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Record Information
Version3.6
Creation Date2006-08-13 06:36:08 UTC
Update Date2017-03-02 21:27:23 UTC
HMDB IDHMDB03882
Secondary Accession NumbersNone
Metabolite Identification
Common NameN1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole
DescriptionN1-(5-Phospho-alpha-D-ribosyl)-5,6-dimethylbenzimidazole (or alpha-ribazole-5'-Phosphate) is an intermediate in Riboflavin metabolism. In particular, alpha-Ribazole 5'-phosphate is converted from Dimethylbenzimidazole via the enzyme nicotinate-nucleotide-dimethylbenzimidazole. phosphoribosyltransferase (EC 2.4.2.21). It is then converted to alpha-Ribazole via the enzyme (EC 3.1.3.-).
Structure
Thumb
Synonyms
ValueSource
5,6-Dimethyl-1-alpha-D-ribofuranosylbenzimidazole 5'-phosphateChEBI
alpha-Ribazole-5'-PChEBI
ALPHA-RIBAZOLE-5'-phosphATEChEBI
N1-(5-phospho-alpha-D-Ribosyl)-5,6-dimethylbenzimidazoleChEBI
N(1)-(5-Phosphoribosyl)-5,6-dimethylbenzimidazoleChEBI
PHOSPHORIC ACID mono-[5-(5,6-dimethyl-benzoimidazol-1-yl)-3,4-dihydroxy-tetrahydro-furan-2ylmethyl] esterChEBI
5,6-Dimethyl-1-a-D-ribofuranosylbenzimidazole 5'-phosphateGenerator
5,6-Dimethyl-1-a-D-ribofuranosylbenzimidazole 5'-phosphoric acidGenerator
5,6-Dimethyl-1-alpha-D-ribofuranosylbenzimidazole 5'-phosphoric acidGenerator
5,6-Dimethyl-1-α-D-ribofuranosylbenzimidazole 5'-phosphateGenerator
5,6-Dimethyl-1-α-D-ribofuranosylbenzimidazole 5'-phosphoric acidGenerator
a-Ribazole-5'-PGenerator
α-ribazole-5'-PGenerator
a-RIBAZOLE-5'-phosphateGenerator
a-RIBAZOLE-5'-phosphoric acidGenerator
alpha-RIBAZOLE-5'-phosphoric acidGenerator
α-ribazole-5'-phosphateGenerator
α-ribazole-5'-phosphoric acidGenerator
N1-(5-phospho-α-D-ribosyl)-5,6-dimethylbenzimidazoleGenerator
PHOSPHate mono-[5-(5,6-dimethyl-benzoimidazol-1-yl)-3,4-dihydroxy-tetrahydro-furan-2ylmethyl] esterGenerator
alpha-Ribazole 5'-phosphateHMDB
alpha-Ribazole-5'-PO4HMDB
N1-(5-phospho-alpha-delta-Ribosyl)-5,6-dimethylbenzimidazoleHMDB
Chemical FormulaC14H19N2O7P
Average Molecular Weight358.2836
Monoisotopic Molecular Weight358.092987484
IUPAC Name{[(2R,3S,4R,5S)-5-(5,6-dimethyl-1H-1,3-benzodiazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional Nameα-ribazole-5'-P
CAS Registry NumberNot Available
SMILES
CC1=CC2=C(C=C1C)N(C=N2)[C@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C14H19N2O7P/c1-7-3-9-10(4-8(7)2)16(6-15-9)14-13(18)12(17)11(23-14)5-22-24(19,20)21/h3-4,6,11-14,17-18H,5H2,1-2H3,(H2,19,20,21)/t11-,12-,13-,14+/m1/s1
InChI KeyZMRGXEJKZPRBPJ-SYQHCUMBSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as benzimidazole ribonucleosides and ribonucleotides. These are nucleosides with a structure that consists of an imidazole moiety of benzimidazole is N-linked to a ribose (or deoxyribose). Nucleotides have a phosphate group linked to the C5 carbon of the ribose (or deoxyribose) moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassBenzimidazole ribonucleosides and ribonucleotides
Direct ParentBenzimidazole ribonucleosides and ribonucleotides
Alternative Parents
Substituents
  • 1-ribofuranosylbenzimidazole
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Benzimidazole
  • Monoalkyl phosphate
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Benzenoid
  • Alkyl phosphate
  • Phosphoric acid ester
  • Heteroaromatic compound
  • Imidazole
  • Oxolane
  • Azole
  • Secondary alcohol
  • 1,2-diol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.524Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.53 mg/mLALOGPS
logP-0.32ALOGPS
logP-1.5ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)5.81ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area134.27 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity82.52 m3·mol-1ChemAxon
Polarizability34.13 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0924000000-ca83b2cabb6f848fb606View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1910000000-f1a785d3193f0d8ff5bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0900000000-047b40eca213cd9b3d4dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6s-7709000000-c0797f58260c9a1a6a6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-8900000000-1229d2ae6136dbe43637View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-e3828a9e7ec68e9998b4View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023243
KNApSAcK IDNot Available
Chemspider ID392720
KEGG Compound IDC04778
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB03882
Metagene LinkHMDB03882
METLIN IDNot Available
PubChem Compound444941
PDB IDRBZ
ChEBI ID16837
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in phosphohistidine phosphatase activity
Specific function:
Exhibits phosphohistidine phosphatase activity.
Gene Name:
PHPT1
Uniprot ID:
Q9NRX4
Molecular weight:
Not Available