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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-10-09 20:59:45 UTC
HMDB IDHMDB0000570
Secondary Accession Numbers
  • HMDB00570
Metabolite Identification
Common NameCoproporphyrin III
DescriptionCoproporphyrin III is a porphyrin metabolite arising from heme synthesis. Porphyrins are pigments found in both animal and plant life. Coproporphyrin III 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, which are inherited disorders. 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 ).
Structure
Data?1582752141
Synonyms
ValueSource
3,8,13,17-Tetramethylporphyrin-2,7,12,18-tetrapropanoic acidChEBI
3,8,13,17-Tetramethylporphyrin-2,7,12,18-tetrapropanoateGenerator
Chemical FormulaC36H38N4O8
Average Molecular Weight654.7089
Monoisotopic Molecular Weight654.268964212
IUPAC Name3-[9,15,19-tris(2-carboxyethyl)-5,10,14,20-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{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-[9,15,19-tris(2-carboxyethyl)-5,10,14,20-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{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 Number14643-66-4
SMILES
CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(CCC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C)=C4CCC(O)=O)/C(CCC(O)=O)=C3C
InChI Identifier
InChI=1S/C36H38N4O8/c1-17-21(5-9-33(41)42)29-14-27-19(3)22(6-10-34(43)44)30(39-27)15-28-20(4)24(8-12-36(47)48)32(40-28)16-31-23(7-11-35(45)46)18(2)26(38-31)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-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-
InChI KeyJWFCYWSMNRLXLX-UJJXFSCMSA-N
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
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg271.13430932474
[M+H]+MetCCS_train_pos257.18630932474
[M+H]+Not Available258.107http://allccs.zhulab.cn/database/detail?ID=AllCCS00000465
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.031 g/LALOGPS
logP10(2.53) g/LALOGPS
logP10(4.95) g/LChemAxon
logS10(-4.3) g/LALOGPS
pKa (Strongest Acidic)3.52ChemAxon
pKa (Strongest Basic)5.16ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area206.56 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity176.26 m³·mol⁻¹ChemAxon
Polarizability73.93 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+31661259
DarkChem[M-H]-31661259
AllCCS[M+H]+252.21832859911
AllCCS[M-H]-250.67632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Coproporphyrin IIICC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(CCC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C)=C4CCC(O)=O)/C(CCC(O)=O)=C3C6805.9Standard polar33892256
Coproporphyrin IIICC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(CCC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C)=C4CCC(O)=O)/C(CCC(O)=O)=C3C4249.7Standard non polar33892256
Coproporphyrin IIICC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(CCC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C)=C4CCC(O)=O)/C(CCC(O)=O)=C3C6677.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Coproporphyrin III,1TMS,isomer #1CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(CCC(=O)O[Si](C)(C)C)=C5C)C(C)=C4CCC(=O)O)[NH]36032.8Semi standard non polar33892256
Coproporphyrin III,1TMS,isomer #2CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(CCC(=O)O)=C5C)C(C)=C4CCC(=O)O)[NH]36032.8Semi standard non polar33892256
Coproporphyrin III,1TMS,isomer #3CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(CCC(=O)O)=C5C)C(C)=C4CCC(=O)O[Si](C)(C)C)[NH]36040.5Semi standard non polar33892256
Coproporphyrin III,1TMS,isomer #4CC1=C(CCC(=O)O)C2=CC3=C(CCC(=O)O)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O)C(C)=C4CCC(=O)O[Si](C)(C)C)[NH]36040.3Semi standard non polar33892256
Coproporphyrin III,1TMS,isomer #5CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(CCC(=O)O)=C5C)C(C)=C4CCC(=O)O)N3[Si](C)(C)C6101.5Semi standard non polar33892256
Coproporphyrin III,1TMS,isomer #6CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O)=C(C=C4N=C(C=C5C(C)=C(CCC(=O)O)C(=CC1=N2)N5[Si](C)(C)C)C(C)=C4CCC(=O)O)[NH]36098.1Semi standard non polar33892256
Coproporphyrin III,2TMS,isomer #1CC1=C(CCC(=O)O)C2=CC3=C(CCC(=O)O)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O[Si](C)(C)C)C(C)=C4CCC(=O)O[Si](C)(C)C)[NH]35921.9Semi standard non polar33892256
Coproporphyrin III,2TMS,isomer #10CC1=C(CCC(=O)O[Si](C)(C)C)C2=CC3=C(C)C(CCC(=O)O)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(CCC(=O)O)=C5C)C(C)=C4CCC(=O)O[Si](C)(C)C)[NH]35920.6Semi standard non polar33892256
Coproporphyrin III,2TMS,isomer #11CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(CCC(=O)O)=C5C)C(C)=C4CCC(=O)O[Si](C)(C)C)N3[Si](C)(C)C5958.5Semi standard non polar33892256
Coproporphyrin III,2TMS,isomer #12CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O)=C(C=C4N=C(C=C5C(C)=C(CCC(=O)O)C(=CC1=N2)N5[Si](C)(C)C)C(C)=C4CCC(=O)O[Si](C)(C)C)[NH]35960.0Semi standard non polar33892256
Coproporphyrin III,2TMS,isomer #13CC1=C(CCC(=O)O)C2=CC3=C(CCC(=O)O)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O)C(C)=C4CCC(=O)O[Si](C)(C)C)N3[Si](C)(C)C5958.4Semi standard non polar33892256
Coproporphyrin III,2TMS,isomer #14CC1=C(CCC(=O)O)C2=CC3=C(CCC(=O)O)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(C)=C4CCC(=O)O[Si](C)(C)C)[NH]35959.4Semi standard non polar33892256
Coproporphyrin III,2TMS,isomer #15CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O)=C(C=C4N=C(C=C5C(C)=C(CCC(=O)O)C(=CC1=N2)N5[Si](C)(C)C)C(C)=C4CCC(=O)O)N3[Si](C)(C)C6049.0Semi standard non polar33892256
Coproporphyrin III,2TMS,isomer #2CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(CCC(=O)O[Si](C)(C)C)=C5C)C(C)=C4CCC(=O)O[Si](C)(C)C)[NH]35922.1Semi standard non polar33892256
Coproporphyrin III,2TMS,isomer #3CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(CCC(=O)O[Si](C)(C)C)=C5C)C(C)=C4CCC(=O)O)[NH]35923.6Semi standard non polar33892256
Coproporphyrin III,2TMS,isomer #4CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(CCC(=O)O[Si](C)(C)C)=C5C)C(C)=C4CCC(=O)O)N3[Si](C)(C)C5952.5Semi standard non polar33892256
Coproporphyrin III,2TMS,isomer #5CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O)=C(C=C4N=C(C=C5C(C)=C(CCC(=O)O[Si](C)(C)C)C(=CC1=N2)N5[Si](C)(C)C)C(C)=C4CCC(=O)O)[NH]35947.4Semi standard non polar33892256
Coproporphyrin III,2TMS,isomer #6CC1=C(CCC(=O)O)C2=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O)C(C)=C4CCC(=O)O[Si](C)(C)C)[NH]35921.8Semi standard non polar33892256
Coproporphyrin III,2TMS,isomer #7CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(CCC(=O)O)=C5C)C(C)=C4CCC(=O)O[Si](C)(C)C)[NH]35921.9Semi standard non polar33892256
Coproporphyrin III,2TMS,isomer #8CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(CCC(=O)O)=C5C)C(C)=C4CCC(=O)O)N3[Si](C)(C)C5947.2Semi standard non polar33892256
Coproporphyrin III,2TMS,isomer #9CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(C=C4N=C(C=C5C(C)=C(CCC(=O)O)C(=CC1=N2)N5[Si](C)(C)C)C(C)=C4CCC(=O)O)[NH]35953.0Semi standard non polar33892256
Coproporphyrin III,3TMS,isomer #1CC1=C(CCC(=O)O[Si](C)(C)C)C2=CC3=C(C)C(CCC(=O)O)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(CCC(=O)O[Si](C)(C)C)=C5C)C(C)=C4CCC(=O)O[Si](C)(C)C)[NH]35850.6Semi standard non polar33892256
Coproporphyrin III,3TMS,isomer #10CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O)=C(C=C4N=C(C=C5C(C)=C(CCC(=O)O[Si](C)(C)C)C(=CC1=N2)N5[Si](C)(C)C)C(C)=C4CCC(=O)O)N3[Si](C)(C)C5933.8Semi standard non polar33892256
Coproporphyrin III,3TMS,isomer #11CC1=C(CCC(=O)O[Si](C)(C)C)C2=CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(CCC(=O)O)=C5C)C(C)=C4CCC(=O)O[Si](C)(C)C)[NH]35851.2Semi standard non polar33892256
Coproporphyrin III,3TMS,isomer #12CC1=C(CCC(=O)O)C2=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O)C(C)=C4CCC(=O)O[Si](C)(C)C)N3[Si](C)(C)C5872.3Semi standard non polar33892256
Coproporphyrin III,3TMS,isomer #13CC1=C(CCC(=O)O)C2=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(C)=C4CCC(=O)O[Si](C)(C)C)[NH]35873.9Semi standard non polar33892256
Coproporphyrin III,3TMS,isomer #14CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(CCC(=O)O)=C5C)C(C)=C4CCC(=O)O[Si](C)(C)C)N3[Si](C)(C)C5872.5Semi standard non polar33892256
Coproporphyrin III,3TMS,isomer #15CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(C=C4N=C(C=C5C(C)=C(CCC(=O)O)C(=CC1=N2)N5[Si](C)(C)C)C(C)=C4CCC(=O)O[Si](C)(C)C)[NH]35874.3Semi standard non polar33892256
Coproporphyrin III,3TMS,isomer #16CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(C=C4N=C(C=C5C(C)=C(CCC(=O)O)C(=CC1=N2)N5[Si](C)(C)C)C(C)=C4CCC(=O)O)N3[Si](C)(C)C5933.2Semi standard non polar33892256
Coproporphyrin III,3TMS,isomer #17CC1=C(CCC(=O)O[Si](C)(C)C)C2=CC3=C(C)C(CCC(=O)O)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(CCC(=O)O)=C5C)C(C)=C4CCC(=O)O[Si](C)(C)C)N3[Si](C)(C)C5875.5Semi standard non polar33892256
Coproporphyrin III,3TMS,isomer #18CC1=C(CCC(=O)O[Si](C)(C)C)C2=CC3=C(C)C(CCC(=O)O)=C(C=C4N=C(C=C5C(C)=C(CCC(=O)O)C(=CC1=N2)N5[Si](C)(C)C)C(C)=C4CCC(=O)O[Si](C)(C)C)[NH]35876.6Semi standard non polar33892256
Coproporphyrin III,3TMS,isomer #19CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O)=C(C=C4N=C(C=C5C(C)=C(CCC(=O)O)C(=CC1=N2)N5[Si](C)(C)C)C(C)=C4CCC(=O)O[Si](C)(C)C)N3[Si](C)(C)C5943.6Semi standard non polar33892256
Coproporphyrin III,3TMS,isomer #2CC1=C(CCC(=O)O)C2=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O[Si](C)(C)C)C(C)=C4CCC(=O)O[Si](C)(C)C)[NH]35845.0Semi standard non polar33892256
Coproporphyrin III,3TMS,isomer #20CC1=C(CCC(=O)O)C2=CC3=C(CCC(=O)O)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(C)=C4CCC(=O)O[Si](C)(C)C)N3[Si](C)(C)C5942.4Semi standard non polar33892256
Coproporphyrin III,3TMS,isomer #3CC1=C(CCC(=O)O)C2=CC3=C(CCC(=O)O)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O[Si](C)(C)C)C(C)=C4CCC(=O)O[Si](C)(C)C)N3[Si](C)(C)C5873.0Semi standard non polar33892256
Coproporphyrin III,3TMS,isomer #4CC1=C(CCC(=O)O)C2=CC3=C(CCC(=O)O)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O[Si](C)(C)C)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(C)=C4CCC(=O)O[Si](C)(C)C)[NH]35872.3Semi standard non polar33892256
Coproporphyrin III,3TMS,isomer #5CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(CCC(=O)O[Si](C)(C)C)=C5C)C(C)=C4CCC(=O)O[Si](C)(C)C)[NH]35845.3Semi standard non polar33892256
Coproporphyrin III,3TMS,isomer #6CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(CCC(=O)O[Si](C)(C)C)=C5C)C(C)=C4CCC(=O)O[Si](C)(C)C)N3[Si](C)(C)C5873.6Semi standard non polar33892256
Coproporphyrin III,3TMS,isomer #7CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O)=C(C=C4N=C(C=C5C(C)=C(CCC(=O)O[Si](C)(C)C)C(=CC1=N2)N5[Si](C)(C)C)C(C)=C4CCC(=O)O[Si](C)(C)C)[NH]35873.1Semi standard non polar33892256
Coproporphyrin III,3TMS,isomer #8CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(CCC(=O)O[Si](C)(C)C)=C5C)C(C)=C4CCC(=O)O)N3[Si](C)(C)C5871.8Semi standard non polar33892256
Coproporphyrin III,3TMS,isomer #9CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O[Si](C)(C)C)=C(C=C4N=C(C=C5C(C)=C(CCC(=O)O[Si](C)(C)C)C(=CC1=N2)N5[Si](C)(C)C)C(C)=C4CCC(=O)O)[NH]35872.2Semi standard non polar33892256
Coproporphyrin III,1TBDMS,isomer #1CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C5C)C(C)=C4CCC(=O)O)[NH]36305.8Semi standard non polar33892256
Coproporphyrin III,1TBDMS,isomer #2CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(CCC(=O)O)=C5C)C(C)=C4CCC(=O)O)[NH]36305.8Semi standard non polar33892256
Coproporphyrin III,1TBDMS,isomer #3CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(CCC(=O)O)=C5C)C(C)=C4CCC(=O)O[Si](C)(C)C(C)(C)C)[NH]36310.1Semi standard non polar33892256
Coproporphyrin III,1TBDMS,isomer #4CC1=C(CCC(=O)O)C2=CC3=C(CCC(=O)O)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O)C(C)=C4CCC(=O)O[Si](C)(C)C(C)(C)C)[NH]36309.6Semi standard non polar33892256
Coproporphyrin III,1TBDMS,isomer #5CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(CCC(=O)O)=C5C)C(C)=C4CCC(=O)O)N3[Si](C)(C)C(C)(C)C6297.4Semi standard non polar33892256
Coproporphyrin III,1TBDMS,isomer #6CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O)=C(C=C4N=C(C=C5C(C)=C(CCC(=O)O)C(=CC1=N2)N5[Si](C)(C)C(C)(C)C)C(C)=C4CCC(=O)O)[NH]36295.3Semi standard non polar33892256
Coproporphyrin III,2TBDMS,isomer #1CC1=C(CCC(=O)O)C2=CC3=C(CCC(=O)O)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=C4CCC(=O)O[Si](C)(C)C(C)(C)C)[NH]36375.0Semi standard non polar33892256
Coproporphyrin III,2TBDMS,isomer #10CC1=C(CCC(=O)O[Si](C)(C)C(C)(C)C)C2=CC3=C(C)C(CCC(=O)O)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(CCC(=O)O)=C5C)C(C)=C4CCC(=O)O[Si](C)(C)C(C)(C)C)[NH]36365.8Semi standard non polar33892256
Coproporphyrin III,2TBDMS,isomer #11CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(CCC(=O)O)=C5C)C(C)=C4CCC(=O)O[Si](C)(C)C(C)(C)C)N3[Si](C)(C)C(C)(C)C6410.2Semi standard non polar33892256
Coproporphyrin III,2TBDMS,isomer #12CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O)=C(C=C4N=C(C=C5C(C)=C(CCC(=O)O)C(=CC1=N2)N5[Si](C)(C)C(C)(C)C)C(C)=C4CCC(=O)O[Si](C)(C)C(C)(C)C)[NH]36411.5Semi standard non polar33892256
Coproporphyrin III,2TBDMS,isomer #13CC1=C(CCC(=O)O)C2=CC3=C(CCC(=O)O)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O)C(C)=C4CCC(=O)O[Si](C)(C)C(C)(C)C)N3[Si](C)(C)C(C)(C)C6410.2Semi standard non polar33892256
Coproporphyrin III,2TBDMS,isomer #14CC1=C(CCC(=O)O)C2=CC3=C(CCC(=O)O)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O)=C(C)C(=CC1=N2)N5[Si](C)(C)C(C)(C)C)C(C)=C4CCC(=O)O[Si](C)(C)C(C)(C)C)[NH]36411.1Semi standard non polar33892256
Coproporphyrin III,2TBDMS,isomer #15CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O)=C(C=C4N=C(C=C5C(C)=C(CCC(=O)O)C(=CC1=N2)N5[Si](C)(C)C(C)(C)C)C(C)=C4CCC(=O)O)N3[Si](C)(C)C(C)(C)C6444.4Semi standard non polar33892256
Coproporphyrin III,2TBDMS,isomer #2CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C5C)C(C)=C4CCC(=O)O[Si](C)(C)C(C)(C)C)[NH]36375.0Semi standard non polar33892256
Coproporphyrin III,2TBDMS,isomer #3CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C5C)C(C)=C4CCC(=O)O)[NH]36380.0Semi standard non polar33892256
Coproporphyrin III,2TBDMS,isomer #4CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C5C)C(C)=C4CCC(=O)O)N3[Si](C)(C)C(C)(C)C6411.0Semi standard non polar33892256
Coproporphyrin III,2TBDMS,isomer #5CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O)=C(C=C4N=C(C=C5C(C)=C(CCC(=O)O[Si](C)(C)C(C)(C)C)C(=CC1=N2)N5[Si](C)(C)C(C)(C)C)C(C)=C4CCC(=O)O)[NH]36405.7Semi standard non polar33892256
Coproporphyrin III,2TBDMS,isomer #6CC1=C(CCC(=O)O)C2=CC3=C(CCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O)C(C)=C4CCC(=O)O[Si](C)(C)C(C)(C)C)[NH]36374.5Semi standard non polar33892256
Coproporphyrin III,2TBDMS,isomer #7CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(CCC(=O)O)=C5C)C(C)=C4CCC(=O)O[Si](C)(C)C(C)(C)C)[NH]36375.0Semi standard non polar33892256
Coproporphyrin III,2TBDMS,isomer #8CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(CCC(=O)O)=C5C)C(C)=C4CCC(=O)O)N3[Si](C)(C)C(C)(C)C6404.8Semi standard non polar33892256
Coproporphyrin III,2TBDMS,isomer #9CC1=C(CCC(=O)O)C2=CC3=C(C)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C(C=C4N=C(C=C5C(C)=C(CCC(=O)O)C(=CC1=N2)N5[Si](C)(C)C(C)(C)C)C(C)=C4CCC(=O)O)[NH]36412.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Coproporphyrin III GC-MS (Non-derivatized) - 70eV, Positivesplash10-052g-2000089000-f03a7599281003918c9d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coproporphyrin III GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coproporphyrin III GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coproporphyrin III GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coproporphyrin III GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coproporphyrin III GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coproporphyrin III GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coproporphyrin III GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coproporphyrin III GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coproporphyrin III GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coproporphyrin III GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coproporphyrin III GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coproporphyrin III GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coproporphyrin III GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coproporphyrin III GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coproporphyrin III GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coproporphyrin III GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coproporphyrin III GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coproporphyrin III GC-MS (TMS_2_12) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coproporphyrin III GC-MS (TMS_2_13) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coproporphyrin III GC-MS (TMS_2_14) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coproporphyrin III GC-MS (TMS_2_15) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coproporphyrin III GC-MS (TMS_3_1) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coproporphyrin III GC-MS (TMS_3_2) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coproporphyrin III GC-MS (TMS_3_3) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coproporphyrin III 10V, Positive-QTOFsplash10-00kr-0000059000-ee622066b0f73e50cf912015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coproporphyrin III 20V, Positive-QTOFsplash10-00kp-0000094000-ee6c72d818b957fec0b62015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coproporphyrin III 40V, Positive-QTOFsplash10-01ot-0000090000-87edb6484e1fd9c985612015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coproporphyrin III 10V, Negative-QTOFsplash10-0f79-0000029000-08747adb62bb52441aeb2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coproporphyrin III 20V, Negative-QTOFsplash10-052u-1000079000-d36d808ce647034f91092015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coproporphyrin III 40V, Negative-QTOFsplash10-052f-7000094000-b86bf714ce0924edc7012015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coproporphyrin III 10V, Positive-QTOFsplash10-05n0-0000019000-dbabbc75ab65e178136e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coproporphyrin III 20V, Positive-QTOFsplash10-05p6-0000079000-ce9c57417ac25b4744d62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coproporphyrin III 40V, Positive-QTOFsplash10-00kf-1000091000-12a4e59244652240a7d02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coproporphyrin III 10V, Negative-QTOFsplash10-0udr-0000029000-acad21a4e05418a58cec2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coproporphyrin III 20V, Negative-QTOFsplash10-00kf-0000094000-84fc3e3b8cde3d282f7e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coproporphyrin III 40V, Negative-QTOFsplash10-03di-0000090000-26e94889c74c71b9b2372021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.006 (0.000 - 0.012) uMAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.0054 +/- 0.0019 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.0051 +/- 0.0014 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.0094 +/- 0.00013 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.00367 +/- 0.00153 umol/mmol creatinineNot SpecifiedNot SpecifiedNormal
    • Geigy Scientific ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0045 (0.0000 - 0.0090) uMAdult (>18 years old)Not Specified
Porphyria
details
BloodDetected and Quantified0.0044 (0.0002 - 0.0087) uMAdult (>18 years old)Not Specified
Porphyria
details
UrineDetected and Quantified0.012 +/- 0.00013 umol/mmol creatinineAdult (>18 years old)BothLiver disease details
UrineDetected and Quantified0.005 umol/mmol creatinineAdult (>18 years old)BothPorphyria cutanea tarda details
UrineDetected and Quantified0.015 +/- 0.00078 umol/mmol creatinineAdult (>18 years old)BothHereditary coproporphyria details
UrineDetected and Quantified0.043 +/- 0.00019 umol/mmol creatinineAdult (>18 years old)BothAcute intermittent porphyria details
Associated Disorders and Diseases
Disease References
Porphyria
  1. Hindmarsh JT, Oliveras L, Greenway DC: Biochemical differentiation of the porphyrias. Clin Biochem. 1999 Nov;32(8):609-19. [PubMed:10638943 ]
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 ]
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
  • 121300 (Hereditary coproporphyria)
  • 176000 (Acute intermittent porphyria)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB005557
KNApSAcK IDNot Available
Chemspider ID16736509
KEGG Compound IDC05770
BioCyc IDCOPROPORPHYRIN_III
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5553
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID27609
Food Biomarker OntologyNot Available
VMH IDC05770
MarkerDB IDMDB00000191
Good Scents IDNot Available
References
Synthesis ReferenceMinoda, Taiji; Takada, Toshihiro; Horii, Shinichi. Coproporphyrin III. Jpn. Kokai Tokkyo Koho (1979), 3 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Doss MO: Porphyrinurias and occupational disease. Ann N Y Acad Sci. 1987;514:204-18. [PubMed:3327428 ]

Enzymes

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:
UROD
Uniprot ID:
P06132
Molecular weight:
40786.58
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
General function:
Involved in coproporphyrinogen oxidase activity
Specific function:
Key enzyme in heme biosynthesis. Catalyzes the oxidative decarboxylation of propionic acid side chains of rings A and B of coproporphyrinogen III.
Gene Name:
CPOX
Uniprot ID:
P36551
Molecular weight:
50151.605