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Showing metabocard for Acetyl adenylate (HMDB0006880)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
enzymes (3) Show 3 proteins
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-08-14 17:18:54 UTC
Update Date2020-02-26 21:26:52 UTC
HMDB IDHMDB0006880
Secondary Accession Numbers
  • HMDB0006947
  • HMDB06880
  • HMDB06947
Metabolite Identification
Common NameAcetyl adenylate
DescriptionAcetyl adenylate, also known as acetyl AMP, belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups. Acetyl adenylate is a strong basic compound (based on its pKa).
Structure
Data?1582752412
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5'-AcetylphosphoadenosineKegg
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 KeyUBPVOHPZRZIJHM-WOUKDFQISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTetrahydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • 26-hydroxysteroid
  • Tetrahydroxy bile acid, alcohol, or derivatives
  • Sulfated steroid skeleton
  • 3-hydroxysteroid
  • 12-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 7-hydroxysteroid
  • Sulfate-ester
  • Sulfuric acid monoester
  • Alkyl sulfate
  • Sulfuric acid ester
  • Organic sulfuric acid or derivatives
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Organic oxide
  • Primary alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Process

Naturally occurring process:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity83.22 m³·mol⁻¹ChemAxon
Polarizability33.79 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gvt-5913000000-4b21305f5ae8862b482aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00pl-4891600000-9a73d48fc64423dadb41Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000j-1819000000-91af5d9e32b06642ebc1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0901000000-afcae5af796629b17092Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-b6122ae0e10da781cb2dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00c9-2809000000-bcbe596d9947ab374421Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-4901000000-e99793fd821fb5ed2ce6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-9600000000-330dd6ff381223198137Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024132
KNApSAcK IDNot Available
Chemspider ID389703
KEGG Compound IDC05993
BioCyc IDACETYL_AMP
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440867
PDB IDNot Available
ChEBI ID37666
Food Biomarker OntologyNot Available
VMH IDHC01672
MarkerDB ID
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:6249595 ]
  9. Krajewski WA, Luchnik AN: Relationship of histone acetylation to DNA topology and transcription. Mol Gen Genet. 1991 Dec;230(3):442-8. [PubMed: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. [PubMed: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. [PubMed:2901103 ]

Enzymes

Enzyme Details
1. Acetyl-coenzyme A synthetase, cytoplasmic
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
Enzyme Details
2. Acetyl-coenzyme A synthetase 2-like, mitochondrial
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
Enzyme Details
3. ACSS2 protein
General function:
Involved in acetate-CoA ligase activity
Specific function:
Not Available
Gene Name:
ACSS2
Uniprot ID:
Q96FY7
Molecular weight:
59346.4