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Record Information
Version3.6
Creation Date2012-09-11 17:35:29 UTC
Update Date2016-02-11 01:47:18 UTC
HMDB IDHMDB30213
Secondary Accession NumbersNone
Metabolite Identification
Common Name(S)-Laudanosine
Description(S)-Laudanosine is found in opium poppy. (S)-Laudanosine is an alkaloid from Papaver somniferum (opium poppy) (S)-Laudanosine belongs to the family of Benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.
Structure
Thumb
Synonyms
ValueSource
LaudanosineHMDB
Chemical FormulaC21H27NO4
Average Molecular Weight357.4434
Monoisotopic Molecular Weight357.194008357
IUPAC Name1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
Traditional Namelaudanosine
CAS Registry Number2688-77-9
SMILES
COC1=C(OC)C=C(CC2N(C)CCC3=CC(OC)=C(OC)C=C23)C=C1
InChI Identifier
InChI=1/C21H27NO4/c1-22-9-8-15-12-20(25-4)21(26-5)13-16(15)17(22)10-14-6-7-18(23-2)19(11-14)24-3/h6-7,11-13,17H,8-10H2,1-5H3
InChI KeyInChIKey=KGPAYJZAMGEDIQ-UHFFFAOYNA-N
Chemical Taxonomy
DescriptionThis compound 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
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • Tetrahydroisoquinoline
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • Aralkylamine
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
  • Endogenous
  • Food
Biofunction
  • Waste products
Application
  • Nutrient
Cellular locations
  • Membrane
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point89 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.021 mg/mLALOGPS
logP2.96ALOGPS
logP3.4ChemAxon
logS-4.2ALOGPS
pKa (Strongest Basic)8.28ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.16 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity102.8 m3·mol-1ChemAxon
Polarizability39.9 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00636
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB002032
KNApSAcK IDC00001876
Chemspider ID14792
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB30213
Metagene LinkHMDB30213
METLIN IDNot Available
PubChem Compound15548
PDB IDNot Available
ChEBI ID444892
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.