ChemFOnt: Showing chemical card for {[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid (CFc000135441)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 22:08:23 UTC

Chemfont ID

CFc000135441

Molecule Identification

Common Name

{[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

Definition

Adenosine monophosphate, also known as adenylic acid or 5'-AMP, 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. Adenosine monophosphate is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Adenosine monophosphate is a strong basic compound (based on its pKa). Adenosine monophosphate exists in all living species, ranging from bacteria to humans. In humans, adenosine monophosphate is involved in the metabolic disorder called the canavan disease pathway. Outside of the human body, Adenosine monophosphate is found, on average, in the highest concentration within beers. Adenosine monophosphate has also been detected, but not quantified in, several different foods, such as spinachs, cowpea, parsley, arctic blackberries, and kumquats. This could make adenosine monophosphate a potential biomarker for the consumption of these foods. A purine ribonucleoside 5'-monophosphate having adenine as the nucleobase.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5'-Adenosine monophosphate	ChEBI
5'-Adenylic acid	ChEBI
5'-AMP	ChEBI
5'-O-Phosphonoadenosine	ChEBI
Adenosine 5'-(dihydrogen phosphate)	ChEBI
Adenosine 5'-phosphate	ChEBI
Adenosine phosphate	ChEBI
Adenosine-5'-monophosphoric acid	ChEBI
Adenosine-5'p	ChEBI
Adenosini phosphas	ChEBI
Adenylate	ChEBI
Adenylic acid	ChEBI
Ado5'p	ChEBI
AMP	ChEBI
Fosfato de adenosina	ChEBI
pA	ChEBI
PAdo	ChEBI
Phosphate d'adenosine	ChEBI
Adenosine 5'-monophosphate	Kegg
Adenyl	Kegg
5'-Adenosine monophosphoric acid	Generator
5'-Adenylate	Generator
Adenosine 5'-(dihydrogen phosphoric acid)	Generator
Adenosine 5'-phosphoric acid	Generator
Adenosine phosphoric acid	Generator
Adenosine-5'-monophosphate	Generator
Phosphoric acid d'adenosine	Generator
Adenosine 5'-monophosphoric acid	Generator
Adenosine monophosphoric acid	Generator
Adenosine 5'-phosphorate	HMDB
Adenosine-5'-monophosphorate	HMDB
Adenosine-5-monophosphorate	HMDB
Adenosine-5-monophosphoric acid	HMDB
Adenosine-monophosphate	HMDB
Adenosine-phosphate	HMDB
Adenovite	HMDB
Cardiomone	HMDB
Lycedan	HMDB
Muscle adenylate	HMDB
Muscle adenylic acid	HMDB
My-b-den	HMDB
My-beta-den	HMDB
Phosaden	HMDB
Phosphaden	HMDB
Phosphentaside	HMDB
5'-Phosphate, adenosine	HMDB
Acid, 2'-adenylic	HMDB
2'-Adenylic acid	HMDB
Adenosine 3' phosphate	HMDB
Disodium, adenosine phosphate	HMDB
Phosphate dipotassium, adenosine	HMDB
Adenosine 2'-phosphate	HMDB
Adenosine 5' phosphate	HMDB
Adenosine phosphate dipotassium	HMDB
Dipotassium, adenosine phosphate	HMDB
2' Adenylic acid	HMDB
5' Adenylic acid	HMDB
Acid, 5'-adenylic	HMDB
Adenosine 3'-phosphate	HMDB
monoPhosphate, 2'-adenosine	HMDB
Phosphate disodium, adenosine	HMDB
2' Adenosine monophosphate	HMDB
2'-AMP	HMDB
2'-Adenosine monophosphate	HMDB
Adenosine 2' phosphate	HMDB
Adenosine phosphate disodium	HMDB

Chemical Formula

C₁₀H₁₄N₅O₇P

Average Molecular Weight

347.2212

Monoisotopic Molecular Weight

347.063084339

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

Traditional Name

adenylate

CAS Registry Number

61-19-8

SMILES

NC1=C2N=CN([C@@H]3O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]3O)C2=NC=N1

InChI Identifier

InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1

InChI Key

UDMBCSSLTHHNCD-KQYNXXCUSA-N

Chemical Taxonomy

Description

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 Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine ribonucleotides

Direct Parent

Purine ribonucleoside monophosphates

Alternative Parents

Substituents

Purine ribonucleoside monophosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Aminopyrimidine
Monoalkyl phosphate
Alkyl phosphate
Monosaccharide
Pyrimidine
Imidolactam
N-substituted imidazole
Organic phosphoric acid derivative
Phosphoric acid ester
Tetrahydrofuran
Azole
Imidazole
Heteroaromatic compound
Secondary alcohol
1,2-diol
Organoheterocyclic compound
Oxacycle
Azacycle
Organonitrogen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Alcohol
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

adenosine 5'-phosphate (CHEBI:16027 )
purine ribonucleoside 5'-monophosphate (CHEBI:16027 )
Ribonucleotides (C00020 )

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.31 g/L	ALOGPS
logP	-3.1	ALOGPS
logP	-4.7	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.22	ChemAxon
pKa (Strongest Basic)	3.92	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	186.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	74.07 m³·mol⁻¹	ChemAxon
Polarizability	29.96 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000045

DrugBank ID

DB00131

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16027

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for {[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid (CFc000135441)

MOL for CFc000135441 ({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid)

3D MOL for CFc000135441 ({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid)

3D SDF for CFc000135441 ({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid)

3D-SDF for CFc000135441 ({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid)

PDB for CFc000135441 ({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid)

3D PDB for CFc000135441 ({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid)

SMILES for CFc000135441 ({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid)

INCHI for CFc000135441 ({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid)

Structure for CFc000135441 ({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid)

3D Structure for CFc000135441 ({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid)