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Chemistry

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Also known as: 5'-adenylic acid, Adenosine 5'-monophosphate, Adenosine phosphate, 61-19-8, Adenylic acid, Adenosine 5'-phosphate

Molecular Formula

C₁₀H₁₄N₅O₇P

Molecular Weight

347.22 g/mol

InChI Key

UDMBCSSLTHHNCD-KQYNXXCUSA-N

FDA UNII

415SHH325A

Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position.

1 2D Structure

Adenosine 5

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate

2.1.2 InChI

InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1

2.1.3 InChI Key

UDMBCSSLTHHNCD-KQYNXXCUSA-N

2.1.4 Canonical SMILES

C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)COP(=O)(O)O)O)O)N

2.1.5 Isomeric SMILES

C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)N

2.2 Other Identifiers

2.2.1 UNII

415SHH325A

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2' Adenosine Monophosphate

2. 2' Adenylic Acid

3. 2'-adenosine Monophosphate

4. 2'-adenylic Acid

5. 2'-amp

6. 5' Adenylic Acid

7. 5'-adenylic Acid

8. 5'-phosphate, Adenosine

9. Acid, 2'-adenylic

10. Acid, 5'-adenylic

11. Adenosine 2' Phosphate

12. Adenosine 2'-phosphate

13. Adenosine 3' Phosphate

14. Adenosine 3'-phosphate

15. Adenosine 5' Phosphate

16. Adenosine 5'-phosphate

17. Adenosine Phosphate Dipotassium

18. Adenosine Phosphate Disodium

19. Adenylic Acid

20. Amp

21. Dipotassium, Adenosine Phosphate

22. Disodium, Adenosine Phosphate

23. Monophosphate, 2'-adenosine

24. Phosphaden

25. Phosphate Dipotassium, Adenosine

26. Phosphate Disodium, Adenosine

2.3.2 Depositor-Supplied Synonyms

1. 5'-adenylic Acid

2. Adenosine 5'-monophosphate

3. Adenosine Phosphate

4. 61-19-8

5. Adenylic Acid

6. Adenosine 5'-phosphate

7. 5'-amp

8. Adenylate

9. Phosphentaside

10. Adenovite

11. Phosphaden

12. Cardiomone

13. Lycedan

14. Phosaden

15. Amp

16. Vitamin B8

17. Adenosine-5'-monophosphate

18. My-b-den

19. Myoston

20. Ergadenylic Acid

21. Monophosphadenine

22. Muscle Adenylic Acid

23. Muskeladenylsaeure

24. 5'-adenosine Monophosphate

25. Amp (nucleotide)

26. Adenosine 5'-(dihydrogen Phosphate)

27. A-5mp

28. Adenosine 5'-phosphoric Acid

29. Adenosini Phosphas

30. Adenosine-5-monophosphoric Acid

31. Adenosine-5'-monophosphoric Acid

32. Adenyl

33. Fosfato De Adenosina

34. Phosphate D'adenosine

35. Adenosine-5-phosphate

36. Adenosine-monophosphate

37. Pado

38. Adenylic Acid (van)

39. Muskeladenosin-phosphorsaeure

40. Adenosine-5'p

41. Adenosine-phosphate

42. Amp (van)

43. Adenosine 5'-monophosphoric Acid

44. Ado5'p

45. 5'-o-phosphonoadenosine

46. A5mp

47. Adenosini Phosphas [inn-latin]

48. Fosfato De Adenosina [inn-spanish]

49. Phosphate D'adenosine [inn-french]

50. Nsc-20264

51. Adenosine, Mono(dihydrogen Phosphate) (ester)

52. Hsdb 3281

53. A 5mp

54. Brn 0054612

55. [(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl Dihydrogen Phosphate

56. Chebi:16027

57. Adenosine5'-monophosphate

58. Adenosine Phosphate [usan:ban:inn]

59. Adenosine 5' Monophosphate

60. Chembl752

61. ((2r,3s,4r,5r)-5-(6-amino-9h-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl Dihydrogen Phosphate

62. 122768-03-0

63. 415shh325a

64. {[(2r,3s,4r,5r)-5-(6-amino-9h-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic Acid

65. Ncgc00163319-01

66. Ncgc00163319-03

67. Dsstox_cid_2560

68. Dsstox_rid_76630

69. Dsstox_gsid_22560

70. 136920-07-5

71. 67583-85-1

72. Adenosine 5-monophosphate

73. Adenosine-5'-monophosphate, Free Acid

74. 7gpb

75. 8gpb

76. Cas-61-19-8

77. Adenosine Phosphate [usan:inn:ban]

78. Acetamide, 2,2,2,2-(1,2-ethanediyldinitrilo)tetrakis-, N,n,n,n,n,n,n,n-octa-c12-18-alkyl Derivs.

79. Adenosin-5'-monophosphat

80. Adenyl (tn)

81. Einecs 200-500-0

82. Nsc 20264

83. Adenosine 5 -monophosphate

84. Adenosine Monophosphate (amp)

85. Unii-415shh325a

86. Muscle Adenylate

87. Mfcd00005750

88. 5'adenylic Acid

89. Adenosine 5'-monophosphate, Free Acid

90. Adenosine Phosphate (usan/inn)

91. 1pyg

92. 2gsu

93. 5'-adenylate

94. My-beta-den

95. 1ua4

96. 1z6s

97. Adenosin-5-monophosphate

98. Adenosine 5'-phosphorate

99. Prestwick0_000356

100. Prestwick1_000356

101. Prestwick2_000356

102. Prestwick3_000356

103. Bmse000005

104. Bmse000873

105. Bmse000992

106. Epitope Id:137353

107. Adenosine-5-monophosphorate

108. Schembl5588

109. Adenosine-5'-monophosphorate

110. Adenosine-5'-phosphoric Acid

111. Bspbio_000451

112. 4-26-00-03615 (beilstein Handbook Reference)

113. Spbio_002372

114. Bpbio1_000497

115. Gtpl2455

116. [3h]adenosine 5'-monophosphate

117. Adenosine Phosphate(vitamin B8)

118. Dtxsid5022560

119. Schembl18287224

120. 5'-adenylic Acid [mi]

121. Bdbm18137

122. 5'-adenylic Acid [fcc]

123. Adenosine Phosphate [inn]

124. [(2r,3s,4r)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-2-oxolanyl]methyl Dihydrogen Phosphate

125. Adenosine Phosphate [hsdb]

126. Adenosine Phosphate [inci]

127. Adenosine Phosphate [usan]

128. Adenosine Phosphate [vandf]

129. 7a8e6d15-9136-44c1-88c9-e1a224638e56

130. Adenosine Phosphate [mart.]

131. Amy30021

132. Hy-a0181

133. Zinc3860156

134. 5'-adenylic Acid [usp-rs]

135. Tox21_112046

136. Adenosine Phosphate [who-dd]

137. S9366

138. Akos015833068

139. Akos015888563

140. Tox21_112046_1

141. Ccg-267996

142. Db00131

143. Adenosine 5'-monophosphate, Free Acid

144. Adenosine 5\'-monophosphate Monohydrate

145. Ncgc00163319-02

146. [(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl Dihydrogen Phosphate

147. As-11783

148. Adenosine Monophosphate (5'-adenylic Acid)

149. Db-022416

150. A0158

151. Cs-0017523

152. Adenosine 5'-(dihydrogen Phosphate).

153. C00020

154. D02769

155. F20323

156. 005a750

157. Adenosine-3(+2')-monophosphoric Acid Monohydrate*

158. Q318369

159. J-700145

160. W-105182

161. Adenosine 5'-monophosphate-agarose, Lyophilized Powder

162. Adenosine 5'-monophosphate-agarose, Saline Suspension

163. 9h-purin-6-amine, 9-(5-o-phosphono-.beta.-d-ribofuranosyl)-

164. 9h-purin-6-amine, 9-(5-o-phosphono-beta-d-ribofuranosyl)-

165. [(2r,3s,4r,5r)-5-adenin-9-yl-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl Dihydrogen Phosphate;hydrate

166. 53624-78-5

167. Adenosine 5'-monophosphate-agarose, Lyophilized Powder, Contains Lactose Stabilizers That Must Be Removed Prior To Use.

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₁₄N₅O₇P
Molecular Weight	347.22 g/mol
XLogP3	-3.5
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	4
Exact Mass	347.06308480 g/mol
Monoisotopic Mass	347.06308480 g/mol
Topological Polar Surface Area	186 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	481
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
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 Therapeutic Uses

ENERGY-RICH PHOSPHATES REPRESENT "ENERGY POOL" FROM WHICH CELLS OBTAIN THEIR ENERGY REQUIREMENTS. IN PATHOLOGICAL SITUATIONS, WHERE METABOLISM IS ALTERED, SPECIFIC DETERMINATION OF NUCLEOTIDES IS OF DIAGNOSTIC VALUE & IS INCREASINGLY USED IN HEART, LIVER & KIDNEY DISEASES.

Bergmeyer, H.W. (ed.). Methods of Enzymatic Analysis. 2nd English ed. New York City: Academic Press, 1974., p. 2127

4.2 Drug Indication

For nutritional supplementation, also for treating dietary shortage or imbalance

5 Pharmacology and Biochemistry

5.1 Pharmacology

Adenosine monophosphate, also known as 5'-adenylic acid and abbreviated AMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside adenosine. AMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase adenine. AMP is used as a dietary supplement to boost immune activity, and is also used as a substitute sweetener to aid in the maintenance of a low-calorie diet.

5.2 Absorption, Distribution and Excretion

AMP ADMIN TO RATS ORALLY WAS RECOVERED INTACT IN BLOOD. IT APPEARED RAPIDLY IN BLOOD (IN 15-30 MIN) & WAS ALSO RAPIDLY DISTRIBUTED, SINCE PLASMA CONCN WAS DECR BY FACTOR OF 5 IN 2 HR.

MALMARY-NEBOT MF ET AL; EUR J DRUG METAB PHARMACOKINET 4(2) 97 (1979)

5.3 Mechanism of Action

Nucleotides such as Adenosine-5'-Monophosphate affect a number of immune functions, including the reversal of malnutrition and starvation-induced immunosuppression, the enhancement of T-cell maturation and function, the enhancement of natural killer cell activity, the improvement of delayed cutaneous hypersensitivity, helping resistance to such infectious agents as Staphylococcus aureus and Candida albicans, and finally the modulation of T-cell responses toward type 1 CD4 helper lymphocytes or Th1 cells. Studies have shown that mice fed a nucleotide-free diet have both impaired humoral and cellular immune responses. The addition of dietary nucleotides normalizes both types of responses. RNA, a delivery form of nucleotides, and ribonucleotides were used in these studies. The mechanism of the immune-enhancing activity of nucleic acids/nucleotides is not clear.

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