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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-08-28 18:06:07 UTC
Update Date2021-09-26 22:47:35 UTC
HMDB IDHMDB0242221
Secondary Accession NumbersNone
Metabolite Identification
Common Name(-)-Tylophorine
Description4,5,10,11-tetramethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2,4,6,8,10,12-heptaene belongs to the class of organic compounds known as phenanthroindolizidines. These are aromatic polycyclic compounds containing the phenanthroindolizidine skeleton, which is structurally characterized by an indolizidine and a phenanthrene, where the indolizidine is fused to the second benzene ring of a phenanthrene. Based on a literature review very few articles have been published on 4,5,10,11-tetramethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2,4,6,8,10,12-heptaene. This compound has been identified in human blood as reported by (PMID: 31557052 ). (-)-tylophorine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (-)-Tylophorine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
DL-TylophorineChEMBL, HMDB
2,3,6,7-Tetramethoxyphenanthro(9,10:6,7')indolizidineMeSH, HMDB
DehydrotylophorineMeSH, HMDB
Chemical FormulaC24H27NO4
Average Molecular Weight393.483
Monoisotopic Molecular Weight393.194008353
IUPAC Name4,5,10,11-tetramethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2,4,6,8,10,12-heptaene
Traditional Nametylophorine
CAS Registry NumberNot Available
SMILES
COC1=C(OC)C=C2C(=C1)C1=C(CN3CCCC3C1)C1=CC(OC)=C(OC)C=C21
InChI Identifier
InChI=1S/C24H27NO4/c1-26-21-9-16-15-8-14-6-5-7-25(14)13-20(15)19-12-24(29-4)23(28-3)11-18(19)17(16)10-22(21)27-2/h9-12,14H,5-8,13H2,1-4H3
InChI KeySSEUDFYBEOIWGF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenanthroindolizidines. These are aromatic polycyclic compounds containing the phenanthroindolizidine skeleton, which is structurally characterized by an indolizidine and a phenanthrene, where the indolizidine is fused to the second benzene ring of a phenanthrene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenanthrenes and derivatives
Sub ClassPhenanthroindolizidines
Direct ParentPhenanthroindolizidines
Alternative Parents
Substituents
  • Phenanthroindolizidine
  • Naphthalene
  • Tetrahydroisoquinoline
  • Indolizidine
  • Anisole
  • Alkyl aryl ether
  • Aralkylamine
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Ether
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • 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
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP4.1ALOGPS
logP3.77ChemAxon
logS-5.1ALOGPS
pKa (Strongest Basic)8.47ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.16 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity113.87 m³·mol⁻¹ChemAxon
Polarizability44.86 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
DeepCCS[M-2H]-231.35430932474
DeepCCS[M+Na]+206.58230932474
AllCCS[M+H]+195.432859911
AllCCS[M+H-H2O]+192.932859911
AllCCS[M+NH4]+197.732859911
AllCCS[M+Na]+198.332859911
AllCCS[M-H]-197.632859911
AllCCS[M+Na-2H]-197.532859911
AllCCS[M+HCOO]-197.632859911

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Tylophorine GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-1009000000-4700c79e827761eac8d42021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Tylophorine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Tylophorine 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 - (-)-Tylophorine 10V, Positive-QTOFsplash10-0006-0009000000-dccac3257825718db11e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Tylophorine 20V, Positive-QTOFsplash10-0006-0009000000-261739ea3dfc26dae4372021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Tylophorine 40V, Positive-QTOFsplash10-0bt9-0029000000-2953d1335c4901bb57b92021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Tylophorine 10V, Negative-QTOFsplash10-0006-0009000000-a1975bb03bf73b8b78802021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Tylophorine 20V, Negative-QTOFsplash10-0006-0009000000-8c315ce55b06723fbf7e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Tylophorine 40V, Negative-QTOFsplash10-0uxv-0009000000-2c2a277440212a8fb7842021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4266625
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5090648
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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]