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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

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 Formula	C₈H₁₀NO₆P
Molecular Weight	247.14 g/mol
XLogP3	-1.1
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	4
Exact Mass	247.02457404 g/mol
Monoisotopic Mass	247.02457404 g/mol
Topological Polar Surface Area	117 Å²
Heavy Atom Count	16
Formal Charge	0
Complexity	292
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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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