748 (Hemin)

3D PDB for NP0046748 (Hemin)

SMILES for NP0046748 (Hemin)

INCHI for NP0046748 (Hemin)

Structure for NP0046748 (Hemin)

3D Structure for NP0046748 (Hemin)