Record Information
Version1.0
Creation date2010-04-08 22:06:10 UTC
Update date2020-09-17 15:38:30 UTC
Primary IDFDB004277
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameProtoporphyrin
DescriptionProtoporphyrin IX, also known as porphyrinogen IX or H2PPIX, 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. Chronically high levels of porphyrins are associated with porphyrias such as porphyria variegate, acute intermittent porphyria, and hereditary coproporphyria (HCP). Protoporphyrin IX is a strong basic compound (based on its pKa). Protoporphyrin IX exists in all living species, ranging from bacteria to humans. Outside of the human body, Protoporphyrin IX has been detected, but not quantified in, red beetroots. This could make protoporphyrin IX a potential biomarker for the consumption of these foods. Protoporphyrin IX is a potentially toxic compound. There are several types of porphyrias (most are inherited). The enzyme ferrochelatase converts it into heme. 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).
CAS Number553-12-8
Structure
Thumb
Synonyms
SynonymSource
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
Lebersdanmanual
Protoporphyrin IXChEBI
Protoporphyrin IX (6CI)biospider
Predicted 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
Chemical FormulaC34H34N4O4
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
InChI IdentifierInChI=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
Isomeric SMILESCC1=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
Average Molecular Weight562.6582
Monoisotopic Molecular Weight562.258005596
Classification
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

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Indirect biological role:

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionReddish-purple cryst.CCD
Mass CompositionC 72.58%; H 6.09%; N 9.96%; O 11.37%CCD
Melting PointMp 300°CCD
Boiling PointNot Available
Experimental Water Solubility0.169 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data[neutral]?max557;582;602 ( dication, aq. HCl)CCD
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSProtoporphyrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0uxu-1000290000-e22236fe3cca8eed1ecfSpectrum
Predicted GC-MSProtoporphyrin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-6000094000-b9c12952e100c5144cabSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000090000-5d5be53410134c5719abSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-1000590000-2d4157b9f73534d95a9cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-1000910000-07524a9291a1921dfafcSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000090000-5df26c1cfb9a0b16a91aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0296-1000190000-2d4bcb49201fc10adc09Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000230000-064fb944a966d08c06bfSpectrum
NMRNot Available
ChemSpider ID10469486
ChEMBL IDCHEMBL1325592
KEGG Compound IDC02191
Pubchem Compound ID4971
Pubchem Substance IDNot Available
ChEBI ID15430
Phenol-Explorer IDNot Available
DrugBank IDDB02285
HMDB IDHMDB00241
CRC / DFC (Dictionary of Food Compounds) IDHDX23-L:HDX23-L
EAFUS IDNot Available
Dr. Duke IDPROTOPORPHYRIN
BIGG ID39293
KNApSAcK IDC00007370
HET ID1HBG
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDProtoporphyrin IX
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
FerrochelataseDKFZp686P18130Q7KZA3
Pathways
NameSMPDB LinkKEGG Link
Porphyrin MetabolismSMP00024 map00860
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).