Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-04-23 20:52:31 UTC
HMDB IDHMDB0000887
Secondary Accession Numbers
  • HMDB00887
Metabolite Identification
Common NameHemin
DescriptionHemin, also known as hemin IX or protohemin, belongs to the class of organic compounds known as metalloporphyrins. These are polycyclic compounds containing a porphyrin moiety and a metal atom. Hemin is a drug which is used in the management of porphyria attacks, particularly in acute intermittent porphyria. Hemin is found, on average, in the highest concentration within sea-buckthornberries (Hippophae rhamnoides). Hemin has also been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make hemin a potential biomarker for the consumption of these foods. Hemin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Hemin.
Structure
Data?1582752162
Synonyms
ValueSource
Chloro(protoporphyrinato)iron(III)ChEBI
Chloro[3,7,12,17-tetramethyl-8,13-divinylporphyrin-2,18-dipropanoato(2-)]iron(III)ChEBI
ChloroheminChEBI
ChloroprotoferrihemChEBI
Ferriprotoporphyrin IX chlorideChEBI
HaeminChEBI
Hemin chlorideChEBI
Hemin IXChEBI
HemineChEBI
PanhematinChEBI
ProtoheminChEBI
Protohemin IXChEBI
NormosangKegg
Chloro(protoporphyrinato)ironHMDB
ChloroprotoferrihemeHMDB
ChloroprotoheminHMDB
Chloroprotoporphyrin IX ironHMDB
Ferric heminHMDB
FerrihemeHMDB
Ferriporphyrin chlorideHMDB
FerriprotoporphyrinHMDB
Ferriprotoporphyrin IXHMDB
HaminHMDB
Hemin porcineHMDB
Hemin ultra-pureHMDB
Iron(III) protoporphyrin chlorideHMDB
ProtoferrihemeHMDB
Protohemin chlorideHMDB
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkNot Available
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+242.52932859911
AllCCS[M-H]-223.56332859911
AllCCS[M+H]+242.532859911
AllCCS[M+H-H2O]+241.532859911
AllCCS[M+NH4]+243.532859911
AllCCS[M+Na]+243.732859911
AllCCS[M-H]-223.632859911
AllCCS[M+Na-2H]-226.032859911
AllCCS[M+HCOO]-228.932859911

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Hemin GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fu-0100094000-9c4857dace576149c6de2017-09-01Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hemin 10V, Positive-QTOFsplash10-0ufr-0000189000-7121ff06cc07cf8c1c092017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hemin 20V, Positive-QTOFsplash10-0kdj-0000594000-f90a5e5b8377ac4bf5d92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hemin 40V, Positive-QTOFsplash10-0a4l-0000930000-53b96c5ba0cb501d7bf42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hemin 10V, Negative-QTOFsplash10-0ufr-0000093000-9e411f7cb2ab4066b7d02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hemin 20V, Negative-QTOFsplash10-114j-0000091000-914d79acd0bcc11f6d8f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hemin 40V, Negative-QTOFsplash10-01tc-6100091000-b2e3291f8e766f9186572017-09-01Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Tissue Locations
  • Erythrocyte
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
FooDB IDFDB005746
KNApSAcK IDC00003385
Chemspider ID401223
KEGG Compound IDC06767
BioCyc IDCPD-11678
BiGG IDNot Available
Wikipedia LinkHemin
METLIN ID5845
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID50385
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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