Record Information
Version1.0
Creation date2010-04-08 22:11:12 UTC
Update date2019-11-26 03:09:52 UTC
Primary IDFDB014332
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGlaucarubin
DescriptionGlaucarubin, also known as alpha-kirondrin or simarubaceae, belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring. Glaucarubin is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number1448-23-3
Structure
Thumb
Synonyms
SynonymSource
alpha-KirondrinHMDB
b-KirondrinHMDB
GlaucarubinaHMDB
SimarubaceaeHMDB
4,5,16,17-Tetrahydroxy-6,14,18-trimethyl-9-oxo-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-8-yl 2-hydroxy-2-methylbutanoic acidGenerator
KirondrinMeSH
α-kirondrinbiospider
Glaucarubindb_source
Predicted Properties
PropertyValueSource
Water Solubility2.1 g/LALOGPS
logP0.4ALOGPS
logP-0.24ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)10.89ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area162.98 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity119.72 m³·mol⁻¹ChemAxon
Polarizability50.73 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC25H36O10
IUPAC name4,5,16,17-tetrahydroxy-6,14,18-trimethyl-9-oxo-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-8-yl 2-hydroxy-2-methylbutanoate
InChI IdentifierInChI=1S/C25H36O10/c1-6-22(4,31)21(30)35-16-15-11(3)17(27)25(32)20-23(5)12(10(2)7-13(26)18(23)28)8-14(34-19(16)29)24(15,20)9-33-25/h7,11-18,20,26-28,31-32H,6,8-9H2,1-5H3
InChI KeyLZKVXMYVBSNXER-UHFFFAOYSA-N
Isomeric SMILESCCC(C)(O)C(=O)OC1C2C(C)C(O)C3(O)OCC22C3C3(C)C(O)C(O)C=C(C)C3CC2OC1=O
Average Molecular Weight496.5473
Monoisotopic Molecular Weight496.230847372
Classification
Description belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentQuassinoids
Alternative Parents
Substituents
  • C-20 quassinoid skeleton
  • Quassinoid
  • Naphthopyran
  • Naphthalene
  • Delta valerolactone
  • Fatty acid ester
  • Delta_valerolactone
  • Oxepane
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Oxane
  • Pyran
  • Tertiary alcohol
  • Tetrahydrofuran
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Hemiacetal
  • Lactone
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 60.47%; H 7.31%; O 32.22%DFC
Melting PointMp 250-255° dec.DFC
Boiling PointNot Available
Experimental Water Solubilityless than]
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D +69 (c, 0.6 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01di-6001900000-e1ce9105bdde68503ee1JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00ba-4520129000-40ed048370ebf98a64c3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-1104900000-7bb6188c59c74e7d63c3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0umi-5109400000-decc9a710ceb50a6c12cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fr-6209000000-9a4e5b75b9a759c4c42dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-1002900000-a716f8c5bf8de2ae5badJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0101-9308800000-cada2918a5e89f56ba06JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-8109000000-017a1d307b0873e107bfJSpectraViewer
ChemSpider ID2568746
ChEMBL IDNot Available
KEGG Compound IDC08760
Pubchem Compound ID3321199
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35626
CRC / DFC (Dictionary of Food Compounds) IDJVB89-V:JPQ44-L
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00003710
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
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference