ChemFOnt: Showing chemical card for Imidazoleacetic acid riboside (CFc000001567)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:13 UTC

Chemfont ID

CFc000001567

Molecule Identification

Common Name

Imidazoleacetic acid riboside

Definition

Imidazoleacetic acid riboside is a metabolite of imidazoleacetic acid (itself histamine's oxidative metabolite). (PMID: 7616240 ). In kidney glomeruli, histamine is predominantly catabolized to acid metabolites of the diamine oxidase (histaminase) pathway, imidazoleacetic acid and Imidazoleacetic acid riboside. (PMID: 7616240 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Imidazoleacetate riboside	Generator
IAA-R	MeSH
Ribosylimidazole-4-acetic acid	MeSH
Ribosylimidazole acetic acid	MeSH
1-b-D-Ribofuranosyl-imidazole-4-acetic acid	HMDB
1-beta-delta-Ribofuranosyl-imidazole-4-acetic acid	HMDB
1-Ribosylimidazole-4-acetic acid	HMDB
Ribosylimidazoleacetate	HMDB
(1-Ribosylimidazole)-4-acetic acid	Generator, HMDB
Imidazoleacetic acid riboside	MeSH

Chemical Formula

C₁₀H₁₄N₂O₆

Average Molecular Weight

258.228

Monoisotopic Molecular Weight

258.08518619

IUPAC Name

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

Traditional Name

ribosylimidazole acetic acid

CAS Registry Number

29605-99-0

SMILES

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

InChI Identifier

InChI=1S/C10H14N2O6/c13-3-6-8(16)9(17)10(18-6)12-2-5(11-4-12)1-7(14)15/h2,4,6,8-10,13,16-17H,1,3H2,(H,14,15)/t6-,8-,9-,10-/m1/s1

InChI Key

AHPWEWASPTZMEK-PEBGCTIMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as imidazole ribonucleosides and ribonucleotides. These are organic compounds in which the C-1 of a ribosyl moiety is N-linked to an imidazole ring. Nucleotides have a phosphate group linked to the C5 carbon of the ribose (or deoxyribose) moiety. This class does not contain benzimidazole nucleosides and nucleotides.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Imidazole ribonucleosides and ribonucleotides

Sub Class

Not Available

Direct Parent

Imidazole ribonucleosides and ribonucleotides

Alternative Parents

Substituents

Imidazole ribonucleoside
Glycosyl compound
N-glycosyl compound
Pentose monosaccharide
Imidazolyl carboxylic acid derivative
Monosaccharide
N-substituted imidazole
Azole
Imidazole
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Alcohol
Organonitrogen compound
Organooxygen compound
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0002331)

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	27 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-3	ChemAxon
logS	-0.98	ALOGPS
pKa (Strongest Acidic)	3.4	ChemAxon
pKa (Strongest Basic)	6.16	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.04 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	56.54 m³·mol⁻¹	ChemAxon
Polarizability	24.33 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

HMDB0002331

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022964

KNApSAcK ID

Not Available

Chemspider ID

389469

KEGG Compound ID

C05131

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6626

PubChem Compound

440569

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Baddiley, J.; Buchanan, J. G.; Hayes, D. H.; Smith, P. A. Synthesis of 1-b-D-ribofuranosyl-4(5)-glyoxalinylacetic acid, a metabolite of histamine. Journal of the Chemical Society (1958), 3743-5.

Showing chemical card for Imidazoleacetic acid riboside (CFc000001567)

MOL for CFc000001567 (Imidazoleacetic acid riboside)

3D MOL for CFc000001567 (Imidazoleacetic acid riboside)

3D SDF for CFc000001567 (Imidazoleacetic acid riboside)

3D-SDF for CFc000001567 (Imidazoleacetic acid riboside)

PDB for CFc000001567 (Imidazoleacetic acid riboside)

3D PDB for CFc000001567 (Imidazoleacetic acid riboside)

SMILES for CFc000001567 (Imidazoleacetic acid riboside)

INCHI for CFc000001567 (Imidazoleacetic acid riboside)

Structure for CFc000001567 (Imidazoleacetic acid riboside)

3D Structure for CFc000001567 (Imidazoleacetic acid riboside)