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Human Metabolome Database Version 2.5

 

Showing metabocard for Coproporphyrin I (HMDB00643)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2005-11-16 15:48:42
Update Date 2009-08-13 10:46:34
Accession Number HMDB00643
Secondary Accession Numbers Not Available
Common Name Coproporphyrin I
Description Coproporhyrin 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)
Synonyms
  1. 3,8,13,18-Tetramethyl-21H,23H-porphine-2,7,12,17-tetrapropionate
  2. 3,8,13,18-Tetramethyl-21H,23H-porphine-2,7,12,17-tetrapropionic acid
  3. 3,8,13,18-tetramethyl-2,7,12,17-Porphinetetrapropionate
  4. 3,8,13,18-tetramethyl-2,7,12,17-Porphinetetrapropionic acid
Chemical IUPAC Name 3,8,13,18-tetramethyl-21H,23H-Porphine-2,7,12,17-tetrapropanoic acid
Chemical Formula C36H38N4O8
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Heterocyclic molecules
Class
  • Porphyrins
Sub Class
  • Miscellaneous porphyrins
Family
  • Mammalian Metabolite
Species
  • carboxylic acid
  • aromatic compound
  • heterocyclic compound
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 654.709
Monoisotopic Molecular Weight 654.268982
Isomeric SMILES CC1=C(CCC(O)=O)/C2=C/C3=N/C(=CC4=C(C)C(CCC(O)=O)=C(N4)C=C4/N=C(/C=C1N2)C(CCC(O)=O)=C/4C)/C(CCC(O)=O)=C3C
Canonical SMILES CC1=C(CCC(O)=O)C2=CC3=NC(=CC4=C(C)C(CCC(O)=O)=C(N4)C=C4N=C(C=C1N2)C(CCC(O)=O)=C4C)C(CCC(O)=O)=C3C
KEGG Compound ID C02667 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB00643 Link Image
Metagene Link HMDB00643 Link Image
METLIN ID 5616 Link Image
PubChem Compound 68271 Link Image
PubChem Substance 210397 Link Image
ChEBI ID 28421 Link Image
CAS Registry Number 531-14-6
InChI Identifier InChI=1/C36H38N4O8/c1-17-21(5-9-33(41)42)29-14-26-19(3)23(7-11-35(45)46)31(39-26)16-28-20(4)24(8-12-36(47)48)32(40-28)15-27-18(2)22(6-10-34(43)44)30(38-27)13-25(17)37-29/h13-16,37,40H,5-12H2,1-4H3,(H,41,42)(H,43,44)(H,45,46)(H,47,48)/b25-13-,26-14-,27-15-,28-16-,29-14-,30-13-,31-16-,32-15-
Synthesis Reference Schonheyder, Fritz. The formation of coproporphyrin I and hemoglobin during embryonic life. Journal of Biological Chemistry (1938), 123 491-7.
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 0.0309 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -4
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 2.53 [Predicted by ALOGPS]; 0.7 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID 1R3Q Link Image
Experimental PDB File Show
Experimental PDB Structure
Experimental 1H NMR Spectrum Download Spectrum
Download FID (Bruker)
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Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
Show Experimental Conditions Link Image
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
Download File
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Medium Energy
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High Energy
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
  • Mitochondria
Biofluid Location
  • Blood
  • Urine
Tissue Location
Tissue References
Liver —
Concentrations (Normal)
Biofluid Blood
Value 0.005 (0.000 - 0.010) uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Hindmarsh JT, Oliveras L, Greenway DC: Biochemical differentiation of the porphyrias. Clin Biochem. 1999 Nov;32(8):609-19. [PubMed Link Image]
Biofluid Blood
Value 0.0073 +/- 0.0035 uM
Age Newborn:0-30 days old
Sex Both
Patient information Normal
Comments Not Available
References
  • Geigy Scientific Tables, 8th Rev edition, pp. 165-177. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.
Biofluid Blood
Value 0.012 +/- 0.005 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Geigy Scientific Tables, 8th Rev edition, pp. 165-177. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.
Biofluid Urine
Value 0.0036 +/- 0.0015 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Geigy Scientific Tables, 8th Rev edition, pp. 165-177. Edited by Cornelius Lentner.
  • West Cadwell, N.J. : Medical education Div., Ciba-Geigy Corp.
  • Basel, Switzerland c1981-1992.
Biofluid Urine
Value 0.0021 +/- 0.001 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Female
Patient information Normal
Comments Not Available
References
  • Li J, Cai Z: Stacking and separation of urinary porphyrins in capillary electrophoresis: optimization of concentration efficiency and resolution. Talanta. 2008 Oct 19;77(1):331-9. Epub 2008 Jul 1. [PubMed Link Image]
Biofluid Urine
Value 0.0020 +/- 0.0011 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Male
Patient information Normal
Comments Not Available
References
  • Li J, Cai Z: Stacking and separation of urinary porphyrins in capillary electrophoresis: optimization of concentration efficiency and resolution. Talanta. 2008 Oct 19;77(1):331-9. Epub 2008 Jul 1. [PubMed Link Image]
Biofluid Urine
Value 0.0049 +/- 0.00019 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • 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 Link Image]
Biofluid Urine
Value 0.0098 (0.0053-0.017) umol/mmol creatinine
Age Newborn:0-30 days old
Sex Both
Patient information Normal
Comments Not Available
References
  • Ozalla D, Herrero C, Ribas-Fito N, To-Figueras J, Toll A, Sala M, Grimalt J, Basagana X, Lecha M, Sunyer J: Evaluation of urinary porphyrin excretion in neonates born to mothers exposed to airborne hexachlorobenzene. Environ Health Perspect. 2002 Feb;110(2):205-9. [PubMed Link Image]
Concentrations (Abnormal)
Biofluid Blood
Value 0.008 (0.000 - 0.016) uM
Age Adult:>18 yrs old
Sex Both
Condition Porphyria
Comments Porphyria cutanea tarda
References
  • Hindmarsh JT, Oliveras L, Greenway DC: Biochemical differentiation of the porphyrias. Clin Biochem. 1999 Nov;32(8):609-19. [PubMed Link Image]
Biofluid Blood
Value 0.0850 (0.0008 - 0.1700) uM
Age Adult:>18 yrs old
Sex Male
Condition Porphyria
Comments Not Available
References
  • Hindmarsh JT, Oliveras L, Greenway DC: Biochemical differentiation of the porphyrias. Clin Biochem. 1999 Nov;32(8):609-19. [PubMed Link Image]
Biofluid Urine
Value 0.0042 +/- 0.00019 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Condition Liver disease
Comments Not Available
References
  • 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 Link Image]
Biofluid Urine
Value 0.002 +/- 0.00019 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Comments Not Available
References
  • 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 Link Image]
Biofluid Urine
Value 0.014 +/- 0.00013 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Comments Not Available
References
  • 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 Link Image]
Biofluid Urine
Value 0.0019 +/- 0.00085 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Comments Not Available
References
  • 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 Link Image]
Biofluid Urine
Value 0.0035 +/- 0.00013 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Comments Not Available
References
  • 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 Link Image]
Biofluid Urine
Value 0.015 (0.0067-0.021) umol/mmol creatinine
Age N/A
Sex Both
Comments Not Available
References
  • Ozalla D, Herrero C, Ribas-Fito N, To-Figueras J, Toll A, Sala M, Grimalt J, Basagana X, Lecha M, Sunyer J: Evaluation of urinary porphyrin excretion in neonates born to mothers exposed to airborne hexachlorobenzene. Environ Health Perspect. 2002 Feb;110(2):205-9. [PubMed Link Image]
Associated Disorders
Condition References
Liver disease
  • 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 Link Image]
Porphyria
  • Hindmarsh JT, Oliveras L, Greenway DC: Biochemical differentiation of the porphyrias. Clin Biochem. 1999 Nov;32(8):609-19. [PubMed Link Image]
OMIM ID Not Available
Pathways
Name SMPDB Link KEGG Link
Porphyrin Metabolism SMP00024 Link Image map00860 Link Image
General References Not Available