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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:39 UTC
HMDB IDHMDB0000839
Secondary Accession Numbers
  • HMDB00839
Metabolite Identification
Common NamePentaporphyrin I
DescriptionPentaporphyrin 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. Pentaporphyrin 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 pentaporphyrin I a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Pentaporphyrin I.
Structure
Data?1582752159
Synonyms
ValueSource
(+)-IsoboldineHMDB
2,10-Dimethoxy-6a-aporphine-1,9-diolHMDB
2,10-Dimethoxy-6alpha-aporphine-1,9-diolHMDB
21H,23H-PorphinHMDB
21H,23H-PorphineHMDB
D-IsoboldineHMDB
delta-IsoboldineHMDB
IsoboldineHMDB
PorphineHMDB
ProlmonHMDB
Protoporphyrin disodiumHMDB
Chemical FormulaC20H14N4
Average Molecular Weight310.352
Monoisotopic Molecular Weight310.121846468
IUPAC Name21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3,5,7,9,11,13(22),14,16,18(21),19-undecaene
Traditional Name21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3,5,7,9,11,13(22),14,16,18(21),19-undecaene
CAS Registry Number3019-51-0
SMILES
N1C2=CC=C1\C=C1\C=CC(\C=C3\C=CC(\C=C4/N\C(\C=C4)=C/2)=N3)=N1
InChI Identifier
InChI=1S/C20H14N4/c1-2-14-10-16-5-6-18(23-16)12-20-8-7-19(24-20)11-17-4-3-15(22-17)9-13(1)21-14/h1-12,21-22H/b13-9-,14-10-,15-9-,16-10-,17-11-,18-12-,19-11-,20-12-
InChI KeyJZRYQZJSTWVBBD-CEVVSZFKSA-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 PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.043 g/LALOGPS
logP3.02ALOGPS
logP4.63ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)14.81ChemAxon
pKa (Strongest Basic)5.13ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.36 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity92.46 m³·mol⁻¹ChemAxon
Polarizability34.75 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+175.82232859911
AllCCS[M-H]-177.43832859911
DeepCCS[M+H]+189.40330932474
DeepCCS[M-H]-187.04530932474
DeepCCS[M-2H]-221.32230932474
DeepCCS[M+Na]+196.46130932474
AllCCS[M+H]+175.832859911
AllCCS[M+H-H2O]+172.232859911
AllCCS[M+NH4]+179.132859911
AllCCS[M+Na]+180.132859911
AllCCS[M-H]-177.432859911
AllCCS[M+Na-2H]-176.032859911
AllCCS[M+HCOO]-174.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Pentaporphyrin IN1C2=CC=C1\C=C1\C=CC(\C=C3\C=CC(\C=C4/N\C(\C=C4)=C/2)=N3)=N15041.5Standard polar33892256
Pentaporphyrin IN1C2=CC=C1\C=C1\C=CC(\C=C3\C=CC(\C=C4/N\C(\C=C4)=C/2)=N3)=N13486.2Standard non polar33892256
Pentaporphyrin IN1C2=CC=C1\C=C1\C=CC(\C=C3\C=CC(\C=C4/N\C(\C=C4)=C/2)=N3)=N13899.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pentaporphyrin I,1TMS,isomer #1C[Si](C)(C)N1C2=CC=C1C=C1C=CC(=CC3=NC(=CC4=NC(=C2)C=C4)C=C3)[NH]13357.5Semi standard non polar33892256
Pentaporphyrin I,1TMS,isomer #1C[Si](C)(C)N1C2=CC=C1C=C1C=CC(=CC3=NC(=CC4=NC(=C2)C=C4)C=C3)[NH]13201.4Standard non polar33892256
Pentaporphyrin I,1TMS,isomer #1C[Si](C)(C)N1C2=CC=C1C=C1C=CC(=CC3=NC(=CC4=NC(=C2)C=C4)C=C3)[NH]14584.2Standard polar33892256
Pentaporphyrin I,2TMS,isomer #1C[Si](C)(C)N1C2=CC=C1C=C1C=CC(=CC3=NC(=CC4=NC(=C2)C=C4)C=C3)N1[Si](C)(C)C3438.9Semi standard non polar33892256
Pentaporphyrin I,2TMS,isomer #1C[Si](C)(C)N1C2=CC=C1C=C1C=CC(=CC3=NC(=CC4=NC(=C2)C=C4)C=C3)N1[Si](C)(C)C3389.2Standard non polar33892256
Pentaporphyrin I,2TMS,isomer #1C[Si](C)(C)N1C2=CC=C1C=C1C=CC(=CC3=NC(=CC4=NC(=C2)C=C4)C=C3)N1[Si](C)(C)C4380.8Standard polar33892256
Pentaporphyrin I,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C2=CC=C1C=C1C=CC(=CC3=NC(=CC4=NC(=C2)C=C4)C=C3)[NH]13561.8Semi standard non polar33892256
Pentaporphyrin I,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C2=CC=C1C=C1C=CC(=CC3=NC(=CC4=NC(=C2)C=C4)C=C3)[NH]13391.2Standard non polar33892256
Pentaporphyrin I,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C2=CC=C1C=C1C=CC(=CC3=NC(=CC4=NC(=C2)C=C4)C=C3)[NH]14671.1Standard polar33892256
Pentaporphyrin I,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C2=CC=C1C=C1C=CC(=CC3=NC(=CC4=NC(=C2)C=C4)C=C3)N1[Si](C)(C)C(C)(C)C3862.7Semi standard non polar33892256
Pentaporphyrin I,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C2=CC=C1C=C1C=CC(=CC3=NC(=CC4=NC(=C2)C=C4)C=C3)N1[Si](C)(C)C(C)(C)C3732.9Standard non polar33892256
Pentaporphyrin I,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C2=CC=C1C=C1C=CC(=CC3=NC(=CC4=NC(=C2)C=C4)C=C3)N1[Si](C)(C)C(C)(C)C4487.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pentaporphyrin I GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-0009000000-c840e918f6f52a0983502017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentaporphyrin I GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentaporphyrin I GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentaporphyrin I 10V, Positive-QTOFsplash10-03di-0009000000-436e5c763ea018a16e832017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentaporphyrin I 20V, Positive-QTOFsplash10-03di-0009000000-436e5c763ea018a16e832017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentaporphyrin I 40V, Positive-QTOFsplash10-03di-0009000000-58421ad29bd1fc585e5f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentaporphyrin I 10V, Negative-QTOFsplash10-0a4i-0009000000-b28534cedcf9900d84482017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentaporphyrin I 20V, Negative-QTOFsplash10-0a4i-0009000000-b28534cedcf9900d84482017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentaporphyrin I 40V, Negative-QTOFsplash10-0a4i-0029000000-f7a2f934fb7fca84713a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentaporphyrin I 10V, Negative-QTOFsplash10-0a4i-0009000000-89f88484153e1092dd792021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentaporphyrin I 20V, Negative-QTOFsplash10-0a4i-0009000000-89f88484153e1092dd792021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentaporphyrin I 40V, Negative-QTOFsplash10-0a59-0059000000-cae8b41cf5f8d57625562021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentaporphyrin I 10V, Positive-QTOFsplash10-03di-0009000000-cace220374bc9ffac2f62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentaporphyrin I 20V, Positive-QTOFsplash10-03di-0009000000-cace220374bc9ffac2f62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentaporphyrin I 40V, Positive-QTOFsplash10-000i-0092000000-988e7d904ce20d755a332021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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 IDFDB112165
KNApSAcK IDNot Available
Chemspider ID60231
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID174230
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceKametani, Tetsuji; Sugahara, Tokuji; Yagi, Haruhiko; Fukumoto, Keiichiro. Synthesis of heterocyclic compounds. CCCXIV. Biogenetic type syntheses of aporphine alkaloids, isoboldine and glaucine. Tetrahedron (1969), 25(17), 3667-73.
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. Ausio X, Grimalt JO, Ozalla D, Herrero C: On-line LC-MS analysis of urinary porphyrins. Anal Chem. 2000 Oct 15;72(20):4874-7. [PubMed:11055702 ]