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Showing metabocard for N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole (HMDB11112)

Record Information
Version 3.5
Creation Date 2008-10-16 16:29:40 -0600
Update Date 2013-02-08 17:25:42 -0700
HMDB ID HMDB11112
Secondary Accession Numbers None
Metabolite Identification
Common Name N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole
Description N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole is an intermediate in riboflavin metabolism. It is converted from N1-(5-Phospho-alpha-D-ribosyl)-5,6-dimethylbenzimidazole via dephosphorylation by the enzyme phosphohistidine phosphatase 1 (EC 3.1.3.-). Humans do not have all the enzymes needed to synthesize or metabolize riboflavin. However, gut microflora do have the necessary enzymatic machinery to produce and metabolize this vitamin. Riboflavin (or vitamin B2) is an easily absorbed micronutrient with a key role in maintaining health in humans and animals. It is the central component of the cofactors FAD and FMN, and is therefore required by all flavoproteins. Riboflavin is yellow or yellow-orange in color and in addition to being used as a food coloring it is also used to fortify some foods including baby foods, breakfast cereals, pastas, sauces, processed cheese, fruit drinks, vitamin-enriched milk products, some energy drinks, and vitamin supplements.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (2S,5R)-2-(5,6 dimethylbenzimidazol-1-yl)-5 (hydroxymethyl)oxolane-3,4-diol
  2. 5,6-Dimethyl-1-a-D-ribofuranosyl-1H-benzimidazole
  3. 5,6-Dimethyl-1-alpha-delta-ribofuranosyl-1H-benzimidazole
  4. a-Ribazole
  5. alpha-Ribazole
  6. N1-(alpha-D-ribosyl)-5,6-dimethylbenzimidazole
  7. N1-(alpha-delta-ribosyl)-5,6-dimethylbenzimidazole
Chemical Formula C14H18N2O4
Average Molecular Weight 278.3037
Monoisotopic Molecular Weight 278.126657074
IUPAC Name (2S,5R)-2-(5,6-dimethyl-1H-1,3-benzodiazol-1-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Traditional IUPAC Name (2S,5R)-2-(5,6-dimethyl-1,3-benzodiazol-1-yl)-5-(hydroxymethyl)oxolane-3,4-diol
CAS Registry Number Not Available
SMILES CC1=CC2=C(C=C1C)N(C=N2)[C@H]1O[C@H](CO)C(O)C1O
InChI Identifier InChI=1S/C14H18N2O4/c1-7-3-9-10(4-8(7)2)16(6-15-9)14-13(19)12(18)11(5-17)20-14/h3-4,6,11-14,17-19H,5H2,1-2H3/t11-,12?,13?,14+/m1/s1
InChI Key HLRUKOJSWOKCPP-RYSNWHEDSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Nucleosides, Nucleotides, and Analogues
Class Benzimidazole Nucleosides and Nucleotides
Sub Class N/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • 1,2 Diol
  • Benzimidazole
  • Glycosyl Compound
  • Imidazole
  • N Glycosyl Compound
  • Oxolane
  • Pentose Monosaccharide
  • Primary Alcohol
  • Saccharide
  • Secondary Alcohol
  • Toluene
Direct Parent Benzimidazole Nucleosides and Nucleotides
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 4.03 g/L ALOGPS
LogP 0.35 ALOGPS
LogP 0.73 ChemAxon
LogS -1.84 ALOGPS
pKa (strongest acidic) 12.46 ChemAxon
pKa (strongest basic) 6 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 87.74 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 71.65 ChemAxon
Polarizability 29.38 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB027894
KNApSAcK ID Not Available
Chemspider ID 389646 Link_out
KEGG Compound ID C05775 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB11112 Link_out
Metagene Link HMDB11112 Link_out
METLIN ID Not Available
PubChem Compound 440780 Link_out
PDB ID Not Available
ChEBI ID 10329 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available
Enzymes
Name: 14 kDa phosphohistidine phosphatase
Reactions:
    Gene Name: PHPT1
    Uniprot ID: Q9NRX4 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA