Record Information
Version1.0
Creation date2011-09-21 00:28:17 UTC
Update date2015-07-21 06:57:38 UTC
Primary IDFDB023336
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameBiotinyl-5'-AMP
Description5'-biotinyl-AMP (B-AMP) is the active form of biotin in mammals. In human cells, 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. Multiple carboxylase deficiency (MCD) is a life-threatening disease characterized by the lack of carboxylase activities because of deficiency of HCS activity. (PMID: 15905112, 11959985) [HMDB]
CAS Number4130-20-5
Structure
Thumb
Synonyms
SynonymSource
(+)-Biotinyl 5'-adenylateHMDB
5'-Adenylic acid anhydride with biotinHMDB
5'-Adenylic acid monoanhydride with biotinHMDB
b-AMPHMDB
beta-AMPHMDB
Bio-5-AMPHMDB
Biotin anhydride with 5'-adenylic acidHMDB
Biotinoyl 5'-adenylateHMDB
Biotinyl 5'-AMPHMDB
[3AS-(3aa,4b,6aa)]-5'-adenylic acid monoanhydride with hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-pentanoateHMDB
[3AS-(3aa,4b,6aa)]-5'-adenylic acid monoanhydride with hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-pentanoic acidHMDB
[3aS-(3aa,4b,6aa)]-5'-Adenylic acid monoanhydride with hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanoatehmdb
[3aS-(3aa,4b,6aa)]-5'-Adenylic acid monoanhydride with hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanoic acidhmdb
B-AMPhmdb
bio-5-AMPhmdb
Predicted PropertiesNot Available
Chemical FormulaC20H28N7O9PS
IUPAC name
InChI IdentifierInChI=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
InChI KeyUTQCSTJVMLODHM-CFYKWCKVSA-N
Isomeric SMILESNC1=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
Average Molecular Weight573.517
Monoisotopic Molecular Weight573.140682731
Classification
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 DescriptorsNot Available
Ontology
Disposition

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MSNot Available
NMRNot Available
ChemSpider ID389681
ChEMBL IDNot Available
KEGG Compound IDC05921
Pubchem Compound ID440839
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04220
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID46920
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Biotin--protein ligaseHLCSP50747
Pathways
NameSMPDB LinkKEGG Link
Biotin MetabolismSMP00066 map00780
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference