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Identification
YMDB IDYMDB00987
NameProtoheme IX
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionProtoheme IX (heme b or heme) is the final product in the heme biosynthesis from uroporphyrinogen-III pathway. It is an iron-containing prosthetic group found in many essential proteins including cytochromes and heme-containing globins. In addition to its role in oxidative metabolism, heme also functions as a regulatory molecule in transcription, translation, protein targeting, protein stability, and cellular differentiation. Different derivatives of protoheme can actually be formed that differ in modifications to the porphyrin ring, including how it is bound to the protein (e.g. heme o, heme a, heme c, and heme d). [Biocyc PWY-5189]
Structure
Thumb
Synonyms
  • (protoporphyrinato)iron
  • [3,7,12,17-tetramethyl-8,13-divinylporphyrin-2,18-dipropanoato(2-)]iron(II)
  • [Fe(ppIX)]
  • Fe(ppIX)
  • Ferroheme
  • Ferroheme b
  • Ferroprotoheme
  • Ferroprotoporphyrin
  • Ferroprotoporphyrin IX
  • Ferrous protoheme
  • Ferrous protoheme IX
  • haem
  • Hem
  • heme
  • heme b
  • hemeb
  • Iron protoporphyrin
  • Iron protoporphyrin IX
  • Iron(II) protoporphyrin IX
  • Protoferroheme
  • Protohaem
  • Protoheme
  • Protoheme IX
  • Protoheme IX (VAN)
  • Reduced hematin
CAS number14875-96-8
WeightAverage: 616.487
Monoisotopic: 616.177297665
InChI KeyKABFMIBPWCXCRK-VXWKYRPVSA-L
InChIInChI=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;+2/p-2/b25-13?,26-13-,27-14-,28-15?,29-14?,30-15?,31-16?,32-16?;
IUPAC Name3-[(12Z)-20-(2-carboxyethyl)-10,15-diethenyl-5,9,14,19-tetramethyl-21,23,24,25-tetraaza-22-ferrahexacyclo[9.9.3.1³,⁶.1¹³,¹⁶.0⁸,²³.0¹⁸,²¹]pentacosa-1,3(25),4,6,8,10,12,14,16(24),17,19-undecaen-4-yl]propanoic acid
Traditional IUPAC Name3-[(12Z)-20-(2-carboxyethyl)-10,15-diethenyl-5,9,14,19-tetramethyl-21,23,24,25-tetraaza-22-ferrahexacyclo[9.9.3.1³,⁶.1¹³,¹⁶.0⁸,²³.0¹⁸,²¹]pentacosa-1,3(25),4,6,8,10,12,14,16(24),17,19-undecaen-4-yl]propanoic acid
Chemical FormulaC34H32FeN4O4
SMILESCC1=C(CCC(O)=O)C2=N\C1=C/C1=C(C)C(C=C)=C3\C=C4/N=C(C=C5N([Fe]N13)C(=C2)C(CCC(O)=O)=C5C)C(C=C)=C4C
Chemical Taxonomy
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.062 g/LALOGPS
logP4.06ALOGPS
logP8.07ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)3.66ChemAxon
pKa (Strongest Basic)2.85ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area110.24 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity165.03 m³·mol⁻¹ChemAxon
Polarizability67.52 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Oxidative phosphorylationPW002461 ThumbThumb?image type=greyscaleThumb?image type=simple
Porphyrin MetabolismPW002462 ThumbThumb?image type=greyscaleThumb?image type=simple
Steroid biosynthesisPW002482 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Oxidative phosphorylationec00190 Map00190
Porphyrin and chlorophyll metabolismec00860 Map00860
Steroid biosynthesisec00100 Map00100
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066r-0000095000-501c4a776d38d61ab89aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gi4-0000092000-31aae4730bdb8c350db1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01sa-6000590000-d7d1dfc3c64946a1a5f7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000049000-80d052f0bff948fb0434JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00r2-1000091000-06d9f6af8c6722e75f27JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kdi-1000090000-55b40ce160d0188375d3JSpectraViewer
References
References:
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Gora, M., Chacinska, A., Rytka, J., Labbe-Bois, R. (1996). "Isolation and functional characterization of mutant ferrochelatases in Saccharomyces cerevisiae." Biochimie 78:144-152.8818224
  • Camadro, J. M., Labbe, P. (1982). "Kinetic studies of ferrochelatase in yeast. Zinc or iron as competing substrates." Biochim Biophys Acta 707:280-288.6753940
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17627
HMDB IDHMDB03178
Pubchem Compound ID26945
Kegg IDC00032
ChemSpider ID21864835
FOODB IDNot Available
WikipediaHeme_b
BioCyc IDPROTOHEME

Enzymes

General function:
Involved in ferrochelatase activity
Specific function:
Catalyzes the ferrous insertion into protoporphyrin IX
Gene Name:
HEM15
Uniprot ID:
P16622
Molecular weight:
44595.80078
Reactions
Protoheme + 2 H(+) → protoporphyrin + Fe(2+).