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Record Information
Version3.6
Creation Date2008-08-14 17:18:54 UTC
Update Date2016-02-11 01:08:04 UTC
HMDB IDHMDB06880
Secondary Accession Numbers
  • HMDB06947
Metabolite Identification
Common NameAcetyl adenylate
DescriptionAcetyl adenylate is an intermediate in acetyl-CoA synthesis. It is converted from acetate via the enzyme acetyl-CoA synthetase. It is involved in the non-enzymatic acetylation of histones in chromatin (PMID:8619849 ). In microbes acetyl adenylate also plays a role in the direction of flagellar rotation (PMID:2901103 ).
Structure
Thumb
Synonyms
ValueSource
Acetyl adenylateChEBI
Acetyl adenylic acidGenerator
5'-O-[Acetoxy(hydroxy)phosphoryl]adenosineHMDB
Acetyl AMPHMDB
AcetyladenylateHMDB
[[(2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl] acetateHMDB
Chemical FormulaC12H16N5O8P
Average Molecular Weight389.2579
Monoisotopic Molecular Weight389.073649025
IUPAC Name(acetyloxy)({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid
Traditional Name5'-acetylphosphoadenosine
CAS Registry Number13015-87-7
SMILES
CC(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N
InChI Identifier
InChI=1S/C12H16N5O8P/c1-5(18)25-26(21,22)23-2-6-8(19)9(20)12(24-6)17-4-16-7-10(13)14-3-15-11(7)17/h3-4,6,8-9,12,19-20H,2H2,1H3,(H,21,22)(H2,13,14,15)/t6-,8-,9-,12-/m1/s1
InChI KeyInChIKey=UBPVOHPZRZIJHM-WOUKDFQISA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine ribonucleoside monophosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Saccharide
  • Heteroaromatic compound
  • Acetate salt
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.02 mg/mLALOGPS
logP-2.4ALOGPS
logP-4.7ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)0.84ChemAxon
pKa (Strongest Basic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area192.14 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity83.22 m3·mol-1ChemAxon
Polarizability33.79 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Leigh SyndromeSMP00196Not Available
Primary hyperoxaluria II, PH2SMP00558Not Available
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)SMP00334Not Available
Pyruvate Dehydrogenase Complex DeficiencySMP00212Not Available
Pyruvate kinase deficiencySMP00559Not Available
Pyruvate MetabolismSMP00060map00620
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB024132
KNApSAcK IDNot Available
Chemspider ID389703
KEGG Compound IDC05993
BioCyc IDACETYL_AMP
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06880
Metagene LinkHMDB06880
METLIN IDNot Available
PubChem Compound440867
PDB IDNot Available
ChEBI ID37666
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. WEBSTER LT Jr: STUDIES OF THE ACETYL COENZYME A SYNTHETASE REACTION. I. ISOLATION AND CHARACTERIZATION OF ENZYME-BOUND ACETYL ADENYLATE. J Biol Chem. 1963 Dec;238:4010-5. [14086739 ]
  2. Webster LT Jr: Studies of the acetyl coenzyme A synthetase reaction. V. The requirement for monovalent and divalent cations in partial reactions involving enzyme-bound acetyl adenylate. J Biol Chem. 1967 Mar 25;242(6):1232-40. [4290317 ]
  3. Hilscher LW, Hanson CD, Russell DH, Raushel FM: Measurement of positional isotope exchange rates in enzyme-catalyzed reactions by fast atom bombardment mass spectrometry: application to argininosuccinate synthetase. Biochemistry. 1985 Oct 8;24(21):5888-93. [2867775 ]
  4. Schmellenkamp H, Eggerer H: Mechanism of enzymic acetylation of des-acetyl citrate lyase. Proc Natl Acad Sci U S A. 1974 May;71(5):1987-91. [4365579 ]
  5. Ramponi G, Manao G, Camici G: Nonenzymatic acetylation of histones with acetyl phosphate and acetyl adenylate. Biochemistry. 1975 Jun 17;14(12):2681-5. [238571 ]
  6. Camici G, Manao G, Ramponi G: Nonenzymatic reactivation of des-acetyl citrate lyase by acetyl adenylate. First example of enzyme activation by chemotrophic modification. Physiol Chem Phys. 1975;7(5):409-14. [698 ]
  7. Shewmaker CK, Wagner TE: Analysis of binding interactions between histone core complex and simian virus 40 DNA. A comparison of acetylated versus non-acetylated histone core complexes. Eur J Biochem. 1980 Jun;107(2):505-10. [6249594 ]
  8. Cohen BN, Blue WT, Wagner TE: Chemically induced gene expression. Manipulation of the transforming ability of simian virus 40 minichromatin by specific chemical hyperacetylation of histones H3 and H4. Eur J Biochem. 1980 Jun;107(2):511-8. [6249595 ]
  9. Krajewski WA, Luchnik AN: Relationship of histone acetylation to DNA topology and transcription. Mol Gen Genet. 1991 Dec;230(3):442-8. [1662766 ]
  10. Krajewski WA: Effect of nonenzymatic histone acetylation on chromatin high-order folding. Biochem Biophys Res Commun. 1996 Apr 16;221(2):295-9. [8619849 ]
  11. Wolfe AJ, Conley MP, Berg HC: Acetyladenylate plays a role in controlling the direction of flagellar rotation. Proc Natl Acad Sci U S A. 1988 Sep;85(18):6711-5. [2901103 ]

Enzymes

General function:
Involved in acetate-CoA ligase activity
Specific function:
Activates acetate so that it can be used for lipid synthesis or for energy generation.
Gene Name:
ACSS2
Uniprot ID:
Q9NR19
Molecular weight:
78579.11
Reactions
Acetyl adenylate + Coenzyme A → Adenosine monophosphate + Acetyl-CoAdetails
Adenosine triphosphate + Acetic acid → Pyrophosphate + Acetyl adenylatedetails
General function:
Involved in acetate-CoA ligase activity
Specific function:
Important for maintaining normal body temperature during fasting and for energy homeostasis. Essential for energy expenditure under ketogenic conditions (By similarity). Converts acetate to acetyl-CoA so that it can be used for oxidation through the tricarboxylic cycle to produce ATP and CO(2).
Gene Name:
ACSS1
Uniprot ID:
Q9NUB1
Molecular weight:
74625.88
Reactions
Acetyl adenylate + Coenzyme A → Adenosine monophosphate + Acetyl-CoAdetails
Adenosine triphosphate + Acetic acid → Pyrophosphate + Acetyl adenylatedetails
General function:
Involved in acetate-CoA ligase activity
Specific function:
Not Available
Gene Name:
ACSS2
Uniprot ID:
Q96FY7
Molecular weight:
59346.4