Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110805
Identification
Name: uroporphyrinogen-III
Description:An octacarboxylic acid anion obtained by deprotonation of all eight carboxy groups of uroporphyrinogen III.
Structure
Thumb
Synonyms:
  • uroporphyrinogen III
Chemical Formula: C40H36N4O16
Average Molecular Weight: 828.74
Monoisotopic Molecular Weight: 836.2752313868
InChI Key: HUHWZXWWOFSFKF-UHFFFAOYSA-F
InChI: 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)/p-8
CAS number: 1976-85-8
IUPAC Name:3,3',3'',3'''-[3,8,13,17-tetrakis(carboxylatomethyl)-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrayl]tetrapropanoate
Traditional IUPAC Name: uroporphyrinogen-III
SMILES:C(=O)([O-])CCC3(C(=C2(CC5(NC(CC4(NC(CC1(NC(=C(C=1CC(=O)[O-])CCC(=O)[O-])CC(N2)=3))=C(CC(=O)[O-])C=4CCC(=O)[O-]))=C(CC([O-])=O)C(CCC(=O)[O-])=5)))CC(=O)[O-])
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities 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.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organoheterocyclic compounds
Sub ClassTetrapyrroles and derivatives
Direct Parent Porphyrins
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 Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-8
Melting point: Not Available
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)3.21ChemAxon
Physiological Charge-8ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area361.56 Å2ChemAxon
Rotatable Bond Count20ChemAxon
Refractivity206.93 m3·mol-1ChemAxon
Polarizability81.55 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-106r-0000000980-8aa242b9a95e3ad92890View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-0000000910-5ea901953b2295eabfb6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-0000000900-fe3587925504317b1a70View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00xr-0000000930-6a464d08b50b7b5e266cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0000000910-22d2fcd94b453076587dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-2000000900-342f06471315f49e3debView in MoNA
References
References:
  • 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. [11112350 ]
  • 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. [11524417 ]
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CAS1976-85-8
ChEBI57308
HMDBHMDB01086
IAF126036704
KEGGC01051
MetaboLightsMTBLC57308
PubChem25202645