Record Information |
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Version | 1.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2021-06-29 00:47:07 UTC |
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NP-MRD ID | NP0000927 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Pyridoxamine 5'-phosphate |
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Description | Pyridoxamine 5'-phosphate belongs to the class of organic compounds known as pyridoxamine 5'-phosphates. These are heterocyclic aromatic compounds containing a pyridoxamine that carries a phosphate group at the 5'-position. Vitamin B6 is a water-soluble compound that was discovered in 1930s during nutrition studies on rats. The vitamin was named pyridoxine to indicate its structural homology to pyridine. Later it was shown that vitamin B6 could exist in two other, slightly different, chemical forms, termed pyridoxal and pyridoxamine. All three forms of vitamin B6 are precursors of an activated compound known as pyridoxal 5-phosphate (PLP), which plays a vital role as the cofactor of a large number of essential enzymes in the human body. Vitamin B6 is a water-soluble vitamin. The three major forms of vitamin B6 are pyridoxine (also known as pyridoxol), pyridoxal, and pyridoxamine, which are all converted in the liver to pyridoxal 5-phosphate (PLP) a cofactor in many reactions of amino acid metabolism. PLP also is necessary for the enzymatic reaction governing the release of glucose from glycogen. |
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Structure | CC1=NC=C(COP(O)(O)=O)C(CN)=C1O InChI=1S/C8H13N2O5P/c1-5-8(11)7(2-9)6(3-10-5)4-15-16(12,13)14/h3,11H,2,4,9H2,1H3,(H2,12,13,14) |
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Synonyms | Value | Source |
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4'-DEOXY-4'-aminopyridoxal-5'-phosphATE | ChEBI | Pyridoxamine 5'-(dihydrogen phosphate) | ChEBI | Pyridoxamine 5'-phosphoric acid | ChEBI | Pyridoxamine 5-phosphate | ChEBI | Pyridoxamine 5-phosphoric acid | ChEBI | Pyridoxamine phosphate | ChEBI | 4'-DEOXY-4'-aminopyridoxal-5'-phosphoric acid | Generator | Pyridoxamine 5'-(dihydrogen phosphoric acid) | Generator | Pyridoxamine phosphoric acid | Generator | Pyridoxamine-p | HMDB | PMP | HMDB | Pyridoxamine 5’-phosphate | HMDB | 4’-deoxy-4’-aminopyridoxal-5’-phosphate | HMDB | 4’-deoxy-4’-aminopyridoxal-5’-phosphoric acid | HMDB | Pyridoxamine 5'-phosphate | HMDB |
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Chemical Formula | C8H13N2O5P |
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Average Mass | 248.1730 Da |
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Monoisotopic Mass | 248.05621 Da |
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IUPAC Name | {[4-(aminomethyl)-5-hydroxy-6-methylpyridin-3-yl]methoxy}phosphonic acid |
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Traditional Name | pyridoxamine-5'-phosphate |
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CAS Registry Number | 529-96-4 |
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SMILES | CC1=NC=C(COP(O)(O)=O)C(CN)=C1O |
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InChI Identifier | InChI=1S/C8H13N2O5P/c1-5-8(11)7(2-9)6(3-10-5)4-15-16(12,13)14/h3,11H,2,4,9H2,1H3,(H2,12,13,14) |
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InChI Key | ZMJGSOSNSPKHNH-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as pyridoxamine 5'-phosphates. These are heterocyclic aromatic compounds containing a pyridoxamine that carries a phosphate group at the 5'-position. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Pyridines and derivatives |
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Sub Class | Pyridoxamines |
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Direct Parent | Pyridoxamine 5'-phosphates |
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Alternative Parents | |
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Substituents | - Pyridoxamine 5'-phosphate
- Monoalkyl phosphate
- Aralkylamine
- Hydroxypyridine
- Methylpyridine
- Organic phosphoric acid derivative
- Alkyl phosphate
- Phosphoric acid ester
- Heteroaromatic compound
- Azacycle
- Primary aliphatic amine
- Hydrocarbon derivative
- Amine
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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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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General References | - Coburn SP, Mahuren JD, Pauly TA, Ericson KL, Townsend DW: Alkaline phosphatase activity and pyridoxal phosphate concentrations in the milk of various species. J Nutr. 1992 Dec;122(12):2348-53. doi: 10.1093/jn/122.12.2348. [PubMed:1453218 ]
- Driskell JA, Chrisley BM, Reynolds LK, Moak SW: Plasma B6 vitamer and plasma and urinary 4-pyridoxic acid concentrations of middle-aged obese black women. J Chromatogr. 1991 Aug 23;568(2):333-40. doi: 10.1016/0378-4347(91)80171-8. [PubMed:1783639 ]
- Smith P, Szu PH, Bui C, Liu HW, Tsai SC: Structure and mutagenic conversion of E1 dehydrase: at the crossroads of dehydration, amino transfer, and epimerization. Biochemistry. 2008 Jun 17;47(24):6329-41. doi: 10.1021/bi702449p. Epub 2008 May 21. [PubMed:18491919 ]
- Jankowska M, Marszall M, Debska-Slizien A, Carrero JJ, Lindholm B, Czarnowski W, Rutkowski B, Trzonkowski P: Vitamin B6 and the immunity in kidney transplant recipients. J Ren Nutr. 2013 Jan;23(1):57-64. doi: 10.1053/j.jrn.2012.01.023. Epub 2012 Mar 21. [PubMed:22445054 ]
- Brandon DL, Corse JW, Windle JJ, Layton LL: Two homogeneous immunoassays for pyridoxamine. J Immunol Methods. 1985 Apr 8;78(1):87-94. doi: 10.1016/0022-1759(85)90331-x. [PubMed:2580028 ]
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