ChemFOnt: Showing chemical card for Biotinyl-5'-AMP (CFc000002089)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:53 UTC

Chemfont ID

CFc000002089

Molecule Identification

Common Name

Biotinyl-5'-AMP

Definition

5'-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 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-Biotinyl 5'-adenylate	HMDB
5'-Adenylic acid anhydride with biotin	HMDB
5'-Adenylic acid monoanhydride with biotin	HMDB
b-AMP	HMDB
beta-AMP	HMDB
Bio-5-AMP	HMDB
Biotin anhydride with 5'-adenylic acid	HMDB
Biotinoyl 5'-adenylate	HMDB
Biotinyl 5'-AMP	HMDB
[3AS-(3aa,4b,6aa)]-5'-adenylic acid monoanhydride with hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-pentanoate	HMDB
[3AS-(3aa,4b,6aa)]-5'-adenylic acid monoanhydride with hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-pentanoic acid	HMDB

Chemical Formula

C₂₀H₂₈N₇O₉PS

Average Molecular Weight

573.517

Monoisotopic Molecular Weight

573.140682731

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 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

CAS Registry Number

4130-20-5

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

InChI Identifier

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

InChI Key

UTQCSTJVMLODHM-CFYKWCKVSA-N

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.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine ribonucleotides

Direct Parent

5'-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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0004220)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Biotin Metabolism (PathBank: SMP0063602)
Biotin Metabolism (HMDB: HMDB0004220)

Disease pathway

Multiple Carboxylase Deficiency, Neonatal or Early Onset Form (PathBank: SMP0120847)
Biotinidase Deficiency (PathBank: SMP0120460)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.24 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-4.1	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	4.99	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	233.27 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	130.63 m³·mol⁻¹	ChemAxon
Polarizability	53.92 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0004220

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023336

KNApSAcK ID

Not Available

Chemspider ID

389681

KEGG Compound ID

C05921

BioCyc ID

Not Available

BiGG ID

46920

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440839

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Christner, James E.; Coon, Minor J. Synthesis of (+)-biotinyl 5'-adenylate. Methods Enzymol. (1970), 18(Pt. A), 386-90.

Showing chemical card for Biotinyl-5'-AMP (CFc000002089)

MOL for CFc000002089 (Biotinyl-5'-AMP)

3D MOL for CFc000002089 (Biotinyl-5'-AMP)

3D SDF for CFc000002089 (Biotinyl-5'-AMP)

3D-SDF for CFc000002089 (Biotinyl-5'-AMP)

PDB for CFc000002089 (Biotinyl-5'-AMP)

3D PDB for CFc000002089 (Biotinyl-5'-AMP)

SMILES for CFc000002089 (Biotinyl-5'-AMP)

INCHI for CFc000002089 (Biotinyl-5'-AMP)

Structure for CFc000002089 (Biotinyl-5'-AMP)

3D Structure for CFc000002089 (Biotinyl-5'-AMP)