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Record Information
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:34 UTC
Secondary Accession NumbersNone
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.
2,7,12,17-Porphinetetrapropionic acidChEBI
3,8,13,18-Tetrakis(carboxymethyl)porphyrin-2,7,12,17-tetrapropionic acidChEBI
3,3',3'',3'''-(3,8,13,18-tetrakis-carboxymethyl-21H,23H-porphine-2,7,12,17-tetrayl)-tetrakis-propionic acidHMDB
3,3',3'',3'''-(3,8,13,18-tetrakis-carboxymethyl-porphyrin-2,7,12,17-tetrayl)-tetra-propionic acidHMDB
3,8,13,18-Tetrakis(carboxymethyl)porphyrin-2,7,12,17-tetrapropanoic acidHMDB
3-[7,12,17-Tris-(2-carboxy-ethyl)-3,8,13,18-tetrakis-carboxymethyl-22,24-dihydro-porphin-2-yl]-propionic acidHMDB
Chemical FormulaC40H38N4O16
Average Molecular Weight830.7469
Monoisotopic Molecular Weight830.228281188
IUPAC Name3-[9,14,19-tris(2-carboxyethyl)-5,10,15,20-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid
Traditional Nameuroporphyrin I
CAS Registry Number607-14-7
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as porphyrins. These 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
  • Porphyrin
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
StatusDetected and Quantified
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.037 mg/mLALOGPS
pKa (Strongest Acidic)3.16ChemAxon
Physiological Charge-8ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area355.76 Å2ChemAxon
Rotatable Bond Count20ChemAxon
Refractivity201.32 m3·mol-1ChemAxon
Polarizability84.92 Å3ChemAxon
Number of Rings5ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
Acute Intermittent PorphyriaSMP00344Not Available
Congenital Erythropoietic Porphyria (CEP) or Gunther DiseaseSMP00345Not Available
Hereditary Coproporphyria (HCP)SMP00342Not Available
Porphyria Variegata (PV)SMP00346Not Available
Porphyrin MetabolismSMP00024map00860
Normal Concentrations
BloodDetected and Quantified0.0006 (0.0000-0.0012) uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
BloodDetected and Quantified0.012 (0.000-0.024) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
UrineDetected and Quantified0.00092 +/- 0.00032 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
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
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00936
Metagene LinkHMDB00936
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID27484
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. [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. [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. [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. 2003 May;81(5):310-20. Epub 2003 Apr 30. [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. [12482484 ]
  6. Fritsch C, Bolsen K, Ruzicka T, Goerz G: Congenital erythropoietic porphyria. J Am Acad Dermatol. 1997 Apr;36(4):594-610. [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. [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. [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. [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. [9861496 ]