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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-23 19:21:49 UTC
Update Date2021-09-23 19:21:49 UTC
HMDB IDHMDB0302643
Secondary Accession NumbersNone
Metabolite Identification
Common NameBenzyladenine 7-O-beta-D-glucoside
Description(3R,4S,5S,6R)-2-[6-(benzylamino)-7H-purin-7-yl]-6-(hydroxymethyl)oxane-3,4,5-triol belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether). Based on a literature review very few articles have been published on (3R,4S,5S,6R)-2-[6-(benzylamino)-7H-purin-7-yl]-6-(hydroxymethyl)oxane-3,4,5-triol.
Structure
Thumb
Synonyms
ValueSource
Benzyladenine 7-O-b-D-glucosideGenerator
Benzyladenine 7-O-β-D-glucosideGenerator
Chemical FormulaC18H21N5O5
Average Molecular Weight387.3898
Monoisotopic Molecular Weight387.154268807
IUPAC Name(3R,4S,5S,6R)-2-[6-(benzylamino)-7H-purin-7-yl]-6-(hydroxymethyl)oxane-3,4,5-triol
Traditional Name(3R,4S,5S,6R)-2-[6-(benzylamino)purin-7-yl]-6-(hydroxymethyl)oxane-3,4,5-triol
CAS Registry NumberNot Available
SMILES
OC[C@H]1OC([C@H](O)[C@@H](O)[C@@H]1O)N1C=NC2=C1C(NCC1=CC=CC=C1)=NC=N2
InChI Identifier
InChI=1S/C18H21N5O5/c24-7-11-13(25)14(26)15(27)18(28-11)23-9-22-17-12(23)16(20-8-21-17)19-6-10-4-2-1-3-5-10/h1-5,8-9,11,13-15,18,24-27H,6-7H2,(H,19,20,21)/t11-,13-,14+,15-,18?/m1/s1
InChI KeyMFMRRPHRZQYKIJ-XPDDWETNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentGlycosylamines
Alternative Parents
Substituents
  • Hexose monosaccharide
  • N-glycosyl compound
  • 6-alkylaminopurine
  • 6-aminopurine
  • Imidazopyrimidine
  • Purine
  • Benzylamine
  • Aminopyrimidine
  • Secondary aliphatic/aromatic amine
  • Monocyclic benzene moiety
  • Monosaccharide
  • N-substituted imidazole
  • Oxane
  • Pyrimidine
  • Imidolactam
  • Benzenoid
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • Polyol
  • Secondary amine
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Amine
  • Organonitrogen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP0.14ALOGPS
logP-0.74ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)12.36ChemAxon
pKa (Strongest Basic)5.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area145.78 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity100.88 m³·mol⁻¹ChemAxon
Polarizability38.23 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+192.29632859911
AllCCS[M+H-H2O]+189.67232859911
AllCCS[M+Na]+195.40532859911
AllCCS[M+NH4]+194.71332859911
AllCCS[M-H]-186.6532859911
AllCCS[M+Na-2H]-186.56732859911
AllCCS[M+HCOO]-186.61732859911
DeepCCS[M+H]+176.45430932474
DeepCCS[M-H]-174.05830932474
DeepCCS[M-2H]-207.18930932474
DeepCCS[M+Na]+182.36630932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Benzyladenine 7-O-beta-D-glucoside,5TMS,isomer #1C[Si](C)(C)OC[C@H]1OC(N2C=NC3=NC=NC(N(CC4=CC=CC=C4)[Si](C)(C)C)=C32)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C3412.9Semi standard non polar33892256
Benzyladenine 7-O-beta-D-glucoside,5TMS,isomer #1C[Si](C)(C)OC[C@H]1OC(N2C=NC3=NC=NC(N(CC4=CC=CC=C4)[Si](C)(C)C)=C32)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C3061.3Standard non polar33892256
Benzyladenine 7-O-beta-D-glucoside,5TMS,isomer #1C[Si](C)(C)OC[C@H]1OC(N2C=NC3=NC=NC(N(CC4=CC=CC=C4)[Si](C)(C)C)=C32)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C3927.0Standard polar33892256
Benzyladenine 7-O-beta-D-glucoside,4TBDMS,isomer #5CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C(N2C=NC3=NC=NC(N(CC4=CC=CC=C4)[Si](C)(C)C(C)(C)C)=C32)O[C@H](CO)[C@H]1O[Si](C)(C)C(C)(C)C4012.9Semi standard non polar33892256
Benzyladenine 7-O-beta-D-glucoside,4TBDMS,isomer #5CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C(N2C=NC3=NC=NC(N(CC4=CC=CC=C4)[Si](C)(C)C(C)(C)C)=C32)O[C@H](CO)[C@H]1O[Si](C)(C)C(C)(C)C3789.1Standard non polar33892256
Benzyladenine 7-O-beta-D-glucoside,4TBDMS,isomer #5CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C(N2C=NC3=NC=NC(N(CC4=CC=CC=C4)[Si](C)(C)C(C)(C)C)=C32)O[C@H](CO)[C@H]1O[Si](C)(C)C(C)(C)C4378.7Standard polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyladenine 7-O-beta-D-glucoside 10V, Positive-QTOFsplash10-004r-3098000000-5bcfeb968ea04127bc6c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyladenine 7-O-beta-D-glucoside 20V, Positive-QTOFsplash10-004l-9371000000-b4f759afab48b98a8ccb2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyladenine 7-O-beta-D-glucoside 40V, Positive-QTOFsplash10-0006-9230000000-bfd0e94ea684e24c5a282016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyladenine 7-O-beta-D-glucoside 10V, Negative-QTOFsplash10-0079-0289000000-d7c350c0a5abd5af9bc22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyladenine 7-O-beta-D-glucoside 20V, Negative-QTOFsplash10-00di-0190000000-dea9bfd1d14fec83e9282016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyladenine 7-O-beta-D-glucoside 40V, Negative-QTOFsplash10-001i-2920000000-84e43287d83dfa2d38e12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyladenine 7-O-beta-D-glucoside 10V, Positive-QTOFsplash10-004r-0097000000-f4d3e78c37d904e3c3692021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyladenine 7-O-beta-D-glucoside 20V, Positive-QTOFsplash10-004l-6091000000-45f136ac046a19d3b06d2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyladenine 7-O-beta-D-glucoside 40V, Positive-QTOFsplash10-0006-9031000000-6b7fb7ca218556e5ed9c2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyladenine 7-O-beta-D-glucoside 10V, Negative-QTOFsplash10-000i-0049000000-cc6d1f83727bd3f369992021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyladenine 7-O-beta-D-glucoside 20V, Negative-QTOFsplash10-00di-0095000000-117c7c5b78a96c09cff92021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyladenine 7-O-beta-D-glucoside 40V, Negative-QTOFsplash10-001i-2920000000-7824c0993af9963c07162021-10-21Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB005550
KNApSAcK IDNot Available
Chemspider ID59696369
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available