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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:30:34 UTC
Update Date2022-03-07 02:53:50 UTC
HMDB IDHMDB0033749
Secondary Accession Numbers
  • HMDB33749
Metabolite Identification
Common NameIsoliensinine
DescriptionIsoliensinine belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached. Isoliensinine has been detected, but not quantified in, a few different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, and robusta coffees (Coffea canephora). This could make isoliensinine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Isoliensinine.
Structure
Data?1563862454
Synonyms
ValueSource
IsoliensininHMDB
Chemical FormulaC37H42N2O6
Average Molecular Weight610.7392
Monoisotopic Molecular Weight610.304287086
IUPAC Name1-{[4-hydroxy-3-({6-methoxy-1-[(4-methoxyphenyl)methyl]-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl}oxy)phenyl]methyl}-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol
Traditional Name1-{[4-hydroxy-3-({6-methoxy-1-[(4-methoxyphenyl)methyl]-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl}oxy)phenyl]methyl}-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol
CAS Registry Number6817-41-0
SMILES
COC1=CC=C(CC2N(C)CCC3=CC(OC)=C(OC4=C(O)C=CC(CC5N(C)CCC6=CC(OC)=C(O)C=C56)=C4)C=C23)C=C1
InChI Identifier
InChI=1S/C37H42N2O6/c1-38-15-13-26-20-36(44-5)37(22-29(26)30(38)16-23-6-9-27(42-3)10-7-23)45-35-18-24(8-11-32(35)40)17-31-28-21-33(41)34(43-4)19-25(28)12-14-39(31)2/h6-11,18-22,30-31,40-41H,12-17H2,1-5H3
InChI KeyAJPXZTKPPINUKN-UHFFFAOYSA-N
Chemical Taxonomy
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
  • Diaryl ether
  • Tetrahydroisoquinoline
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ether
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.017 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0049 g/LALOGPS
logP5.71ALOGPS
logP5.23ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)7.16ChemAxon
pKa (Strongest Basic)10.9ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.86 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity177.43 m³·mol⁻¹ChemAxon
Polarizability68.01 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+241.17731661259
DarkChem[M-H]-237.91131661259
DeepCCS[M-2H]-267.730932474
DeepCCS[M+Na]+242.32930932474
AllCCS[M+H]+251.132859911
AllCCS[M+H-H2O]+250.032859911
AllCCS[M+NH4]+252.232859911
AllCCS[M+Na]+252.532859911
AllCCS[M-H]-230.932859911
AllCCS[M+Na-2H]-232.732859911
AllCCS[M+HCOO]-234.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IsoliensinineCOC1=CC=C(CC2N(C)CCC3=CC(OC)=C(OC4=C(O)C=CC(CC5N(C)CCC6=CC(OC)=C(O)C=C56)=C4)C=C23)C=C16114.2Standard polar33892256
IsoliensinineCOC1=CC=C(CC2N(C)CCC3=CC(OC)=C(OC4=C(O)C=CC(CC5N(C)CCC6=CC(OC)=C(O)C=C56)=C4)C=C23)C=C14550.8Standard non polar33892256
IsoliensinineCOC1=CC=C(CC2N(C)CCC3=CC(OC)=C(OC4=C(O)C=CC(CC5N(C)CCC6=CC(OC)=C(O)C=C56)=C4)C=C23)C=C14949.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isoliensinine,1TMS,isomer #1COC1=CC=C(CC2C3=CC(OC4=CC(CC5C6=CC(O)=C(OC)C=C6CCN5C)=CC=C4O[Si](C)(C)C)=C(OC)C=C3CCN2C)C=C14814.8Semi standard non polar33892256
Isoliensinine,1TMS,isomer #2COC1=CC=C(CC2C3=CC(OC4=CC(CC5C6=CC(O[Si](C)(C)C)=C(OC)C=C6CCN5C)=CC=C4O)=C(OC)C=C3CCN2C)C=C14787.6Semi standard non polar33892256
Isoliensinine,2TMS,isomer #1COC1=CC=C(CC2C3=CC(OC4=CC(CC5C6=CC(O[Si](C)(C)C)=C(OC)C=C6CCN5C)=CC=C4O[Si](C)(C)C)=C(OC)C=C3CCN2C)C=C14762.4Semi standard non polar33892256
Isoliensinine,1TBDMS,isomer #1COC1=CC=C(CC2C3=CC(OC4=CC(CC5C6=CC(O)=C(OC)C=C6CCN5C)=CC=C4O[Si](C)(C)C(C)(C)C)=C(OC)C=C3CCN2C)C=C15004.1Semi standard non polar33892256
Isoliensinine,1TBDMS,isomer #2COC1=CC=C(CC2C3=CC(OC4=CC(CC5C6=CC(O[Si](C)(C)C(C)(C)C)=C(OC)C=C6CCN5C)=CC=C4O)=C(OC)C=C3CCN2C)C=C14982.0Semi standard non polar33892256
Isoliensinine,2TBDMS,isomer #1COC1=CC=C(CC2C3=CC(OC4=CC(CC5C6=CC(O[Si](C)(C)C(C)(C)C)=C(OC)C=C6CCN5C)=CC=C4O[Si](C)(C)C(C)(C)C)=C(OC)C=C3CCN2C)C=C15139.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isoliensinine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-0901200000-43445c0cbd9e61218af02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoliensinine GC-MS (1 TMS) - 70eV, Positivesplash10-0006-0900011000-44d33e0a94a433ba65b82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoliensinine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoliensinine GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoliensinine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoliensinine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoliensinine GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoliensinine GC-MS ("Isoliensinine,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-20Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoliensinine 10V, Positive-QTOFsplash10-03di-0010049000-f92861be9144168f23a72015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoliensinine 20V, Positive-QTOFsplash10-000x-0920581000-aafcd46c56623ec7e1092015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoliensinine 40V, Positive-QTOFsplash10-0005-0951130000-8e08f5055c96fd9d54c62015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoliensinine 10V, Negative-QTOFsplash10-0a4i-0001019000-bfccca31b1f37c4471b42015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoliensinine 20V, Negative-QTOFsplash10-08fv-0086096000-2b529b7029c519cd23242015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoliensinine 40V, Negative-QTOFsplash10-0002-0191000000-e69f3518fbbffdde92fa2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoliensinine 10V, Negative-QTOFsplash10-0a4i-0000009000-1bf6ad4873b01da32e142021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoliensinine 20V, Negative-QTOFsplash10-0a7i-0010093000-6d082c6b8293d39a450d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoliensinine 40V, Negative-QTOFsplash10-0a4i-0110196000-e0cfe7d42ee294df36d32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoliensinine 10V, Positive-QTOFsplash10-03di-0001009000-d812cf5f7d77bfd1e6b22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoliensinine 20V, Positive-QTOFsplash10-0ir0-3520295000-96d3ba0336886eb64ebd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoliensinine 40V, Positive-QTOFsplash10-05ox-7752294000-9f325a8331ce660142d42021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB011881
KNApSAcK IDC00050943
Chemspider ID8275812
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10100278
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1838171
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.. .