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ferroheme b (M2MDB006369)

Record Information
Version2.0
Creation Date2015-09-08 17:50:26 -0600
Update Date2015-09-14 16:46:06 -0600
Secondary Accession Numbers
  • ECMDB24252
Identification
Name:ferroheme b
DescriptionFerroheme b or heme B (also known as protoheme IX) is the most abundant heme in nature. E. coli 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.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:Not Available
Chemical Formula:C34H30FeN4O4
Weight:Average: 614.485
Monoisotopic: 614.163836
InChI Key:RNQMHXMGXVQRMV-RGGAHWMASA-J
InChI:InChI=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);/p-4/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;
CAS number:Not Available
IUPAC Name:5,9-bis(2-carboxylatoethyl)-14,19-diethenyl-4,10,15,20-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),4,6,8(23),9,11,13,15,17,19-undecaene-21,22-diide iron
Traditional IUPAC Name:5,9-bis(2-carboxylatoethyl)-14,19-diethenyl-4,10,15,20-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),4,6,8(23),9,11,13,15,17,19-undecaene-21,22-diide iron
SMILES:[Fe].CC1=C(CCC([O-])=O)C2=N\C\1=C/C1=C(C=C)C(C)=C([N-]1)\C=C1/[N-]\C(=C/C3=N/C(=C\2)/C(CCC([O-])=O)=C3C)C(C)=C1C=C
Chemical Taxonomy
ClassificationNot classified
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.053 g/LALOGPS
logP4.05ALOGPS
logP6.85ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)3.52ChemAxon
pKa (Strongest Basic)4.94ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area131.82 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity186.71 m³·mol⁻¹ChemAxon
Polarizability64.32 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
Protoporphyrin IX + Iron >2 Hydrogen ion + ferroheme b
ferroheme b + Water + Farnesyl pyrophosphate + Farnesyl pyrophosphate > Heme O + Pyrophosphate
ferroheme b + Hydrogen peroxide > Heme D
SMPDB Pathways:
Oxidative phosphorylationPW000919 ThumbThumb?image type=greyscaleThumb?image type=simple
Phenylalanine metabolismPW000921 ThumbThumb?image type=greyscaleThumb?image type=simple
Porphyrin metabolismPW000936 ThumbThumb?image type=greyscaleThumb?image type=simple
TCA cyclePW000779 ThumbThumb?image type=greyscaleThumb?image type=simple
TCA cycle (ubiquinol-0)PW002023 ThumbThumb?image type=greyscaleThumb?image type=simple
TCA cycle (ubiquinol-10)PW001010 ThumbThumb?image type=greyscaleThumb?image type=simple
TCA cycle (ubiquinol-2)PW001002 ThumbThumb?image type=greyscaleThumb?image type=simple
TCA cycle (ubiquinol-3)PW001003 ThumbThumb?image type=greyscaleThumb?image type=simple
TCA cycle (ubiquinol-4)PW001004 ThumbThumb?image type=greyscaleThumb?image type=simple
TCA cycle (ubiquinol-5)PW001005 ThumbThumb?image type=greyscaleThumb?image type=simple
TCA cycle (ubiquinol-6)PW001006 ThumbThumb?image type=greyscaleThumb?image type=simple
TCA cycle (ubiquinol-7)PW001007 ThumbThumb?image type=greyscaleThumb?image type=simple
TCA cycle (ubiquinol-8)PW001008 ThumbThumb?image type=greyscaleThumb?image type=simple
TCA cycle (ubiquinol-9)PW001009 ThumbThumb?image type=greyscaleThumb?image type=simple
pyruvate to cytochrome bd terminal oxidase electron transferPW002087 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000009000-0965983505b13997f5d8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000009000-0965983505b13997f5d8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0000009000-0965983505b13997f5d8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000009000-c2a4b379666e8bdcbddfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000009000-c2a4b379666e8bdcbddfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0000009000-c2a4b379666e8bdcbddfView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Catalase HPII
General function:
Involved in catalase activity
Specific function:
Decomposes hydrogen peroxide into water and oxygen; serves to protect cells from the toxic effects of hydrogen peroxide
Gene Name:
katE
Uniprot ID:
P21179
Molecular weight:
84162
Reactions
2 H(2)O(2) = O(2) + 2 H(2)O.
Protein Details
2. Ferrochelatase
General function:
Involved in ferrochelatase activity
Specific function:
Catalyzes the ferrous insertion into protoporphyrin IX
Gene Name:
hemH
Uniprot ID:
P23871
Molecular weight:
35884
Reactions
Protoheme + 2 H(+) = protoporphyrin + Fe(2+).
Protein Details
3. Protoheme IX farnesyltransferase
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:
cyoE
Uniprot ID:
P0AEA5
Molecular weight:
32248