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Record Information
Version	2.0
Creation Date	2012-05-31 14:00:30 -0600
Update Date	2015-06-03 15:54:32 -0600
Secondary Accession Numbers	ECMDB03882
Identification
Name:	N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole
Description	N1-(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
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x99e63d10> Close
Synonyms:	α-ribazole-5'-P a-Ribazole 5'-phosphate a-Ribazole 5'-phosphoric acid a-Ribazole-5'-P a-Ribazole-5'-PO4 Alpha-Ribazole 5'-phosphate alpha-Ribazole 5'-phosphoric acid Alpha-Ribazole-5'-P Alpha-Ribazole-5'-PO4 DMB-ribose-5'-P N1-(5'-phospho-α-D-ribosyl)-5,6-dimethylbenzimidazole N1-(5'-phospho-a-D-Ribosyl)-5,6-dimethylbenzimidazole N1-(5'-phospho-alpha-D-ribosyl)-5,6-dimethylbenzimidazole N1-(5'-phospho-α-D-Ribosyl)-5,6-dimethylbenzimidazole N1-(5-phospho-a-delta-Ribosyl)-5,6-dimethylbenzimidazole N1-(5-phospho-a-δ-Ribosyl)-5,6-dimethylbenzimidazole N1-(5-Phospho-alpha-D-ribosyl)-5,6-dimethylbenzimidazole N1-(5-Phospho-alpha-delta-ribosyl)-5,6-dimethylbenzimidazole N1-(5-phospho-α-D-Ribosyl)-5,6-dimethylbenzimidazole N1-(5-phospho-α-δ-Ribosyl)-5,6-dimethylbenzimidazole Ribazole5'P α-Ribazole 5'-phosphate α-Ribazole 5'-phosphoric acid α-Ribazole-5'-P α-Ribazole-5'-PO4
Chemical Formula:	C14H19N2O7P
Weight:	Average: 358.2836 Monoisotopic: 358.092987484
InChI Key:	ZMRGXEJKZPRBPJ-SYQHCUMBSA-N
InChI:	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
CAS number:	Not Available
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 IUPAC Name:	α-ribazole-5'-P
SMILES:	CC1=CC2=C(C=C1C)N(C=N2)[C@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
Chemical Taxonomy
Description	belongs to the class of organic compounds 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.
Kingdom	Organic compounds
Super Class	Nucleosides, nucleotides, and analogues
Class	Benzimidazole ribonucleosides and ribonucleotides
Sub Class	Not Available
Direct Parent	Benzimidazole ribonucleosides and ribonucleotides
Alternative Parents	Pentose phosphates Glycosylamines Monosaccharide phosphates Benzimidazoles Monoalkyl phosphates N-substituted imidazoles Benzenoids Heteroaromatic compounds Tetrahydrofurans 1,2-diols Secondary alcohols Oxacyclic compounds Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
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 Phosphoric acid ester Alkyl phosphate Benzenoid Azole Tetrahydrofuran Imidazole Heteroaromatic compound 1,2-diol Secondary alcohol Oxacycle Organoheterocyclic compound Azacycle Hydrocarbon derivative Organonitrogen compound Organooxygen compound Organic oxygen compound Organic nitrogen compound Organopnictogen compound Organic oxide Alcohol Aromatic heteropolycyclic compound
Molecular Framework	Aromatic heteropolycyclic compounds
External Descriptors	ribose monophosphate (CHEBI:16837 ) 1-ribosylbenzimidazole (CHEBI:16837 ) dimethylbenzimidazole (CHEBI:16837 )
Physical Properties
State:	Solid
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source LogP: -0.524 PhysProp
Predicted Properties	Property Value Source Water Solubility 1.53 g/L ALOGPS logP -0.32 ALOGPS logP -1.5 ChemAxon logS -2.4 ALOGPS pKa (Strongest Acidic) 1.22 ChemAxon pKa (Strongest Basic) 5.81 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 134.27 Ų ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 82.52 m³·mol⁻¹ ChemAxon Polarizability 34.13 ų ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole + Water > Phosphate + N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole Dimethylbenzimidazole + Nicotinamide ribotide <> N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole + Hydrogen ion + Nicotinic acid N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole + Water <> N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole + Phosphate Adenosylcobinamide-GDP + N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole > adenosylcobalamin 5'-phosphate + Guanosine monophosphate + Hydrogen ion Nicotinamide ribotide + Dimethylbenzimidazole > Hydrogen ion + Nicotinic acid + N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole + Water > alpha-ribazole + Inorganic phosphate Nicotinamide ribotide + Dimethylbenzimidazole > Nicotinic acid + N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole Adenosylcobinamide-GDP + N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole + N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole <> Guanosine monophosphate + Adenosylcobalamin + Adenosylcobalamin 5'-phosphate Dimethylbenzimidazole + nicotinate beta-D-ribonucleotide + Nicotinamide ribotide > Hydrogen ion + Nicotinic acid + N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole + Adenosylcobinamide-GDP + Adenosylcobinamide-GDP > Hydrogen ion + GMP + Adenosylcobalamin 5'-phosphate N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole + Water > Phosphate + N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole + Water > Phosphate + N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole
SMPDB Pathways:	adenosylcobalamin salvage from cobinamide PW001884
KEGG Pathways:	Metabolic pathways eco01100 Porphyrin and chlorophyll metabolism ec00860 Riboflavin metabolism ec00740
EcoCyc Pathways:	adenosylcobalamin salvage from cobinamide I COBALSYN-PWY-1
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0002-9612000000-fb21cfa813df9fff3f0d View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive splash10-01vk-5943100000-cb128df76b1b27f96534 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0002-0924000000-ca83b2cabb6f848fb606 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0002-1910000000-f1a785d3193f0d8ff5bc View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0002-0900000000-047b40eca213cd9b3d4d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0a6s-7709000000-c0797f58260c9a1a6a6c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-002b-8900000000-1229d2ae6136dbe43637 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9200000000-e3828a9e7ec68e9998b4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0a4i-3009000000-6535ffb46debd0ae1f34 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9001000000-578749d5ff31e4fab5ea View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9100000000-d4ee221347b2259634d2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0a4j-0719000000-2538d2d5f670e5ddcec9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0002-0923000000-40c17e787a25cabb848e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0002-4900000000-6c85eaa5dbac4013d383 View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer
References
References:	Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 16837 HMDB ID HMDB03882 Pubchem Compound ID 444941 Kegg ID C04778 ChemSpider ID 392720 Wikipedia ID Not Available BioCyc ID ALPHA-RIBAZOLE-5-P EcoCyc ID ALPHA-RIBAZOLE-5-P Ligand Expo RIC

Enzymes