Record Information
Version2.0
Creation Date2012-05-31 14:32:29 -0600
Update Date2015-06-03 17:19:30 -0600
Secondary Accession Numbers
  • ECMDB20194
Identification
Name:Siroheme
DescriptionSiroheme belongs to the class of Precorrins. These are intermediates formed by methylation at one or more of the four rings prior to the formation of the macrocyclic corrin ring. (inferred from compound structure)Siroheme (or sirohaem) is a heme-like prosthetic group used by some enzymes to accomplish the six-electron reduction of sulfur and nitrogen. Siroheme is synthesized from uroporphyrinogen III, a heme and vitamin B12 precursor. It plays a major role in the sulfur assimilation pathway: converting sulfite to a biologically useful sulfide, which can be incorporated into the organic compound homocysteine. (WikiPedia)
Structure
Thumb
Synonyms:
  • Iron(2+) (2S,3S,7S,8S)-2,7,13,17-tetrakis(2-carboxyethyl)-3,8,12,18-tetrakis(carboxymethyl)-3,8-dimethyl-7,8-dihydro-2H,3H-porphine-21,23-diide
  • Iron(2+); 3-(2S,3S,7S,8S)-7,13,17-tris(2-carboxyethyl)-3,8,12,18-tetrakis(carboxymethyl)-3,8-dimethyl-2,7-dihydroporphyrin-21,23-diid-2-ylpropanoate
  • Iron(2+); 3-(2S,3S,7S,8S)-7,13,17-tris(2-carboxyethyl)-3,8,12,18-tetrakis(carboxymethyl)-3,8-dimethyl-2,7-dihydroporphyrin-21,23-diid-2-ylpropanoic acid
Chemical Formula:C42H44FeN4O16
Weight:Average: 916.661
Monoisotopic: 916.210173513
InChI Key:DLKSSIHHLYNIKN-QIISWYHFSA-L
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
CAS number:52553-42-1
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
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
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
Chemical Taxonomy
Description belongs to the class of organic compounds known as metallotetrapyrroles. These are polycyclic compounds containing a tetrapyrrole skeleton combined with a metal atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrapyrroles and derivatives
Sub ClassMetallotetrapyrroles
Direct ParentMetallotetrapyrroles
Alternative Parents
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
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-8
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP1.07ALOGPS
logS-3.9ALOGPS
pKa (Strongest Acidic)2.79ChemAxon
Physiological Charge-8ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Flavin biosynthesisPW001971 ThumbThumb?image type=greyscaleThumb?image type=simple
Porphyrin metabolismPW000936 ThumbThumb?image type=greyscaleThumb?image type=simple
Sulfur metabolismPW000922 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05i1-0000000090-f46f6449060cf2ca1980View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00b9-0000000090-84962b34725f7a689488View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01t9-0000000090-00a96804df0e7027208cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00xr-0000000092-0b4a42172e52e76b6f63View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ufr-0000000090-e9c0f647cacbe1d93a40View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0000000090-191e040b23bfd9ce6a65View in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • 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
  • 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
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID28599
HMDB IDNot Available
Pubchem Compound ID439303
Kegg IDC00748
ChemSpider ID108937
Wikipedia IDSiroheme
BioCyc IDSIROHEME
EcoCyc IDSIROHEME

Enzymes

General function:
Involved in methyltransferase activity
Specific function:
Multifunctional enzyme that catalyzes the SAM-dependent methylation of uroporphyrinogen III at position C-2 and C-7 to form precorrin-2 and then position C-12 or C-18 to form trimethylpyrrocorphin 2. It also catalyzes the conversion of precorrin-2 into siroheme. This reaction consists of the NAD- dependent oxidation of precorrin-2 into sirohydrochlorin and its subsequent ferrochelation into siroheme
Gene Name:
cysG
Uniprot ID:
P0AEA8
Molecular weight:
49951
Reactions
S-adenosyl-L-methionine + uroporphyrinogen III = S-adenosyl-L-homocysteine + precorrin-1.
S-adenosyl-L-methionine + precorrin-1 = S-adenosyl-L-homocysteine + precorrin-2.
Precorrin-2 + NAD(+) = sirohydrochlorin + NADH.
Siroheme + 2 H(+) = sirohydrochlorin + Fe(2+).