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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:28:11 UTC
Update Date2022-03-07 02:54:09 UTC
HMDB IDHMDB0034592
Secondary Accession Numbers
  • HMDB34592
Metabolite Identification
Common NameLansamide 4
DescriptionLansamide 4 belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Lansamide 4 has been detected, but not quantified in, fruits. This could make lansamide 4 a potential biomarker for the consumption of these foods. Lansamide 4 is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on Lansamide 4.
Structure
Data?1563862587
Synonyms
ValueSource
3-Hydroxy-6-methoxy-1-methyl-4,5-diphenyl-2-piperidinonChEBI
3-Hydroxy-6-methoxy-1-methyl-4,5-diphenyl-2-piperidinoneHMDB
Lansimide 4HMDB
Chemical FormulaC19H21NO3
Average Molecular Weight311.3749
Monoisotopic Molecular Weight311.152143543
IUPAC Name3-hydroxy-6-methoxy-1-methyl-4,5-diphenylpiperidin-2-one
Traditional Name3-hydroxy-6-methoxy-1-methyl-4,5-diphenylpiperidin-2-one
CAS Registry Number211505-00-9
SMILES
COC1C(C(C(O)C(=O)N1C)C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C19H21NO3/c1-20-18(22)17(21)15(13-9-5-3-6-10-13)16(19(20)23-2)14-11-7-4-8-12-14/h3-12,15-17,19,21H,1-2H3
InChI KeyHGOXSQCBJLZRJO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Phenylpiperidine
  • Delta-lactam
  • Piperidinone
  • Monocyclic benzene moiety
  • Benzenoid
  • Piperidine
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Lactam
  • Secondary alcohol
  • Azacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point187 - 188 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.4 g/LALOGPS
logP2.04ALOGPS
logP2.38ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)12.8ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.77 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity88.22 m³·mol⁻¹ChemAxon
Polarizability33.59 ųChemAxon
Number of Rings3ChemAxon
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]+171.72231661259
DarkChem[M-H]-171.06231661259
DeepCCS[M+H]+173.38530932474
DeepCCS[M-H]-171.02730932474
DeepCCS[M-2H]-204.91630932474
DeepCCS[M+Na]+180.32830932474
AllCCS[M+H]+175.032859911
AllCCS[M+H-H2O]+171.532859911
AllCCS[M+NH4]+178.332859911
AllCCS[M+Na]+179.332859911
AllCCS[M-H]-179.832859911
AllCCS[M+Na-2H]-179.732859911
AllCCS[M+HCOO]-179.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Lansamide 4COC1C(C(C(O)C(=O)N1C)C1=CC=CC=C1)C1=CC=CC=C13708.4Standard polar33892256
Lansamide 4COC1C(C(C(O)C(=O)N1C)C1=CC=CC=C1)C1=CC=CC=C12522.0Standard non polar33892256
Lansamide 4COC1C(C(C(O)C(=O)N1C)C1=CC=CC=C1)C1=CC=CC=C12521.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Lansamide 4,1TMS,isomer #1COC1C(C2=CC=CC=C2)C(C2=CC=CC=C2)C(O[Si](C)(C)C)C(=O)N1C2434.3Semi standard non polar33892256
Lansamide 4,1TBDMS,isomer #1COC1C(C2=CC=CC=C2)C(C2=CC=CC=C2)C(O[Si](C)(C)C(C)(C)C)C(=O)N1C2673.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Lansamide 4 GC-MS (Non-derivatized) - 70eV, Positivesplash10-001l-1930000000-0cff559141d8524d92a92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lansamide 4 GC-MS (1 TMS) - 70eV, Positivesplash10-0036-3951000000-3b0aae81bc235033ace22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lansamide 4 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 - Lansamide 4 10V, Negative-QTOFsplash10-03di-0009000000-ff5ecec3f5761d8319602016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lansamide 4 20V, Negative-QTOFsplash10-03di-2896000000-456f8e4c4de50ea8600a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lansamide 4 40V, Negative-QTOFsplash10-0a4i-9210000000-270a81024d3cf12d2d3b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lansamide 4 10V, Negative-QTOFsplash10-03di-0009000000-9bf675b2e28db05b0d3b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lansamide 4 20V, Negative-QTOFsplash10-03di-0169000000-8d2ea231d305ff6c5b282021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lansamide 4 40V, Negative-QTOFsplash10-004i-3932000000-a450800a70d9514c2d6d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lansamide 4 10V, Positive-QTOFsplash10-03di-0039000000-983af54750d2fcf9c95e2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lansamide 4 20V, Positive-QTOFsplash10-03dl-4195000000-c38b92a5091845a79d782016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lansamide 4 40V, Positive-QTOFsplash10-0006-9310000000-af961ee1346a36f0c4382016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lansamide 4 10V, Positive-QTOFsplash10-03di-0039000000-5f9b875c4e3d4c439a922021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lansamide 4 20V, Positive-QTOFsplash10-03e9-0395000000-db8e75418eb8c7e984a52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lansamide 4 40V, Positive-QTOFsplash10-0f8c-3920000000-be8953720c9fc6f42b022021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013108
KNApSAcK IDNot Available
Chemspider ID8694499
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10519101
PDB IDNot Available
ChEBI ID141548
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.. .