Showing metabocard for Nordihydroguaiaretate (BMDB0012270)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:35:19 UTC
Update Date2020-04-22 15:49:24 UTC
BMDB IDBMDB0012270
Secondary Accession Numbers
  • BMDB12270
Metabolite Identification
Common NameNordihydroguaiaretate
DescriptionNordihydroguaiaretate belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety. Nordihydroguaiaretate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Nordihydroguaiaretic acidGenerator
1,4-Bis(3,4-dihydroxyphenyl)-2,3-dimethyl-butaneHMDB
2,3-Bis(3,4-dihydroxyphenylmethyl)butaneHMDB
4, 4'-(2,3-Dimethyl-1,4-butanediyl)bis(pyrocatechol)HMDB
4,4'- (2,3-Diemthyltetramethylene)-dipyrocatecholHMDB
4,4'-(2, 3-Dimethyltetramethylene)dipyrocatecholHMDB
4,4'-(2,3-Dimethyl-1,4-butanediyl)bis(pyrocatechol)HMDB
4,4'-(2,3-Dimethyl-1,4-butanediyl)bis-1, 2-benzenediolHMDB
4,4'-(2,3-Dimethyltetramethylene)dipyrocatecholHMDB
dihydro-Dinorguaiaretic acidHMDB
dihydro-Norguaiaretic acidHMDB
Dihydronorguaiaretic acidHMDB
NDGAHMDB
Nordihydroguairaretic acidHMDB
Chemical FormulaC18H22O4
Average Molecular Weight302.3649
Monoisotopic Molecular Weight302.151809192
IUPAC Name4-[(2S,3S)-3-[(3,4-dihydroxyphenyl)methyl]-2-methylbutyl]benzene-1,2-diol
Traditional Name4-[(2S,3S)-3-[(3,4-dihydroxyphenyl)methyl]-2-methylbutyl]benzene-1,2-diol
CAS Registry Number500-38-9
SMILES
C[C@@H](CC1=CC=C(O)C(O)=C1)[C@@H](C)CC1=CC=C(O)C(O)=C1
InChI Identifier
InChI=1S/C18H22O4/c1-11(7-13-3-5-15(19)17(21)9-13)12(2)8-14-4-6-16(20)18(22)10-14/h3-6,9-12,19-22H,7-8H2,1-2H3/t11-,12-/m0/s1
InChI KeyHCZKYJDFEPMADG-RYUDHWBXSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassDibenzylbutane lignans
Sub ClassNot Available
Direct ParentDibenzylbutane lignans
Alternative Parents
Substituents
  • Dibenzylbutane lignan skeleton
  • Phenylpropane
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.44ALOGPS
logP4.76ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)9.21ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area80.92 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity86.62 m³·mol⁻¹ChemAxon
Polarizability32.37 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fk9-0900000000-c156a7beced7bc5559ceView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-004i-1152090000-b4208f8d034e20d028bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0209000000-f3e0ee613835e76b1cf8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0umj-0912000000-0a697c743212ba4c7fcfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pvi-9650000000-c8d7bafb9c1c2aa852abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-f8459bb82f2ade44ba1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0019000000-47fe21f1ba5817a6a693View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-0490000000-4bc770bf2a65897466ffView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0012270
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNordihydroguaiaretic acid
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available