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Record Information
Version2.0
Creation Date2014-08-29 06:25:21 UTC
Update Date2018-03-21 17:46:22 UTC
Accession NumberT3D4322
Identification
Common NameUroporphyrin III
ClassSmall Molecule
DescriptionUroporphyrin is the porphyrin produced by oxidation of the methylene bridges in uroporphyrinogen. Uroporphyrins have four acetic acid and four propionic acid side chains attached to their pyrrole rings. The enzyme uroporphyrinogen I synthase catalyzes the formation of hydroxymethylbilane from four molecules of porphobilinogen. Uroporphyrinogen III cosynthase then catalyzes the conversion of hydroxymethylbilane into uroporphyrinogen III. Otherwise, hydroxymethylbilane cyclizes nonenzymatically to form uroporphyrinogen I. Uroporphyrinogen I and III yield their respective uroporphyrins via autooxidation or their respective coproporphyrinogens via decarboxylation. Excessive amounts of uroporphyrin I are excreted in congenital erythropoietic porphyria, and both uroporphyrin I and uroporphyrin III are excreted in porphyria cutanea tarda. Uroporphyrin I and III are the most common isomers. Under certain conditions, uroporphyrin III can act as a phototoxin, a neurotoxin, and a metabotoxin. A phototoxin leads to cell damage upon exposure to light. A neurotoxin causes damage to nerve cells and nerve tissues. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of porphyrins are associated with porphyrias such as porphyria variegate, acute intermittent porphyria, porphyria cutanea tarda, and hereditary coproporphyria (HCP). There are several types of porphyrias (most are inherited). Hepatic porphyrias are characterized by acute neurological attacks (seizures, psychosis, extreme back and abdominal pain, and an acute polyneuropathy), while the erythropoietic forms present with skin problems (usually a light-sensitive blistering rash and increased hair growth). The neurotoxicity of porphyrins may be due to their selective interactions with tubulin, which disrupt microtubule formation and cause neural malformations (PMID: 3441503).
Compound Type
  • Animal Toxin
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
Synonyms
Synonym
3,8,13,17-Tetrakis(carboxymethyl)porphyrin-2,7,12,18-tetrapropanoate
3,8,13,17-Tetrakis(carboxymethyl)porphyrin-2,7,12,18-tetrapropanoic acid
3,8,13,17-Tetramethyl-2,7,12,18-Porphinetetrapropionate
3,8,13,17-Tetramethyl-2,7,12,18-Porphinetetrapropionic acid
Coproporphyrin III
Chemical FormulaC40H38N4O16
Average Molecular Mass830.747 g/mol
Monoisotopic Mass830.228 g/mol
CAS Registry Number18273-06-8
IUPAC Name3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoic acid
Traditional Name3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoic acid
SMILES[H]\C-1=C2\N\C(=C([H])/C3=N/C(=C([H])\C4=C(CCC(O)=O)C(CC(O)=O)=C(N4)\C([H])=C4/N=C-1C(CCC(O)=O)=C4CC(O)=O)/C(CC(O)=O)=C3CCC(O)=O)C(CC(O)=O)=C2CCC(O)=O
InChI IdentifierInChI=1S/C40H38N4O16/c45-33(46)5-1-17-21(9-37(53)54)29-14-27-19(3-7-35(49)50)22(10-38(55)56)30(43-27)15-28-20(4-8-36(51)52)24(12-40(59)60)32(44-28)16-31-23(11-39(57)58)18(2-6-34(47)48)26(42-31)13-25(17)41-29/h13-16,41,44H,1-12H2,(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)(H,59,60)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-
InChI KeyInChIKey=VZVFNUAIRVUCEW-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
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Membrane
  • Mitochondria
Biofluid LocationsNot Available
Tissue Locations
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Porphyrin MetabolismSMP00024 map00860
Congenital Erythropoietic Porphyria (CEP) or Gunther DiseaseSMP00345 Not Available
Porphyria Variegata (PV)SMP00346 Not Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.038 g/LALOGPS
logP0.79ALOGPS
logP3.51ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)3.11ChemAxon
Physiological Charge-8ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area355.76 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity201.32 m³·mol⁻¹ChemAxon
Polarizability85.12 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0hft-0000000920-cc03b9bed8ec1e3756f2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gbi-0000000900-b9c5416788c41a1b932dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ftr-0000000900-ddf789a09baa29543062JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02t9-0000000940-171f6daf64defe53ba6eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000000910-e893ced4f4069e732360JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-2000000900-e8e4a229f7baf3810285JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014r-0000000900-1ba54d2ecd921bbf981cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014u-0000000900-8dfb85a7347e408fafaeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-0000000900-cc696857ebd0630cc06aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02t9-0000000930-9dd5499b3b084b8cef39JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00or-0000000900-e6018a2ba33c9cad4454JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0173-0000000900-24c512158030a2f09176JSpectraViewer
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsChronically high levels of porophyrins are associated with porphyrias such as Porphyria variegate, Acute Intermittent Porphyria and Hereditary Coproporphyria (HCP).
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB04461
HMDB IDHMDB00916
PubChem Compound IDNot Available
ChEMBL IDNot Available
ChemSpider ID16736727
KEGG IDC02469
UniProt IDNot Available
OMIM ID
ChEBI ID15436
BioCyc IDUROPORPHYRIN_III
CTD IDNot Available
Stitch IDNot Available
PDB IDUFE
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis Reference

Ichiro Kojima, Kenji Maruhashi, Yasuo Fujiwara, “Process for producing coproporphyrin III.” U.S. Patent US4334021, issued September, 1978.

MSDST3D4322.pdf
General References
  1. Tsai SF, Bishop DF, Desnick RJ: Purification and properties of uroporphyrinogen III synthase from human erythrocytes. J Biol Chem. 1987 Jan 25;262(3):1268-73. [3805019 ]
  2. Bozek P, Hutta M, Hrivnakova B: Rapid analysis of porphyrins at low ng/l and microg/l levels in human urine by a gradient liquid chromatography method using octadecylsilica monolithic columns. J Chromatogr A. 2005 Aug 19;1084(1-2):24-32. [16114232 ]
  3. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [12829005 ]
  4. Luo J, Lim CK: Isolation and characterization of new porphyrin metabolites in human porphyria cutanea tarda and in rats treated with hexachlorobenzene by HPTLC, HPLC and liquid secondary ion mass spectrometry. Biomed Chromatogr. 1995 May-Jun;9(3):113-22. [7655298 ]
  5. Schonning C, Leeming R, Stenstrom TA: Faecal contamination of source-separated human urine based on the content of faecal sterols. Water Res. 2002 Apr;36(8):1965-72. [12092571 ]
  6. Hernandez-Zavala A, Del Razo LM, Garcia-Vargas GG, Aguilar C, Borja VH, Albores A, Cebrian ME: Altered activity of heme biosynthesis pathway enzymes in individuals chronically exposed to arsenic in Mexico. Arch Toxicol. 1999 Mar;73(2):90-5. [10350189 ]
  7. Salen G, Berginer V, Shore V, Horak I, Horak E, Tint GS, Shefer S: Increased concentrations of cholestanol and apolipoprotein B in the cerebrospinal fluid of patients with cerebrotendinous xanthomatosis. Effect of chenodeoxycholic acid. N Engl J Med. 1987 May 14;316(20):1233-8. [3106810 ]
  8. To-Figueras J, Ozalla D, Mateu CH: Long-standing changes in the urinary profile of porphyrin isomers after clinical remission of porphyria cutanea tarda. Ann Clin Lab Sci. 2003 Summer;33(3):251-6. [12956438 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
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 Da
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. [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. [17016423 ]