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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-01-11 19:15:15 UTC
HMDB IDHMDB0000887
Secondary Accession Numbers
  • HMDB00887
Metabolite Identification
Common NameHemin
DescriptionHemin is an iron containing metalloporphyrin. Specifically, the Fe3+ oxidation product of heme is termed hemin. Hemin acts as a feed-back inhibitor on ALA synthase. Hemin also inhibits transport of ALA synthase from the cytosol (its' site of synthesis) into the mitochondria (its' site of action) as well as represses synthesis of the enzyme. Hemin is also known as a drug that is derived from processed red blood cells. Hemin for injection was known previously as hematin.
Structure
Data?1547234115
Synonyms
ValueSource
Chloro(protoporphyrinato)iron(III)ChEBI
Chloro[3,7,12,17-tetramethyl-8,13-divinylporphyrin-2,18-dipropanoato(2-)]iron(III)ChEBI
HaeminChEBI
HemineChEBI
ProtoheminChEBI
NormosangKegg
Chloro(protoporphyrinato)ironHMDB
ChloroprotoferrihemeHMDB
ChloroprotoheminHMDB
Chloroprotoporphyrin IX ironHMDB
Ferric heminHMDB
FerrihemeHMDB
Ferriporphyrin chlorideHMDB
FerriprotoporphyrinHMDB
Ferriprotoporphyrin IXHMDB
Ferriprotoporphyrin IX chlorideHMDB
HaminHMDB
Hemin chlorideHMDB
Hemin IXHMDB
Hemin porcineHMDB
Hemin ultra-pureHMDB
Iron(III) protoporphyrin chlorideHMDB
PanhematinHMDB
ProtoferrihemeHMDB
Protohemin chlorideHMDB
Protohemin IXHMDB
Teichmann'S crystalsHMDB
Chemical FormulaC34H32ClFeN4O4
Average Molecular Weight651.94
Monoisotopic Molecular Weight651.146150372
IUPAC Name3-[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 Name3-[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
CAS Registry Number16009-13-5
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 KeyBTIJJDXEELBZFS-HXFTUNQESA-K
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrapyrroles and derivatives
Sub ClassMetallotetrapyrroles
Direct ParentMetalloporphyrins
Alternative Parents
Substituents
  • Metalloporphyrin
  • Porphyrin
  • Dicarboxylic acid or derivatives
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Carboxylic acid salt
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic metal halide
  • Azacycle
  • Organic transition metal salt
  • Carbonyl group
  • Organic zwitterion
  • Organic salt
  • Hydrochloride
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.017 g/LALOGPS
logP1.58ALOGPS
logS-5.1ALOGPS
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area121.19 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity182.32 m³·mol⁻¹ChemAxon
Polarizability71.81 ųChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fu-0100094000-9c4857dace576149c6deJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ufr-0000189000-7121ff06cc07cf8c1c09JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kdj-0000594000-f90a5e5b8377ac4bf5d9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-0000930000-53b96c5ba0cb501d7bf4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ufr-0000093000-9e411f7cb2ab4066b7d0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-114j-0000091000-914d79acd0bcc11f6d8fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01tc-6100091000-b2e3291f8e766f918657JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Tissue Locations
  • Erythrocyte
  • Erythroleukemia
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03404
Phenol Explorer Compound IDNot Available
FoodDB IDFDB005746
KNApSAcK IDNot Available
Chemspider ID401223
KEGG Compound IDC06767
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHemin
METLIN ID5845
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID50385
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. 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. [PubMed:2537104 ]
  3. 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 ]
  4. Alter BP, Schofield JM, He LY, Weinberg RS: Effects of hemin on erythropoiesis. Adv Exp Med Biol. 1989;271:95-102. [PubMed:2486293 ]
  5. 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. [PubMed:1895756 ]
  6. 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. [PubMed:1998709 ]
  7. 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. [PubMed:108889 ]
  8. 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 ]
  9. 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. [PubMed:15962939 ]
  10. 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. Epub 2003 Jul 7. [PubMed:12846933 ]
  11. 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. [PubMed:4297976 ]
  12. 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 ]
  13. 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. [PubMed:4063370 ]

Enzymes

General function:
Involved in protein serine/threonine kinase activity
Specific function:
Mediates down-regulation of protein synthesis in response to various stress conditions by the phosphorylation of EIF2S1 at 'Ser-48' and 'Ser-51'. Protein synthesis is inhibited at the level of initiation
Gene Name:
EIF2AK1
Uniprot ID:
Q9BQI3
Molecular weight:
71105.9