Showing Compound Card for cis-Zeatin O-glucoside (CDB005008)

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Record Information
Version1.0
Created at2020-04-17 18:59:51 UTC
Updated at2020-12-07 19:11:26 UTC
CannabisDB IDCDB005008
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namecis-Zeatin O-glucoside
Descriptioncis-Zeatin O-glucoside, also known as O-b-D-glucosyl-cis-zeatin, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. cis-Zeatin O-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). cis-Zeatin O-glucoside is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
cis-Zeatin-O-glucosideChEBI
O-b-D-Glucosyl-cis-zeatinHMDB
O-Β-D-glucosyl-cis-zeatinHMDB
(2Z)-2-Methyl-4-(1H-purin-6-ylamino)-2-buten-1-yl beta-D-glucopyranosideHMDB
(2Z)-2-Methyl-4-(1H-purin-6-ylamino)-2-buten-1-yl β-D-glucopyranosideHMDB
O-beta-D-Glucopyranosyl-cis-zeatinHMDB
O-beta-D-Glucosyl-cis-zeatinHMDB
O-Β-D-glucopyranosyl-cis-zeatinHMDB
cis-Zeatin O-glucosideHMDB
Chemical FormulaC16H23N5O6
Average Molecular Weight381.39
Monoisotopic Molecular Weight381.1648
IUPAC Name(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2Z)-2-methyl-4-[(1H-purin-6-yl)amino]but-2-en-1-yl]oxy}oxane-3,4,5-triol
Traditional Name(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2Z)-2-methyl-4-(1H-purin-6-ylamino)but-2-en-1-yl]oxy}oxane-3,4,5-triol
CAS Registry Number71866-93-8
SMILES
C\C(CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)=C\CNC1=C2N=CN=C2N=CN1
InChI Identifier
InChI=1S/C16H23N5O6/c1-8(2-3-17-14-10-15(19-6-18-10)21-7-20-14)5-26-16-13(25)12(24)11(23)9(4-22)27-16/h2,6-7,9,11-13,16,22-25H,3-5H2,1H3,(H2,17,18,19,20,21)/b8-2-/t9-,11-,12+,13-,16-/m1/s1
InChI KeyUUPDCCPAOMDMPT-MTQUCLQASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl glycosides
Direct ParentFatty acyl glycosides of mono- and disaccharides
Alternative Parents
Substituents
  • Fatty acyl glycoside of mono- or disaccharide
  • Alkyl glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • 6-alkylaminopurine
  • 6-aminopurine
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Secondary aliphatic/aromatic amine
  • Monosaccharide
  • Oxane
  • Pyrimidine
  • Imidolactam
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Secondary alcohol
  • Organoheterocyclic compound
  • Secondary amine
  • Polyol
  • Acetal
  • Azacycle
  • Oxacycle
  • Primary alcohol
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organopnictogen compound
  • Amine
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Route of exposure:

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.5ALOGPS
logP-2.1ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)6.11ChemAxon
pKa (Strongest Basic)0.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area165.87 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity95.71 m³·mol⁻¹ChemAxon
Polarizability37.44 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MScis-Zeatin O-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 19V, positivesplash10-00di-0291000000-8ff78feb3055c54c68032020-07-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0319000000-09a2cada4b696df940782021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0j4i-5389000000-7ffde7d78e85e3603b5f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-5910000000-86999dda86df003974452021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0019000000-2c70425e036b227bbae32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0292000000-187056877f7e89f290412021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-3890000000-cef5c68fcd71b09170ee2021-09-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0012203
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB112395
KNApSAcK IDNot Available
Chemspider ID4444204
KEGG Compound IDC15546
BioCyc IDCPD-4620
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280589
PDB IDNot Available
ChEBI ID29043
References
General ReferencesNot Available