Hmdb loader
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-04-23 20:56:37 UTC
HMDB IDHMDB0000241
Secondary Accession Numbers
  • HMDB00241
Metabolite Identification
Common NameProtoporphyrin IX
DescriptionProtoporphyrins are tetrapyrroles containing 4 methyl, 2 propionic, and 2 vinyl side chains. Protoporphyrin is produced by oxidation of the methylene bridge of protoporphyrinogen. Protoporphyrin IX is the only naturally occurring isomer; it is an intermediate in heme biosynthesis, combining with ferrous iron to form protoheme IX, the heme prosthetic group of hemoglobin. Protoporphyrin IX is created by the enzyme protoporphyrinogen oxidase. The enzyme ferrochelatase converts it into heme. Protoporphyrin IX naturally occurs in small amounts in feces. Protoporphyrin IX is also responsible for the brown pigment (ooporphyrin) of birds' eggs. Protoporphyrin IX is used as a branch point in the biosynthetic pathway leading to heme (by insertion of iron) and chlorophylls (by insertion of Mg and further side-chain transformation). Protoporphyrin IX can be used to treat liver disorders, mainly as the sodium salt. Under certain conditions, protoporphyrin IX can act as a neurotoxin, a phototoxin, and a metabotoxin. A neurotoxin causes damage to nerve cells and nerve tissues. A phototoxin causes cell damage upon exposure to light. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of porphyrins are associated with porphyrias such as porphyria variegate, acute intermittent porphyria, and hereditary coproporphyria (HCP). In particular, it is accumulated and excreted excessively in the feces in acute intermittent porphyria, protoporphyria, and variegate porphyria. There are several types of porphyrias (most are inherited). Hepatic porphyrias are characterized by acute neurological attacks (seizures, psychosis, extreme back and abdominal pain, and an acute polyneuropathy), while the erythropoietic forms present with skin problems (usually a light-sensitive blistering rash and increased hair growth). The neurotoxicity of porphyrins may be due to their selective interactions with tubulin, which disrupt microtubule formation and cause neural malformations (PMID: 3441503 ).
Structure
Data?1582752118
Synonyms
ValueSource
3,3'-(3,7,12,17-Tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acidChEBI
3,7,12,17-Tetramethyl-8,13-divinylporphyrin-2,18-dipropanoic acidChEBI
H2PpIXChEBI
Kammerer's prophyrinChEBI
OoporphyrinChEBI
Porphyrinogen IXChEBI
3,3'-(3,7,12,17-Tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionateGenerator
3,7,12,17-Tetramethyl-8,13-divinylporphyrin-2,18-dipropanoateGenerator
3,3'-(3,7,12,17-Tetramethyl-8,13-divinylporphine-2,18-diyl)diHMDB
PpIXHMDB
ProtoporphyrinHMDB
Protoporphyrin-"ix"HMDB
Protoporphyrin-IXHMDB
Chemical FormulaC34H34N4O4
Average Molecular Weight562.6582
Monoisotopic Molecular Weight562.258005596
IUPAC Name3-[20-(2-carboxyethyl)-9,14-diethenyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid
Traditional Name3-[20-(2-carboxyethyl)-9,14-diethenyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid
CAS Registry Number553-12-8
SMILES
CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(C=C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C=C)=C4C)/C(C)=C3CCC(O)=O
InChI Identifier
InChI=1S/C34H34N4O4/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25/h7-8,13-16,35,38H,1-2,9-12H2,3-6H3,(H,39,40)(H,41,42)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-
InChI KeyKSFOVUSSGSKXFI-UJJXFSCMSA-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
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point300 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.17 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg245.23230932474
[M+H]+MetCCS_train_pos241.41930932474
[M-H]-Not Available245.232http://allccs.zhulab.cn/database/detail?ID=AllCCS00000317
[M+H]+Not Available242.26http://allccs.zhulab.cn/database/detail?ID=AllCCS00000317
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.022 g/LALOGPS
logP4.4ALOGPS
logP6.78ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)3.68ChemAxon
pKa (Strongest Basic)4.96ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area131.96 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity163.81 m³·mol⁻¹ChemAxon
Polarizability66.03 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]+237.43532859911
AllCCS[M-H]-230.79232859911
DeepCCS[M+H]+251.03830932474
DeepCCS[M-H]-249.21330932474
DeepCCS[M-2H]-282.45630932474
DeepCCS[M+Na]+256.64430932474
AllCCS[M+H]+237.432859911
AllCCS[M+H-H2O]+235.832859911
AllCCS[M+NH4]+239.032859911
AllCCS[M+Na]+239.432859911
AllCCS[M-H]-230.832859911
AllCCS[M+Na-2H]-232.332859911
AllCCS[M+HCOO]-234.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Protoporphyrin IXCC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(C=C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C=C)=C4C)/C(C)=C3CCC(O)=O6245.9Standard polar33892256
Protoporphyrin IXCC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(C=C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C=C)=C4C)/C(C)=C3CCC(O)=O3858.4Standard non polar33892256
Protoporphyrin IXCC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(C=C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C=C)=C4C)/C(C)=C3CCC(O)=O5813.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Protoporphyrin IX,1TMS,isomer #1C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O[Si](C)(C)C)C(CCC(=O)O)=C4C)[NH]35372.5Semi standard non polar33892256
Protoporphyrin IX,1TMS,isomer #2C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O)C(CCC(=O)O[Si](C)(C)C)=C4C)[NH]35357.7Semi standard non polar33892256
Protoporphyrin IX,1TMS,isomer #3C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O)C(CCC(=O)O)=C4C)N3[Si](C)(C)C5429.1Semi standard non polar33892256
Protoporphyrin IX,1TMS,isomer #4C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O)=C4C)[NH]35403.2Semi standard non polar33892256
Protoporphyrin IX,2TMS,isomer #1C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C4C)[NH]35260.4Semi standard non polar33892256
Protoporphyrin IX,2TMS,isomer #2C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O[Si](C)(C)C)C(CCC(=O)O)=C4C)N3[Si](C)(C)C5350.2Semi standard non polar33892256
Protoporphyrin IX,2TMS,isomer #3C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O[Si](C)(C)C)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O)=C4C)[NH]35328.0Semi standard non polar33892256
Protoporphyrin IX,2TMS,isomer #4C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O)C(CCC(=O)O[Si](C)(C)C)=C4C)N3[Si](C)(C)C5332.6Semi standard non polar33892256
Protoporphyrin IX,2TMS,isomer #5C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C4C)[NH]35309.9Semi standard non polar33892256
Protoporphyrin IX,2TMS,isomer #6C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O)=C4C)N3[Si](C)(C)C5368.9Semi standard non polar33892256
Protoporphyrin IX,3TMS,isomer #1C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C4C)N3[Si](C)(C)C5237.9Semi standard non polar33892256
Protoporphyrin IX,3TMS,isomer #1C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C4C)N3[Si](C)(C)C4475.5Standard non polar33892256
Protoporphyrin IX,3TMS,isomer #1C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C4C)N3[Si](C)(C)C6148.1Standard polar33892256
Protoporphyrin IX,3TMS,isomer #2C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O[Si](C)(C)C)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C4C)[NH]35213.5Semi standard non polar33892256
Protoporphyrin IX,3TMS,isomer #2C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O[Si](C)(C)C)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C4C)[NH]34461.0Standard non polar33892256
Protoporphyrin IX,3TMS,isomer #2C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O[Si](C)(C)C)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C4C)[NH]36237.9Standard polar33892256
Protoporphyrin IX,3TMS,isomer #3C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O[Si](C)(C)C)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O)=C4C)N3[Si](C)(C)C5282.5Semi standard non polar33892256
Protoporphyrin IX,3TMS,isomer #3C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O[Si](C)(C)C)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O)=C4C)N3[Si](C)(C)C4484.5Standard non polar33892256
Protoporphyrin IX,3TMS,isomer #3C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O[Si](C)(C)C)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O)=C4C)N3[Si](C)(C)C6111.8Standard polar33892256
Protoporphyrin IX,3TMS,isomer #4C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C4C)N3[Si](C)(C)C5277.2Semi standard non polar33892256
Protoporphyrin IX,3TMS,isomer #4C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C4C)N3[Si](C)(C)C4480.4Standard non polar33892256
Protoporphyrin IX,3TMS,isomer #4C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C4C)N3[Si](C)(C)C6123.2Standard polar33892256
Protoporphyrin IX,4TMS,isomer #1C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O[Si](C)(C)C)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C4C)N3[Si](C)(C)C5182.6Semi standard non polar33892256
Protoporphyrin IX,4TMS,isomer #1C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O[Si](C)(C)C)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C4C)N3[Si](C)(C)C4462.6Standard non polar33892256
Protoporphyrin IX,4TMS,isomer #1C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O[Si](C)(C)C)=C(C)C(=CC1=N2)N5[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C4C)N3[Si](C)(C)C5851.9Standard polar33892256
Protoporphyrin IX,1TBDMS,isomer #1C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O[Si](C)(C)C(C)(C)C)C(CCC(=O)O)=C4C)[NH]35616.8Semi standard non polar33892256
Protoporphyrin IX,1TBDMS,isomer #2C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C4C)[NH]35602.5Semi standard non polar33892256
Protoporphyrin IX,1TBDMS,isomer #3C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O)C(CCC(=O)O)=C4C)N3[Si](C)(C)C(C)(C)C5595.2Semi standard non polar33892256
Protoporphyrin IX,1TBDMS,isomer #4C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O)=C(C)C(=CC1=N2)N5[Si](C)(C)C(C)(C)C)C(CCC(=O)O)=C4C)[NH]35583.3Semi standard non polar33892256
Protoporphyrin IX,2TBDMS,isomer #1C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O[Si](C)(C)C(C)(C)C)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C4C)[NH]35648.2Semi standard non polar33892256
Protoporphyrin IX,2TBDMS,isomer #2C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O[Si](C)(C)C(C)(C)C)C(CCC(=O)O)=C4C)N3[Si](C)(C)C(C)(C)C5674.6Semi standard non polar33892256
Protoporphyrin IX,2TBDMS,isomer #3C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C(C)C(=CC1=N2)N5[Si](C)(C)C(C)(C)C)C(CCC(=O)O)=C4C)[NH]35664.1Semi standard non polar33892256
Protoporphyrin IX,2TBDMS,isomer #4C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5[NH]C(=CC1=N2)C(C)=C5CCC(=O)O)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C4C)N3[Si](C)(C)C(C)(C)C5666.9Semi standard non polar33892256
Protoporphyrin IX,2TBDMS,isomer #5C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O)=C(C)C(=CC1=N2)N5[Si](C)(C)C(C)(C)C)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C4C)[NH]35660.8Semi standard non polar33892256
Protoporphyrin IX,2TBDMS,isomer #6C=CC1=C(C)C2=CC3=C(C=C)C(C)=C(C=C4N=C(C=C5C(CCC(=O)O)=C(C)C(=CC1=N2)N5[Si](C)(C)C(C)(C)C)C(CCC(=O)O)=C4C)N3[Si](C)(C)C(C)(C)C5687.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Protoporphyrin IX GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uxu-1000290000-e22236fe3cca8eed1ecf2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Protoporphyrin IX GC-MS (1 TMS) - 70eV, Positivesplash10-00di-6000094000-b9c12952e100c5144cab2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Protoporphyrin IX GC-MS ("Protoporphyrin IX,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TBDMS_2_4) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TBDMS_2_5) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Protoporphyrin IX GC-MS (TBDMS_2_6) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protoporphyrin IX 10V, Positive-QTOFsplash10-0002-0000090000-5d5be53410134c5719ab2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protoporphyrin IX 20V, Positive-QTOFsplash10-00kb-1000590000-2d4157b9f73534d95a9c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protoporphyrin IX 40V, Positive-QTOFsplash10-0a4l-1000910000-07524a9291a1921dfafc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protoporphyrin IX 10V, Negative-QTOFsplash10-03di-0000090000-5df26c1cfb9a0b16a91a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protoporphyrin IX 20V, Negative-QTOFsplash10-0296-1000190000-2d4bcb49201fc10adc092017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protoporphyrin IX 40V, Negative-QTOFsplash10-0a4l-9000230000-064fb944a966d08c06bf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protoporphyrin IX 10V, Negative-QTOFsplash10-03di-0000090000-87c1740ecd1a28f4a2d92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protoporphyrin IX 20V, Negative-QTOFsplash10-03xu-0000590000-99160b987bb7e62ab3622021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protoporphyrin IX 40V, Negative-QTOFsplash10-00di-0000900000-f2d9118441a9c8c47d792021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protoporphyrin IX 10V, Positive-QTOFsplash10-03dj-0000090000-d428ac6dc2fc4794cc412021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protoporphyrin IX 20V, Positive-QTOFsplash10-0j4j-0000090000-2b065966ec57bb97d5112021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protoporphyrin IX 40V, Positive-QTOFsplash10-0uk9-1000970000-b435817e4dc349e65ab32021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
  • Mitochondria
Biospecimen Locations
  • Blood
Tissue Locations
  • Adipose Tissue
  • Adrenal Medulla
  • Bladder
  • Epidermis
  • Erythrocyte
  • Fibroblasts
  • Intestine
  • Kidney
  • Leukocyte
  • Liver
  • Platelet
  • Spleen
  • Testis
  • Thyroid Gland
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.66 +/- 0.18 uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.53 +/- 0.13 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified1.09 +/- 0.57 uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0-1.244 uMAdult (>18 years old)MaleProtoporphyria, Erythropoietic details
Associated Disorders and Diseases
Disease References
Protoporphyria, Erythropoietic
  1. MAGNUS IA, JARRETT A, PRANKERD TA, RIMINGTON C: Erythropoietic protoporphyria. A new porphyria syndrome with solar urticaria due to protoporphyrinaemia. Lancet. 1961 Aug 26;2(7200):448-51. [PubMed:13765301 ]
Associated OMIM IDs
  • 177000 (Protoporphyria, Erythropoietic)
DrugBank IDDB02285
Phenol Explorer Compound IDNot Available
FooDB IDFDB004277
KNApSAcK IDC00007370
Chemspider ID10469486
KEGG Compound IDC02191
BioCyc IDPROTOPORPHYRIN_IX
BiGG IDNot Available
Wikipedia LinkProtoporphyrin_IX
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID15430
Food Biomarker OntologyNot Available
VMH IDPPP9
MarkerDB IDNot Available
Good Scents IDrw1279251
References
Synthesis ReferenceGames, David E.; Jackson, Anthony H.; Jackson, J. Richard; Belcher, Roderick V.; Smith, Sydney G. Biosynthesis of protoporphyrin-IX from coproporphyrinogen-III. Journal of the Chemical Society, Chemical Communications (1976), (6), 187-8.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Messmann H, Knuchel R, Baumler W, Holstege A, Scholmerich J: Endoscopic fluorescence detection of dysplasia in patients with Barrett's esophagus, ulcerative colitis, or adenomatous polyps after 5-aminolevulinic acid-induced protoporphyrin IX sensitization. Gastrointest Endosc. 1999 Jan;49(1):97-101. [PubMed:9869731 ]
  2. Stankiewicz A, Lutz W, Krajewska B, Szulc B: [Plasma indicators of iron metabolism in persons occupationally exposed to organic solvents with normal and increased levels of protoporphyrin IX in erythrocytes]. Pol Tyg Lek. 1986 Jul 7;41(27):851-4. [PubMed:3763462 ]
  3. Stankiewicz A: [Erythrocyte protoporphyrin IX in occupational exposure to asbestos]. Med Pr. 1984;35(5):351-4. [PubMed:6530952 ]
  4. Sudworth CD, Stringer MR, Cruse-Sawyer JE, Brown SB: Fluorescence microspectroscopy technique for the study of intracellular protoporphyrin IX dynamics. Appl Spectrosc. 2003 Jun;57(6):682-8. [PubMed:14658702 ]
  5. Kufner G, Schlegel H, Jager R: A spectrophotometric micromethod for determining erythrocyte protoporphyrin-IX in whole blood or erythrocytes. Clin Chem Lab Med. 2005;43(2):183-91. [PubMed:15843214 ]
  6. Stankiewicz A: The concentration of protoporphyrin IX in workers occupationally exposed to lead. Mater Med Pol. 1989 Apr-Jun;21(2):100-2. [PubMed:2488459 ]
  7. Krieg RC, Fickweiler S, Wolfbeis OS, Knuechel R: Cell-type specific protoporphyrin IX metabolism in human bladder cancer in vitro. Photochem Photobiol. 2000 Aug;72(2):226-33. [PubMed:10946577 ]
  8. Bailey GG, Needham LL: Simultaneous quantification of erythrocyte zinc protoporphyrin and protoporphyrin IX by liquid chromatography. Clin Chem. 1986 Dec;32(12):2137-42. [PubMed:3779978 ]
  9. Chisolm J Jr, Brown DH: Micro-scale photofluorometric determination of "free erythrocyte pophyrin" (protoporphyrin IX). Clin Chem. 1975 Oct;21(11):1669-82. [PubMed:1164799 ]
  10. Casas A, Batlle AM, Butler AR, Robertson D, Brown EH, MacRobert A, Riley PA: Comparative effect of ALA derivatives on protoporphyrin IX production in human and rat skin organ cultures. Br J Cancer. 1999 Jul;80(10):1525-32. [PubMed:10408393 ]
  11. Smits T, Robles CA, van Erp PE, van de Kerkhof PC, Gerritsen MJ: Correlation between macroscopic fluorescence and protoporphyrin IX content in psoriasis and actinic keratosis following application of aminolevulinic acid. J Invest Dermatol. 2005 Oct;125(4):833-9. [PubMed:16185285 ]
  12. Bartosova J, Hrkal Z: Accumulation of protoporphyrin-IX (PpIX) in leukemic cell lines following induction by 5-aminolevulinic acid (ALA). Comp Biochem Physiol C Toxicol Pharmacol. 2000 Jul;126(3):245-52. [PubMed:11048674 ]
  13. Sakai T, Takeuchi Y, Ikeya Y, Araki T, Ushio K: [Automated HPLC method for determining zinc protoporphyrin IX and protoporphyrin IX in erythrocytes of workers exposed to lead]. Sangyo Igaku. 1988 Nov;30(6):467-74. [PubMed:3221502 ]
  14. Stankiewicz A, Lutz W, Szeszko A: [Protoporphyrin IX level in erythrocytes of persons with alcoholic liver cirrhosis]. Pol Tyg Lek. 1985 Jul 15;40(28):787-9. [PubMed:4059100 ]
  15. Star WM, Aalders MC, Sac A, Sterenborg HJ: Quantitative model calculation of the time-dependent protoporphyrin IX concentration in normal human epidermis after delivery of ALA by passive topical application or lontophoresis. Photochem Photobiol. 2002 Apr;75(4):424-32. [PubMed:12003134 ]
  16. von Beckerath M, Juzenas P, Ma LW, Iani V, Lofgren L, Moan J: The influence of UV exposure on 5-aminolevulinic acid-induced protoporphyrin IX production in skin. Photochem Photobiol. 2001 Dec;74(6):825-8. [PubMed:11783939 ]
  17. Gottsch JD, Graham CR Jr, Hairston RJ, Chen CH, Green WR, Stark WJ: Protoporphyrin IX photosensitization of corneal endothelium. Arch Ophthalmol. 1989 Oct;107(10):1497-500. [PubMed:2803100 ]
  18. Bissonnette R, Zeng H, McLean DI, Korbelik M, Lui H: Oral aminolevulinic acid induces protoporphyrin IX fluorescence in psoriatic plaques and peripheral blood cells. Photochem Photobiol. 2001 Aug;74(2):339-45. [PubMed:11547574 ]
  19. Rick K, Sroka R, Stepp H, Kriegmair M, Huber RM, Jacob K, Baumgartner R: Pharmacokinetics of 5-aminolevulinic acid-induced protoporphyrin IX in skin and blood. J Photochem Photobiol B. 1997 Oct;40(3):313-9. [PubMed:9372622 ]
  20. De Rosa FS, Marchetti JM, Thomazini JA, Tedesco AC, Bentley MV: A vehicle for photodynamic therapy of skin cancer: influence of dimethylsulphoxide on 5-aminolevulinic acid in vitro cutaneous permeation and in vivo protoporphyrin IX accumulation determined by confocal microscopy. J Control Release. 2000 Apr 3;65(3):359-66. [PubMed:10699294 ]
  21. Winkelman JW, Collins GH: Neurotoxicity of tetraphenylporphinesulfonate TPPS4 and its relation to photodynamic therapy. Photochem Photobiol. 1987 Nov;46(5):801-7. [PubMed:3441503 ]

Enzymes

General function:
Involved in coproporphyrinogen oxidase activity
Specific function:
Key enzyme in heme biosynthesis. Catalyzes the oxidative decarboxylation of propionic acid side chains of rings A and B of coproporphyrinogen III.
Gene Name:
CPOX
Uniprot ID:
P36551
Molecular weight:
50151.605
General function:
Involved in catalytic activity
Specific function:
Catalyzes the 6-electron oxidation of protoporphyrinogen-IX to form protoporphyrin-IX.
Gene Name:
PPOX
Uniprot ID:
P50336
Molecular weight:
50764.8
Reactions
Protoporphyrinogen IX + Oxygen → Protoporphyrin IX + Hydrogen peroxidedetails
Protoporphyrinogen IX + Oxygen → Protoporphyrin IX + Hydrogen peroxidedetails
General function:
Involved in ferrochelatase activity
Specific function:
Catalyzes the ferrous insertion into protoporphyrin IX.
Gene Name:
FECH
Uniprot ID:
P22830
Molecular weight:
47861.77
Reactions
Heme + Hydrogen Ion → Protoporphyrin IX + Fe2+details
Protoporphyrin IX + Fe2+ → Heme + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Stores iron in a soluble, non-toxic, readily available form. Important for iron homeostasis. Iron is taken up in the ferrous form and deposited as ferric hydroxides after oxidation. Also plays a role in delivery of iron to cells. Mediates iron uptake in capsule cells of the developing kidney
Gene Name:
FTL
Uniprot ID:
P02792
Molecular weight:
20019.5
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
General function:
Involved in ferrochelatase activity
Specific function:
Catalyzes the ferrous insertion into protoporphyrin IX
Gene Name:
Not Available
Uniprot ID:
Q53FU1
Molecular weight:
47488.3
General function:
Involved in ferrochelatase activity
Specific function:
Catalyzes the ferrous insertion into protoporphyrin IX
Gene Name:
Not Available
Uniprot ID:
Q5TZY0
Molecular weight:
47680.5
General function:
Involved in ferrochelatase activity
Specific function:
Catalyzes the ferrous insertion into protoporphyrin IX
Gene Name:
DKFZp686P18130
Uniprot ID:
Q7KZA3
Molecular weight:
47131.9