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Record Information
Version1.0
Created at2006-08-13 19:32:00 UTC
Updated at2021-06-29 00:53:48 UTC
NP-MRD IDNP0000034
Secondary Accession NumbersNone
Natural Product 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
Thumb
Synonyms
ValueSource
(-)-AnatabineKegg
Chemical FormulaC10H12N2
Average Mass160.2157 Da
Monoisotopic Mass160.10005 Da
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, simulated)Varshavi.d262021-08-12View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, simulated)Varshavi.d262021-08-12View Spectrum
Species
Species of Origin
Species NameSourceReference
Nicotiana acaulisKNApSAcK Database
Nicotiana acuminataKNApSAcK Database
Nicotiana africanaKNApSAcK Database
Nicotiana alataKNApSAcK Database
Nicotiana ameghinoiKNApSAcK Database
Nicotiana amplexicaulisKNApSAcK Database
Nicotiana arentsiiKNApSAcK Database
Nicotiana attenuataKNApSAcK Database
Nicotiana benavidesiiKNApSAcK Database
Nicotiana benthamianaKNApSAcK Database
Nicotiana bigeloviiKNApSAcK Database
Nicotiana bonariensisKNApSAcK Database
Nicotiana cavicolaKNApSAcK Database
Nicotiana clevelandiiKNApSAcK Database
Nicotiana cordifoliaKNApSAcK Database
Nicotiana corymbosaKNApSAcK Database
Nicotiana debneyiKNApSAcK Database
Nicotiana excelsiorKNApSAcK Database
Nicotiana exiguaKNApSAcK Database
Nicotiana forgetianaKNApSAcK Database
Nicotiana fragransKNApSAcK Database
Nicotiana glaucaKNApSAcK Database
Nicotiana glutinosaKNApSAcK Database
Nicotiana goodspeediiKNApSAcK Database
Nicotiana gosseiKNApSAcK Database
Nicotiana hesperisKNApSAcK Database
Nicotiana ingulbaKNApSAcK Database
Nicotiana kawakamiiKNApSAcK Database
Nicotiana knightianaKNApSAcK Database
Nicotiana langsdorffiiKNApSAcK Database
Nicotiana linearisKNApSAcK Database
Nicotiana longibracteataKNApSAcK Database
Nicotiana longifloraKNApSAcK Database
Nicotiana maritimaKNApSAcK Database
Nicotiana megalosiphonKNApSAcK Database
Nicotiana miersiiKNApSAcK Database
Nicotiana nesophilaKNApSAcK Database
Nicotiana noctifloraKNApSAcK Database
Nicotiana nudicaulisKNApSAcK Database
Nicotiana occidentalisKNApSAcK Database
Nicotiana otophoraKNApSAcK Database
Nicotiana paniculataKNApSAcK Database
Nicotiana paucifloraKNApSAcK Database
Nicotiana petunioidesKNApSAcK Database
Nicotiana plumbaginifoliaKNApSAcK Database
Nicotiana raimondiiKNApSAcK Database
Nicotiana repandaKNApSAcK Database
Nicotiana rosulataKNApSAcK Database
Nicotiana rotundifoliaKNApSAcK Database
Nicotiana rusticaKNApSAcK Database
Nicotiana setchelliiKNApSAcK Database
Nicotiana simulansKNApSAcK Database
Nicotiana solanifoliaKNApSAcK Database
Nicotiana spegazziniiKNApSAcK Database
Nicotiana stocktoniiKNApSAcK Database
Nicotiana suaveolensKNApSAcK Database
Nicotiana sylvestrisKNApSAcK Database
Nicotiana tabacumKNApSAcK Database
Nicotiana thyrosifloraKNApSAcK Database
Nicotiana tobacumKNApSAcK Database
Nicotiana tomentosaKNApSAcK Database
Nicotiana tomentosiformisKNApSAcK Database
Nicotiana trigonophyllaKNApSAcK Database
Nicotiana undulataKNApSAcK Database
Nicotiana velutinaKNApSAcK Database
Nicotiana wigandioidesKNApSAcK Database
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point145.5 °CNot Available
Water Solubility1000 mg/mLNot Available
LogPNot AvailableNot Available
Predicted 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
External Links
HMDB IDHMDB0004476
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
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 ]
  4. Patalas-Krawczyk P, Malinska D, Walczak J, Kratzer G, Prill M, Michalska B, Drabik K, Titz B, Eb-Levadoux Y, Schneider T, Szymanski J, Hoeng J, Peitsch MC, Duszynski J, Szczepanowska J, Van der Toorn M, Mathis C, Wieckowski MR: Effects of plant alkaloids on mitochondrial bioenergetic parameters. Food Chem Toxicol. 2021 Aug;154:112316. doi: 10.1016/j.fct.2021.112316. Epub 2021 Jun 3. [PubMed:34089800 ]
  5. Callahan PM, Terry AV Jr, Peitsch MC, Hoeng J, Koshibu K: Differential effects of alkaloids on memory in rodents. Sci Rep. 2021 May 10;11(1):9843. doi: 10.1038/s41598-021-89245-w. [PubMed:33972592 ]