Record Information
Version2.0
Creation Date2012-05-31 14:31:55 -0600
Update Date2015-06-03 17:19:28 -0600
Secondary Accession Numbers
  • ECMDB20183
Identification
Name:Precorrin 2
DescriptionPrecorrin 2 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. Precorrin 2 is invovled in Proto- and siroheme biosynthesis. Precorrin-2 is a precursor of both siroheme and B12. (PMID 8955319)
Structure
Thumb
Synonyms:
  • 15,23-Dihydrosirohydrochlorin
  • Dihydrosirohydrochlorin
  • Precorrin-2
Chemical Formula:C42H46N4O16
Weight:Average: 862.8318
Monoisotopic: 862.290881444
InChI Key:KVFNZYKFDBWLHT-ZTKUHGNGSA-N
InChI:InChI=1S/C42H46N4O16/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/h14-16,23-24H,3-13,17-18H2,1-2H3,(H9,43,44,47,48,49,50,51,52,53,54,55,56,57,58,59,60,61,62)/t23-,24-,41+,42+/m1/s1
CAS number:82542-92-5
IUPAC Name:(4S,5S,9S,10S)-4,9,15,19-tetrakis(2-carboxyethyl)-5,10,14,20-tetrakis(carboxymethyl)-5,10-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(20),2,6(24),7,11(23),12,14,16(22),18-nonaen-22-ium-21-ide
Traditional IUPAC Name:(4S,5S,9S,10S)-4,9,15,19-tetrakis(2-carboxyethyl)-5,10,14,20-tetrakis(carboxymethyl)-5,10-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(20),2,6(24),7,11(23),12,14,16(22),18-nonaen-22-ium-21-ide
SMILES:[H][C@@]1(CCC(O)=O)C2=CC3=C(CC(O)=O)C(CCC(O)=O)=C(CC4=[NH+]C(=CC5=NC(=CC(=N2)[C@@]1(C)CC(O)=O)[C@@]([H])(CCC(O)=O)[C@]5(C)CC(O)=O)C(CC(O)=O)=C4CCC(O)=O)[N-]3
Chemical Taxonomy
Description belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrapyrroles and derivatives
Sub ClassNot Available
Direct ParentTetrapyrroles and derivatives
Alternative Parents
Substituents
  • Tetrapyrrole skeleton
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrroline
  • Pyrrole
  • Ketimine
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic zwitterion
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-8
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.026 g/LALOGPS
logP1.04ALOGPS
logP1.57ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)3.15ChemAxon
Physiological Charge-8ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area349.98 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity227.83 m³·mol⁻¹ChemAxon
Polarizability86.93 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Porphyrin metabolismPW000936 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, Positivesplash10-01t9-0000000090-3fed12fcc4f9b8f249e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000090-457d3e08ad7483db3c02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bt9-0120001090-deb3d0f24e6ef8da71baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000090-bcea32de04cd450f7babView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fr-1000000090-b4be0b8b43691ca31dcfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-7000001090-52f742092fbf18c1b905View in MoNA
References
References:
  • Fazzio, T. G., Roth, J. R. (1996). "Evidence that the CysG protein catalyzes the first reaction specific to B12 synthesis in Salmonella typhimurium, insertion of cobalt." J Bacteriol 178:6952-6959. Pubmed: 8955319
  • 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 ID50602
HMDB IDNot Available
Pubchem Compound ID5280516
Kegg IDC02463
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDDIHYDROSIROHYDROCHLORIN
EcoCyc IDDIHYDROSIROHYDROCHLORIN

Enzymes

General function:
Coenzyme transport and metabolism
Specific function:
S-adenosyl-L-methionine + uroporphyrinogen III = S-adenosyl-L-homocysteine + precorrin-1
Gene Name:
hemX
Uniprot ID:
P09127
Molecular weight:
42963
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.
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+).