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Record Information
Version2.0
Creation Date2014-08-29 06:27:08 UTC
Update Date2018-03-21 17:46:22 UTC
Accession NumberT3D4324
Identification
Common NameUroporphyrin I
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 I 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
2,7,12,17-Porphinetetrapropionate
2,7,12,17-Porphinetetrapropionic acid
3,3',3'',3'''-(3,8,13,18-Tetrakis-carboxymethyl-21H,23H-porphine-2,7,12,17-tetrayl)-tetrakis-propionate
3,3',3'',3'''-(3,8,13,18-Tetrakis-carboxymethyl-21H,23H-porphine-2,7,12,17-tetrayl)-tetrakis-propionic acid
3,3',3'',3'''-(3,8,13,18-Tetrakis-carboxymethyl-porphyrin-2,7,12,17-tetrayl)-tetra-propionate
3,3',3'',3'''-(3,8,13,18-Tetrakis-carboxymethyl-porphyrin-2,7,12,17-tetrayl)-tetra-propionic acid
3,8,13,18-Tetrakis(carboxymethyl)porphyrin-2,7,12,17-tetrapropanoate
3,8,13,18-Tetrakis(carboxymethyl)porphyrin-2,7,12,17-tetrapropanoic acid
3-[7,12,17-Tris-(2-carboxy-ethyl)-3,8,13,18-tetrakis-carboxymethyl-22,24-dihydro-porphin-2-yl]-propionate
3-[7,12,17-Tris-(2-carboxy-ethyl)-3,8,13,18-tetrakis-carboxymethyl-22,24-dihydro-porphin-2-yl]-propionic acid
Chemical FormulaC40H38N4O16
Average Molecular Mass830.747 g/mol
Monoisotopic Mass830.228 g/mol
CAS Registry Number607-14-7
IUPAC Name3-[9,14,19-tris(2-carboxyethyl)-5,10,15,20-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid
Traditional Nameuroporphyrin I
SMILES[H]\C-1=C2\N\C(=C([H])/C3=N/C(=C([H])\C4=C(CC(O)=O)C(CCC(O)=O)=C(N4)\C([H])=C4/N=C-1C(CCC(O)=O)=C4CC(O)=O)/C(CCC(O)=O)=C3CC(O)=O)C(CCC(O)=O)=C2CC(O)=O
InChI IdentifierInChI=1S/C40H38N4O16/c45-33(46)5-1-17-21(9-37(53)54)29-14-26-19(3-7-35(49)50)23(11-39(57)58)31(43-26)16-28-20(4-8-36(51)52)24(12-40(59)60)32(44-28)15-27-18(2-6-34(47)48)22(10-38(55)56)30(42-27)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-,26-14-,27-15-,28-16-,29-14-,30-13-,31-16-,32-15-
InChI KeyInChIKey=DAFUFNRZWDWXJP-JRHDEHKPSA-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
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 Solubility0.037 g/LALOGPS
logP0.76ALOGPS
logP3.51ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)3.16ChemAxon
Physiological Charge-8ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area355.76 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity201.32 m³·mol⁻¹ChemAxon
Polarizability84.92 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, Positivesplash10-03xs-0000000940-dfb6a1c5995e614eac9aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gbi-0000000910-609babbc27a206d09ad4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f9i-0000000900-ffd2454f165fe2594021JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000790-377067e19f6ade3d5860JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02vi-1000000940-9415a48c2a747a58ce1dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066r-5000000900-22e5a1d377afd75f3366JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03xr-0000000980-fa8ef8e410767e523954JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00p0-0000000900-d455288feb5e6056af12JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0170-0000000900-e223edb8a02cb6503ce4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00ku-0000000900-b16843991f1b653b1397JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ku-0000000900-5880fbaaad32a34fdb0fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-0000000900-dddaee25a158e99d04c4JSpectraViewer
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 EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB00936
PubChem Compound IDNot Available
ChEMBL IDNot Available
ChemSpider ID16736725
KEGG IDC05767
UniProt IDNot Available
OMIM ID
ChEBI ID27484
BioCyc IDUROPORPHYRIN_I
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General References
  1. Ding Y, Lin B, Huie CW: Binding studies of porphyrins to human serum albumin using affinity capillary electrophoresis. Electrophoresis. 2001 Jul;22(11):2210-6. [11504054 ]
  2. Sunyer J, Herrero C, Ozalla D, Sala M, Ribas-Fito N, Grimalt J, Basagana X: Serum organochlorines and urinary porphyrin pattern in a population highly exposed to hexachlorobenzene. Environ Health. 2002 Jul 19;1(1):1. [12495451 ]
  3. Ged C, Moreau-Gaudry F, Taine L, Hombrados I, Calvas P, Colombies P, De Verneuil H: Prenatal diagnosis in congenital erythropoietic porphyria by metabolic measurement and DNA mutation analysis. Prenat Diagn. 1996 Jan;16(1):83-6. [8821859 ]
  4. Geronimi F, Richard E, Lamrissi-Garcia I, Lalanne M, Ged C, Redonnet-Vernhet I, Moreau-Gaudry F, de Verneuil H: Lentivirus-mediated gene transfer of uroporphyrinogen III synthase fully corrects the porphyric phenotype in human cells. J Mol Med (Berl). 2003 May;81(5):310-20. Epub 2003 Apr 30. [12721665 ]
  5. Bu W, Myers N, McCarty JD, O'Neill T, Hollar S, Stetson PL, Sved DW: Simultaneous determination of six urinary porphyrins using liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jan 15;783(2):411-23. [12482484 ]
  6. Fritsch C, Bolsen K, Ruzicka T, Goerz G: Congenital erythropoietic porphyria. J Am Acad Dermatol. 1997 Apr;36(4):594-610. [9092747 ]
  7. Zhang W, Zhang L, Ping G, Zhang Y, Kettrup A: Study on the multiple sites binding of human serum albumin and porphyrin by affinity capillary electrophoresis. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Feb 25;768(1):211-4. [11939554 ]
  8. Oguz F, Sidal M, Bayram C, Sansoy N, Hekim N: Ocular involvement in two symptomatic congenital erythropoietic porphyria. Eur J Pediatr. 1993 Aug;152(8):671-3. [8404971 ]
  9. Akhtar MK, Kaderbhai NN, Hopper DJ, Kelly SL, Kaderbhai MA: Export of a heterologous cytochrome P450 (CYP105D1) in Escherichia coli is associated with periplasmic accumulation of uroporphyrin. J Biol Chem. 2003 Nov 14;278(46):45555-62. Epub 2003 Aug 20. [12930844 ]
  10. Gorchein A, Guo R, Lim CK, Raimundo A, Pullon HW, Bellingham AJ: Porphyrins in urine, plasma, erythrocytes, bile and faeces in a case of congenital erythropoietic porphyria (Gunther's disease) treated with blood transfusion and iron chelation: lack of benefit from oral charcoal. Biomed Chromatogr. 1998 Nov-Dec;12(6):350-6. [9861496 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available