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    Chemistry

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    Also known as: 54-47-7, Codecarboxylase, Pyridoxal 5'-phosphate, Pyridoxal 5-phosphate, Pyridoxyl phosphate, (4-formyl-5-hydroxy-6-methylpyridin-3-yl)methyl dihydrogen phosphate
    Molecular Formula
    C8H10NO6P
    Molecular Weight
    247.14  g/mol
    InChI Key
    NGVDGCNFYWLIFO-UHFFFAOYSA-N
    FDA UNII
    F06SGE49M6
    Pyridoxal Phosphate
    This is the active form of VITAMIN B 6 serving as a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into pyridoxamine phosphate (PYRIDOXAMINE).
    1 2D Structure

    Pyridoxal Phosphate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (4-formyl-5-hydroxy-6-methylpyridin-3-yl)methyl dihydrogen phosphate
    2.1.2 InChI
    InChI=1S/C8H10NO6P/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14/h2-3,11H,4H2,1H3,(H2,12,13,14)
    2.1.3 InChI Key
    NGVDGCNFYWLIFO-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=NC=C(C(=C1O)C=O)COP(=O)(O)O
    2.2 Other Identifiers
    2.2.1 UNII
    F06SGE49M6
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Phosphate, Pyridoxal

    2. Pyridoxal 5 Phosphate

    3. Pyridoxal 5-phosphate

    4. Pyridoxal P

    5. Pyridoxal-p

    2.3.2 Depositor-Supplied Synonyms

    1. 54-47-7

    2. Codecarboxylase

    3. Pyridoxal 5'-phosphate

    4. Pyridoxal 5-phosphate

    5. Pyridoxyl Phosphate

    6. (4-formyl-5-hydroxy-6-methylpyridin-3-yl)methyl Dihydrogen Phosphate

    7. Pyridoxal P

    8. Biosechs

    9. Hairoxal

    10. Pyromijin

    11. Vitazechs

    12. Pyridoxal-5'-phosphate

    13. Hiadelon

    14. Pidopidon

    15. Himitan

    16. Phosphopyridoxal

    17. Pyridoxal-5-phosphate

    18. 853645-22-4

    19. Pal-p

    20. Sechvitan

    21. Pydoxal

    22. Piodel

    23. Apolon B6

    24. Hi-pyridoxin

    25. Pyridoxal-p

    26. Phosphopyridoxal Coenzyme

    27. Vitahexin P

    28. Hexermin P

    29. Coenzyme B6

    30. Pyridoxal Monophosphate

    31. Pyridoxaldehyde Phosphate

    32. Apolon B(sub 6)

    33. Plp

    34. Phosphoridoxal Coenzyme

    35. Pyridoxal 5'-phosphate Hydrate

    36. Vitamin B6 Phosphate

    37. Pyridoxal 5'-(dihydrogen Phosphate)

    38. Pyridoxal-5p

    39. Pyridoxal 5-monophosphoric Acid Ester

    40. Vitahexin-p

    41. Hexermin-p

    42. Pyridoxal Phosphate [jan]

    43. 3-hydroxy-2-methyl-5-((phosphonooxy)methyl)-4-pyridinecarboxaldehyde

    44. 4-pyridinecarboxaldehyde, 3-hydroxy-2-methyl-5-((phosphonooxy)methyl)-

    45. Pyridoxal 5/'-phosphate (hydrate)

    46. Pyridoxal, 5-(dihydrogen Phosphate)

    47. 3-hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-phosphate

    48. 3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinecarboxaldehyde

    49. Pyridoxal Phosphate Anhydrous

    50. 2-methyl-3-hydroxy-4-formyl-5-hydroxymethylpyridine-5-calcium Phosphate

    51. 4-pyridinecarboxaldehyde, 3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]-

    52. Chembl82202

    53. F06sge49m6

    54. Chebi:18405

    55. Pyridoxal-phosphate

    56. Nsc82388

    57. Nsc-82388

    58. Mc-1

    59. Pyridoxal 5'-phosphate;pyridoxyl Phosphate

    60. 3-hydroxy-2-methyl-5-([phosphonooxy]methyl)-4-pyridinecarboxaldehyde

    61. 2-methyl-3-hydroxy-4-formyl-5-hydroxymethylpyridine-5-calcium Phosphate Trihydrate

    62. (4-formyl-5-hydroxy-6-methyl-3-pyridyl)methyl Dihydrogen Phosphate

    63. [(4-formyl-5-hydroxy-6-methylpyridin-3-yl)methoxy]phosphonic Acid

    64. Pyridoxalphosphate

    65. Sechvitan, Vitahexin P

    66. Ncgc00166300-01

    67. Pyridoxal-5-monophosphate

    68. Einecs 200-208-3

    69. Nsc 82388

    70. Pyridoxal 5'-phosphate 5

    71. Pyridoxal Phosphate (6ci)

    72. Unii-f06sge49m6

    73. Vitamin B6 Phosphate (ester)

    74. Pyridoxal, 5-(dihydrogenphosphate)

    75. Sri 2392

    76. Pyridoxal Phosphate

    77. P-5'-p

    78. Pridoxal-5-phosphate

    79. Pyridoxal 5 Inverted Exclamation Marka-phosphate Hydrate

    80. Pyridoxal 5''-phosphate

    81. P5p

    82. Pyridoxal, 5-(dihydrogen Phosphate) (8ci)

    83. (4-formyl-5-hydroxy-6-methyl(3-pyridyl))methyl Dihydrogen Phosphate

    84. Bmse000111

    85. Pyridoxal 5'-phosphate Monohydrate, Vitamin B6

    86. Schembl23158

    87. Pyridoxal 5'-phosphoric Acid

    88. Gtpl5249

    89. Sgcut00188

    90. Dtxsid4048351

    91. Pyridoxal 5'-phosphate Anhydrous

    92. 2-methyl-3-hydroxy-4-formyl-5-pyridylmethylphosphoric Acid

    93. Ex-a980

    94. 4-formyl-5-hydroxy-6-methyl-pyridin-3-yl)methoxyphosphonic Acid

    95. Act03489

    96. Bcp34576

    97. Hy-b1744

    98. Pyridoxal 5-phosphate [mi]

    99. Pyridoxal Phosphate Treated .beta.-lactoglobulin From Bovine Whey

    100. To_000077

    101. Zinc1532514

    102. (4-formyl-5-hydroxy-6-methyl-3-pyridinyl)methyl Dihydrogen Phosphate

    103. Bdbm50118216

    104. Mfcd00006333

    105. Pyridoxal Phosphate [who-dd]

    106. S5311

    107. Stl185213

    108. Pyridoxal 5''-(dihydrogen Phosphate)

    109. Pyridoxal 5-phosphate [inci]

    110. Akos015891654

    111. Phosphoric Acid Mono-(4-formyl-5-hydroxy-6-methyl-pyridin-3-ylmethyl) Ester

    112. Pyridoxal 5'-phosphate;codecarboxylase

    113. Ccg-266929

    114. Cs-7767

    115. Db00114

    116. Sb18794

    117. Pyridoxal 5'-phosphate [vandf]

    118. Pyridoxal 5'-phosphate Hydrate, >=98%

    119. As-19314

    120. Db-052584

    121. Vitamin B6 (pyridoxal 5-phosphate)

    122. Ft-0631236

    123. Ft-0655876

    124. Isonicotinaldehyde, 5-(dihydrogen Phosphate)

    125. C00018

    126. F17391

    127. Pyridoxal 5 Inverted Exclamation Marka-phosphate

    128. Pyridoxal 5'-phosphate Monohydrate - Vitamin B6

    129. 468c251

    130. A841303

    131. Q418957

    132. Sr-01000944534

    133. Q-201645

    134. Sr-01000944534-1

    135. A26bdb6a-282a-4d13-a916-7b2b215b0fd6

    136. (4-formyl-5-hydroxy-6-methylpyridin-3-yl)methyldihydrogenphosphate

    137. 3-hydroxy-2-methyl-5-([phosphonooxy]methyl)-4-pyridinecarbaldehyde

    138. (4-methanoyl-6-methyl-5-oxidanyl-pyridin-3-yl)methyl Dihydrogen Phosphate

    139. 4-pyridinecarboxaldehyde,3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]-

    140. 4-pyridinecarboxaldehyde, 3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]- (9ci)

    141. Pyridoxal 5'-phosphate Hydrate, Powder, Bioreagent, Suitable For Cell Culture

    2.4 Create Date
    2004-09-16
    3 Chemical and Physical Properties
    Molecular Weight 247.14 g/mol
    Molecular Formula C8H10NO6P
    XLogP3-1.1
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count4
    Exact Mass247.02457404 g/mol
    Monoisotopic Mass247.02457404 g/mol
    Topological Polar Surface Area117 Ų
    Heavy Atom Count16
    Formal Charge0
    Complexity292
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For nutritional supplementation and for treating dietary shortage or imbalance.

    Investigated for use/treatment in coronary artery disease.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    The two major forms of vitamin B6 are pyridoxine and pyridoxamine. In the liver they are converted to pyridoxal phosphate (PLP) which is a cofactor in many reactions of amino acid metabolism. PLP also is necessary for the enzymatic reaction governing the release of glucose from glycogen. Pyroluria is one potential cause of vitamin B6 deficiency.

    5.2 MeSH Pharmacological Classification

    Vitamin B Complex

    A group of water-soluble vitamins, some of which are COENZYMES. (See all compounds classified as Vitamin B Complex.)

    5.3 ATC Code

    A - Alimentary tract and metabolism

    A11 - Vitamins

    A11H - Other plain vitamin preparations

    A11HA - Other plain vitamin preparations

    A11HA06 - Pyridoxal phosphate

    5.4 Mechanism of Action

    Pyridoxal Phosphate is a coenzyme of many enzymatic reactions. It is the active form of vitamin B6 which comprises three natural organic compounds, pyridoxal, pyridoxamine and pyridoxine. Pyridoxal phosphate acts as a coenzyme in all transamination reactions, and in some oxylation and deamination reactions of amino acids. The aldehyde group of pyridoxal phosphate forms a Schiff-base linkage with the epsilon-amino group of a specific lysine group of the aminotransferase enzyme. The alpha-amino group of the amino acid substrate displaces the epsilon-amino group of the active-site lysine residue. The resulting aldimine becomes deprotonated to become a quinoid intermediate, which in turn accepts a proton at a different position to become a ketimine. Ketimine becomes hydrolyzed so that the amino group remains on the protein complex.

    MC-1 is a biologically active natural product which can be regarded as a chemical entity that has been evolutionarily selected and validated for binding to particular protein domains. Thus, its underlying structural architecture, or scaffold, has already been biologically established as safe and active, providing a powerful guiding principle for novel drug and library development.

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