Np mrd loader

Record Information
Version2.0
Created at2022-09-11 14:17:56 UTC
Updated at2022-09-11 14:17:56 UTC
NP-MRD IDNP0315589
Secondary Accession NumbersNone
Natural Product Identification
Common Namepyridoxine-α-glucoside
Description5'-O-beta-D-glucosylpyridoxine, also known as beta-D-glucopyranoside pyridoxol or 5'-O-(glucopyranosyl)pyridoxine, belongs to the class of organic compounds known as pyridoxines. These are pyridoxal derivatives in which the carbaldehyde group at position 2 of the pyridoxal moiety is replaced by a hydroxymethyl group. pyridoxine-α-glucoside is found in Pisum sativum. pyridoxine-α-glucoside was first documented in 1992 (PMID: 1552357). Based on a literature review a small amount of articles have been published on 5'-O-beta-D-glucosylpyridoxine (PMID: 12023280) (PMID: 12221231) (PMID: 12730423) (PMID: 15051835).
Structure
Thumb
Synonyms
ValueSource
5'-O-(beta-D-Glucopyranosyl)pyridoxineChEBI
5'-O-(Glucopyranosyl)pyridoxineChEBI
5'-Pyridoxine glucosideChEBI
beta-D-Glucopyranoside pyridoxolChEBI
Pyridoxine beta-glucosideChEBI
Pyridoxine-5'-beta-D-glucosideChEBI
5'-O-(b-D-Glucopyranosyl)pyridoxineGenerator
5'-O-(Β-D-glucopyranosyl)pyridoxineGenerator
b-D-Glucopyranoside pyridoxolGenerator
Β-D-glucopyranoside pyridoxolGenerator
Pyridoxine b-glucosideGenerator
Pyridoxine β-glucosideGenerator
Pyridoxine-5'-b-D-glucosideGenerator
Pyridoxine-5'-β-D-glucosideGenerator
5'-O-b-D-GlucosylpyridoxineGenerator
5'-O-Β-D-glucosylpyridoxineGenerator
5'-O-(Glucopyranosyl)pyridoxine, (alpha)-isomerMeSH
5'-O-(Glucopyranosyl)pyridoxine, (5'alpha)-isomerMeSH
Pyridoxine-alpha-glucosideMeSH
Pyridoxine-5'-glucosideMeSH
Chemical FormulaC14H21NO8
Average Mass331.3210 Da
Monoisotopic Mass331.12672 Da
IUPAC Name(2R,3R,4S,5S,6R)-2-{[5-hydroxy-4-(hydroxymethyl)-6-methylpyridin-3-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Traditional Namepyridoxine-α-glucoside
CAS Registry NumberNot Available
SMILES
CC1=NC=C(CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(CO)=C1O
InChI Identifier
InChI=1S/C14H21NO8/c1-6-10(18)8(3-16)7(2-15-6)5-22-14-13(21)12(20)11(19)9(4-17)23-14/h2,9,11-14,16-21H,3-5H2,1H3/t9-,11-,12+,13-,14-/m1/s1
InChI KeyMDLTWTOQCHCLSZ-RGCYKPLRSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Pisum sativumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyridoxines. These are pyridoxal derivatives in which the carbaldehyde group at position 2 of the pyridoxal moiety is replaced by a hydroxymethyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridoxines
Direct ParentPyridoxines
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Pyridoxine
  • Glycosyl compound
  • O-glycosyl compound
  • Hydroxypyridine
  • Methylpyridine
  • Monosaccharide
  • Oxane
  • Heteroaromatic compound
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Azacycle
  • Polyol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organopnictogen compound
  • Primary alcohol
  • Organic oxygen compound
  • Aromatic alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.7ChemAxon
pKa (Strongest Acidic)9.4ChemAxon
pKa (Strongest Basic)5.58ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area152.73 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity76.52 m³·mol⁻¹ChemAxon
Polarizability32.7 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID389176
KEGG Compound IDC03996
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440188
PDB IDNot Available
ChEBI ID17382
Good Scents IDNot Available
References
General References
  1. Mackey AD, Henderson GN, Gregory JF 3rd: Enzymatic hydrolysis of pyridoxine-5'-beta-D-glucoside is catalyzed by intestinal lactase-phlorizin hydrolase. J Biol Chem. 2002 Jul 26;277(30):26858-64. doi: 10.1074/jbc.M201774200. Epub 2002 May 21. [PubMed:12023280 ]
  2. Armada LJ, Mackey AD, Gregory JF 3rd: Intestinal brush border membrane catalyzes hydrolysis of pyridoxine-5'-beta-D-glucoside and exhibits parallel developmental changes of hydrolytic activities toward pyridoxine-5'-beta-D-glucoside and lactose in rats. J Nutr. 2002 Sep;132(9):2695-9. doi: 10.1093/jn/132.9.2695. [PubMed:12221231 ]
  3. Mackey AD, Lieu SO, Carman C, Gregory JF 3rd: Hydrolytic activity toward pyridoxine-5'-beta-D-glucoside in rat intestinal mucosa is not increased by vitamin B-6 deficiency: effect of basal diet composition and pyridoxine intake. J Nutr. 2003 May;133(5):1362-7. doi: 10.1093/jn/133.5.1362. [PubMed:12730423 ]
  4. Mackey AD, McMahon RJ, Townsend JH, Gregory JF 3rd: Uptake, hydrolysis, and metabolism of pyridoxine-5'-beta-D-glucoside in Caco-2 cells. J Nutr. 2004 Apr;134(4):842-6. doi: 10.1093/jn/134.4.842. [PubMed:15051835 ]
  5. Gilbert JA, Gregory JF 3rd: Pyridoxine-5'-beta-D-glucoside affects the metabolic utilization of pyridoxine in rats. J Nutr. 1992 Apr;122(4):1029-35. doi: 10.1093/jn/122.4.1029. [PubMed:1552357 ]
  6. LOTUS database [Link]