Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110478
Identification
Name: AMP
Description:A nucleoside 5'-monophosphate(2−) that results from the removal of two protons from the phosphate group of AMP.
Structure
Thumb
Synonyms:
  • 5'-AMP
  • adenosine-monophosphate
  • adenylic acid
  • adenosine 5'-phosphate
  • adenosine 5'-monophosphate
  • adenylate
  • 5'-adenylic acid
  • 5'-adenosine monophosphate
Chemical Formula: C10H12N5O7P
Average Molecular Weight: 345.21
Monoisotopic Molecular Weight: 347.0630843401
InChI Key: UDMBCSSLTHHNCD-KQYNXXCUSA-L
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)/p-2/t4-,6-,7-,10-/m1/s1
CAS number: 61-19-8
IUPAC Name:5'-O-phosphonatoadenosine
Traditional IUPAC Name: adenylate
SMILES:C(C3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))OP([O-])([O-])=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Nucleosides, nucleotides, and analogues
Sub ClassPurine nucleotides
Direct Parent Purine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Alkyl phosphate
  • Pyrimidine
  • Monosaccharide
  • Primary aromatic amine
  • Imidolactam
  • Phosphoric acid ester
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Heteroaromatic compound
  • Oxolane
  • Azole
  • Imidazole
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organic oxide
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Amine
  • Alcohol
  • Primary amine
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: 195 °C
Experimental Properties:
PropertyValueReference
Melting Point195 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility10 mg/mL at 20 °CBEILSTEIN
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.31 mg/mLALOGPS
logP-3.1ALOGPS
logP-4.8ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)4.97ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area186.07 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity74.07 m3·mol-1ChemAxon
Polarizability30 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Odd-Straight-Chain-234-Sat-FA + ATP + coenzyme A → Odd-Saturated-Fatty-Acyl-CoA + AMP + diphosphate
Citronellates + coenzyme A + ATP → citronellyll-CoA + AMP + diphosphate
coenzyme A + acetoacetate + ATP → acetoacetyl-CoA + diphosphate + AMP
thiamin + ATP → Hydrogen ion + thiamin diphosphate + AMP
3-Methyl-Saturated-Fatty-Acids + coenzyme A + ATP → 3-Methyl-Saturated-Fatty-Acyl-CoA + AMP + diphosphate
ADP-D-ribose + Water → AMP + CPD-15317 + Hydrogen ion
Water → AMP
NADH + Water → Hydrogen ion + NMNH + AMP
trans-cinnamate + coenzyme A + ATP → (E)-cinnamoyl-CoA + AMP + diphosphate
tRNA-uridine34 + TusE-S-sulfanylcysteine + ATP → tRNA-2-thiouridine34 + TusE-L-cysteine + AMP + diphosphate
Selenite + AMP + glutathione disulfide + Hydrogen ion → adenosine 5'-phosphoselenate + glutathione
coenzyme A + propanoate + ATP → propanoyl-CoA + diphosphate + AMP
linoleate + coenzyme A + ATP → linoleoyl-CoA + diphosphate + AMP
L-Glutamine + L-aspartate + ATP + Water → Hydrogen ion + L-glutamate + L-Asparagine + diphosphate + AMP
ATP + α-linolenate + coenzyme A → α-linolenoyl-CoA + diphosphate + AMP
oleate + coenzyme A + ATP → oleoyl-CoA + AMP + diphosphate
Long-Chain-Fatty-Acids + coenzyme A + ATP → Long-Chain-Acyl-CoAs + diphosphate + AMP
undecaprenyl-diphospho-(N-acetylglucosamine)-N-acetylmuramoyl-L-alanyl-γ-D-isoglutaminyl-N-(β-D-asparatyl)-L-lysyl-D-alanyl-D-alanine + Ammonium + ATP → Hydrogen ion + undecaprenyl-diphospho-(N-acetylglucosamine)-N-acetylmuramoyl-L-alanyl-γ-D-isoglutaminyl-N-(β-D-asparaginyl)-L-lysyl-D-alanyl-D-alanine + AMP + diphosphate
eicosapentaenoate + ATP + coenzyme A → eicosapentaenoyl-CoA + diphosphate + AMP
3-oxocholest-4-en-26-oate + ATP + coenzyme A → 3-oxocholest-4-en-26-oyl-CoA + AMP + diphosphate
cyclic-AMP + Water → Hydrogen ion + AMP
Hydrogen ion + L-Serine + ATP → diphosphate + AMP
DEOXYNUCLEOTIDESM + ATP + Deoxynucleotides → AMP + diphosphate + Deoxynucleotides
CPD66-39 + coenzyme A + ATP → Saturated-Fatty-Acyl-CoA + diphosphate + AMP
phytenate + ATP + coenzyme A → phytenoyl-CoA + AMP + diphosphate
ATP → AMP + diphosphate
biotin + ATP → diphosphate + AMP
phenylacetate + ATP + coenzyme A → phenylacetyl-CoA + AMP + diphosphate
(R)-4'-phosphopantothenate + L-Cysteine + ATP → Hydrogen ion + R-4'-phosphopantothenoyl-L-cysteine + diphosphate + AMP
R2OH-Straight-Chain-234-Sat-FA + ATP + coenzyme A → R2-2OH-Straight-Chain-234-Sat-FA-CoA + AMP + diphosphate
(15Z)-tetracosenoate + coenzyme A + ATP → (Z)-15-tetracosenoyl-CoA + diphosphate + AMP
O-ureidohomoserine + L-aspartate + ATP → Hydrogen ion + canavaninosuccinate + AMP + diphosphate
palmitate + coenzyme A + ATP → palmitoyl-CoA + diphosphate + AMP
GDP + ADP → GTP + AMP
3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoate + ATP + coenzyme A → 3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoyl-CoA + AMP + diphosphate
L-glutamate + ATP + Hydrogen ion → AMP + diphosphate
pristanate + coenzyme A + ATP → pristanoyl-CoA + diphosphate + AMP
2-Me-Branched-234-Sat-FA + coenzyme A + ATP → 2-Me-Branched-234-Sat-Fatty-Acyl-CoA + diphosphate + AMP
β-D-fructofuranose 6-phosphate + ADP → Hydrogen ion + fructose 1,6-bisphosphate + AMP
tRNAs-Asp-with-queuosine + ATP + L-glutamate → tRNAs-with-glutamylated-queuosine + AMP + diphosphate + Hydrogen ion
Sulfite + AMP + Acceptor + Hydrogen ion → adenosine 5'-phosphosulfate + Donor-H2
More...

Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-014i-0974000000-7ce25c09f93913b81e9bView in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-014i-0975000000-8175538459abaf92d36fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-052b-0209001000-f6c3cf706bb3b839d180View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-053s-0395300000-e2a342872025e6e960aeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-2b9fb262817de641a5cdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-053r-0007920000-ee7bab39079e225a1b07View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0109000000-52331e416cbdd8218b97View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-3900000000-ddc799b6e2bb5d5ac9a6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-68d6660e0cfbfb8f02adView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-27f73c3a0a9566986a0eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03dm-0007009001-639c5cafae90b10dfc5fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0290000000-e0b5612abd24736e70daView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0039210000-3e5b716531d739ca25d9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0009000000-9232b7438abb1f6256b6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0007-2109007000-3e1cf347bd9e054b9368View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-0002009000-b840e6edcca65562937bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0190000000-948ec97ae442eda212cbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0009000000-bd1c10704f289141803aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-0109000000-433eab5bd833cd92f290View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-000b-0709000000-fa268a51905a453bc6f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-002b-9104000000-bc358c1d8c03290fc49dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Eells JT, Spector R: Purine and pyrimidine base and nucleoside concentrations in human cerebrospinal fluid and plasma. Neurochem Res. 1983 Nov;8(11):1451-7. [6656991 ]
  • Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2(1):18. [15882454 ]
  • BISHOP C, RANKINE DM, TALBOTT JH: The nucleotides in normal human blood. J Biol Chem. 1959 May;234(5):1233-7. [13654353 ]
  • Lin CY, Ishida M: Elevation of cAMP levels in cerebrospinal fluid of patients with neonatal meningitis. Pediatrics. 1983 Jun;71(6):932-4. [6304612 ]
  • Pagani R, Tabucchi A, Carlucci F, Leoncini R, Consolmagno E, Molinelli M, Valerio P: Some aspects of purine nucleotide metabolism in human lymphocytes before and after infection with HIV-1 virus: nucleotide content. Adv Exp Med Biol. 1991;309B:43-6. [1781403 ]
  • Drezner MK, Neelon FA, Curtis HB, Lebovitz HE: Renal cyclic adenosine monophosphate: an accurate index of parathyroid function. Metabolism. 1976 Oct;25(10):1103-12. [184364 ]
  • Aschenbach WG, Sakamoto K, Goodyear LJ: 5' adenosine monophosphate-activated protein kinase, metabolism and exercise. Sports Med. 2004;34(2):91-103. [14965188 ]
  • Subramanian GM, Cronin PW, Poley G, Weinstein A, Stoughton SM, Zhong J, Ou Y, Zmuda JF, Osborn BL, Freimuth WW: A phase 1 study of PAmAb, a fully human monoclonal antibody against Bacillus anthracis protective antigen, in healthy volunteers. Clin Infect Dis. 2005 Jul 1;41(1):12-20. Epub 2005 May 24. [15937757 ]
  • Aurbach GD: Genetic disorders involving parathyroid hormone and calcitonin. Birth Defects Orig Artic Ser. 1971 May;7(6):48-54. [4155962 ]
  • Post RM, Cramer H, Goodwin FK: Cyclic AMP in cerebrospinal fluid of manic and depressive patients. Psychol Med. 1977 Nov;7(4):599-605. [201957 ]
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CAS61-19-8
ChEBI456215
ChemSpider10239183
HMDBHMDB00045
IAF126033534
KEGGC00020
MetaboLightsMTBLC456215
NCI20264
PubChem15938965