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Record Information
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-10-09 20:59:58 UTC
Secondary Accession Numbers
  • HMDB00643
Metabolite Identification
Common NameCoproporphyrin I
DescriptionCoproporphyrin I is a porphyrin metabolite arising from heme synthesis. Porphyrins are pigments found in both animal and plant life. Coproporphyrin I is a tetrapyrrole dead-end product from the spontaneous oxidation of the methylene bridges of coproporphynogen, arising from heme synthesis and secreted in feces and urine. Increased levels of coproporphyrins can indicate congenital erythropoietic porphyria or sideroblastic anaemia. Porphyria is a pathological state characterised by abnormalities of porphyrin metabolism and results in the excretion of large quantities of porphyrins in the urine and in extreme sensitivity to light. A large number of factors are capable of increasing porphyrin excretion, owing to different and multiple causes and etiologies: 1) the main site of the chronic hepatic porphyria disease process concentrates on the liver, 2) a functional and morphologic liver injury is almost regularly associated with this chronic porphyria, 3) the toxic form due to occupational and environmental exposure takes mainly a subclinical course. Hepatic factors includes disturbance in coproporphyrinogen metabolism, which results from inhibition of coproporphyrinogen oxidase as well as from the rapid loss from, and diminished utilization of coproporphyrinogen in the hepatocytes, which may also explain why coproporphyrin, its autoxidation product, predominates physiologically in the urine; decreased biliary excretion of coproporphyrin leading to a compensatory urinary excretion, so that the coproporphyrin ring isomer ratio (1:III) becomes a sensitive index for impaired liver function and intrahepatic cholestasis; and disturbed activity of hepatic uroporphyrinogen decarboxylase. In itself, secondary coproporphyrinuria is not associated with porphyria symptoms of a hepatologic-gastroenterologic, neurologic, or dermatologic order, even though coproporphyrinuria can occur with such symptoms. (PMID: 3327428 ).
3,8,13,17-Tetramethylporphyrin-2,7,12,18-tetrapropanoic acidChEBI
3,8,13,18-Tetramethyl-2,7,12,17-porphinetetrapropionic acidHMDB
3,8,13,18-Tetramethyl-21H,23H-porphine-2,7,12,17-tetrapropionic acidHMDB
Chemical FormulaC36H38N4O8
Average Molecular Weight654.7089
Monoisotopic Molecular Weight654.268964212
IUPAC Name3-[9,14,19-tris(2-carboxyethyl)-5,10,15,20-tetramethyl-21,22,23,24-tetraazapentacyclo[^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoic acid
Traditional Name3-[9,14,19-tris(2-carboxyethyl)-5,10,15,20-tetramethyl-21,22,23,24-tetraazapentacyclo[^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoic acid
CAS Registry Number531-14-6
InChI Identifier
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkNot Available
External DescriptorsNot Available
Physiological effect

Health effect:



Biological location:


Naturally occurring process:


Industrial application:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.031 g/LALOGPS
pKa (Strongest Acidic)3.56ChemAxon
pKa (Strongest Basic)5.18ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area206.56 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity176.26 m³·mol⁻¹ChemAxon
Polarizability74.04 ųChemAxon
Number of Rings5ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052g-2000069000-b0400ff816c8bb479aa9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0000039000-f3b4207c1c84e6625cb5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4u-0000097000-25bf85caccefc18e4e75Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ot-1000090000-f4fcb2a24b23cd617b5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000009000-9d1a49bb4b1cf969e8e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zg0-1000039000-f24da7ff41769ba0e5beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000042000-ef49befaf8862d948c2bSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Liver
Normal Concentrations
BloodDetected and Quantified0.0073 +/- 0.0035 uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
BloodDetected and Quantified0.012 +/- 0.005 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
BloodDetected and Quantified0.005 (0.000 - 0.010) uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0021 +/- 0.001 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.0020 +/- 0.0011 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.0049 +/- 0.00019 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0036 +/- 0.0015 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
UrineDetected and Quantified0.0098 (0.0053-0.017) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
Abnormal Concentrations
BloodDetected and Quantified0.008 (0.000 - 0.016) uMAdult (>18 years old)Both
BloodDetected and Quantified0.0850 (0.0008 - 0.1700) uMAdult (>18 years old)MalePorphyria details
BloodDetected and Quantified0 uMAdult (>18 years old)MaleProtoporphyria, Erythropoietic details
UrineDetected and Quantified0.0042 +/- 0.00019 umol/mmol creatinineAdult (>18 years old)BothLiver disease details
UrineDetected and Quantified0.002 +/- 0.00019 umol/mmol creatinineAdult (>18 years old)BothPorphyria cutanea tarda details
UrineDetected and Quantified0.014 +/- 0.00013 umol/mmol creatinineAdult (>18 years old)BothPorphyria variegata details
UrineDetected and Quantified0.0019 +/- 0.00085 umol/mmol creatinineAdult (>18 years old)BothHereditary coproporphyria details
UrineDetected and Quantified0.0035 +/- 0.00013 umol/mmol creatinineAdult (>18 years old)BothAcute intermittent porphyria details
UrineDetected and Quantified0.015 (0.0067-0.021) umol/mmol creatinineNot SpecifiedBothHexachlorobenzene exposure details
UrineDetected and Quantified0.00326-0.00916 umol/mmol creatinineAdult (>18 years old)MaleProtoporphyria, Erythropoietic details
Associated Disorders and Diseases
Disease References
  1. Hindmarsh JT, Oliveras L, Greenway DC: Biochemical differentiation of the porphyrias. Clin Biochem. 1999 Nov;32(8):609-19. [PubMed:10638943 ]
Protoporphyria, Erythropoietic
  1. MAGNUS IA, JARRETT A, PRANKERD TA, RIMINGTON C: Erythropoietic protoporphyria. A new porphyria syndrome with solar urticaria due to protoporphyrinaemia. Lancet. 1961 Aug 26;2(7200):448-51. [PubMed:13765301 ]
Liver disease
  1. Zuijderhoudt FM, Koehorst SG, Kluitenberg WE, Dorresteijn-de Bok J: On accuracy and precision of a HPLC method for measurement of urine porphyrin concentrations. Clin Chem Lab Med. 2000 Mar;38(3):227-30. [PubMed:10905759 ]
Porphyria cutanea tarda
  1. Zuijderhoudt FM, Koehorst SG, Kluitenberg WE, Dorresteijn-de Bok J: On accuracy and precision of a HPLC method for measurement of urine porphyrin concentrations. Clin Chem Lab Med. 2000 Mar;38(3):227-30. [PubMed:10905759 ]
Variegate porphyria
  1. Zuijderhoudt FM, Koehorst SG, Kluitenberg WE, Dorresteijn-de Bok J: On accuracy and precision of a HPLC method for measurement of urine porphyrin concentrations. Clin Chem Lab Med. 2000 Mar;38(3):227-30. [PubMed:10905759 ]
Hereditary coproporphyria
  1. Zuijderhoudt FM, Koehorst SG, Kluitenberg WE, Dorresteijn-de Bok J: On accuracy and precision of a HPLC method for measurement of urine porphyrin concentrations. Clin Chem Lab Med. 2000 Mar;38(3):227-30. [PubMed:10905759 ]
Acute intermittent porphyria
  1. Zuijderhoudt FM, Koehorst SG, Kluitenberg WE, Dorresteijn-de Bok J: On accuracy and precision of a HPLC method for measurement of urine porphyrin concentrations. Clin Chem Lab Med. 2000 Mar;38(3):227-30. [PubMed:10905759 ]
Associated OMIM IDs
  • 177000 (Protoporphyria, Erythropoietic)
  • 176200 (Variegate porphyria)
  • 121300 (Hereditary coproporphyria)
  • 176000 (Acute intermittent porphyria)
DrugBank IDDB03727
Phenol Explorer Compound IDNot Available
FooDB IDFDB022159
KNApSAcK IDNot Available
Chemspider ID16736701
KEGG Compound IDC05769
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID28421
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000206
Synthesis ReferenceSchonheyder, Fritz. The formation of coproporphyrin I and hemoglobin during embryonic life. Journal of Biological Chemistry (1938), 123 491-7.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Doss MO: Porphyrinurias and occupational disease. Ann N Y Acad Sci. 1987;514:204-18. [PubMed:3327428 ]
  2. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]