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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:51:07 UTC
Update Date2022-03-07 02:54:16 UTC
HMDB IDHMDB0034923
Secondary Accession Numbers
  • HMDB34923
Metabolite Identification
Common NameLettowianthine
DescriptionLettowianthine, also known as annobraine, 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. Lettowianthine is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, lettowianthine has been detected, but not quantified in, alcoholic beverages and fruits. This could make lettowianthine a potential biomarker for the consumption of these foods.
Structure
Data?1563862636
Synonyms
ValueSource
AnnobraineHMDB
LettowianthineMeSH
Chemical FormulaC19H11NO4
Average Molecular Weight317.2949
Monoisotopic Molecular Weight317.068807845
IUPAC Name3,5-dioxa-11-azahexacyclo[9.9.2.0²,⁶.0⁸,²¹.0¹⁴,²².0¹⁵,²⁰]docosa-1(21),2(6),7,14(22),15,17,19-heptaene-12,13-dione
Traditional Name3,5-dioxa-11-azahexacyclo[9.9.2.0²,⁶.0⁸,²¹.0¹⁴,²².0¹⁵,²⁰]docosa-1(21),2(6),7,14(22),15,17,19-heptaene-12,13-dione
CAS Registry NumberNot Available
SMILES
O=C1N2CCC3=CC4=C(OCO4)C4=C3C2=C(C1=O)C1=CC=CC=C41
InChI Identifier
InChI=1S/C19H11NO4/c21-17-15-11-4-2-1-3-10(11)14-13-9(7-12-18(14)24-8-23-12)5-6-20(16(13)15)19(17)22/h1-4,7H,5-6,8H2
InChI KeyFMLHJJVSHOCVAU-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
  • Quinoline
  • Benzodioxole
  • Indole or derivatives
  • Aryl ketone
  • Benzenoid
  • Vinylogous amide
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Ketone
  • Lactam
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen 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 Point314 - 317 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.083 g/LALOGPS
logP2.24ALOGPS
logP2.46ChemAxon
logS-3.6ALOGPS
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area55.84 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity85.57 m³·mol⁻¹ChemAxon
Polarizability32.36 ųChemAxon
Number of Rings6ChemAxon
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]+170.37131661259
DarkChem[M-H]-171.42531661259
DeepCCS[M-2H]-208.42630932474
DeepCCS[M+Na]+183.65330932474
AllCCS[M+H]+171.932859911
AllCCS[M+H-H2O]+168.532859911
AllCCS[M+NH4]+175.032859911
AllCCS[M+Na]+175.932859911
AllCCS[M-H]-178.332859911
AllCCS[M+Na-2H]-176.932859911
AllCCS[M+HCOO]-175.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LettowianthineO=C1N2CCC3=CC4=C(OCO4)C4=C3C2=C(C1=O)C1=CC=CC=C414679.8Standard polar33892256
LettowianthineO=C1N2CCC3=CC4=C(OCO4)C4=C3C2=C(C1=O)C1=CC=CC=C413111.0Standard non polar33892256
LettowianthineO=C1N2CCC3=CC4=C(OCO4)C4=C3C2=C(C1=O)C1=CC=CC=C413558.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Lettowianthine GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0092000000-9e89e9fe7d52ccf28ba92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lettowianthine 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 - Lettowianthine 10V, Positive-QTOFsplash10-014i-0019000000-95327c7827d0194b89952016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lettowianthine 20V, Positive-QTOFsplash10-014i-0029000000-6d71d316f416721f4ece2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lettowianthine 40V, Positive-QTOFsplash10-0310-0090000000-3c98d1efe4b186c050af2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lettowianthine 10V, Negative-QTOFsplash10-014i-0009000000-8d463ca6bf3eeb8115dd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lettowianthine 20V, Negative-QTOFsplash10-02t9-0096000000-a84d45628a8f2ec4689e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lettowianthine 40V, Negative-QTOFsplash10-08g0-0090000000-88db4609af2a4d78ab7c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lettowianthine 10V, Negative-QTOFsplash10-014i-0009000000-cdb697e9f2878552c94c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lettowianthine 20V, Negative-QTOFsplash10-014i-0009000000-0c180e871813a20167352021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lettowianthine 40V, Negative-QTOFsplash10-0wmr-0098000000-ef5fa2a1d42687d1bc6e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lettowianthine 10V, Positive-QTOFsplash10-014i-0009000000-7a22534e87f602b14ab32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lettowianthine 20V, Positive-QTOFsplash10-014i-0009000000-7a22534e87f602b14ab32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lettowianthine 40V, Positive-QTOFsplash10-02tc-0094000000-63db42333d87563cf7922021-09-23Wishart 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 IDFDB013509
KNApSAcK IDC00027280
Chemspider ID10216687
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21593830
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.. .