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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-12 23:23:28 UTC
Update Date2018-05-20 00:02:49 UTC
HMDB IDHMDB0003540
Secondary Accession Numbers
  • HMDB0006550
  • HMDB03540
  • HMDB06550
Metabolite Identification
Common Name3'-AMP
Description3'-AMP, also known as 3'-adenylic acid or AMP 3'-phosphate, belongs to the class of organic compounds known as ribonucleoside 3'-phosphates. These are ribonucleosides that contain a phosphate group attached to the C-3 carbon of the ribose or deoxyribose moiety. The nucleobases here are limited to purine, pyrimidine, and pyridine derivatives. 3'-AMP exists as a solid, slightly soluble (in water), and an extremely strong acidic compound (based on its pKa). 3'-AMP has been primarily detected in saliva. In humans, 3'-AMP is involved in the tryptophan metabolism pathway, the cerebrotendinous xanthomatosis (CTX) pathway, bile acid biosynthesis pathway, and congenital bile acid synthesis defect type II pathway. 3'-AMP is also involved in several metabolic disorders, some of which include Beta ureidopropionase deficiency, 27-hydroxylase deficiency, the familial hypercholanemia (fhca) pathway, and the zellweger syndrome pathway.
Structure
Thumb
Synonyms
ValueSource
3'-Adenosine monophosphateChEBI
3'-Adenylic acidChEBI
Adenosine 3'-monophosphateChEBI
Adenosine 3'-phosphateChEBI
Adenosine-3'-monophosphateChEBI
AMP 3'-PhosphateChEBI
Synadenylic acidChEBI
3'-Adenosine monophosphoric acidGenerator
3'-AdenylateGenerator
Adenosine 3'-monophosphoric acidGenerator
Adenosine 3'-phosphoric acidGenerator
Adenosine-3'-monophosphoric acidGenerator
AMP 3'-Phosphoric acidGenerator
SynadenylateGenerator
Adenosine-3'-phosphateHMDB
Yeast adenylic acidHMDB
2' Adenylic acidMeSH
5' Adenylic acidMeSH
Phosphate dipotassium, adenosineMeSH
5'-Adenylic acidMeSH
Adenylic acidMeSH
5'-Phosphate, adenosineMeSH
Adenosine 2'-phosphateMeSH
Dipotassium, adenosine phosphateMeSH
Phosphate disodium, adenosineMeSH
Monophosphate, 2'-adenosineMeSH
2'-AMPMeSH
2'-Adenosine monophosphateMeSH
Adenosine 2' phosphateMeSH
Adenosine phosphate dipotassiumMeSH
Adenosine 3' phosphateMeSH
Disodium, adenosine phosphateMeSH
PhosphadenMeSH
2'-Adenylic acidMeSH
AMPMeSH
Adenosine monophosphateMeSH
Adenosine phosphate disodiumMeSH
2' Adenosine monophosphateMeSH
Acid, 2'-adenylicMeSH
Acid, 5'-adenylicMeSH
Adenosine 5' phosphateMeSH
Adenosine 5'-phosphateMeSH
Chemical FormulaC10H14N5O7P
Average Molecular Weight347.2212
Monoisotopic Molecular Weight347.063084339
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}phosphonic acid
Traditional Nameadenosine-3'-phosphate
CAS Registry Number84-21-9
SMILES
NC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](OP(O)(O)=O)[C@H]3O)C2=NC=N1
InChI Identifier
InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(17)7(4(1-16)21-10)22-23(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
InChI KeyLNQVTSROQXJCDD-KQYNXXCUSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as ribonucleoside 3'-phosphates. These are ribonucleosides that contain a phosphate group attached to the C-3 carbon of the ribose or deoxyribose moiety. The nucleobases here are limited to purine, pyrimidine, and pyridine derivatives.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassRibonucleoside 3'-phosphates
Sub ClassNot Available
Direct ParentRibonucleoside 3'-phosphates
Alternative Parents
Substituents
  • Pentose phosphate
  • Ribonucleoside 3'-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Pentose monosaccharide
  • Monosaccharide phosphate
  • Purine
  • Imidazopyrimidine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • N-substituted imidazole
  • Monosaccharide
  • Pyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Primary amine
  • Amine
  • Alcohol
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point197 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility500 mg/L at 15 °CNot Available
LogP-1.453Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.48 g/LALOGPS
logP-3.1ALOGPS
logP-4.8ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)0.87ChemAxon
pKa (Strongest Basic)4.94ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area186.07 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity74.07 m³·mol⁻¹ChemAxon
Polarizability29.67 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0kuv-0973000000-eb7c71515eea7eb1a837View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0kuv-0973000000-eb7c71515eea7eb1a837View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9511000000-80f5030da41a88c5adf7View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03xr-7973700000-7630afa3708fa5e5ab9eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-03di-2093000000-f9389aa723f687dcb780View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-01u1-9463000000-deedf4a3a159267bf008View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-1900000000-3070b457af9f8caf95aeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0901000000-01666f7ac8779350ae53View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2913000000-583726ba8cf3132ced34View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-3743b8381504a528e937View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-3900000000-674aca6f0bee774491a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0032-4709000000-0e304c018489ee824b4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3900000000-28c48abec776120de260View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9500000000-64e6e28bb636afabd554View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified0.137 +/- 0.204 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.269 +/- 0.162 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023193
KNApSAcK IDC00019350
Chemspider ID37610
KEGG Compound IDC01367
BioCyc IDNot Available
BiGG ID2224997
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound41211
PDB ID3AM
ChEBI ID28931
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Jackson EK, Ren J, Gillespie DG: 2',3'-cAMP, 3'-AMP, and 2'-AMP inhibit human aortic and coronary vascular smooth muscle cell proliferation via A2B receptors. Am J Physiol Heart Circ Physiol. 2011 Aug;301(2):H391-401. doi: 10.1152/ajpheart.00336.2011. Epub 2011 May 27. [PubMed:21622827 ]