ChemFOnt: Showing chemical card for Imidazoleacetic acid ribotide (CFc000002628)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:33 UTC

Chemfont ID

CFc000002628

Molecule Identification

Common Name

Imidazoleacetic acid ribotide

Definition

Imidazoleacetic acid ribotide (IAA-RP) is an endogenous ligand that stimulates imidazol(in)e receptors. Experimental data suggest that IAA-RP may participate in transsynaptic signaling in brain, because it exists in brainstem neurons, exhibits depolarization-induced Ca2+-dependent release from P2 synaptosomal elements, has relatively high affinity for membrane-bound I-R sites, and produces physiological effects on exogenous application. IAA-RP is rapidly metabolized by phosphatases and ecto-5'-nucleotidases. (PMID: 15365189 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-(5-Phosphoribosyl)imidazole-4-acetate	ChEBI
1-(5-Phosphoribosyl)imidazole-4-acetic acid	Generator
Imidazoleacetate ribotide	Generator
IAA-RP	MeSH
1-(5-Phosphoribosyl)imidazol-4-ylacetic acid	ChEBI, HMDB
1-(5-Phosphoribosyl)imidazol-4-ylacetate	Generator, HMDB
1-(5-O-phosphono-b-D-Ribofuranosyl)-1H-imidazole-4-acetic acid	HMDB
1-(5-O-phosphono-beta-delta-Ribofuranosyl)-1H-imidazole-4-acetic acid	HMDB
1-b-D-Ribofuranosyl-imidazole-4-acetic acid 5'-(dihydrogen phosphate)	HMDB
1-b-D-Ribofuranosyl-imidazole-4-acetic acid 5'-phosphate	HMDB
1-beta-delta-Ribofuranosyl-imidazole-4-acetic acid 5'-(dihydrogen phosphate)	HMDB
1-beta-delta-Ribofuranosyl-imidazole-4-acetic acid 5'-phosphate	HMDB
1-Ribosylimidazole-4-acetic acid 5'-phosphate	HMDB
Imidazole-4-acetic acid ribotide	HMDB
[1-(5-Phosphoribofuranosyl)imidazol-4-yl]acetic acid	HMDB
[1-(5-Phosphoribosyl)imidazol-4-yl]acetic acid	HMDB
[1-(5-Phosphoribosyl)imidazol-4-yl]acetate	Generator, HMDB
Imidazoleacetic acid ribotide	MeSH

Chemical Formula

C₁₀H₁₅N₂O₉P

Average Molecular Weight

338.2079

Monoisotopic Molecular Weight

338.0515166

IUPAC Name

2-{1-[(3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1H-imidazol-4-yl}acetic acid

Traditional Name

{1-[(3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]imidazol-4-yl}acetic acid

CAS Registry Number

2888-19-9

SMILES

O[C@@H]1[C@@H](COP(O)(O)=O)OC([C@@H]1O)N1C=NC(CC(O)=O)=C1

InChI Identifier

InChI=1S/C10H15N2O9P/c13-7(14)1-5-2-12(4-11-5)10-9(16)8(15)6(21-10)3-20-22(17,18)19/h2,4,6,8-10,15-16H,1,3H2,(H,13,14)(H2,17,18,19)/t6-,8-,9-,10?/m1/s1

InChI Key

RDQUQBHPMYFYMX-XIWVQZPPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Not Available

Direct Parent

Purine nucleosides

Alternative Parents

Substituents

Purine nucleoside
Glycosyl compound
N-glycosyl compound
6-aminopurine
Imidazopyrimidine
Purine
Aminopyrimidine
Imidolactam
Pyrimidine
Monosaccharide
N-substituted imidazole
Azole
Heteroaromatic compound
Imidazole
Tetrahydrofuran
Secondary alcohol
Dialkyl ether
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organic oxygen compound
Amine
Hydrocarbon derivative
Alcohol
Organic nitrogen compound
Organopnictogen compound
Primary amine
Primary alcohol
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0006032)

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

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.74 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-3.6	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.22	ChemAxon
pKa (Strongest Basic)	5.9	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	171.57 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	67.42 m³·mol⁻¹	ChemAxon
Polarizability	28.94 Å³	ChemAxon
Number of Rings	2	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

HMDB0006032

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023810

KNApSAcK ID

Not Available

Chemspider ID

13148709

KEGG Compound ID

C04437

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16019958

PDB ID

Not Available

ChEBI ID

16805

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Matulic-Adamic, Jasenka; Watanabe, Kyoichi A. Nucleosides. 163. Synthesis of ribosides and ribotides of imidazole-4(5)-acetic acid and 1-methylimidazole-4(5)-acetic acid. Korean Journal of Medicinal Chemistry (1991), 1(1), 54-64.

Showing chemical card for Imidazoleacetic acid ribotide (CFc000002628)

MOL for CFc000002628 (Imidazoleacetic acid ribotide)

3D MOL for CFc000002628 (Imidazoleacetic acid ribotide)

3D SDF for CFc000002628 (Imidazoleacetic acid ribotide)

3D-SDF for CFc000002628 (Imidazoleacetic acid ribotide)

PDB for CFc000002628 (Imidazoleacetic acid ribotide)

3D PDB for CFc000002628 (Imidazoleacetic acid ribotide)

SMILES for CFc000002628 (Imidazoleacetic acid ribotide)

INCHI for CFc000002628 (Imidazoleacetic acid ribotide)

Structure for CFc000002628 (Imidazoleacetic acid ribotide)

3D Structure for CFc000002628 (Imidazoleacetic acid ribotide)