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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 07:55:32 UTC
HMDB IDHMDB0000936
Secondary Accession Numbers
  • HMDB00936
Metabolite Identification
Common NameUroporphyrin I
DescriptionUroporphyrin is the porphyrin produced by oxidation of the methylene bridges in uroporphyrinogen. They have four acetic acid and four propionic acid side chains attached to the pyrrole rings. Uroporphyrinogen I and III are formed from polypyrryl methane in the presence of uroporphyrinogen III cosynthetase and uroporphyrin I synthetase, respectively. They can yield uroporphyrins by autooxidation or coproporphyrinogens by decarboxylation.Excessive amounts of uroporphyrin I are excreted in congenital erythropoietic porphyria, and both types I and III are excreted in porphyria cutanea tarda.Uroporphyrin I and III are the most common isomers.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC40H38N4O16
Average Molecular Weight830.7469
Monoisotopic Molecular Weight830.228281188
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number607-14-7
SMILESNot Available
InChI Identifier
InChI=1S/C40H38N4O16/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/h13-16,41,44H,1-12H2,(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)(H,59,60)/b25-13-,26-14-,27-15-,28-16-,29-14-,30-13-,31-16-,32-15-
InChI KeyDAFUFNRZWDWXJP-JRHDEHKPSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03xs-0000000940-dfb6a1c5995e614eac9aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gbi-0000000910-609babbc27a206d09ad4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f9i-0000000900-ffd2454f165fe2594021View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000790-377067e19f6ade3d5860View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02vi-1000000940-9415a48c2a747a58ce1dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066r-5000000900-22e5a1d377afd75f3366View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Acute Intermittent PorphyriaPw000174Pw000174 greyscalePw000174 simpleNot Available
Congenital Erythropoietic Porphyria (CEP) or Gunther DiseasePw000176Pw000176 greyscalePw000176 simpleNot Available
Hereditary Coproporphyria (HCP)Pw000211Pw000211 greyscalePw000211 simpleNot Available
Porphyria Variegata (PV)Pw000175Pw000175 greyscalePw000175 simpleNot Available
Porphyrin MetabolismPw000158Pw000158 greyscalePw000158 simpleMap00860
Displaying all 5 entries
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0006 (0.0000-0.0012) uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.012 (0.000-0.024) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified0.00092 +/- 0.00032 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022326
KNApSAcK IDNot Available
Chemspider ID16736725
KEGG Compound IDC05767
BioCyc IDUROPORPHYRIN_I
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5885
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID27484
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Ding Y, Lin B, Huie CW: Binding studies of porphyrins to human serum albumin using affinity capillary electrophoresis. Electrophoresis. 2001 Jul;22(11):2210-6. [PubMed:11504054 ]
  2. Sunyer J, Herrero C, Ozalla D, Sala M, Ribas-Fito N, Grimalt J, Basagana X: Serum organochlorines and urinary porphyrin pattern in a population highly exposed to hexachlorobenzene. Environ Health. 2002 Jul 19;1(1):1. [PubMed:12495451 ]
  3. Ged C, Moreau-Gaudry F, Taine L, Hombrados I, Calvas P, Colombies P, De Verneuil H: Prenatal diagnosis in congenital erythropoietic porphyria by metabolic measurement and DNA mutation analysis. Prenat Diagn. 1996 Jan;16(1):83-6. [PubMed:8821859 ]
  4. Geronimi F, Richard E, Lamrissi-Garcia I, Lalanne M, Ged C, Redonnet-Vernhet I, Moreau-Gaudry F, de Verneuil H: Lentivirus-mediated gene transfer of uroporphyrinogen III synthase fully corrects the porphyric phenotype in human cells. J Mol Med (Berl). 2003 May;81(5):310-20. Epub 2003 Apr 30. [PubMed:12721665 ]
  5. Bu W, Myers N, McCarty JD, O'Neill T, Hollar S, Stetson PL, Sved DW: Simultaneous determination of six urinary porphyrins using liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jan 15;783(2):411-23. [PubMed:12482484 ]
  6. Fritsch C, Bolsen K, Ruzicka T, Goerz G: Congenital erythropoietic porphyria. J Am Acad Dermatol. 1997 Apr;36(4):594-610. [PubMed:9092747 ]
  7. Zhang W, Zhang L, Ping G, Zhang Y, Kettrup A: Study on the multiple sites binding of human serum albumin and porphyrin by affinity capillary electrophoresis. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Feb 25;768(1):211-4. [PubMed:11939554 ]
  8. Oguz F, Sidal M, Bayram C, Sansoy N, Hekim N: Ocular involvement in two symptomatic congenital erythropoietic porphyria. Eur J Pediatr. 1993 Aug;152(8):671-3. [PubMed:8404971 ]
  9. Akhtar MK, Kaderbhai NN, Hopper DJ, Kelly SL, Kaderbhai MA: Export of a heterologous cytochrome P450 (CYP105D1) in Escherichia coli is associated with periplasmic accumulation of uroporphyrin. J Biol Chem. 2003 Nov 14;278(46):45555-62. Epub 2003 Aug 20. [PubMed:12930844 ]
  10. Gorchein A, Guo R, Lim CK, Raimundo A, Pullon HW, Bellingham AJ: Porphyrins in urine, plasma, erythrocytes, bile and faeces in a case of congenital erythropoietic porphyria (Gunther's disease) treated with blood transfusion and iron chelation: lack of benefit from oral charcoal. Biomed Chromatogr. 1998 Nov-Dec;12(6):350-6. [PubMed:9861496 ]