Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:06:10 UTC |
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Update date | 2020-09-17 15:38:30 UTC |
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Primary ID | FDB004277 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Protoporphyrin |
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Description | Protoporphyrin 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). |
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CAS Number | 553-12-8 |
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Structure | |
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Synonyms | Synonym | Source |
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3,3'-(3,7,12,17-Tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid | ChEBI | 3,7,12,17-Tetramethyl-8,13-divinylporphyrin-2,18-dipropanoic acid | ChEBI | H2PpIX | ChEBI | Kammerer's prophyrin | ChEBI | Ooporphyrin | ChEBI | Porphyrinogen IX | ChEBI | 3,3'-(3,7,12,17-Tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionate | Generator | 3,7,12,17-Tetramethyl-8,13-divinylporphyrin-2,18-dipropanoate | Generator | 3,3'-(3,7,12,17-Tetramethyl-8,13-divinylporphine-2,18-diyl)di | HMDB | PpIX | HMDB | Protoporphyrin | HMDB | Protoporphyrin-"ix" | HMDB | Protoporphyrin-IX | HMDB | Lebersdan | manual | Protoporphyrin IX | ChEBI | Protoporphyrin IX (6CI) | biospider |
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Predicted Properties | |
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Chemical Formula | C34H34N4O4 |
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IUPAC name | 3-[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 |
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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- |
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InChI Key | KSFOVUSSGSKXFI-UJJXFSCMSA-N |
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Isomeric 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 |
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Average Molecular Weight | 562.6582 |
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Monoisotopic Molecular Weight | 562.258005596 |
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Classification |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Tetrapyrroles and derivatives |
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Sub Class | Porphyrins |
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Direct Parent | Porphyrins |
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Alternative Parents | Not Available |
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Substituents | Not Available |
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Molecular Framework | Not Available |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Indirect biological role: Biological role: Industrial application: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Reddish-purple cryst. | CCD |
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Mass Composition | C 72.58%; H 6.09%; N 9.96%; O 11.37% | CCD |
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Melting Point | Mp 300° | CCD |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 0.169 mg/mL at 25 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | [neutral]?max557;582;602 ( dication, aq. HCl) | CCD |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | Protoporphyrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0uxu-1000290000-e22236fe3cca8eed1ecf | Spectrum | Predicted GC-MS | Protoporphyrin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00di-6000094000-b9c12952e100c5144cab | Spectrum | Predicted GC-MS | Protoporphyrin, "Protoporphyrin IX,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Protoporphyrin, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Protoporphyrin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Protoporphyrin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Protoporphyrin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Protoporphyrin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Protoporphyrin, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Protoporphyrin, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Protoporphyrin, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Protoporphyrin, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Protoporphyrin, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Protoporphyrin, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Protoporphyrin, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Protoporphyrin, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Protoporphyrin, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Protoporphyrin, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Protoporphyrin, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Protoporphyrin, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Protoporphyrin, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Protoporphyrin, TBDMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Protoporphyrin, TBDMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0000090000-5d5be53410134c5719ab | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00kb-1000590000-2d4157b9f73534d95a9c | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4l-1000910000-07524a9291a1921dfafc | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0000090000-5df26c1cfb9a0b16a91a | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0296-1000190000-2d4bcb49201fc10adc09 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9000230000-064fb944a966d08c06bf | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0000090000-87c1740ecd1a28f4a2d9 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03xu-0000590000-99160b987bb7e62ab362 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00di-0000900000-f2d9118441a9c8c47d79 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03dj-0000090000-d428ac6dc2fc4794cc41 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0j4j-0000090000-2b065966ec57bb97d511 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0uk9-1000970000-b435817e4dc349e65ab3 | 2021-09-23 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 10469486 |
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ChEMBL ID | CHEMBL1325592 |
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KEGG Compound ID | C02191 |
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Pubchem Compound ID | 4971 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 15430 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB02285 |
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HMDB ID | HMDB00241 |
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CRC / DFC (Dictionary of Food Compounds) ID | HDX23-L:HDX23-L |
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EAFUS ID | Not Available |
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Dr. Duke ID | PROTOPORPHYRIN |
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BIGG ID | 39293 |
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KNApSAcK ID | C00007370 |
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HET ID | 1HBG |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Protoporphyrin IX |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Name | Gene Name | UniProt ID |
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Ferrochelatase | DKFZp686P18130 | Q7KZA3 |
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Pathways | |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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