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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:33 UTC
HMDB IDHMDB00916
Secondary Accession NumbersNone
Metabolite Identification
Common NameUroporphyrin III
DescriptionUroporphyrin is the porphyrin produced by oxidation of the methylene bridges in uroporphyrinogen. They have four acetic acid and four propionic acid side chains attached to the pyrrole rings. Uroporphyrinogen I and III are formed from polypyrryl methane in the presence of uroporphyrinogen III cosynthetase and uroporphyrin I synthetase, respectively. They can yield uroporphyrins by autooxidation or coproporphyrinogens by decarboxylation. Excessive amounts of uroporphyrin I are excreted in congenital erythropoietic porphyria, and both types I and III are excreted in porphyria cutanea tarda. Uroporphyrin I and III are the most common isomers.
Structure
Thumb
Synonyms
ValueSource
3,8,13,17-Tetrakis(carboxymethyl)porphyrin-2,7,12,18-tetrapropionic acidChEBI
3,8,13,17-Tetrakis(carboxymethyl)porphyrin-2,7,12,18-tetrapropionateGenerator
3,8,13,17-Tetrakis(carboxymethyl)porphyrin-2,7,12,18-tetrapropanoateHMDB
3,8,13,17-Tetrakis(carboxymethyl)porphyrin-2,7,12,18-tetrapropanoic acidHMDB
3,8,13,17-Tetramethyl-2,7,12,18-porphinetetrapropionateHMDB
3,8,13,17-Tetramethyl-2,7,12,18-porphinetetrapropionic acidHMDB
Coproporphyrin IIIHMDB
Chemical FormulaC40H38N4O16
Average Molecular Weight830.7469
Monoisotopic Molecular Weight830.228281188
IUPAC Name3-[10,14,19-tris(2-carboxyethyl)-5,9,15,20-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 Name3-[10,14,19-tris(2-carboxyethyl)-5,9,15,20-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
CAS Registry Number18273-06-8
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(CCC(O)=O)=C3CC(O)=O
InChI Identifier
InChI=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
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
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
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 mg/mLALOGPS
logP0.75ALOGPS
logP3.51ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)3.11ChemAxon
Physiological Charge-8ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area355.76 Å2ChemAxon
Rotatable Bond Count20ChemAxon
Refractivity201.32 m3·mol-1ChemAxon
Polarizability85.12 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biofluid Locations
  • Urine
Tissue Location
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Acute Intermittent PorphyriaSMP00344Not Available
Congenital Erythropoietic Porphyria (CEP) or Gunther DiseaseSMP00345Not Available
Hereditary Coproporphyria (HCP)SMP00342Not Available
Porphyria Variegata (PV)SMP00346Not Available
Porphyrin MetabolismSMP00024map00860
Normal Concentrations
Not Available
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.00005 (0.00005-0.0007) umol/mmol creatinineNewborn (0-30 days old)BothHexachlorobenzene exposure details
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 IDFDB005664
KNApSAcK IDNot Available
Chemspider ID16736727
KEGG Compound IDC02469
BioCyc IDUROPORPHYRIN_III
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00916
Metagene LinkHMDB00916
METLIN ID5870
PubChem CompoundNot Available
PDB ID1R3T
ChEBI ID15436
References
Synthesis ReferenceKajiwara, Masahiro; Mizutani, Minoru; Kojima, Ichiro. Manufacture of uroporphyrin III with Arthrobacter. Jpn. Kokai Tokkyo Koho (1993), 7 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  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 ]