| Record Information |
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| Version | 1.0 |
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| Creation date | 2015-10-09 22:29:40 UTC |
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| Update date | 2017-01-19 02:36:19 UTC |
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| FoodComEx ID | PC000286 |
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| FoodDB Record | FDB004277 |
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| Chemical Information |
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| 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-propionate | Generator | | 3,3'-(3,7,12,17-Tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid | ChEBI | | 3,3'-(3,7,12,17-Tetramethyl-8,13-divinylporphine-2,18-diyl)di | HMDB | | 3,7,12,17-Tetramethyl-8,13-divinylporphyrin-2,18-dipropanoate | Generator | | 3,7,12,17-Tetramethyl-8,13-divinylporphyrin-2,18-dipropanoic acid | ChEBI | | H2PpIX | ChEBI | | Kammerer's prophyrin | ChEBI | | Lebersdan | manual | | Ooporphyrin | manual | | Porphyrinogen IX | ChEBI | | PpIX | HMDB | | Protoporphyrin IX | ChEBI | | Protoporphyrin IX (6CI) | biospider | | Protoporphyrin-"ix" | HMDB | | Protoporphyrin-IX | HMDB |
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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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| Chemical Taxonomy |
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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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| Physico-Chemical Properties - Experimental |
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| Property | Value | Reference |
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| Experimental logP | 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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| Melting Point | Mp 300° | CCD |
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| Foods of Origin |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Production Data |
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| Production Method | commercial |
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| Production Method Reference | Not Available |
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| Production Method Reference File | Not Available |
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| Quantity Available | Production upon request, up to 1 g |
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| Delivery Time | Not Available |
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| Storage Form | solid |
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| Storage Conditions | -80°C |
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| Stability | Not Available |
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| Purity | Not Available |
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| Spectra |
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| Spectral Data Upon Request | Not Available |
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| Provider Information |
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| Commercial Vendors |
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| AKSci | V0221 |
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| Toronto Research Chemicals | P839138 |
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