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Uroporphyrinogen I (M2MDB000447)

Record Information
Version2.0
Creation Date2012-05-31 13:56:04 -0600
Update Date2015-06-03 15:54:15 -0600
Secondary Accession Numbers
  • ECMDB02211
Identification
Name:Uroporphyrinogen I
DescriptionUroporphyrinogens are porphyrinogen variants in which each pyrrole ring has one acetate side chain and one propionate side chain; it is formed by condensation 4 four molecules of porphobilinogen. 4 isomers are possible but only 2 commoly are found, types and I. Uroporphyrinogen I is a functional intermediate in heme biosynthesis while Uroporphyrinogen is produced in an abortive side reaction.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 3,8,13,18-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydro-(8CI)-2,7,12,17-Porphinetetrapropionate
  • 3,8,13,18-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydro-(8CI)-2,7,12,17-Porphinetetrapropionic acid
  • 3,8,13,18-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydro-21H,23H-Porphine-2,7,12,17-tetrapropanoate
  • 3,8,13,18-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydro-21H,23H-Porphine-2,7,12,17-tetrapropanoic acid
  • 3,8,13,18-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,17-tetrapropanoate
  • 3,8,13,18-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,17-tetrapropanoic acid
  • Uroporphyrinogen I
  • Uroporphyrinogen III
  • Uroporphyrinogen-I
Chemical Formula:C40H44N4O16
Weight:Average: 836.7946
Monoisotopic: 836.27523138
InChI Key:QTTNOSKSLATGQB-UHFFFAOYSA-N
InChI:InChI=1S/C40H44N4O16/c45-33(46)5-1-17-21(9-37(53)54)29-14-26-19(3-7-35(49)50)23(11-39(57)58)31(43-26)16-28-20(4-8-36(51)52)24(12-40(59)60)32(44-28)15-27-18(2-6-34(47)48)22(10-38(55)56)30(42-27)13-25(17)41-29/h41-44H,1-16H2,(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)(H,59,60)
CAS number:1867-62-5
IUPAC Name:3-[9,14,19-tris(2-carboxyethyl)-5,10,15,20-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid
Traditional IUPAC Name:uroporphyrinogen I
SMILES:OC(=O)CCC1=C2CC3=C(CC(O)=O)C(CCC(O)=O)=C(CC4=C(CC(O)=O)C(CCC(O)=O)=C(CC5=C(CC(O)=O)C(CCC(O)=O)=C(CC(N2)=C1CC(O)=O)N5)N4)N3
Chemical Taxonomy
Description belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrapyrroles and derivatives
Sub ClassPorphyrins
Direct ParentPorphyrins
Alternative Parents
Substituents
  • Porphyrin
  • Substituted pyrrole
  • Pyrrole
  • Heteroaromatic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-8
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.044 g/LALOGPS
logP0.67ALOGPS
logP1.39ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)3.27ChemAxon
Physiological Charge-8ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area361.56 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity206.93 m³·mol⁻¹ChemAxon
Polarizability84.05 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Uroporphyrinogen I <> Coproporphyrinogen I +4 Carbon dioxide
Uroporphyrinogen I + 4 Hydrogen ion >4 Carbon dioxide + Coproporphyrinogen I
SMPDB Pathways:
Porphyrin metabolismPW000936 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Porphyrin and chlorophyll metabolism ec00860
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gi0-0000000790-66d58d00c9ac805a86ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-0000000910-4ff4ea54a281f8d6b0d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0adi-0000000900-919f095ae5cb2c3e6cd2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000790-5f547e23817fab228be1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00y0-1000000940-4d4fc3a395b4bfdd41dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-5000000900-f49d69c9724b023caf67View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0g4i-0000000960-0125e055eb61d33157a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-0000000910-6066cce322481af52283View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000t-0000000900-a0d3dd169d62d3b9101aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000000900-e9ab543d3cd6074dec5dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0000000900-d45cf1d17beafd43554eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kb-0000000900-b910cfcdb3042465a8f1View in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot 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
  • Maines MD, Mayer RD: Inhibition of testicular cytochrome P-450-dependent steroid biosynthesis by cis-platinum. Reversal by human chorionic gonadotropin. J Biol Chem. 1985 May 25;260(10):6063-8. Pubmed: 4039724
  • Mukerji SK, Pimstone NR: Defective human erythrocyte uroporphyrinogen decarboxylase in familial porphyria cutanea tarda: the metabolic lesion or the result of endogenous porphyrinemia? Biochem Biophys Res Commun. 1988 Jul 15;154(1):39-46. Pubmed: 3395340
Synthesis Reference:Burton, Gerardo; Fagerness, Paul E.; Hosozawa, Shigeki; Jordan, Peter M.; Scott, A. Ian. Carbon-13 NMR evidence for a new intermediate, pre-uroporphyrinogen, in the enzymic transformation of porphobilinogen into uroporphyrinogens I and III. Journal of
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID28766
HMDB IDHMDB02211
Pubchem Compound ID440775
Kegg IDC05766
ChemSpider ID389644
WikipediaUroporphyrinogen I
BioCyc IDUROPORPHYRINOGEN-III
EcoCyc IDUROPORPHYRINOGEN-III

Enzymes

Protein Details
1. Uroporphyrinogen decarboxylase
General function:
Involved in uroporphyrinogen decarboxylase activity
Specific function:
Catalyzes the decarboxylation of four acetate groups of uroporphyrinogen-III to yield coproporphyrinogen-III
Gene Name:
hemE
Uniprot ID:
P29680
Molecular weight:
39248
Reactions
Uroporphyrinogen III = coproporphyrinogen + 4 CO(2).