| Record Information |
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| Version | 4.0 |
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| Status | Expected but not Quantified |
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| Creation Date | 2009-02-04 10:38:54 UTC |
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| Update Date | 2020-02-26 21:35:37 UTC |
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| HMDB ID | HMDB0011680 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Inosine 2',3'-cyclic phosphate |
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| Description | Coproporphyrinogen I 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. Coproporphyrinogen I is a weakly acidic compound (based on its pKa). Coproporphyrinogen I exists in all living species, ranging from bacteria to humans. In humans, coproporphyrinogen I is involved in the metabolic disorder called the acute intermittent porphyria pathway. A large number of factors are capable of increasing porphyrin excretion, owing to different and multiple causes and etiologies: (1) the main site of the chronic hepatic porphyria disease process concentrates on the liver, (2) a functional and morphologic liver injury is almost regularly associated with this chronic porphyria, and (3) the toxic form due to occupational and environmental exposure takes mainly a subclinical course. 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). Outside of the human body, Coproporphyrinogen I has been detected, but not quantified in, several different foods, such as pak choy, pepper (c. chinense), tea leaf willows, rosemaries, and mung beans. This could make coproporphyrinogen I a potential biomarker for the consumption of these foods. A neurotoxin causes damage to nerve cells and nerve tissues. Coproporphyrinogen I is a porphyrin metabolite arising from heme synthesis. Coproporphyrinogen I is biosynthesized from the tetrapyrrole hydroxymethylbilane, which is converted by the action of uroporphyrinogen synthase to uroporphyrinogen I. Uroporphyrinogen I is subsequently converted into coproporphyrinogen I through a series of four decarboxylations. Decreased biliary excretion of coproporphyrin leading to a compensatory urinary excretion. Coproporphyrinogen I can be found in a number of food items, including cascade huckleberry, hyacinth bean, horseradish tree, and watercress. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 3,8,13,18-Tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,17-tetrapropionic acid | ChEBI | | COPROPORPHYRIN I | ChEBI | | 3,8,13,18-Tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,17-tetrapropionate | Generator | | 3,8,13,18-Tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,17-tetrapropanoate | HMDB | | 3,8,13,18-Tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,17-tetrapropanoic acid | HMDB | | 2',3' Cyclic imp | HMDB | | Inosine cyclic 2',3'-(hydrogen phosphate) | HMDB | | Inosine cyclic 2',3'-monophosphate | HMDB | | Inosine cyclic 2,3 monophosphate | HMDB | | Inosine cyclic-2',3'-monophosphate | HMDB | | 2',3'-Cyclic imp | MeSH, HMDB | | Inosine 2',3'-cyclic phosphoric acid | Generator |
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| Chemical Formula | C10H11N4O7P |
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| Average Molecular Weight | 330.1907 |
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| Monoisotopic Molecular Weight | 330.036535238 |
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| IUPAC Name | 9-[(3aR,4R,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxo-tetrahydro-2H-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-4-yl]-6,9-dihydro-3H-purin-6-one |
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| Traditional Name | 9-[(3aR,4R,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxo-tetrahydro-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-4-yl]-3H-purin-6-one |
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| CAS Registry Number | 15569-30-9 |
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| SMILES | OC[C@H]1O[C@H]([C@@H]2OP(O)(=O)O[C@H]12)N1C=NC2=C1NC=NC2=O |
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| InChI Identifier | InChI=1S/C10H11N4O7P/c15-1-4-6-7(21-22(17,18)20-6)10(19-4)14-3-13-5-8(14)11-2-12-9(5)16/h2-4,6-7,10,15H,1H2,(H,17,18)(H,11,12,16)/t4-,6-,7-,10-/m1/s1 |
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| InChI Key | SBJVDTBACUMFFD-KQYNXXCUSA-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 | |
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| Substituents | - Porphyrin
- Tetracarboxylic acid or derivatives
- Substituted pyrrole
- Pyrrole
- Heteroaromatic compound
- Carboxylic acid derivative
- Carboxylic acid
- Azacycle
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Disposition | Source: |
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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 | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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