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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-14 17:18:54 UTC
Update Date2021-09-14 14:57:19 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 pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. In microbes acetyl adenylate also plays a role in the direction of flagellar rotation (PMID:2901103 ). Acetyl adenylate is a strong basic compound (based on its pKa). Acetyl adenylate exists in all living species, ranging from bacteria to humans. In humans, acetyl adenylate is involved in pyruvate metabolism.
Structure
Data?1582752412
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 pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentose phosphates
Alternative Parents
Substituents
  • Pentose phosphate
  • Pentose-5-phosphate
  • C-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Tetrahydrofuran
  • Secondary alcohol
  • Hemiacetal
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Primary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.02 g/LALOGPS
logP10(-2.4) g/LALOGPS
logP10(-4.7) g/LChemAxon
logS10(-2.1) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+191.06831661259
DarkChem[M-H]-180.65331661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Acetyl adenylateCC(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N3987.1Standard polar33892256
Acetyl adenylateCC(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N2433.9Standard non polar33892256
Acetyl adenylateCC(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N3329.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Acetyl adenylate,1TMS,isomer #1CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O3161.9Semi standard non polar33892256
Acetyl adenylate,1TMS,isomer #2CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C3162.1Semi standard non polar33892256
Acetyl adenylate,1TMS,isomer #3CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1O)O[Si](C)(C)C3178.7Semi standard non polar33892256
Acetyl adenylate,1TMS,isomer #4CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O3225.9Semi standard non polar33892256
Acetyl adenylate,2TMS,isomer #1CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C3059.5Semi standard non polar33892256
Acetyl adenylate,2TMS,isomer #2CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O)O[Si](C)(C)C3084.2Semi standard non polar33892256
Acetyl adenylate,2TMS,isomer #3CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O3113.6Semi standard non polar33892256
Acetyl adenylate,2TMS,isomer #4CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3096.1Semi standard non polar33892256
Acetyl adenylate,2TMS,isomer #5CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C3116.3Semi standard non polar33892256
Acetyl adenylate,2TMS,isomer #6CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O)O[Si](C)(C)C3157.6Semi standard non polar33892256
Acetyl adenylate,2TMS,isomer #7CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O3150.6Semi standard non polar33892256
Acetyl adenylate,3TMS,isomer #1CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3041.8Semi standard non polar33892256
Acetyl adenylate,3TMS,isomer #1CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3103.6Standard non polar33892256
Acetyl adenylate,3TMS,isomer #1CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C4962.8Standard polar33892256
Acetyl adenylate,3TMS,isomer #2CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C3084.0Semi standard non polar33892256
Acetyl adenylate,3TMS,isomer #2CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C3169.1Standard non polar33892256
Acetyl adenylate,3TMS,isomer #2CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C4896.6Standard polar33892256
Acetyl adenylate,3TMS,isomer #3CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O)O[Si](C)(C)C3111.5Semi standard non polar33892256
Acetyl adenylate,3TMS,isomer #3CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O)O[Si](C)(C)C3187.2Standard non polar33892256
Acetyl adenylate,3TMS,isomer #3CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O)O[Si](C)(C)C4698.9Standard polar33892256
Acetyl adenylate,3TMS,isomer #4CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O3101.9Semi standard non polar33892256
Acetyl adenylate,3TMS,isomer #4CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O3219.6Standard non polar33892256
Acetyl adenylate,3TMS,isomer #4CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O4665.8Standard polar33892256
Acetyl adenylate,3TMS,isomer #5CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3116.2Semi standard non polar33892256
Acetyl adenylate,3TMS,isomer #5CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3175.9Standard non polar33892256
Acetyl adenylate,3TMS,isomer #5CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C4668.2Standard polar33892256
Acetyl adenylate,3TMS,isomer #6CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C3112.1Semi standard non polar33892256
Acetyl adenylate,3TMS,isomer #6CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C3212.7Standard non polar33892256
Acetyl adenylate,3TMS,isomer #6CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C4645.9Standard polar33892256
Acetyl adenylate,3TMS,isomer #7CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O)O[Si](C)(C)C3138.4Semi standard non polar33892256
Acetyl adenylate,3TMS,isomer #7CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O)O[Si](C)(C)C3226.3Standard non polar33892256
Acetyl adenylate,3TMS,isomer #7CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O)O[Si](C)(C)C4487.4Standard polar33892256
Acetyl adenylate,4TMS,isomer #1CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3107.7Semi standard non polar33892256
Acetyl adenylate,4TMS,isomer #1CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3132.7Standard non polar33892256
Acetyl adenylate,4TMS,isomer #1CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C4416.6Standard polar33892256
Acetyl adenylate,4TMS,isomer #2CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C3105.9Semi standard non polar33892256
Acetyl adenylate,4TMS,isomer #2CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C3183.8Standard non polar33892256
Acetyl adenylate,4TMS,isomer #2CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C4323.5Standard polar33892256
Acetyl adenylate,4TMS,isomer #3CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O)O[Si](C)(C)C3127.1Semi standard non polar33892256
Acetyl adenylate,4TMS,isomer #3CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O)O[Si](C)(C)C3184.5Standard non polar33892256
Acetyl adenylate,4TMS,isomer #3CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O)O[Si](C)(C)C4166.9Standard polar33892256
Acetyl adenylate,4TMS,isomer #4CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3145.5Semi standard non polar33892256
Acetyl adenylate,4TMS,isomer #4CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3174.1Standard non polar33892256
Acetyl adenylate,4TMS,isomer #4CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C4128.7Standard polar33892256
Acetyl adenylate,5TMS,isomer #1CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3160.2Semi standard non polar33892256
Acetyl adenylate,5TMS,isomer #1CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3109.8Standard non polar33892256
Acetyl adenylate,5TMS,isomer #1CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3920.7Standard polar33892256
Acetyl adenylate,1TBDMS,isomer #1CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3362.1Semi standard non polar33892256
Acetyl adenylate,1TBDMS,isomer #2CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3368.4Semi standard non polar33892256
Acetyl adenylate,1TBDMS,isomer #3CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1O)O[Si](C)(C)C(C)(C)C3387.7Semi standard non polar33892256
Acetyl adenylate,1TBDMS,isomer #4CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O3404.9Semi standard non polar33892256
Acetyl adenylate,2TBDMS,isomer #1CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3457.4Semi standard non polar33892256
Acetyl adenylate,2TBDMS,isomer #2CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O)O[Si](C)(C)C(C)(C)C3474.4Semi standard non polar33892256
Acetyl adenylate,2TBDMS,isomer #3CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3483.7Semi standard non polar33892256
Acetyl adenylate,2TBDMS,isomer #4CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3491.9Semi standard non polar33892256
Acetyl adenylate,2TBDMS,isomer #5CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3492.8Semi standard non polar33892256
Acetyl adenylate,2TBDMS,isomer #6CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O)O[Si](C)(C)C(C)(C)C3529.8Semi standard non polar33892256
Acetyl adenylate,2TBDMS,isomer #7CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O3544.2Semi standard non polar33892256
Acetyl adenylate,3TBDMS,isomer #1CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3589.2Semi standard non polar33892256
Acetyl adenylate,3TBDMS,isomer #1CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3609.1Standard non polar33892256
Acetyl adenylate,3TBDMS,isomer #1CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C5025.6Standard polar33892256
Acetyl adenylate,3TBDMS,isomer #2CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3628.5Semi standard non polar33892256
Acetyl adenylate,3TBDMS,isomer #2CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3737.5Standard non polar33892256
Acetyl adenylate,3TBDMS,isomer #2CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C4930.7Standard polar33892256
Acetyl adenylate,3TBDMS,isomer #3CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O)O[Si](C)(C)C(C)(C)C3636.3Semi standard non polar33892256
Acetyl adenylate,3TBDMS,isomer #3CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O)O[Si](C)(C)C(C)(C)C3716.5Standard non polar33892256
Acetyl adenylate,3TBDMS,isomer #3CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O)O[Si](C)(C)C(C)(C)C4789.2Standard polar33892256
Acetyl adenylate,3TBDMS,isomer #4CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3649.0Semi standard non polar33892256
Acetyl adenylate,3TBDMS,isomer #4CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3788.0Standard non polar33892256
Acetyl adenylate,3TBDMS,isomer #4CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O4688.2Standard polar33892256
Acetyl adenylate,3TBDMS,isomer #5CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3649.1Semi standard non polar33892256
Acetyl adenylate,3TBDMS,isomer #5CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3711.6Standard non polar33892256
Acetyl adenylate,3TBDMS,isomer #5CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4758.3Standard polar33892256
Acetyl adenylate,3TBDMS,isomer #6CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3660.5Semi standard non polar33892256
Acetyl adenylate,3TBDMS,isomer #6CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3787.1Standard non polar33892256
Acetyl adenylate,3TBDMS,isomer #6CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C4671.3Standard polar33892256
Acetyl adenylate,3TBDMS,isomer #7CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O)O[Si](C)(C)C(C)(C)C3671.0Semi standard non polar33892256
Acetyl adenylate,3TBDMS,isomer #7CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O)O[Si](C)(C)C(C)(C)C3761.2Standard non polar33892256
Acetyl adenylate,3TBDMS,isomer #7CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O)O[Si](C)(C)C(C)(C)C4569.9Standard polar33892256
Acetyl adenylate,4TBDMS,isomer #1CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3796.2Semi standard non polar33892256
Acetyl adenylate,4TBDMS,isomer #1CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3798.5Standard non polar33892256
Acetyl adenylate,4TBDMS,isomer #1CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4596.7Standard polar33892256
Acetyl adenylate,4TBDMS,isomer #2CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3808.7Semi standard non polar33892256
Acetyl adenylate,4TBDMS,isomer #2CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3883.4Standard non polar33892256
Acetyl adenylate,4TBDMS,isomer #2CC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C4438.4Standard polar33892256
Acetyl adenylate,4TBDMS,isomer #3CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O)O[Si](C)(C)C(C)(C)C3806.8Semi standard non polar33892256
Acetyl adenylate,4TBDMS,isomer #3CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O)O[Si](C)(C)C(C)(C)C3847.7Standard non polar33892256
Acetyl adenylate,4TBDMS,isomer #3CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O)O[Si](C)(C)C(C)(C)C4345.0Standard polar33892256
Acetyl adenylate,4TBDMS,isomer #4CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3818.1Semi standard non polar33892256
Acetyl adenylate,4TBDMS,isomer #4CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3845.0Standard non polar33892256
Acetyl adenylate,4TBDMS,isomer #4CC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4313.9Standard polar33892256
Spectra
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 IDNot Available
Good Scents IDNot Available
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

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