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Showing Compound Laudanine (FDB002030)

Record Information
Version1.0
Creation date2010-04-08 22:05:12 UTC
Update date2019-11-26 02:56:54 UTC
Primary IDFDB002030
Secondary Accession Numbers
  • FDB002029
Chemical Information
FooDB NameLaudanine
Description(R)-Laudanidine, also known as tritopin or DL-laudanine, belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached (R)-Laudanidine has been detected, but not quantified in, opium poppies (Papaver somniferum). This could make (R)-laudanidine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on (R)-Laudanidine.
CAS Number301-21-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(-)-LaudanidineHMDB
DL-LaudanineHMDB
TritopinHMDB
TritopineHMDB
Laudaninedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.038 g/LALOGPS
logP3.19ALOGPS
logP3.13ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)10.02ChemAxon
pKa (Strongest Basic)8.27ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area51.16 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity98.32 m³·mol⁻¹ChemAxon
Polarizability37.92 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H25NO4
IUPAC name5-[(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]-2-methoxyphenol
InChI IdentifierInChI=1S/C20H25NO4/c1-21-8-7-14-11-19(24-3)20(25-4)12-15(14)16(21)9-13-5-6-18(23-2)17(22)10-13/h5-6,10-12,16,22H,7-9H2,1-4H3
InChI KeyMPYHGNAJOKCMAQ-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(O)C=C(CC2N(C)CCC3=CC(OC)=C(OC)C=C23)C=C1
Average Molecular Weight343.4168
Monoisotopic Molecular Weight343.178358293
Classification
Description Belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsoquinolines and derivatives
Sub ClassBenzylisoquinolines
Direct ParentBenzylisoquinolines
Alternative Parents
Substituents
  • Benzylisoquinoline
  • Methoxyphenol
  • Tetrahydroisoquinoline
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ether
  • Azacycle
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 69.95%; H 7.34%; N 4.08%; O 18.64%DFC
Melting PointMp 166-167°DFC
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-MS(R)-Laudanidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0zfr-1981000000-cc68b102f172fbb3ade9Spectrum
Predicted GC-MS(R)-Laudanidine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0r6r-2950200000-906a1df54edede6d4608Spectrum
Predicted GC-MS(R)-Laudanidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-2a2a7726cd989268ed122016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0btc-0679000000-b728082320290c20a63b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fr-1930000000-b96edd90b8e3a35f2fe02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-e51949b59b42fd6231882016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-0019000000-31ff5cd819e6d3c3fed92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006t-0092000000-e09e7fc4b625837e1bed2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-4684e4ff69877ecc76512021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-0395000000-b3225b24861eb85964c72021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-0932000000-3773eccbac0b02e2fe302021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-5a516184c230fa2e7a582021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0029000000-f9df69fb6470379eaf182021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-0393000000-f28f42c4f79e561f07302021-09-23View Spectrum
NMRNot Available
ChemSpider ID83710
ChEMBL IDNot Available
KEGG Compound IDC17592
Pubchem Compound ID92732
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30211
CRC / DFC (Dictionary of Food Compounds) IDCDG23-B:CDG30-B
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00028453
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— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.