Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 18:15:44 UTC
Update Date2022-09-22 18:34:25 UTC
HMDB IDHMDB0033524
Secondary Accession Numbers
  • HMDB33524
Metabolite Identification
Common NameLambertine
DescriptionLambertine, also known as dihydroberberine, belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton. Lambertine is a strong basic compound (based on its pKa). Outside of the human body, lambertine has been detected, but not quantified in, fruits and tea. This could make lambertine a potential biomarker for the consumption of these foods.
Structure
Data?1563862419
Synonyms
ValueSource
DihydroberberineHMDB
Dihydroberberine hydrochlorideHMDB
Chemical FormulaC20H19NO4
Average Molecular Weight337.3692
Monoisotopic Molecular Weight337.131408101
IUPAC Name16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaene
Traditional Name16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaene
CAS Registry Number120834-89-1
SMILES
COC1=CC=C2C=C3N(CCC4=CC5=C(OCO5)C=C34)CC2=C1OC
InChI Identifier
InChI=1S/C20H19NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,7-9H,5-6,10-11H2,1-2H3
InChI KeyFZAGOOYMTPGPGF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassProtoberberine alkaloids and derivatives
Sub ClassNot Available
Direct ParentProtoberberine alkaloids and derivatives
Alternative Parents
Substituents
  • Protoberberine skeleton
  • Tetrahydroisoquinoline
  • Benzodioxole
  • Anisole
  • Alkyl aryl ether
  • Aralkylamine
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Azacycle
  • Enamine
  • Ether
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point163 - 164 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.073 g/LALOGPS
logP3.36ALOGPS
logP2.84ChemAxon
logS-3.7ALOGPS
pKa (Strongest Basic)4.02ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.16 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity95.69 m³·mol⁻¹ChemAxon
Polarizability37.11 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+179.33231661259
DarkChem[M-H]-179.84231661259
DeepCCS[M-2H]-221.46530932474
DeepCCS[M+Na]+196.69230932474
AllCCS[M+H]+180.732859911
AllCCS[M+H-H2O]+177.532859911
AllCCS[M+NH4]+183.732859911
AllCCS[M+Na]+184.632859911
AllCCS[M-H]-187.132859911
AllCCS[M+Na-2H]-186.532859911
AllCCS[M+HCOO]-185.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LambertineCOC1=CC=C2C=C3N(CCC4=CC5=C(OCO5)C=C34)CC2=C1OC4761.9Standard polar33892256
LambertineCOC1=CC=C2C=C3N(CCC4=CC5=C(OCO5)C=C34)CC2=C1OC2786.6Standard non polar33892256
LambertineCOC1=CC=C2C=C3N(CCC4=CC5=C(OCO5)C=C34)CC2=C1OC3170.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Lambertine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-0937000000-0c51681a533aea1542e82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lambertine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lambertine 10V, Positive-QTOFsplash10-000i-0009000000-71e9dc30e119186620ae2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lambertine 20V, Positive-QTOFsplash10-000i-0109000000-811a0237d57b2724db6b2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lambertine 40V, Positive-QTOFsplash10-002g-0891000000-70473923c1a156f458832016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lambertine 10V, Negative-QTOFsplash10-000i-0009000000-a4fa7b371323f46c26ef2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lambertine 20V, Negative-QTOFsplash10-000i-0019000000-f71cc29f31c9f84190662016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lambertine 40V, Negative-QTOFsplash10-0fdo-0092000000-a15fa22a545766a000f52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lambertine 10V, Negative-QTOFsplash10-000i-0009000000-e425d548b88b813581922021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lambertine 20V, Negative-QTOFsplash10-000i-0009000000-875cb50d577bc475b1662021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lambertine 40V, Negative-QTOFsplash10-0076-0093000000-545328ff2003bc0bf8bd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lambertine 10V, Positive-QTOFsplash10-000i-0009000000-195152c9499dc2b0f3dd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lambertine 20V, Positive-QTOFsplash10-000i-0009000000-177debf6280ad456cbfd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lambertine 40V, Positive-QTOFsplash10-000i-0369000000-0a5b23cfa362b926caa02021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011580
KNApSAcK IDC00028445
Chemspider ID9800
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10217
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.. .