| Record Information |
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| Version | 2.0 |
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| Creation Date | 2012-05-31 14:50:53 -0600 |
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| Update Date | 2015-10-02 02:25:52 -0600 |
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| Secondary Accession Numbers | |
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| Identification |
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| Name: | Heme D |
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| Description | Heme D is a member of the chemical class known as tetrapyrroles and Derivatives. These are polycyclic aromatic compounds containing four pyrrole rings joined by one-carbon units linking position 2 of one pyrrole ring to position 5 of the next. (inferred from compound structure). A heme (American English) or haem (British English) is a prosthetic group that consists of an iron atom contained in the center of a large heterocyclic organic ring called a porphyrin. Heme D is a derivative of heme B, but in which the propionic acid side chain at the carbon of position 6, which is also hydroxylated, forms a γ-spirolactone. Ring III is also hydroxylated at position 5, in a conformation trans to the new lactone group. Heme D is the site for oxygen reduction to water of many types of bacteria at low oxygen tension. In E coli, heme D is formed from protoheme in the interior of the catalase hydroperoxidase II (HPII) molecule through a self-catalyzed reaction. [PMID: 8621527] |
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| Structure | |
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| Synonyms: | Not Available |
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| Chemical Formula: | C34H34N4O10 |
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| Weight: | Average: 658.6546
Monoisotopic: 658.227493328 |
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| InChI Key: | ZAKGXCNMJBQQNZ-CXJCYTKDSA-N |
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| InChI: | InChI=1S/C34H34N4O10/c1-15-17(5-7-27(39)40)21-10-22-18(6-8-28(41)42)16(2)20(36-22)11-25-33(3,13-29(43)44)32(48)24(38-25)12-26-34(4,14-30(45)46)31(47)23(37-26)9-19(15)35-21/h9-12,35-36H,5-8,13-14H2,1-4H3,(H,39,40)(H,41,42)(H,43,44)(H,45,46)/b19-9-,20-11-,21-10-,22-10-,23-9-,24-12-,25-11-,26-12- |
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| CAS number: | 60318-31-2 |
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| IUPAC Name: | 3-[20-(2-carboxyethyl)-10,15-bis(carboxymethyl)-5,10,15,19-tetramethyl-9,14-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(20),2,4,6,8(23),11,13(22),16,18-nonaen-4-yl]propanoic acid |
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| Traditional IUPAC Name: | 3-[20-(2-carboxyethyl)-10,15-bis(carboxymethyl)-5,10,15,19-tetramethyl-9,14-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(20),2,4,6,8(23),11,13(22),16,18-nonaen-4-yl]propanoic acid |
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| SMILES: | CC1=C(CCC(O)=O)/C2=C/C3=C(CCC(O)=O)C(C)=C(N3)\C=C3/N=C(/C=C4\N=C(\C=C\1/N\2)C(=O)C4(C)CC(O)=O)C(=O)C3(C)CC(O)=O |
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| Chemical Taxonomy |
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| Classification | Not classified |
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| Physical Properties |
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| State: | Not Available |
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| Charge: | -4 |
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| Melting point: | Not Available |
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| Experimental Properties: | |
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| Predicted Properties | |
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| Biological Properties |
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| Cellular Locations: | Membrane |
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| Reactions: | |
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| SMPDB Pathways: | | Oxidative phosphorylation | PW000919 |    | | Porphyrin metabolism | PW000936 |    | | pyruvate to cytochrome bd terminal oxidase electron transfer | PW002087 |    |
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| KEGG Pathways: | |
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| EcoCyc Pathways: | Not Available |
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| Concentrations |
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| Not Available |
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| Spectra |
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| Spectra: | |
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| References |
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| References: | - 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
- Murshudov, G. N., Grebenko, A. I., Barynin, V., Dauter, Z., Wilson, K. S., Vainshtein, B. K., Melik-Adamyan, W., Bravo, J., Ferran, J. M., Ferrer, J. C., Switala, J., Loewen, P. C., Fita, I. (1996). "Structure of the heme d of Penicillium vitale and Escherichia coli catalases." J Biol Chem 271:8863-8868. Pubmed: 8621527
- 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
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| Synthesis Reference: | Not Available |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| Links |
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| External Links: | | Resource | Link |
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| CHEBI ID | Not Available | | HMDB ID | Not Available | | Pubchem Compound ID | 3582 | | Kegg ID | Not Available | | ChemSpider ID | Not Available | | Wikipedia ID | Heme | | BioCyc ID | HEME_D | | EcoCyc ID | HEME_D |
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