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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-19 21:49:05 UTC
HMDB IDHMDB0000936
Secondary Accession Numbers
  • HMDB00936
Metabolite Identification
Common NameUroporphyrin I
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 ).
Structure
Thumb
Synonyms
ValueSource
2,7,12,17-Porphinetetrapropionic acidChEBI
3,8,13,18-Tetrakis(carboxymethyl)porphyrin-2,7,12,17-tetrapropionic acidChEBI
2,7,12,17-PorphinetetrapropionateGenerator
3,8,13,18-Tetrakis(carboxymethyl)porphyrin-2,7,12,17-tetrapropionateGenerator
3,3',3'',3'''-(3,8,13,18-tetrakis-carboxymethyl-21H,23H-porphine-2,7,12,17-tetrayl)-tetrakis-propionateHMDB
3,3',3'',3'''-(3,8,13,18-tetrakis-carboxymethyl-21H,23H-porphine-2,7,12,17-tetrayl)-tetrakis-propionic acidHMDB
3,3',3'',3'''-(3,8,13,18-tetrakis-carboxymethyl-porphyrin-2,7,12,17-tetrayl)-tetra-propionateHMDB
3,3',3'',3'''-(3,8,13,18-tetrakis-carboxymethyl-porphyrin-2,7,12,17-tetrayl)-tetra-propionic acidHMDB
3,8,13,18-Tetrakis(carboxymethyl)porphyrin-2,7,12,17-tetrapropanoateHMDB
3,8,13,18-Tetrakis(carboxymethyl)porphyrin-2,7,12,17-tetrapropanoic acidHMDB
3-[7,12,17-Tris-(2-carboxy-ethyl)-3,8,13,18-tetrakis-carboxymethyl-22,24-dihydro-porphin-2-yl]-propionateHMDB
3-[7,12,17-Tris-(2-carboxy-ethyl)-3,8,13,18-tetrakis-carboxymethyl-22,24-dihydro-porphin-2-yl]-propionic acidHMDB
Chemical FormulaC40H38N4O16
Average Molecular Weight830.7469
Monoisotopic Molecular Weight830.228281188
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
CAS Registry Number607-14-7
SMILES
OC(=O)CCC1=C(CC(O)=O)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(CC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CC(O)=O)=C4CCC(O)=O)/C(CC(O)=O)=C3CCC(O)=O
InChI Identifier
InChI=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 KeyDAFUFNRZWDWXJP-JRHDEHKPSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrapyrroles and derivatives
Sub ClassPorphyrins
Direct ParentPorphyrins
Alternative Parents
Substituents
  • Porphyrin
  • 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 DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

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 Solubility0.037 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 Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03xs-0000000940-dfb6a1c5995e614eac9aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gbi-0000000910-609babbc27a206d09ad4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f9i-0000000900-ffd2454f165fe2594021View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000790-377067e19f6ade3d5860View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02vi-1000000940-9415a48c2a747a58ce1dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066r-5000000900-22e5a1d377afd75f3366View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Blood
  • Urine
Tissue Location
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0006 (0.0000-0.0012) uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.012 (0.000-0.024) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified0.00092 +/- 0.00032 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0 uMAdult (>18 years old)MaleProtoporphyria, Erythropoietic details
UrineDetected and Quantified0 umol/mmol creatinineAdult (>18 years old)MaleProtoporphyria, Erythropoietic details
Associated Disorders and Diseases
Disease References
Protoporphyria, Erythropoietic
  1. MAGNUS IA, JARRETT A, PRANKERD TA, RIMINGTON C: Erythropoietic protoporphyria. A new porphyria syndrome with solar urticaria due to protoporphyrinaemia. Lancet. 1961 Aug 26;2(7200):448-51. [PubMed:13765301 ]
Associated OMIM IDs
  • 177000 (Protoporphyria, Erythropoietic)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022326
KNApSAcK IDNot Available
Chemspider ID16736725
KEGG Compound IDC05767
BioCyc IDUROPORPHYRIN_I
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5885
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID27484
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:12482484 ]
  6. Fritsch C, Bolsen K, Ruzicka T, Goerz G: Congenital erythropoietic porphyria. J Am Acad Dermatol. 1997 Apr;36(4):594-610. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:9861496 ]
  11. Doss MO: Porphyrinurias and occupational disease. Ann N Y Acad Sci. 1987;514:204-18. [PubMed:3327428 ]
  12. Winkelman JW, Collins GH: Neurotoxicity of tetraphenylporphinesulfonate TPPS4 and its relation to photodynamic therapy. Photochem Photobiol. 1987 Nov;46(5):801-7. [PubMed:3441503 ]