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Human Metabolome Database Version 3.5

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Showing metabocard for Uroporphyrinogen III (HMDB01086)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:51 -0700
HMDB ID HMDB01086
Secondary Accession Numbers None
Metabolite Identification
Common Name Uroporphyrinogen III
Description Uroporphyrinogens 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydro-2,7,12,18-Porphinetetrapropionate
  2. 3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydro-2,7,12,18-Porphinetetrapropionic acid
  3. 3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydro-21H,23H-Porphine-2,7,12,18-tetrapropanoate
  4. 3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydro-21H,23H-Porphine-2,7,12,18-tetrapropanoic acid
  5. 3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropanoate
  6. 3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropanoic acid
  7. Urogen III
  8. Uroporphyrinogen III
  9. Uroporphyrinogen-III
Chemical Formula C40H44N4O16
Average Molecular Weight 836.7946
Monoisotopic Molecular Weight 836.27523138
IUPAC Name 3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid
Traditional IUPAC Name uroporphyrinogen III
CAS Registry Number 1976-85-8
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 Key HUHWZXWWOFSFKF-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Tetrapyrroles and Derivatives
Sub Class Corrinoids
Other Descriptors
  • Organic Compounds
  • uroporphyrinogen(ChEBI)
Substituents
  • Carboxylic Acid
  • Porphyrin
  • Pyrrole
Direct Parent Precorrins
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Porphyrin and chlorophyll metabolism
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.044 g/L ALOGPS
LogP 0.67 ALOGPS
LogP 1.39 ChemAxon
LogS -4.28 ALOGPS
pKa (strongest acidic) 3.21 ChemAxon
Hydrogen Acceptor Count 16 ChemAxon
Hydrogen Donor Count 12 ChemAxon
Polar Surface Area 361.56 A2 ChemAxon
Rotatable Bond Count 20 ChemAxon
Refractivity 206.93 ChemAxon
Polarizability 81.55 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -8 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Porphyrin Metabolism SMP00024 map00860 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Expected and not Quantified
Not Applicable Not Available Not Available Normal Inferred from detection in urine
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022417
KNApSAcK ID Not Available
Chemspider ID 1146 Link_out
KEGG Compound ID C01051 Link_out
BioCyc ID UROPORPHYRINOGEN-III Link_out
BiGG ID 36704 Link_out
Wikipedia Link Uroporphyrinogen III Link_out
NuGOwiki Link HMDB01086 Link_out
Metagene Link HMDB01086 Link_out
METLIN ID 79 Link_out
PubChem Compound 1179 Link_out
PDB ID UP2 Link_out
ChEBI ID 15437 Link_out
References
Synthesis Reference Not 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 Link_out
  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 Link_out
Enzymes
Name: Uroporphyrinogen decarboxylase
Reactions:
  • uroporphyrinogen III = coproporphyrinogen III + 4 CO2 [RN:R03197]
Gene Name: UROD
Uniprot ID: P06132 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Uroporphyrinogen-III synthase
Reactions:
  • hydroxymethylbilane = uroporphyrinogen III + H2O [RN:R03165]
Gene Name: UROS
Uniprot ID: P10746 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA