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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:33 UTC
HMDB IDHMDB0000737
Secondary Accession Numbers
  • HMDB00737
Metabolite Identification
Common NameHeptacarboxylporphyrin I
DescriptionHeptacarboxylporphyrin I, also known as heptaporphyrin, 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. Heptacarboxylporphyrin I is a very strong basic compound (based on its pKa). Heptacarboxylporphyrin I has been found to be associated with several diseases such as porphyria cutanea tarda, variegate porphyria, acute intermittent porphyria, and liver disease; also heptacarboxylporphyrin I has been linked to the inborn metabolic disorders including hereditary coproporphyria.
Structure
Data?1582752153
Synonyms
ValueSource
Heptacarboxylic acid porphyrin IHMDB
HeptaporphyrinHMDB
3-[9,14,19-Tris(2-carboxyethyl)-10,15,20-tris(carboxymethyl)-5-methyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),4,6,8,10,12,14,16(22),17,19-undecaen-4-yl]propanoateHMDB
Chemical FormulaC39H38N4O14
Average Molecular Weight786.7374
Monoisotopic Molecular Weight786.238451944
IUPAC Name3-[9,14,19-tris(2-carboxyethyl)-10,15,20-tris(carboxymethyl)-5-methyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoic acid
Traditional Name3-[9,14,19-tris(2-carboxyethyl)-10,15,20-tris(carboxymethyl)-5-methyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoic acid
CAS Registry Number65406-45-3
SMILES
CC1=C(CCC(O)=O)\C2=C\C3=C(CC(O)=O)C(CCC(O)=O)=C(N3)\C=C3/N=C(/C=C4\N\C(=C/C1=N2)C(CCC(O)=O)=C4CC(O)=O)C(CCC(O)=O)=C3CC(O)=O
InChI Identifier
InChI=1S/C39H38N4O14/c1-17-18(2-6-33(44)45)26-14-30-23(11-38(54)55)20(4-8-35(48)49)28(42-30)16-32-24(12-39(56)57)21(5-9-36(50)51)29(43-32)15-31-22(10-37(52)53)19(3-7-34(46)47)27(41-31)13-25(17)40-26/h13-16,41-42H,2-12H2,1H3,(H,44,45)(H,46,47)(H,48,49)(H,50,51)(H,52,53)(H,54,55)(H,56,57)/b25-13-,26-14-,27-13-,28-16-,29-15-,30-14-,31-15-,32-16-
InChI KeyGWTVAIDNCPVMLP-YBWGHNILSA-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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkNot Available
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point208 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.039 g/LALOGPS
logP1.17ALOGPS
logP2.87ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)3.23ChemAxon
pKa (Strongest Basic)5.15ChemAxon
Physiological Charge-7ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area318.46 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity195.06 m³·mol⁻¹ChemAxon
Polarizability82.37 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-106r-0000000900-1a5659367722a3b91d07Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-0000002900-85dfdd282818a628f93aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-0000009700-49b4b052511c4ae6e5abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00xu-0000000900-ab85973f83598078c240Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0000001900-1a9755eb8354eff16f28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-2000000900-453451d4dc4aab7fd692Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Urine
Tissue Locations
  • Liver
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.00026 +/- 0.00078 umol/mmol creatinineAdult (>18 years old)BothLiver disease details
UrineDetected and Quantified0.0076 +/- 0.00026 umol/mmol creatinineAdult (>18 years old)BothPorphyria cutanea tarda details
UrineDetected and Quantified0.0013 +/- 0.00052 umol/mmol creatinineAdult (>18 years old)BothVariegate porphyria details
UrineDetected and Quantified0.0015 +/- 0.00039 umol/mmol creatinineAdult (>18 years old)BothHereditary coproporphyria details
UrineDetected and Quantified0.002 +/- 0.00039 umol/mmol creatinineAdult (>18 years old)BothAcute intermittent porphyria details
Associated Disorders and Diseases
Disease References
Liver disease
  1. Zuijderhoudt FM, Koehorst SG, Kluitenberg WE, Dorresteijn-de Bok J: On accuracy and precision of a HPLC method for measurement of urine porphyrin concentrations. Clin Chem Lab Med. 2000 Mar;38(3):227-30. [PubMed:10905759 ]
Porphyria cutanea tarda
  1. Zuijderhoudt FM, Koehorst SG, Kluitenberg WE, Dorresteijn-de Bok J: On accuracy and precision of a HPLC method for measurement of urine porphyrin concentrations. Clin Chem Lab Med. 2000 Mar;38(3):227-30. [PubMed:10905759 ]
Variegate porphyria
  1. Zuijderhoudt FM, Koehorst SG, Kluitenberg WE, Dorresteijn-de Bok J: On accuracy and precision of a HPLC method for measurement of urine porphyrin concentrations. Clin Chem Lab Med. 2000 Mar;38(3):227-30. [PubMed:10905759 ]
Hereditary coproporphyria
  1. Zuijderhoudt FM, Koehorst SG, Kluitenberg WE, Dorresteijn-de Bok J: On accuracy and precision of a HPLC method for measurement of urine porphyrin concentrations. Clin Chem Lab Med. 2000 Mar;38(3):227-30. [PubMed:10905759 ]
Acute intermittent porphyria
  1. Zuijderhoudt FM, Koehorst SG, Kluitenberg WE, Dorresteijn-de Bok J: On accuracy and precision of a HPLC method for measurement of urine porphyrin concentrations. Clin Chem Lab Med. 2000 Mar;38(3):227-30. [PubMed:10905759 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022214
KNApSAcK IDNot Available
Chemspider ID13628138
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5705
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID89912
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceRinguet, Michel; Pottier, Roy H.; Kennedy, James C. Preparation of porphyrin amides as photosensitizing neoplasm inhibitors. PCT Int. Appl. (1992), 35 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Apostoli P, Sarnico M, Bavazzano P, Bartoli D: Arsenic and porphyrins. Am J Ind Med. 2002 Sep;42(3):180-7. [PubMed:12210687 ]
  2. 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. [PubMed:12829005 ]
  3. Sinclair PR, Gorman N, Shedlofsky SI, Honsinger CP, Sinclair JF, Karagas MR, Anderson KE: Ascorbic acid deficiency in porphyria cutanea tarda. J Lab Clin Med. 1997 Aug;130(2):197-201. [PubMed:9280147 ]

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