| Identification |
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| YMDB ID | YMDB00987 |
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| Name | Protoheme IX |
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| Species | Saccharomyces cerevisiae |
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| Strain | Baker's yeast |
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| Description | Protoheme 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] |
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| Structure | |
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| 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
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| CAS number | 14875-96-8 |
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| Weight | Average: 616.487
Monoisotopic: 616.177297665 |
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| InChI Key | KABFMIBPWCXCRK-VXWKYRPVSA-L |
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| 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);/q;+2/p-2/b25-13?,26-13-,27-14-,28-15?,29-14?,30-15?,31-16?,32-16?; |
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| IUPAC Name | 3-[(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 |
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| Traditional IUPAC Name | 3-[(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 |
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| Chemical Formula | C34H32FeN4O4 |
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| SMILES | CC1=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 |
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| Chemical Taxonomy |
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| Physical Properties |
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| State | Solid |
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| Charge | 0 |
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| Melting point | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Water Solubility | Not Available | PhysProp | | LogP | Not Available | PhysProp |
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| Predicted Properties | |
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| Biological Properties |
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| Cellular Locations | Not Available |
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| Organoleptic Properties | Not Available |
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| SMPDB Pathways | |
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| KEGG Pathways | |
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| SMPDB Reactions | Not Available |
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| KEGG Reactions | Not Available |
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| Concentrations |
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| Intracellular Concentrations | Not Available |
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| Extracellular Concentrations | Not Available |
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| Spectra |
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| Spectra | |
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| References |
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| 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
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| Synthesis Reference: | Not Available |
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| External Links: | |
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