Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000481
Name: Heme
Description:Heme B or haem B (also known as protoheme IX) is the most abundant heme in nature. Pseudomonas aeruginosa 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.
  • (protoporphyrinato)iron
  • Ferroheme
  • Ferroheme b
  • Ferroprotoheme
  • Ferroprotoporphyrin
  • Ferroprotoporphyrin IX
  • Ferrous protoheme
  • Ferrous protoheme IX
  • Haem
  • Hem
  • Heme
  • Heme b
  • Heme b
  • Iron protoporphyrin
  • Iron protoporphyrin IX
  • Iron(II) protoporphyrin IX
  • Protoferroheme
  • Protohaem
  • Protoheme
  • Protoheme IX
  • Reduced hematin
Chemical Formula: C34H32FeN4O4
Average Molecular Weight: 616.487
Monoisotopic Molecular Weight: 616.177297665
CAS number: 14875-96-8
IUPAC Name:(1R)-15,19-bis(2-carboxyethyl)-5,10-diethenyl-4,9,14,20-tetramethyl-2???22,23???25-tetraaza-1-ferraoctacyclo[,??1?,??.0?,??0?????.0?????.0??,???pentacosa-2,4,6,8,10,12,14,16(23),17,19,21(24)-undecaene-2,23-bis(ylium)
Traditional IUPAC Name: Heme
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as metallotetrapyrroles. These are polycyclic compounds containing a tetrapyrrole skeleton combined with a metal atom.
Kingdom Organic compounds
Super ClassOrganoheterocyclic compounds
Class Tetrapyrroles and derivatives
Sub ClassMetallotetrapyrroles
Direct Parent Metallotetrapyrroles
Alternative Parents
  • Metallotetrapyrrole skeleton
  • Substituted pyrrole
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Organic metal salt
  • Metalloheterocycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic transition metal salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Melting point: Not Available
Experimental Properties:
Predicted Properties
Water Solubility0.00161 mg/mLALOGPS
pKa (Strongest Acidic)3.28ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area92.22 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity169.77 m3·mol-1ChemAxon
Polarizability69.61 Å3ChemAxon
Number of Rings8ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000009000-08e94d7c2cff81987ae6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00or-0000039000-150b04b26bd0fad6c95eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-4000091000-4c81932d5d5b64f74979View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000009000-77439249aa1341eca15bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-4000019000-d5852f40e204e6105174View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000074000-cdc39a1b5fe31aa6657eView in MoNA
  • 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. Pubmed: 12925227
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Kuhnel A, Gross U, Doss MO: Hereditary coproporphyria in Germany: clinical-biochemical studies in 53 patients. Clin Biochem. 2000 Aug;33(6):465-73. Pubmed: 11074238
  • 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. Pubmed: 15955097
  • 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. Pubmed: 14644357
  • 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. Pubmed: 8944032
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Walczyk T, von Blanckenburg F: Natural iron isotope variations in human blood. Science. 2002 Mar 15;295(5562):2065-6. Pubmed: 11896276
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • Zhang JP, Normark S: Induction of gene expression in Escherichia coli after pilus-mediated adherence. Science. 1996 Aug 30;273(5279):1234-6. Pubmed: 8703059
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
Pubchem Compound ID26945
Kegg IDC00032
ChemSpider ID24604415


General function:
Involved in ferrochelatase activity
Specific function:
Catalyzes the ferrous insertion into protoporphyrin IX
Gene Name:
Locus Tag:
Molecular weight:
38.6 kDa
Protoheme + 2 H(+) = protoporphyrin + Fe(2+).
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex CcmAB involved in the biogenesis of c-type cytochromes; once thought to export heme, this seems not to be the case, but its exact role is uncertain. Responsible for energy coupling to the transport system
Gene Name:
Locus Tag:
Molecular weight:
25 kDa
ATP + H(2)O + heme(In) = ADP + phosphate + heme(Out).
General function:
Involved in protein complex assembly
Specific function:
Required for the export of heme to the periplasm for the biogenesis of c-type cytochromes
Gene Name:
Locus Tag:
Molecular weight:
28.3 kDa
General function:
Involved in heme transporter activity
Specific function:
Required for the export of heme to the periplasm for the biogenesis of c-type cytochromes
Gene Name:
Locus Tag:
Molecular weight:
23.4 kDa
General function:
Involved in protoheme IX farnesyltransferase activity
Specific function:
Converts heme B (protoheme IX) to heme O by substitution of the vinyl group on carbon 2 of heme B porphyrin ring with a hydroxyethyl farnesyl side group
Gene Name:
Locus Tag:
Molecular weight:
31.8 kDa
General function:
Involved in protein-heme linkage
Specific function:
Heme chaperone required for the biogenesis of c-type cytochromes. Transiently binds heme delivered by CcmC and transfers the heme to apo-cytochromes in a process facilitated by CcmF and CcmH
Gene Name:
Locus Tag:
Molecular weight:
17.2 kDa