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Record Information
Version3.6
Creation Date2006-05-22 14:17:42 UTC
Update Date2016-05-13 19:12:36 UTC
HMDB IDHMDB02211
Secondary Accession NumbersNone
Metabolite Identification
Common NameUroporphyrinogen I
DescriptionUroporphyrinogens are porphyrinogen variants in which each pyrrole ring has one acetate side chain and one propionate side chain; it is formed by condensation 4 four molecules of porphobilinogen. 4 isomers are possible but only 2 commoly are found, types I and III. Uroporphyrinogen III is a functional intermediate in heme biosynthesis while Uroporphyrinogen I is produced in an abortive side reaction.
Structure
Thumb
Synonyms
ValueSource
3,8,13,18-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,17-tetrapropionic acidChEBI
Uro'gen IChEBI
Uroporphyrinogen-IChEBI
3,8,13,18-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,17-tetrapropionateGenerator
3,8,13,18-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydro-(8ci)-2,7,12,17-porphinetetrapropionateHMDB
3,8,13,18-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydro-(8ci)-2,7,12,17-porphinetetrapropionic acidHMDB
3,8,13,18-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydro-21H,23H-porphine-2,7,12,17-tetrapropanoateHMDB
3,8,13,18-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydro-21H,23H-porphine-2,7,12,17-tetrapropanoic acidHMDB
3,8,13,18-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,17-tetrapropanoateHMDB
3,8,13,18-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,17-tetrapropanoic acidHMDB
Chemical FormulaC40H44N4O16
Average Molecular Weight836.7946
Monoisotopic Molecular Weight836.27523138
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(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid
Traditional Nameuroporphyrinogen I
CAS Registry Number1867-62-5
SMILES
OC(=O)CCC1=C2CC3=C(CC(O)=O)C(CCC(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)29-14-26-19(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/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 KeyInChIKey=QTTNOSKSLATGQB-UHFFFAOYSA-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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 Solubility0.044 mg/mLALOGPS
logP0.67ALOGPS
logP1.39ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)3.27ChemAxon
Physiological Charge-8ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area361.56 Å2ChemAxon
Rotatable Bond Count20ChemAxon
Refractivity206.93 m3·mol-1ChemAxon
Polarizability84.05 Å3ChemAxon
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, Positivesplash10-0gi0-0000000790-66d58d00c9ac805a86ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-0000000910-4ff4ea54a281f8d6b0d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0adi-0000000900-919f095ae5cb2c3e6cd2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000790-5f547e23817fab228be1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00y0-1000000940-4d4fc3a395b4bfdd41dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-5000000900-f49d69c9724b023caf67View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue Location
  • Testes
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
Not Available
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 IDFDB022910
KNApSAcK IDNot Available
Chemspider ID389644
KEGG Compound IDC05766
BioCyc IDCPD-11444
BiGG IDNot Available
Wikipedia LinkUroporphyrinogen I
NuGOwiki LinkHMDB02211
Metagene LinkHMDB02211
METLIN ID6550
PubChem Compound440775
PDB IDNot Available
ChEBI ID28766
References
Synthesis ReferenceBurton, Gerardo; Fagerness, Paul E.; Hosozawa, Shigeki; Jordan, Peter M.; Scott, A. Ian. Carbon-13 NMR evidence for a new intermediate, pre-uroporphyrinogen, in the enzymic transformation of porphobilinogen into uroporphyrinogens I and III. Journal of the Chemical Society, Chemical Communications (1979), (5), 202-4.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Maines MD, Mayer RD: Inhibition of testicular cytochrome P-450-dependent steroid biosynthesis by cis-platinum. Reversal by human chorionic gonadotropin. J Biol Chem. 1985 May 25;260(10):6063-8. [4039724 ]
  2. Mukerji SK, Pimstone NR: Defective human erythrocyte uroporphyrinogen decarboxylase in familial porphyria cutanea tarda: the metabolic lesion or the result of endogenous porphyrinemia? Biochem Biophys Res Commun. 1988 Jul 15;154(1):39-46. [3395340 ]

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 I → Coproporphyrinogen I + 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