Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB006369
Identification
Name: ferroheme b
Description:Ferroheme b or heme 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.
Structure
Thumb
Synonyms:Not Available
Chemical Formula: C34H30FeN4O4
Average Molecular Weight: 614.485
Monoisotopic Molecular Weight: 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:Not Available
Traditional IUPAC Name: Not Available
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
Taxonomy DescriptionNot Available
Kingdom Not Available
Super ClassNot Available
Class Not Available
Sub ClassNot Available
Direct Parent Not Available
Alternative Parents Not Available
Substituents Not Available
Molecular Framework Not Available
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:Not Available
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Oxidative phosphorylationPW000919 Pw000919Pw000919 greyscalePw000919 simple
Phenylalanine metabolismPW000921 Pw000921Pw000921 greyscalePw000921 simple
Porphyrin metabolismPW000936 Pw000936Pw000936 greyscalePw000936 simple
TCA cyclePW000779 Pw000779Pw000779 greyscalePw000779 simple
TCA cycle (ubiquinol-0)PW002023 Pw002023Pw002023 greyscalePw002023 simple
TCA cycle (ubiquinol-10)PW001010 Pw001010Pw001010 greyscalePw001010 simple
TCA cycle (ubiquinol-2)PW001002 Pw001002Pw001002 greyscalePw001002 simple
TCA cycle (ubiquinol-3)PW001003 Pw001003Pw001003 greyscalePw001003 simple
TCA cycle (ubiquinol-4)PW001004 Pw001004Pw001004 greyscalePw001004 simple
TCA cycle (ubiquinol-5)PW001005 Pw001005Pw001005 greyscalePw001005 simple
TCA cycle (ubiquinol-6)PW001006 Pw001006Pw001006 greyscalePw001006 simple
TCA cycle (ubiquinol-7)PW001007 Pw001007Pw001007 greyscalePw001007 simple
TCA cycle (ubiquinol-8)PW001008 Pw001008Pw001008 greyscalePw001008 simple
TCA cycle (ubiquinol-9)PW001009 Pw001009Pw001009 greyscalePw001009 simple
pyruvate to cytochrome bd terminal oxidase electron transferPW002087 Pw002087Pw002087 greyscalePw002087 simple
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
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
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink

Enzymes

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
Locus Tag:
PA2147
Molecular weight:
78 kDa
Reactions
2 H(2)O(2) = O(2) + 2 H(2)O.
General function:
Involved in ferrochelatase activity
Specific function:
Catalyzes the ferrous insertion into protoporphyrin IX
Gene Name:
hemH
Locus Tag:
PA4655
Molecular weight:
38.6 kDa
Reactions
Protoheme + 2 H(+) = protoporphyrin + Fe(2+).
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
Locus Tag:
PA1321
Molecular weight:
31.8 kDa