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| Identification |
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| YMDB ID | YMDB00968 |
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| Name | Siroheme |
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| Species | Saccharomyces cerevisiae |
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| Strain | Baker's yeast |
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| Description | Siroheme is an iron-containing isobacteriochlorin, a modified tetrapyrrole similar in structure to both heme and chlorophyll. Siroheme is found as a prosthetic group of several enzymes, including sulfite and nitrite reductases, which catalyze the six-electron reductions of sulfite to sulfide and nitrite to ammonia, respectively. Siroheme biosynthesis starts by the same route as other tetrapyrroles, the synthesis of the intermediate uroporphyrinogen-III. [Biocyc PWY-5194] |
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| Structure | |
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| Synonyms | - sirohaem
- Siroheme
- Octacarboxylate iron-tetrahydroporphyrin
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| CAS number | 52553-42-1 |
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| Weight | Average: 916.661
Monoisotopic: 916.210173513 |
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| InChI Key | DLKSSIHHLYNIKN-QIISWYHFSA-L |
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| InChI | InChI=1S/C42H46N4O16.Fe/c1-41(17-39(59)60)23(5-9-35(51)52)29-14-27-21(11-37(55)56)19(3-7-33(47)48)25(43-27)13-26-20(4-8-34(49)50)22(12-38(57)58)28(44-26)15-31-42(2,18-40(61)62)24(6-10-36(53)54)30(46-31)16-32(41)45-29;/h13-16,23-24H,3-12,17-18H2,1-2H3,(H10,43,44,45,46,47,48,49,50,51,52,53,54,55,56,57,58,59,60,61,62);/q;+2/p-2/t23-,24-,41+,42+;/m1./s1 |
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| IUPAC Name | 3-[(4S,5S,9S,10S,11Z,16Z)-9,15,19-tris(2-carboxyethyl)-5,10,14,20-tetrakis(carboxymethyl)-5,10-dimethyl-21,23,24,25-tetraaza-22-ferrahexacyclo[9.9.3.1³,⁶.1¹³,¹⁶.0⁸,²³.0¹⁸,²¹]pentacosa-1(20),2,6(25),7,11,13(24),14,16,18-nonaen-4-yl]propanoic acid |
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| Traditional IUPAC Name | 3-[(4S,5S,9S,10S,11Z,16Z)-9,15,19-tris(2-carboxyethyl)-5,10,14,20-tetrakis(carboxymethyl)-5,10-dimethyl-21,23,24,25-tetraaza-22-ferrahexacyclo[9.9.3.1³,⁶.1¹³,¹⁶.0⁸,²³.0¹⁸,²¹]pentacosa-1(20),2,6(25),7,11,13(24),14,16,18-nonaen-4-yl]propanoic acid |
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| Chemical Formula | C42H44FeN4O16 |
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| SMILES | C[C@]1(CC(O)=O)[C@H](CCC(O)=O)\C2=C\C3=C(CC(O)=O)C(CCC(O)=O)=C4\C=C5/N=C(/C=C6\N([Fe]N34)\C(=C/C1=N2)[C@@H](CCC(O)=O)[C@]6(C)CC(O)=O)C(CC(O)=O)=C5CCC(O)=O |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as metallotetrapyrroles. These are polycyclic compounds containing a tetrapyrrole skeleton combined with a metal atom. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Tetrapyrroles and derivatives |
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| Sub Class | Metallotetrapyrroles |
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| Direct Parent | Metallotetrapyrroles |
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| Alternative Parents | |
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| Substituents | - Metallotetrapyrrole skeleton
- Substituted pyrrole
- Pyrrole
- Heteroaromatic compound
- Azacycle
- Organic transition metal salt
- Carboxylic acid
- Carboxylic acid derivative
- Hydrocarbon derivative
- Carbonyl group
- Organic salt
- Organic zwitterion
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Organic oxide
- Organopnictogen compound
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State | Not Available |
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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 | |
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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 | |
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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: | - UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
- 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
- Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
- Schubert, H. L., Raux, E., Matthews, M. A., Phillips, J. D., Wilson, K. S., Hill, C. P., Warren, M. J. (2002). "Structural diversity in metal ion chelation and the structure of uroporphyrinogen III synthase." Biochem Soc Trans 30:595-600.12196144
- Schubert, H. L., Raux, E., Brindley, A. A., Leech, H. K., Wilson, K. S., Hill, C. P., Warren, M. J. (2002). "The structure of Saccharomyces cerevisiae Met8p, a bifunctional dehydrogenase and ferrochelatase." EMBO J 21:2068-2075.11980703
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| Synthesis Reference: | Not Available |
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| External Links: | |
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