Precorrin 2 (PAMDB001029)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB001029
Identification
Name: Precorrin 2
Description:Precorrin 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
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 15,23-Dihydrosirohydrochlorin
  • Dihydrosirohydrochlorin
  • Precorrin-2
Chemical Formula: C42H46N4O16
Average Molecular Weight: 862.8318
Monoisotopic Molecular Weight: 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[16.2.1.1?,??1????.1??,???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[16.2.1.1?,??1????.1??,???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
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassOrganoheterocyclic compounds
Class Tetrapyrroles and derivatives
Sub ClassNot Available
Direct Parent Tetrapyrroles 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
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Carbonyl group
  • Organic zwitterion
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:-8
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0258 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count20ChemAxon
Refractivity227.83 m3·mol-1ChemAxon
Polarizability86.93 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
2 S-Adenosylmethionine + Uroporphyrinogen III >2 S-Adenosylhomocysteine + Precorrin 2 + Hydrogen ion
Precorrin 2 + NAD > Hydrogen ion + NADH + Sirohydrochlorin
2 S-Adenosylmethionine + Uroporphyrinogen III <>2 S-Adenosylhomocysteine + Precorrin 2
S-Adenosylmethionine + precorrin-1 > S-Adenosylhomocysteine + Precorrin 2
2 S-Adenosylmethionine + Uroporphyrinogen III + Precorrin-1 <>2 S-Adenosylhomocysteine + Precorrin 2
Pathways:
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