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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-13 19:32:00 UTC
Update Date2022-09-22 18:34:18 UTC
HMDB IDHMDB0004476
Secondary Accession Numbers
  • HMDB04476
Metabolite Identification
Common NameAnatabine
DescriptionAnatabine is one of the minor alkaloids found in plants in the family Solanaceae, which includes the tobacco plant and tomato. Commercial tobacco plants typically produce alkaloids at levels between 2% and 4% of total dry weight, with nicotine accounting for about 90% of the total alkaloid content, and the related compounds anabatine, nornicotine, and anabasine making up nearly all the rest. These compounds are thought to be biologically active, and part of plants' natural defense system against insects. It belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group. Anatabine is tobacco alkaloid in urine of smokers and smokeless tobacco users (PMID: 8245163 ). This Nicotine-related alkaloid is an inhibitor of human cytochrome P-450 2A6 (PMID:14757175 ).
Structure
Data?1582752308
Synonyms
ValueSource
(-)-AnatabineKegg
Chemical FormulaC10H12N2
Average Molecular Weight160.2157
Monoisotopic Molecular Weight160.100048394
IUPAC Name(2S)-1,2,3,6-tetrahydro-2,3'-bipyridine
Traditional Nameanatabine
CAS Registry Number581-49-7
SMILES
C1N[C@@H](CC=C1)C1=CN=CC=C1
InChI Identifier
InChI=1S/C10H12N2/c1-2-7-12-10(5-1)9-4-3-6-11-8-9/h1-4,6,8,10,12H,5,7H2/t10-/m0/s1
InChI KeySOPPBXUYQGUQHE-JTQLQIEISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • Pyridine
  • Hydropyridine
  • Heteroaromatic compound
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Secondary aliphatic amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point145.5 °CNot Available
Water Solubility1000 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility10.6 g/LALOGPS
logP1.03ALOGPS
logP1.02ChemAxon
logS-1.2ALOGPS
pKa (Strongest Basic)8.52ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area24.92 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.92 m³·mol⁻¹ChemAxon
Polarizability17.55 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.3831661259
DarkChem[M-H]-136.49431661259
DeepCCS[M+H]+136.94930932474
DeepCCS[M-H]-134.55330932474
DeepCCS[M-2H]-169.37930932474
DeepCCS[M+Na]+143.83830932474
AllCCS[M+H]+135.232859911
AllCCS[M+H-H2O]+130.532859911
AllCCS[M+NH4]+139.732859911
AllCCS[M+Na]+141.032859911
AllCCS[M-H]-137.932859911
AllCCS[M+Na-2H]-138.632859911
AllCCS[M+HCOO]-139.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AnatabineC1N[C@@H](CC=C1)C1=CN=CC=C12143.8Standard polar33892256
AnatabineC1N[C@@H](CC=C1)C1=CN=CC=C11533.3Standard non polar33892256
AnatabineC1N[C@@H](CC=C1)C1=CN=CC=C11514.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Anatabine,1TMS,isomer #1C[Si](C)(C)N1CC=CC[C@H]1C1=CC=CN=C11594.2Semi standard non polar33892256
Anatabine,1TMS,isomer #1C[Si](C)(C)N1CC=CC[C@H]1C1=CC=CN=C11575.2Standard non polar33892256
Anatabine,1TMS,isomer #1C[Si](C)(C)N1CC=CC[C@H]1C1=CC=CN=C12044.3Standard polar33892256
Anatabine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CC=CC[C@H]1C1=CC=CN=C11767.9Semi standard non polar33892256
Anatabine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CC=CC[C@H]1C1=CC=CN=C11790.3Standard non polar33892256
Anatabine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CC=CC[C@H]1C1=CC=CN=C12231.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Anatabine GC-MS (Non-derivatized) - 70eV, Positivesplash10-07cu-1900000000-83089eec362cad1f93f62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Anatabine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Anatabine 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 - Anatabine 10V, Positive-QTOFsplash10-03di-0900000000-972f6de458718e02613b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anatabine 20V, Positive-QTOFsplash10-03e9-1900000000-7baac9dff046273f5a282017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anatabine 40V, Positive-QTOFsplash10-0udl-9200000000-f060db2ea029ecd78a782017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anatabine 10V, Negative-QTOFsplash10-0a4i-0900000000-32258a0e4b3989d0533f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anatabine 20V, Negative-QTOFsplash10-0a4i-0900000000-ffc8f788de93316624242017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anatabine 40V, Negative-QTOFsplash10-004i-7900000000-cac0a5ea86d517e754112017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anatabine 10V, Negative-QTOFsplash10-056r-9700000000-4ed7ee7465de65e911002021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anatabine 20V, Negative-QTOFsplash10-056r-9400000000-c2cb4e83d6aa78ce7b112021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anatabine 40V, Negative-QTOFsplash10-004i-9200000000-0e0e70179caacf58851b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anatabine 10V, Positive-QTOFsplash10-03di-0900000000-ec9dd3a4861a20c6f98c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anatabine 20V, Positive-QTOFsplash10-03di-0900000000-d43f6eaf3f1dd72eec342021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anatabine 40V, Positive-QTOFsplash10-053r-5900000000-19a118d5150f724690502021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, experimental)2021-10-10Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023374
KNApSAcK IDC00002017
Chemspider ID10910
KEGG Compound IDC10126
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAnatabine
METLIN ID7061
PubChem Compound11388
PDB IDNot Available
ChEBI ID2705
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceBalasubramanian, Thiagarajan; Hassner, Alfred. Synthetic methods. 48. Asymmetric synthesis of functionalized piperidine derivatives: synthesis of (S)-anatabine. Tetrahedron: Asymmetry (1998), 9(13), 2201-2205.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Jacob P 3rd, Yu L, Liang G, Shulgin AT, Benowitz NL: Gas chromatographic-mass spectrometric method for determination of anabasine, anatabine and other tobacco alkaloids in urine of smokers and smokeless tobacco users. J Chromatogr. 1993 Sep 8;619(1):49-61. [PubMed:8245163 ]
  2. Denton TT, Zhang X, Cashman JR: Nicotine-related alkaloids and metabolites as inhibitors of human cytochrome P-450 2A6. Biochem Pharmacol. 2004 Feb 15;67(4):751-6. [PubMed:14757175 ]
  3. Jacob P 3rd, Hatsukami D, Severson H, Hall S, Yu L, Benowitz NL: Anabasine and anatabine as biomarkers for tobacco use during nicotine replacement therapy. Cancer Epidemiol Biomarkers Prev. 2002 Dec;11(12):1668-73. [PubMed:12496059 ]