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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:33 UTC
HMDB IDHMDB0000743
Secondary Accession Numbers
  • HMDB00743
Metabolite Identification
Common NameHexacarboxylporphyrin I
DescriptionHexacarboxylporphyrin I 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. Hexacarboxylporphyrin I has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make hexacarboxylporphyrin I a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Hexacarboxylporphyrin I.
Structure
Data?1582752153
Synonyms
ValueSource
Hexacarboxylic acid prophyrin IHMDB
Hexacarboxyporphyrin IHMDB
3-[9,14,19-Tris(2-carboxyethyl)-10,15-bis(carboxymethyl)-5,20-dimethyl-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 FormulaC38H38N4O12
Average Molecular Weight742.7279
Monoisotopic Molecular Weight742.2486227
IUPAC Name3-[9,14,19-tris(2-carboxyethyl)-10,15-bis(carboxymethyl)-5,20-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3(24),4,6,8,10,12,14,16(22),17,19-undecaen-4-yl]propanoic acid
Traditional Name3-[9,14,19-tris(2-carboxyethyl)-10,15-bis(carboxymethyl)-5,20-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3(24),4,6,8,10,12,14,16(22),17,19-undecaen-4-yl]propanoic acid
CAS Registry Number73913-56-1
SMILES
CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(CC(O)=O)C(CCC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CCC(O)=O)=C4C)/C(CCC(O)=O)=C3CC(O)=O
InChI Identifier
InChI=1S/C38H38N4O12/c1-17-19(3-7-33(43)44)27-13-25-18(2)20(4-8-34(45)46)28(40-25)15-31-24(12-38(53)54)22(6-10-36(49)50)30(42-31)16-32-23(11-37(51)52)21(5-9-35(47)48)29(41-32)14-26(17)39-27/h13-16,40-41H,3-12H2,1-2H3,(H,43,44)(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)/b25-13-,26-14-,27-13-,28-15-,29-14-,30-16-,31-15-,32-16-
InChI KeyAFHLWIUSJBEMJE-ZMXCOFNRSA-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 effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point208 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.035 g/LALOGPS
logP1.48ALOGPS
logP2.74ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)3.29ChemAxon
pKa (Strongest Basic)5.23ChemAxon
Physiological Charge-6ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area281.16 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity188.79 m³·mol⁻¹ChemAxon
Polarizability79.54 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+263.27732859911
AllCCS[M-H]-263.87632859911
DeepCCS[M+H]+273.42130932474
DeepCCS[M-H]-271.6730932474
DeepCCS[M-2H]-305.70630932474
DeepCCS[M+Na]+279.48130932474
AllCCS[M+H]+263.332859911
AllCCS[M+H-H2O]+262.732859911
AllCCS[M+NH4]+263.832859911
AllCCS[M+Na]+263.932859911
AllCCS[M-H]-263.932859911
AllCCS[M+Na-2H]-267.932859911
AllCCS[M+HCOO]-272.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Hexacarboxylporphyrin ICC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(CC(O)=O)C(CCC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CCC(O)=O)=C4C)/C(CCC(O)=O)=C3CC(O)=O7440.7Standard polar33892256
Hexacarboxylporphyrin ICC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(CC(O)=O)C(CCC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CCC(O)=O)=C4C)/C(CCC(O)=O)=C3CC(O)=O4560.7Standard non polar33892256
Hexacarboxylporphyrin ICC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(CC(O)=O)C(CCC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CCC(O)=O)=C4C)/C(CCC(O)=O)=C3CC(O)=O7403.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Hexacarboxylporphyrin I GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexacarboxylporphyrin I GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexacarboxylporphyrin I GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexacarboxylporphyrin I GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexacarboxylporphyrin I GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexacarboxylporphyrin I GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexacarboxylporphyrin I GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexacarboxylporphyrin I GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexacarboxylporphyrin I GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexacarboxylporphyrin I GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexacarboxylporphyrin I GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexacarboxylporphyrin I GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexacarboxylporphyrin I GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexacarboxylporphyrin I GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexacarboxylporphyrin I GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexacarboxylporphyrin I GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexacarboxylporphyrin I GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexacarboxylporphyrin I GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexacarboxylporphyrin I GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexacarboxylporphyrin I GC-MS (TMS_2_12) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexacarboxylporphyrin I GC-MS (TMS_2_13) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexacarboxylporphyrin I GC-MS (TMS_2_14) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexacarboxylporphyrin I GC-MS (TMS_2_15) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexacarboxylporphyrin I GC-MS (TMS_2_16) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexacarboxylporphyrin I GC-MS (TMS_2_17) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexacarboxylporphyrin I 10V, Positive-QTOFsplash10-056r-0000006900-c7b0f6210ebd3dd792452017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexacarboxylporphyrin I 20V, Positive-QTOFsplash10-00or-0000009200-bf6d71def09551da36942017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexacarboxylporphyrin I 40V, Positive-QTOFsplash10-000i-0000009000-907019a41b59554e8fcc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexacarboxylporphyrin I 10V, Negative-QTOFsplash10-00fv-0000008900-4d81ad3957c5de1f037c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexacarboxylporphyrin I 20V, Negative-QTOFsplash10-00b9-0000009400-1129842b62b6eff096262017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexacarboxylporphyrin I 40V, Negative-QTOFsplash10-0a6r-4000009200-976122ebaaa0d6b1e75c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexacarboxylporphyrin I 10V, Negative-QTOFsplash10-004i-0000009000-946c7d847cb3aaba69952021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexacarboxylporphyrin I 20V, Negative-QTOFsplash10-0ufr-0000009000-9b6fee0babe7438573502021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexacarboxylporphyrin I 40V, Negative-QTOFsplash10-0udi-0000009000-6af7dc488caae9f0b3e52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexacarboxylporphyrin I 10V, Positive-QTOFsplash10-004i-0000009600-40175966eda4e6eae1eb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexacarboxylporphyrin I 20V, Positive-QTOFsplash10-0f9i-0000009000-c841884267d2d4738e5e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexacarboxylporphyrin I 40V, Positive-QTOFsplash10-0udr-0000009000-d70a85e08a880ee035ad2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen LocationsNot Available
Tissue Locations
  • Liver
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022216
KNApSAcK IDNot Available
Chemspider ID13628139
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5711
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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. CODEN: PIXXD2 WO 9206097 A1 19920416 CAN 117:48227 AN 1992:448227
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. Apostoli P, Sarnico M, Bavazzano P, Bartoli D: Arsenic and porphyrins. Am J Ind Med. 2002 Sep;42(3):180-7. [PubMed:12210687 ]

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