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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-05-07 19:45:19 UTC
HMDB IDHMDB0001086
Secondary Accession Numbers
  • HMDB01086
Metabolite Identification
Common NameUroporphyrinogen III
DescriptionUroporphyrinogen III, also known as uro'gen III, 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. Uroporphyrinogen III exists in all living species, ranging from bacteria to plants to humans. In humans, uroporphyrinogen III is involved in the metabolic disorder called the acute intermittent porphyria pathway. Uroporphyrinogen III has been detected, but not quantified in, several different foods, such as evening primroses (Oenothera biennis), cloves (Syzygium aromaticum), common thymes (Thymus vulgaris), purple lavers (Porphyra laciniata), and coconuts (Cocos nucifera). This could make uroporphyrinogen III a potential biomarker for the consumption of these foods. Uroporphyrinogen III is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Uroporphyrinogen III.
Structure
Data?1588880719
Synonyms
ValueSource
3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydro-21H,23H-porphine-2,7,12,18-tetrapropanoic acidChEBI
3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropionic acidChEBI
Uro'gen IIIChEBI
3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydro-21H,23H-porphine-2,7,12,18-tetrapropanoateGenerator
3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropionateGenerator
UroporphyrinogensMeSH
3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydro-2,7,12,18-porphinetetrapropionateHMDB
3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydro-2,7,12,18-porphinetetrapropionic acidHMDB
3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropanoateHMDB
3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropanoic acidHMDB
Urogen IIIHMDB
Uroporphyrinogen-IIIHMDB
Chemical FormulaC40H44N4O16
Average Molecular Weight836.7946
Monoisotopic Molecular Weight836.27523138
IUPAC Name3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetrakis(carboxymethyl)-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 Nameuroporphyrinogen-III
CAS Registry Number1976-85-8
SMILES
OC(=O)CCC1=C2CC3=C(CCC(O)=O)C(CC(O)=O)=C(CC4=C(CC(O)=O)C(CCC(O)=O)=C(CC5=C(CC(O)=O)C(CCC(O)=O)=C(CC(N2)=C1CC(O)=O)N5)N4)N3
InChI Identifier
InChI=1S/C40H44N4O16/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/h41-44H,1-16H2,(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)(H,59,60)
InChI KeyHUHWZXWWOFSFKF-UHFFFAOYSA-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 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 Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.044 g/LALOGPS
logP10(0.67) g/LALOGPS
logP10(1.39) g/LChemAxon
logS10(-4.3) g/LALOGPS
pKa (Strongest Acidic)3.21ChemAxon
Physiological Charge-8ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area361.56 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity206.93 m³·mol⁻¹ChemAxon
Polarizability81.55 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+31661259
DarkChem[M-H]-31661259
AllCCS[M+H]+276.37232859911
AllCCS[M-H]-270.85332859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uroporphyrinogen III 10V, Positive-QTOFsplash10-106r-0000000980-8aa242b9a95e3ad928902015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uroporphyrinogen III 20V, Positive-QTOFsplash10-05fr-0000000910-5ea901953b2295eabfb62015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uroporphyrinogen III 40V, Positive-QTOFsplash10-0ab9-0000000900-fe3587925504317b1a702015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uroporphyrinogen III 10V, Negative-QTOFsplash10-00xr-0000000930-6a464d08b50b7b5e266c2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uroporphyrinogen III 20V, Negative-QTOFsplash10-00di-0000000910-22d2fcd94b453076587d2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uroporphyrinogen III 40V, Negative-QTOFsplash10-00di-2000000900-342f06471315f49e3deb2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uroporphyrinogen III 10V, Positive-QTOFsplash10-00xr-0000000950-9b8035c556d329d65d922021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uroporphyrinogen III 20V, Positive-QTOFsplash10-008a-0000000900-ca31eaf24646ca5e90042021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uroporphyrinogen III 40V, Positive-QTOFsplash10-0032-0000000900-42e2c47ece780e68ce9c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uroporphyrinogen III 10V, Negative-QTOFsplash10-00dj-0000000900-efbf67512274450743752021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uroporphyrinogen III 20V, Negative-QTOFsplash10-0002-0000000900-1faa99e113ce7b175d672021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uroporphyrinogen III 40V, Negative-QTOFsplash10-00kb-0000000900-479f518906c52f496e892021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022417
KNApSAcK IDC00007373
Chemspider ID1146
KEGG Compound IDC01051
BioCyc IDUROPORPHYRINOGEN-III
BiGG ID36704
Wikipedia LinkUroporphyrinogen III
METLIN ID79
PubChem Compound1179
PDB IDNot Available
ChEBI ID15437
Food Biomarker OntologyNot Available
VMH IDUPPG3
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Aizencang G, Solis C, Bishop DF, Warner C, Desnick RJ: Human uroporphyrinogen-III synthase: genomic organization, alternative promoters, and erythroid-specific expression. Genomics. 2000 Dec 1;70(2):223-31. [PubMed:11112350 ]
  2. Martins BM, Grimm B, Mock HP, Huber R, Messerschmidt A: Crystal structure and substrate binding modeling of the uroporphyrinogen-III decarboxylase from Nicotiana tabacum. Implications for the catalytic mechanism. J Biol Chem. 2001 Nov 23;276(47):44108-16. Epub 2001 Aug 27. [PubMed:11524417 ]

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 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
Reactions
Hydroxymethylbilane → Uroporphyrinogen III + Waterdetails