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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 19:03:49 UTC
HMDB IDHMDB0001261
Secondary Accession Numbers
  • HMDB01261
Metabolite Identification
Common NameCoproporphyrinogen III
DescriptionCoproporphyrinogen III oxidase is deficient in hereditary coproporphyria. These persons usually have enhanced excretion even in a subclinical state of the disease.(PubMed ID 14605502 ).
Structure
Thumb
Synonyms
ValueSource
3,8,13,17-Tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropionic acidChEBI
5,10,15,20,22,24-hexahydro-3,8,13,17-Tetramethyl-21H,23H-porphine-2,7,12,18-tetrapropanoic acidChEBI
COPROPORPHYRIN IIIChEBI
3,8,13,17-Tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropionateGenerator
5,10,15,20,22,24-hexahydro-3,8,13,17-Tetramethyl-21H,23H-porphine-2,7,12,18-tetrapropanoateGenerator
3,8,13,17-Tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropanoateHMDB
3,8,13,17-Tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropanoic acidHMDB
5,10,15,20,22,24-hexahydro-3,8,13,17-Tetramethyl-2,7,12,18-porphinetetrapropionateHMDB
5,10,15,20,22,24-hexahydro-3,8,13,17-Tetramethyl-2,7,12,18-porphinetetrapropionic acidHMDB
CoproporphyrinogenHMDB
Coproporphyrinogen-IIIHMDB
Chemical FormulaC36H44N4O8
Average Molecular Weight660.7566
Monoisotopic Molecular Weight660.315914404
IUPAC Name3-[10,14,19-tris(2-carboxyethyl)-5,9,15,20-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid
Traditional Namecoproporphyrinogen
CAS Registry Number2624-63-7
SMILES
CC1=C2CC3=C(C)C(CCC(O)=O)=C(CC4=C(CCC(O)=O)C(C)=C(CC5=C(CCC(O)=O)C(C)=C(CC(N2)=C1CCC(O)=O)N5)N4)N3
InChI Identifier
InChI=1S/C36H44N4O8/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/h37-40H,5-16H2,1-4H3,(H,41,42)(H,43,44)(H,45,46)(H,47,48)
InChI KeyNIUVHXTXUXOFEB-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassTetrapyrroles and derivatives
Direct ParentPorphyrins
Alternative Parents
Substituents
  • Porphyrin
  • Tetracarboxylic acid or derivatives
  • Substituted pyrrole
  • Pyrrole
  • Heteroaromatic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Industrial application:

  Pharmaceutical industry:

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 Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP1.96ALOGPS
logP4.89ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)3.8ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area212.36 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity181.86 m³·mol⁻¹ChemAxon
Polarizability72.88 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uxu-1000029000-41e3094ebb1945eeb049View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0000049000-0387f74262a47cf81121View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05mn-0000095000-92704e3251119447de7cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0000190000-117c439eaa250aa4b3b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0000049000-0387f74262a47cf81121View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05mn-0000095000-92704e3251119447de7cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0000190000-117c439eaa250aa4b3b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052f-0000029000-96c0bca58c9caf08416fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052g-1000079000-1da57e7f8a138a6c5516View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052g-7000097000-2c52075e18d7d944ae80View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052f-0000029000-96c0bca58c9caf08416fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052g-1000079000-1da57e7f8a138a6c5516View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052g-7000097000-2c52075e18d7d944ae80View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
Tissue LocationNot Available
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
BloodExpected but not Quantified Not AvailableNot Available
Normal
    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 IDFDB022518
    KNApSAcK IDNot Available
    Chemspider ID315
    KEGG Compound IDC03263
    BioCyc IDCOPROPORPHYRINOGEN_III
    BiGG ID41515
    Wikipedia LinkCoproporphyrinogen III
    METLIN ID6116
    PubChem Compound321
    PDB IDCP3
    ChEBI ID15439
    References
    Synthesis ReferenceShoolingin-Jordan, Peter M. The biosynthesis of coproporphyrinogen III. Porphyrin Handbook (2003), 12 33-74.
    Material Safety Data Sheet (MSDS)Not Available
    General ReferencesNot Available

    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
    Reactions
    Uroporphyrinogen III → Coproporphyrinogen III + CO(2)details
    Uroporphyrinogen III → Coproporphyrinogen III + Carbon dioxidedetails
    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
    Reactions
    Coproporphyrinogen III + Oxygen + Hydrogen Ion → Protoporphyrinogen IX + CO(2) + Waterdetails
    Coproporphyrinogen III + Oxygen → Protoporphyrinogen IX + Carbon dioxide + Waterdetails
    General function:
    Involved in uroporphyrinogen-III synthase activity
    Specific function:
    Catalyzes cyclization of the linear tetrapyrrole, hydroxymethylbilane, to the macrocyclic uroporphyrinogen III, the branch point for the various sub-pathways leading to the wide diversity of porphyrins. Porphyrins act as cofactors for a multitude of enzymes that perform a variety of processes within the cell such as methionine synthesis (vitamin B12) or oxygen transport (heme).
    Gene Name:
    UROS
    Uniprot ID:
    P10746
    Molecular weight:
    28627.37
    General function:
    Involved in N-acetyltransferase activity
    Specific function:
    Probable acetyltransferase that binds the 5'-GGACTACAG- 3' sequence of coproporphyrinogen oxidase promoter. Able to activate transcription of a reporter construct in vitro
    Gene Name:
    NAT14
    Uniprot ID:
    Q8WUY8
    Molecular weight:
    21650.2