Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:29 UTC
Update Date2021-09-14 14:57:58 UTC
HMDB IDHMDB0001957
Secondary Accession Numbers
  • HMDB01957
Metabolite Identification
Common NamePentacarboxyl porphyrinogen III
DescriptionPentacarboxyl porphyrinogen III 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. Pentacarboxyl porphyrinogen III is a very strong basic compound (based on its pKa). Substrate for erythrocyte uroporphyrinogen decarboxylase in patients with porphyria cutanea tarda (PubNed ID 1610684 ).
Structure
Data?1582752219
Synonyms
ValueSource
Pentacarboxylporphyrinogen IIIHMDB
Pentacarboxyporphyrinogen IIIHMDB
3-[10,14,19-Tris(2-carboxyethyl)-15-(carboxymethyl)-5,9,20-trimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3,5,9,11(23),12,14,16,18(21),19-decaen-4-yl]propanoateHMDB
Chemical FormulaC37H40N4O10
Average Molecular Weight700.7343
Monoisotopic Molecular Weight700.27444352
IUPAC Name3-[(12Z,17Z)-10,15,20-tris(2-carboxyethyl)-19-(carboxymethyl)-5,9,14-trimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),4,8,10,12,14,16(22),17,19-decaen-4-yl]propanoic acid
Traditional Name3-[(12Z,17Z)-10,15,20-tris(2-carboxyethyl)-19-(carboxymethyl)-5,9,14-trimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),4,8,10,12,14,16(22),17,19-decaen-4-yl]propanoic acid
CAS Registry NumberNot Available
SMILES
CC1=C(CCC(O)=O)C2=NC1CC1=C(C)C(CCC(O)=O)=C(N1)\C=C1/N=C(/C=C3\N\C(=C/2)C(CCC(O)=O)=C3CC(O)=O)C(CCC(O)=O)=C1C
InChI Identifier
InChI=1S/C37H40N4O10/c1-17-20(4-8-33(42)43)28-14-27-19(3)22(6-10-35(46)47)30(40-27)16-32-24(12-37(50)51)23(7-11-36(48)49)31(41-32)15-29-21(5-9-34(44)45)18(2)26(39-29)13-25(17)38-28/h14-16,26,38,41H,4-13H2,1-3H3,(H,42,43)(H,44,45)(H,46,47)(H,48,49)(H,50,51)/b27-14-,31-15-,32-16-
InChI KeyQDDLLFZOMVJQEQ-XJTMSCLRSA-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 Parents
Substituents
  • Porphyrin
  • Pentacarboxylic acid or derivatives
  • Dipyrrin
  • Substituted pyrrole
  • Pyrrole
  • Heteroaromatic compound
  • Ketimine
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.034 g/LALOGPS
logP1.65ALOGPS
logP-2.5ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)3.12ChemAxon
pKa (Strongest Basic)8.97ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area239.04 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity189.67 m³·mol⁻¹ChemAxon
Polarizability77.36 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]+255.26232859911
AllCCS[M-H]-255.22732859911
DeepCCS[M+H]+264.33330932474
DeepCCS[M-H]-262.50830932474
DeepCCS[M-2H]-296.2430932474
DeepCCS[M+Na]+270.01430932474
AllCCS[M+H]+255.332859911
AllCCS[M+H-H2O]+254.532859911
AllCCS[M+NH4]+255.932859911
AllCCS[M+Na]+256.132859911
AllCCS[M-H]-255.232859911
AllCCS[M+Na-2H]-259.232859911
AllCCS[M+HCOO]-263.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Pentacarboxyl porphyrinogen IIICC1=C(CCC(O)=O)C2=NC1CC1=C(C)C(CCC(O)=O)=C(N1)\C=C1/N=C(/C=C3\N\C(=C/2)C(CCC(O)=O)=C3CC(O)=O)C(CCC(O)=O)=C1C8231.8Standard polar33892256
Pentacarboxyl porphyrinogen IIICC1=C(CCC(O)=O)C2=NC1CC1=C(C)C(CCC(O)=O)=C(N1)\C=C1/N=C(/C=C3\N\C(=C/2)C(CCC(O)=O)=C3CC(O)=O)C(CCC(O)=O)=C1C3851.8Standard non polar33892256
Pentacarboxyl porphyrinogen IIICC1=C(CCC(O)=O)C2=NC1CC1=C(C)C(CCC(O)=O)=C(N1)\C=C1/N=C(/C=C3\N\C(=C/2)C(CCC(O)=O)=C3CC(O)=O)C(CCC(O)=O)=C1C6427.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pentacarboxyl porphyrinogen III GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-0000009000-c6229a8f5be34f37d5b72017-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentacarboxyl porphyrinogen III GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentacarboxyl porphyrinogen III GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentacarboxyl porphyrinogen III GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentacarboxyl porphyrinogen III GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentacarboxyl porphyrinogen III GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentacarboxyl porphyrinogen III GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentacarboxyl porphyrinogen III GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentacarboxyl porphyrinogen III GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentacarboxyl porphyrinogen III GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentacarboxyl porphyrinogen III GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentacarboxyl porphyrinogen III GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentacarboxyl porphyrinogen III GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentacarboxyl porphyrinogen III GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentacarboxyl porphyrinogen III GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentacarboxyl porphyrinogen III GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentacarboxyl porphyrinogen III GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentacarboxyl porphyrinogen III GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentacarboxyl porphyrinogen III GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentacarboxyl porphyrinogen III GC-MS (TMS_2_12) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentacarboxyl porphyrinogen III GC-MS (TMS_2_13) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentacarboxyl porphyrinogen III GC-MS (TMS_2_14) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentacarboxyl porphyrinogen III GC-MS (TMS_2_15) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentacarboxyl porphyrinogen III GC-MS (TMS_2_16) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentacarboxyl porphyrinogen III 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 - Pentacarboxyl porphyrinogen III 10V, Positive-QTOFsplash10-00m0-0000009000-60bf8894eaaaf6a177242017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentacarboxyl porphyrinogen III 20V, Positive-QTOFsplash10-059i-0000019000-41d90b495889efa7854c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentacarboxyl porphyrinogen III 40V, Positive-QTOFsplash10-052b-0000097000-59db139a730f0f8648bc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentacarboxyl porphyrinogen III 10V, Negative-QTOFsplash10-0541-0000009000-30e6e25284087477fc442017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentacarboxyl porphyrinogen III 20V, Negative-QTOFsplash10-053i-0000009000-b0761d90fa878bf315902017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentacarboxyl porphyrinogen III 40V, Negative-QTOFsplash10-0bti-3000009000-6b79b9b723c84095d9f02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentacarboxyl porphyrinogen III 10V, Positive-QTOFsplash10-001i-0000009100-4a659b177e7c164028242021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentacarboxyl porphyrinogen III 20V, Positive-QTOFsplash10-05v1-0000019000-b70c01a1be94d634957d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentacarboxyl porphyrinogen III 40V, Positive-QTOFsplash10-0a4s-1000039000-56176c39d0504c79b1db2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentacarboxyl porphyrinogen III 10V, Negative-QTOFsplash10-001j-0000009000-fc2175754d3f335a39552021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentacarboxyl porphyrinogen III 20V, Negative-QTOFsplash10-01p9-0000009000-c7879a801c68406a4bda2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentacarboxyl porphyrinogen III 40V, Negative-QTOFsplash10-0a4i-0000019000-5411b5f5ee8751137b262021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
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 IDFDB022764
KNApSAcK IDNot Available
Chemspider ID13628281
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6401
PubChem Compound21252264
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. de Catabbi SB, de Calmanovici RW, Minutolo C, Aldonatti C, San Martin de Viale LC: Porphyria-induced hepatic porphyrinogen carboxy-lyase inhibitor and its interaction with the active site(s) of the enzyme. Biochem Mol Biol Int. 1999 Jun;47(6):945-56. [PubMed:10410240 ]