| Record Information |
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| Version | 1.0 |
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| Created at | 2020-04-17 18:40:57 UTC |
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| Updated at | 2020-12-07 19:11:03 UTC |
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| CannabisDB ID | CDB004828 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | Protoporphyrin IX |
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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). Protoporphyrin IX is expected to be in Cannabis as all living plants are known to produce and metabolize it. |
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| Structure | |
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| Synonyms | | Value | 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 |
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| Chemical Formula | C34H34N4O4 |
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| Average Molecular Weight | 562.66 |
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| Monoisotopic Molecular Weight | 562.258 |
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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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| Traditional 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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| CAS Registry Number | 553-12-8 |
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| 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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| 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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| 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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| Ontology |
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| Physiological effect | Health effect: |
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| Disposition | Route of exposure: Source: Biological location: |
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| Role | Indirect biological role: Biological role: Industrial application: |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 300 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 0.17 mg/mL at 25 °C | Not Available | | logP | Not Available | Not Available |
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| Predicted Properties | [] |
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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| Predicted GC-MS | Protoporphyrin IX, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0uxu-1000290000-e22236fe3cca8eed1ecf | Spectrum | | Predicted GC-MS | Protoporphyrin IX, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00di-6000094000-b9c12952e100c5144cab | Spectrum | | Predicted GC-MS | Protoporphyrin IX, "Protoporphyrin IX,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Protoporphyrin IX, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Protoporphyrin IX, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Protoporphyrin IX, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Protoporphyrin IX, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Protoporphyrin IX, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Protoporphyrin IX, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Protoporphyrin IX, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Protoporphyrin IX, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Protoporphyrin IX, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Protoporphyrin IX, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Protoporphyrin IX, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Protoporphyrin IX, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Protoporphyrin IX, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Protoporphyrin IX, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Protoporphyrin IX, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Protoporphyrin IX, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Protoporphyrin IX, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Protoporphyrin IX, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Protoporphyrin IX, TBDMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Protoporphyrin IX, 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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