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Identification
YMDB IDYMDB00602
NameBiotinyl-5'-AMP
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionBiotinyl-5'-AMP belongs to the class of organic compounds known as 5'-acylphosphoadenosines. These are ribonucleoside derivatives containing an adenoside moiety, where the phosphate group is acylated. Biotinyl-5'-AMP is a strong basic compound (based on its pKa). Biotinyl-5'-AMP may be a unique S. cerevisiae (yeast) metabolite.
Structure
Thumb
Synonyms
  • (+)-Biotinyl 5'-adenylate
  • 5'-Adenylic acid anhydride with biotin
  • 5'-Adenylic acid monoanhydride with biotin
  • B-AMP
  • beta-AMP
  • bio-5-AMP
  • Biotin anhydride with 5'-adenylic acid
  • Biotinoyl 5'-adenylate
  • Biotinyl 5'-AMP
  • Biotinyl-5'-AMP
CAS number4130-20-5
WeightAverage: 573.517
Monoisotopic: 573.140682731
InChI KeyUTQCSTJVMLODHM-RHCAYAJFSA-N
InChIInChI=1S/C20H28N7O9PS/c21-17-14-18(23-7-22-17)27(8-24-14)19-16(30)15(29)10(35-19)5-34-37(32,33)36-12(28)4-2-1-3-11-13-9(6-38-11)25-20(31)26-13/h7-11,13,15-16,19,29-30H,1-6H2,(H,32,33)(H2,21,22,23)(H2,25,26,31)/t9-,10+,11-,13-,15+,16+,19+/m0/s1
IUPAC Name({5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanoyl}oxy)({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid
Traditional IUPAC Nameβ-amp
Chemical FormulaC20H28N7O9PS
SMILES[H][C@]12CS[C@@H](CCCCC(=O)OP(O)(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3O)N3C=NC4=C3N=CN=C4N)[C@@]1([H])NC(=O)N2
Chemical Taxonomy
Description belongs to the class of organic compounds known as 5'-acylphosphoadenosines. These are ribonucleoside derivatives containing an adenoside moiety, where the phosphate group is acylated.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct Parent5'-acylphosphoadenosines
Alternative Parents
Substituents
  • 5'-acylphosphoadenosine
  • Biotin_derivative
  • Biotin
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Thienoimidazolidine
  • Acyl phosphate
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Imidazolidinone
  • Imidolactam
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Pyrimidine
  • Thiophene
  • Thiolane
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Imidazolidine
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Carbonic acid derivative
  • Urea
  • Secondary alcohol
  • 1,2-diol
  • Carboxylic acid salt
  • Dialkylthioether
  • Oxacycle
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Thioether
  • Organoheterocyclic compound
  • Primary amine
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic salt
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Alcohol
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.24 g/LALOGPS
logP-1.2ALOGPS
logP-4.1ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area233.27 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity130.63 m³·mol⁻¹ChemAxon
Polarizability53.48 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Biotin metabolismec00780 Map00780
SMPDB ReactionsNot Available
KEGG Reactions
Adenosine triphosphate + Biotin + hydronPyrophosphate + Biotinyl-5'-AMP
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0932030000-9fc6a8392ffae33e1669JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0910000000-2446591c42df4f29b9dcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2900000000-4520d832999df4668da5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00c0-2319030000-2145defc8444c115071fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-6902000000-b1fc9db8b42178ed1000JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-9500000000-184eb594d205789edea6JSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Hoja, U., Wellein, C., Greiner, E., Schweizer, E. (1998). "Pleiotropic phenotype of acetyl-CoA-carboxylase-defective yeast cells--viability of a BPL1-amber mutation depending on its readthrough by normal tRNA(Gln)(CAG)." Eur J Biochem 254:520-526.9688262
Synthesis Reference:Christner, James E.; Coon, Minor J. Synthesis of (+)-biotinyl 5'-adenylate. Methods Enzymol. (1970), 18(Pt. A), 386-90.
External Links:
ResourceLink
CHEBI ID3110
HMDB IDHMDB04220
Pubchem Compound ID440839
Kegg IDC05921
ChemSpider IDNot Available
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in biotin-[acetyl-CoA-carboxylase] ligase activity
Specific function:
Post-translational modification of specific protein by attachment of biotin. Acts on various carboxylases such as acetyl- CoA-carboxylase, pyruvate carboxylase, propionyl CoA carboxylase, and 3-methylcrotonyl CoA carboxylase
Gene Name:
BPL1
Uniprot ID:
P48445
Molecular weight:
76362.39844
Reactions
ATP + biotin + apo-[methylmalonyl-CoA:pyruvate carboxytransferase] → AMP + diphosphate + [methylmalonyl-CoA:pyruvate carboxytransferase].
ATP + biotin + apo-[propionyl-CoA:carbon-dioxide ligase (ADP-forming)] → AMP + diphosphate + [propionyl-CoA:carbon-dioxide ligase (ADP-forming)].
ATP + biotin + apo-[3-methylcrotonoyl-CoA:carbon-dioxide ligase (ADP-forming)] → AMP + diphosphate + [3-methylcrotonoyl-CoA:carbon-dioxide ligase (ADP-forming)].
ATP + biotin + apo-[acetyl-CoA:carbon-dioxide ligase (ADP-forming)] → AMP + diphosphate + [acetyl-CoA:carbon-dioxide ligase (ADP-forming)].