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Showing Compound 16,17-Dihydro-16a,17-dihydroxygibberellin A4 17-glucoside (FDB020440)

Record Information
Version1.0
Creation date2010-04-08 22:15:01 UTC
Update date2019-11-26 03:18:56 UTC
Primary IDFDB020440
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name16,17-Dihydro-16a,17-dihydroxygibberellin A4 17-glucoside
Description16,17-Dihydro-16a,17-dihydroxygibberellin A4 17-glucoside belongs to the class of organic compounds known as cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]octane moiety. 16,17-Dihydro-16a,17-dihydroxygibberellin A4 17-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). 16,17-Dihydro-16a,17-dihydroxygibberellin A4 17-glucoside has been detected, but not quantified in, cereals and cereal products. This could make 16,17-dihydro-16a,17-dihydroxygibberellin A4 17-glucoside a potential biomarker for the consumption of these foods.
CAS Number159858-83-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
6,12-Dihydroxy-11-methyl-16-oxo-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylateGenerator
16,17-Dihydro-16a,17-dihydroxygibberellin A4 17-glucosidemanual
16,17-Dihydro-16a,17-dihydroxygibberellin A4 17-O-b-D-glucopyranosidemanual
16,17-Dihydro-16a,17-dihydroxygibberellin A4 17-O-b-D-glucosidemanual
Predicted Properties
PropertyValueSource
Water Solubility8.42 g/LALOGPS
logP-0.97ALOGPS
logP-2.2ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.93ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area203.44 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity119.94 m³·mol⁻¹ChemAxon
Polarizability52.57 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC25H36O12
IUPAC name6,12-dihydroxy-11-methyl-16-oxo-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylic acid
InChI IdentifierInChI=1S/C25H36O12/c1-22-13(27)4-5-25(37-21(22)33)12-3-2-10-6-23(12,14(18(22)25)19(31)32)8-24(10,34)9-35-20-17(30)16(29)15(28)11(7-26)36-20/h10-18,20,26-30,34H,2-9H2,1H3,(H,31,32)
InChI KeyXKXOQMAKWNRIFD-UHFFFAOYSA-N
Isomeric SMILESCC12C3C(C(O)=O)C45CC(CCC4C3(CCC1O)OC2=O)C(O)(COC1OC(CO)C(O)C(O)C1O)C5
Average Molecular Weight528.5461
Monoisotopic Molecular Weight528.220676616
Classification
Description Belongs to the class of organic compounds known as cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]Octane moiety.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassCinchona alkaloids
Sub ClassNot Available
Direct ParentCinchona alkaloids
Alternative Parents
Substituents
  • Cinchonan-skeleton
  • 4-quinolinemethanol
  • Quinoline
  • Anisole
  • Quinuclidine
  • Alkyl aryl ether
  • Aralkylamine
  • Piperidine
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • 1,2-aminoalcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Alcohol
  • Organic oxygen compound
  • Aromatic alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 56.81%; H 6.86%; O 36.32%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS16,17-Dihydro-16a,17-dihydroxygibberellin A4 17-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-08fr-9523630000-d6128596c604908a5539Spectrum
Predicted GC-MS16,17-Dihydro-16a,17-dihydroxygibberellin A4 17-glucoside, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-8800229000-ce52ce83a2e50183ccdcSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0004590000-4ca69cfe58aba4f399882017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0295-0209420000-e5ed7b608311c0d2bda52017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7y-3719300000-a6f23fe54ff2e91567962017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1403690000-c5eaa2da559c75948f302017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0859-4707940000-2ad0e5bde056e84182272017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9217000000-69567a291650f4c2cb822017-09-01View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID85110572
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB40647
CRC / DFC (Dictionary of Food Compounds) IDJFT78-V:MSL98-H
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference