Biotinyl-5'-AMP (PAMDB000655)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000655
Identification
Name: Biotinyl-5'-AMP
Description:5'-biotinyl-AMP (B-AMP) is the active form of biotin. Biotin is essential to maintain metabolic homeostasis and as regulator of gene expression. The vitamin biotin plays an essential role in gluconeogenesis, fatty acid synthesis, and carbohydrate metabolism because of its role as cofactor of five carboxylases; pyruvate carboxylase (PC), propionyl-CoA carboxylase (PCC), methylcrotonyl-CoA carboxylase, and two forms of acetyl-CoA carboxylase (ACC-1 and ACC-2). Carboxylase biotinylation is catalyzed by the enzyme holocarboxylase synthetase (HCS) through a reaction that involves the transformation of biotin into B-AMP and its subsequent attachment to a specific lysine residue in the carboxylases. B-AMP is also required to activate a signal transduction cascade that includes a soluble guanylate cyclase (sGC) and cGMP-dependent protein kinase (PKG). The regulatory role of biotin in the biotin cycle seems to be limited to the expression of proteins involved in the transport and utilization of exogenous vitamin while having no effect on biotinidase mRNA levels, enzyme responsible for biotin recycling during carboxylase turnover.
Structure
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🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (+)-Biotinyl 5'-adenylate
  • (+)-Biotinyl 5'-adenylic acid
  • 5'-Adenylate anhydride with biotin
  • 5'-Adenylate monoanhydride with biotin
  • 5'-Adenylic acid anhydride with biotin
  • 5'-Adenylic acid monoanhydride with biotin
  • B-AMP
  • Beta-AMP
  • Bio-5-AMP
  • Biotin anhydride with 5'-adenylate
  • Biotin anhydride with 5'-adenylic acid
  • Biotinoyl 5'-adenylate
  • Biotinoyl 5'-adenylic acid
  • Biotinyl 5'-AMP
  • Biotinyl-AMP
  • [3aS-(3aa,4b,6aa)]-5'-Adenylate monoanhydride with hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-pentanoate
  • [3aS-(3aa,4b,6aa)]-5'-Adenylate monoanhydride with hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-pentanoic acid
  • [3aS-(3aa,4b,6aa)]-5'-Adenylic acid monoanhydride with hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-pentanoate
  • [3aS-(3aa,4b,6aa)]-5'-Adenylic acid monoanhydride with hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-pentanoic acid
  • β-AMP
Chemical Formula: C20H28N7O9PS
Average Molecular Weight: 573.517
Monoisotopic Molecular Weight: 573.140682731
InChI Key: UTQCSTJVMLODHM-CFYKWCKVSA-N
InChI:InChI=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-/m1/s1
CAS number: 4130-20-5
IUPAC Name:{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({5-[(4S)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanoyl}oxy)phosphinic acid
Traditional IUPAC Name: [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({5-[(4S)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanoyl}oxy)phosphinic acid
SMILES:NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OC(=O)CCCC[C@@H]2SCC3NC(=O)NC23)[C@@H](O)[C@H]1O
Chemical Taxonomy
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.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class Purine nucleotides
Sub ClassPurine ribonucleotides
Direct Parent Purine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine ribonucleoside monophosphate
  • Biotin
  • Biotin_derivative
  • N-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Thienoimidazolidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Imidazolidinone
  • Heteroaromatic compound
  • Thiophene
  • Oxolane
  • Imidazolidine
  • Imidazole
  • Azole
  • Urea
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Dialkylthioether
  • Thioether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility2.24 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity130.63 m3·mol-1ChemAxon
Polarizability53.92 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Adenosine triphosphate + Biotin <> Pyrophosphate + Biotinyl-5'-AMP
Biotinyl-5'-AMP + Apo-[carboxylase] <> Adenosine monophosphate + Holo-[carboxylase]
Adenosine triphosphate + Biotin > Biotinyl-5'-AMP + Pyrophosphate
Biotinyl-5'-AMP > Biotin-Carboxyl Carrying Protein
Biotin + Adenosine triphosphate > diphosphate + Biotinyl-5'-AMP + Pyrophosphate
Biotinyl-5'-AMP + apo-[carboxylase] > Adenosine monophosphate + Biotin-Carboxyl Carrying Protein
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0942030000-e61e914c7ef0f87ef7ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0910000000-90a339c73ce7d6e18307View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2900000000-4473efe13a9fdcd356f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00c0-2309030000-db991b74538e5511fc08View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-7902000000-c38c4f3a31b23503bb6dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-9400000000-f14ea50608a771c5ffc0View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Pacheco-Alvarez D, Solorzano-Vargas RS, Gonzalez-Noriega A, Michalak C, Zempleni J, Leon-Del-Rio A: Biotin availability regulates expression of the sodium-dependent multivitamin transporter and the rate of biotin uptake in HepG2 cells. Mol Genet Metab. 2005 Aug;85(4):301-7. Pubmed: 15905112
  • Solorzano-Vargas RS, Pacheco-Alvarez D, Leon-Del-Rio A: Holocarboxylase synthetase is an obligate participant in biotin-mediated regulation of its own expression and of biotin-dependent carboxylases mRNA levels in human cells. Proc Natl Acad Sci U S A. 2002 Apr 16;99(8):5325-30. Pubmed: 11959985
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference: Christner, James E.; Coon, Minor J. Synthesis of (+)-biotinyl 5'-adenylate. Methods Enzymol. (1970), 18(Pt. A), 386-90.
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB04220
Pubchem Compound ID440839
Kegg IDC05921
ChemSpider ID389681
Wikipedia IDNot Available
BioCyc IDNot Available