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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:35:31 UTC
Update Date2022-03-07 02:52:28 UTC
HMDB IDHMDB0030220
Secondary Accession Numbers
  • HMDB30220
Metabolite Identification
Common NameLaurotetanine
DescriptionLaurotetanine, also known as litsoeine, belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. Laurotetanine is a very strong basic compound (based on its pKa). Outside of the human body, laurotetanine has been detected, but not quantified in, cherimoya. This could make laurotetanine a potential biomarker for the consumption of these foods.
Structure
Data?1563861955
Synonyms
ValueSource
(+)-LaurotetanineHMDB
6Aalpha 1,2,10-trimethoxy--noraporphin-9-olHMDB
9-Hydroxy-1,2,10-trimethoxynoraporphineHMDB
LaurotetaninHMDB
LitsoeineHMDB
LitsoeneHMDB
LaurotetanineMeSH
1,2,10-Trimethoxy-9-hydroxynoraporphineMeSH
Chemical FormulaC19H21NO4
Average Molecular Weight327.3743
Monoisotopic Molecular Weight327.147058165
IUPAC Name4,15,16-trimethoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,13,15-hexaen-5-ol
Traditional Name4,15,16-trimethoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,13,15-hexaen-5-ol
CAS Registry Number128-76-7
SMILES
COC1=C(O)C=C2CC3NCCC4=CC(OC)=C(OC)C(C2=C1)=C34
InChI Identifier
InChI=1S/C19H21NO4/c1-22-15-9-12-11(7-14(15)21)6-13-17-10(4-5-20-13)8-16(23-2)19(24-3)18(12)17/h7-9,13,20-21H,4-6H2,1-3H3
InChI KeyGVVXPMORGFYVOO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassAporphines
Sub ClassNot Available
Direct ParentAporphines
Alternative Parents
Substituents
  • Aporphine
  • Benzoquinoline
  • Phenanthrene
  • Naphthalene
  • Tetrahydroisoquinoline
  • Quinoline
  • Anisole
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Benzenoid
  • Secondary aliphatic amine
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point125 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.038 g/LALOGPS
logP1.61ALOGPS
logP1.97ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)9.95ChemAxon
pKa (Strongest Basic)9.23ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area59.95 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity92.1 m³·mol⁻¹ChemAxon
Polarizability35.64 ųChemAxon
Number of Rings4ChemAxon
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]+177.22631661259
DarkChem[M-H]-175.71731661259
DeepCCS[M-2H]-210.5430932474
DeepCCS[M+Na]+186.72730932474
AllCCS[M+H]+177.732859911
AllCCS[M+H-H2O]+174.532859911
AllCCS[M+NH4]+180.732859911
AllCCS[M+Na]+181.632859911
AllCCS[M-H]-184.432859911
AllCCS[M+Na-2H]-184.032859911
AllCCS[M+HCOO]-183.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LaurotetanineCOC1=C(O)C=C2CC3NCCC4=CC(OC)=C(OC)C(C2=C1)=C344285.1Standard polar33892256
LaurotetanineCOC1=C(O)C=C2CC3NCCC4=CC(OC)=C(OC)C(C2=C1)=C342793.8Standard non polar33892256
LaurotetanineCOC1=C(O)C=C2CC3NCCC4=CC(OC)=C(OC)C(C2=C1)=C342984.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Laurotetanine,1TMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C)CC1NCCC3=C1C2=C(OC)C(OC)=C32894.8Semi standard non polar33892256
Laurotetanine,1TMS,isomer #2COC1=CC2=C(C=C1O)CC1C3=C(C=C(OC)C(OC)=C23)CCN1[Si](C)(C)C2854.1Semi standard non polar33892256
Laurotetanine,2TMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C)CC1C3=C(C=C(OC)C(OC)=C23)CCN1[Si](C)(C)C2810.5Semi standard non polar33892256
Laurotetanine,2TMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C)CC1C3=C(C=C(OC)C(OC)=C23)CCN1[Si](C)(C)C2998.7Standard non polar33892256
Laurotetanine,1TBDMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CC1NCCC3=C1C2=C(OC)C(OC)=C33134.7Semi standard non polar33892256
Laurotetanine,1TBDMS,isomer #2COC1=CC2=C(C=C1O)CC1C3=C(C=C(OC)C(OC)=C23)CCN1[Si](C)(C)C(C)(C)C3088.4Semi standard non polar33892256
Laurotetanine,2TBDMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CC1C3=C(C=C(OC)C(OC)=C23)CCN1[Si](C)(C)C(C)(C)C3242.1Semi standard non polar33892256
Laurotetanine,2TBDMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CC1C3=C(C=C(OC)C(OC)=C23)CCN1[Si](C)(C)C(C)(C)C3441.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Laurotetanine GC-MS (Non-derivatized) - 70eV, Positivesplash10-01q9-0093000000-4a2d9a46dc0f5b9fa88a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Laurotetanine GC-MS (1 TMS) - 70eV, Positivesplash10-05ai-1019000000-c62af0509c8ab6844c082017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Laurotetanine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Laurotetanine , positive-QTOFsplash10-00m0-0190000000-65f5217cc745d745c6bf2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laurotetanine 10V, Positive-QTOFsplash10-004i-0019000000-6e4c101a52ba3c8052692016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laurotetanine 20V, Positive-QTOFsplash10-004i-0059000000-d66fc144960738730cb12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laurotetanine 40V, Positive-QTOFsplash10-001l-0190000000-36b048ab4b509c2c1b922016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laurotetanine 10V, Negative-QTOFsplash10-004i-0009000000-bad89b6504d850983aee2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laurotetanine 20V, Negative-QTOFsplash10-01t9-0029000000-cc0b1a9f23be31e894ed2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laurotetanine 40V, Negative-QTOFsplash10-01q9-0090000000-b9aa2cd54c822be083872016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laurotetanine 10V, Negative-QTOFsplash10-004i-0009000000-82e8b7e0c70cdc0f9fe62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laurotetanine 20V, Negative-QTOFsplash10-004i-0009000000-610458ce85bb917f5cc42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laurotetanine 40V, Negative-QTOFsplash10-00dl-0095000000-5d3de9a7d15a236542b42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laurotetanine 10V, Positive-QTOFsplash10-004i-0009000000-354160c39518aa1987e32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laurotetanine 20V, Positive-QTOFsplash10-004i-0019000000-7b28233b2a0c3889df0a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laurotetanine 40V, Positive-QTOFsplash10-0gxx-0092000000-92ccc2aebefeed83a8732021-09-24Wishart 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 IDFDB002039
KNApSAcK IDC00027409
Chemspider ID235026
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound267400
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.. .