ChemFOnt: Showing chemical card for N-Ribosylhistidine (CFc000001402)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:01 UTC

Chemfont ID

CFc000001402

Molecule Identification

Common Name

N-Ribosylhistidine

Definition

N tau-ribosylhistidine (His-R) is a histidine derivative found in the urine of histidinemic patients (histidinemia is an autosomal recessive metabolic disorder characterized by increased levels of histidine in blood, urine, and cerebrospinal fluid). The enzymes responsible for the formation of His-R are NAD (P) + nucleosidase [EC 3.2.2.5], nucleotide pyrophosphatase [EC 3.5.1.9] and 5'-nucleotidase [EC 3.1.3.5] (PMID: 2992472 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
His-R	HMDB, MeSH
N(Tau)-ribosylhistidine	HMDB, MeSH
(2S)-2-Amino-3-{1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-imidazol-4-yl}propanoate	Generator, HMDB

Chemical Formula

C₁₁H₁₇N₃O₆

Average Molecular Weight

287.2692

Monoisotopic Molecular Weight

287.111735291

IUPAC Name

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

Traditional Name

his-R

CAS Registry Number

98379-91-0

SMILES

N[C@@H](CC1=CN(C=N1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C11H17N3O6/c12-6(11(18)19)1-5-2-14(4-13-5)10-9(17)8(16)7(3-15)20-10/h2,4,6-10,15-17H,1,3,12H2,(H,18,19)/t6-,7+,8+,9+,10+/m0/s1

InChI Key

TTYCFBAOLXCFAB-VAPHQMJDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Histidine and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 4030756)

Cellular substructure

Membrane (HMDB: HMDB0002089)
Cell membrane (HMDB: HMDB0002089)

Excreta

Biofluid or Excreta

Urine (PMID: 4030756)

Source

Endogenous

Endogenous (HMDB: HMDB0002089)

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

Industrial application

Pharmaceutical industry

Biomarker

Histidinemia (MarkerDB: MDB00000375)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	20 g/L	ALOGPS
logP	-3	ALOGPS
logP	-4.9	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	1.53	ChemAxon
pKa (Strongest Basic)	9.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	151.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	64.09 m³·mol⁻¹	ChemAxon
Polarizability	27.15 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

HMDB0002089

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022840

KNApSAcK ID

Not Available

Chemspider ID

112711

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6481

PubChem Compound

126923

PDB ID

Not Available

ChEBI ID

90055

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for N-Ribosylhistidine (CFc000001402)

MOL for CFc000001402 (N-Ribosylhistidine)

3D MOL for CFc000001402 (N-Ribosylhistidine)

3D SDF for CFc000001402 (N-Ribosylhistidine)

3D-SDF for CFc000001402 (N-Ribosylhistidine)

PDB for CFc000001402 (N-Ribosylhistidine)

3D PDB for CFc000001402 (N-Ribosylhistidine)

SMILES for CFc000001402 (N-Ribosylhistidine)

INCHI for CFc000001402 (N-Ribosylhistidine)

Structure for CFc000001402 (N-Ribosylhistidine)

3D Structure for CFc000001402 (N-Ribosylhistidine)