Adenosine monophosphate

Adenosine monophosphate
Names
	IUPAC name 5′-Adenylic acid
	Systematic IUPAC name [(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
	Other names Adenosine 5'-monophosphate; Vitamin B8
Identifiers
CAS Number	61-19-8 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:16027 ;
ChEMBL	ChEMBL752 ;
ChemSpider	5858 ;
DrugBank	DB00131 ;
ECHA InfoCard	100.000.455
IUPHAR/BPS	2455;
KEGG	C00020 ;
MeSH	Adenosine+monophosphate
PubChem CID	6083;
UNII	415SHH325A ;
CompTox Dashboard (EPA)	DTXSID5022560 ;
	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 Key: UDMBCSSLTHHNCD-KQYNXXCUSA-N ; InChI=1/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 Key: UDMBCSSLTHHNCD-KQYNXXCUBP;
	SMILES O=P(O)(O)OC[C@H]3O[C@@H](n2cnc1c(ncnc12)N)[C@H](O)[C@@H]3O; c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)N;
Properties
Chemical formula	C10H14N5O7P
Molar mass	347.22 g/mol
Appearance	white crystalline powder
Density	2.32 g/mL
Melting point	178 to 185 °C (352 to 365 °F; 451 to 458 K)
Boiling point	798.5 °C (1,469.3 °F; 1,071.7 K)
Acidity (pKa)	0.9, 3.8, 6.1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Adenosine monophosphate (AMP), also known as 5'-adenylic acid, is a nucleotide. AMP consists of a phosphate group, the sugar ribose, and the nucleobase adenine. It is an ester of phosphoric acid and the nucleoside adenosine. As a substituent it takes the form of the prefix adenylyl-.

AMP plays an important role in many cellular metabolic processes, being interconverted to adenosine triphosphate (ATP) and adenosine diphosphate (ADP), as well as allosterically activating enzymes such as myophosphorylase-b. AMP is also a component in the synthesis of RNA. AMP is present in all known forms of life.

Names


IUPAC name 5′-Adenylic acid
Systematic IUPAC name [(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
Other names Adenosine 5'-monophosphate Vitamin B8
Identifiers
CAS Number	61-19-8^Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:16027^Y
ChEMBL	ChEMBL752^Y
ChemSpider	5858^Y
DrugBank	DB00131^Y
ECHA InfoCard	100.000.455
IUPHAR/BPS	2455
KEGG	C00020^Y
MeSH	Adenosine+monophosphate
PubChem CID	6083
UNII	415SHH325A^Y
CompTox Dashboard (EPA)	DTXSID5022560
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^Y Key: UDMBCSSLTHHNCD-KQYNXXCUSA-N^Y InChI=1/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 Key: UDMBCSSLTHHNCD-KQYNXXCUBP
SMILES O=P(O)(O)OC[C@H]3O[C@@H](n2cnc1c(ncnc12)N)[C@H](O)[C@@H]3O c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)N
Properties
Chemical formula	C₁₀H₁₄N₅O₇P
Molar mass	347.22 g/mol
Appearance	white crystalline powder
Density	2.32 g/mL
Melting point	178 to 185 °C (352 to 365 °F; 451 to 458 K)
Boiling point	798.5 °C (1,469.3 °F; 1,071.7 K)
Acidity (pK_a)	0.9, 3.8, 6.1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references