Showing NP-Card for Anatabine (NP0000034)

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Record Information
Version2.0
Created at2006-08-13 19:32:00 UTC
Updated at2025-02-11 15:42:16 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000034 (Anatabine)

  Mrv1652304272018412D          

 12 13  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7144    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0625    2.1434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  5  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  2  0  0  0  0
  3  6  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6 11  2  0  0  0  0
  7 12  1  0  0  0  0
  8  9  2  0  0  0  0
  8 11  1  0  0  0  0
 10  9  1  6  0  0  0
 10 12  1  0  0  0  0
M  END
Download

3D MOL for NP0000034 (Anatabine)

HMDB0004476
     RDKit          3D
Anatabine
 24 25  0  0  0  0  0  0  0  0999 V2000
   -3.0152    0.4221    0.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6768   -0.0224   -0.8599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2334   -0.1422   -1.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4691   -0.3430    0.0678 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0032   -0.3871   -0.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8652   -0.2342    0.9220 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2365   -0.2657    0.7743 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7563   -0.4538   -0.4799 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9145   -0.6001   -1.5157 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5710   -0.5724   -1.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7348    0.7631    0.9378 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0860    0.8278    1.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0868    0.4984    0.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4159   -0.3043   -1.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9195    0.8330   -1.6759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0702   -0.9792   -1.9274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8428   -1.2636    0.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4069   -0.0867    1.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8785   -0.1449    1.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8345   -0.4901   -0.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9199   -0.6958   -2.2635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3121    1.6550    0.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3403    1.8659    1.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1835    0.1200    2.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  1  0
 12  1  1  0
 10  5  1  0
  1 13  1  0
  2 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  1
  6 18  1  0
  7 19  1  0
  8 20  1  0
 10 21  1  0
 11 22  1  0
 12 23  1  0
 12 24  1  0
M  END
Download

3D SDF for NP0000034 (Anatabine)

  Mrv1652304272018412D          

 12 13  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7144    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0625    2.1434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  5  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  2  0  0  0  0
  3  6  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6 11  2  0  0  0  0
  7 12  1  0  0  0  0
  8  9  2  0  0  0  0
  8 11  1  0  0  0  0
 10  9  1  6  0  0  0
 10 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000034

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
SOPPBXUYQGUQHE-JTQLQIEISA-N

> <FORMULA>
C10H12N2

> <MOLECULAR_WEIGHT>
160.2157

> <EXACT_MASS>
160.100048394

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
17.553405950590758

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-1,2,3,6-tetrahydro-2,3'-bipyridine

> <ALOGPS_LOGP>
1.03

> <JCHEM_LOGP>
1.0180412236666667

> <ALOGPS_LOGS>
-1.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.517863095340788

> <JCHEM_POLAR_SURFACE_AREA>
24.92

> <JCHEM_REFRACTIVITY>
49.9239

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
anatabine

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0000034 (Anatabine)

HMDB0004476
     RDKit          3D
Anatabine
 24 25  0  0  0  0  0  0  0  0999 V2000
   -3.0152    0.4221    0.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6768   -0.0224   -0.8599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2334   -0.1422   -1.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4691   -0.3430    0.0678 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0032   -0.3871   -0.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8652   -0.2342    0.9220 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2365   -0.2657    0.7743 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7563   -0.4538   -0.4799 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9145   -0.6001   -1.5157 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5710   -0.5724   -1.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7348    0.7631    0.9378 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0860    0.8278    1.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0868    0.4984    0.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4159   -0.3043   -1.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9195    0.8330   -1.6759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0702   -0.9792   -1.9274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8428   -1.2636    0.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4069   -0.0867    1.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8785   -0.1449    1.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8345   -0.4901   -0.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9199   -0.6958   -2.2635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3121    1.6550    0.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3403    1.8659    1.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1835    0.1200    2.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  1  0
 12  1  1  0
 10  5  1  0
  1 13  1  0
  2 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  1
  6 18  1  0
  7 19  1  0
  8 20  1  0
 10 21  1  0
 11 22  1  0
 12 23  1  0
 12 24  1  0
M  END
Download

PDB for NP0000034 (Anatabine)

HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.540   5.335   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770   4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.080   5.335   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.080   2.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.540   2.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -3.850   4.001   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      -1.540   0.000   0.000  0.00  0.00           N+0
CONECT    1    2    5                                                       
CONECT    2    1    7                                                       
CONECT    3    4    6                                                       
CONECT    4    3    9                                                       
CONECT    5    1   10                                                       
CONECT    6    3   11                                                       
CONECT    7    2   12                                                       
CONECT    8    9   11                                                       
CONECT    9    4    8   10                                                  
CONECT   10    5    9   12                                                  
CONECT   11    6    8                                                       
CONECT   12    7   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END
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3D PDB for NP0000034 (Anatabine)

COMPND    HMDB0004476
HETATM    1  C1  UNL     1      -3.015   0.422   0.334  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.677  -0.022  -0.860  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.233  -0.142  -1.206  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.469  -0.343   0.068  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.003  -0.387  -0.160  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.865  -0.234   0.922  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.237  -0.266   0.774  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.756  -0.454  -0.480  1.00  0.00           C  
HETATM    9  N1  UNL     1       2.914  -0.600  -1.516  1.00  0.00           N  
HETATM   10  C9  UNL     1       1.571  -0.572  -1.393  1.00  0.00           C  
HETATM   11  N2  UNL     1      -0.735   0.763   0.938  1.00  0.00           N  
HETATM   12  C10 UNL     1      -2.086   0.828   1.400  1.00  0.00           C  
HETATM   13  H1  UNL     1      -4.087   0.498   0.557  1.00  0.00           H  
HETATM   14  H2  UNL     1      -3.416  -0.304  -1.599  1.00  0.00           H  
HETATM   15  H3  UNL     1      -0.919   0.833  -1.676  1.00  0.00           H  
HETATM   16  H4  UNL     1      -1.070  -0.979  -1.927  1.00  0.00           H  
HETATM   17  H5  UNL     1      -0.843  -1.264   0.562  1.00  0.00           H  
HETATM   18  H6  UNL     1       1.407  -0.087   1.903  1.00  0.00           H  
HETATM   19  H7  UNL     1       3.878  -0.145   1.627  1.00  0.00           H  
HETATM   20  H8  UNL     1       4.834  -0.490  -0.675  1.00  0.00           H  
HETATM   21  H9  UNL     1       0.920  -0.696  -2.263  1.00  0.00           H  
HETATM   22  H10 UNL     1      -0.312   1.655   0.664  1.00  0.00           H  
HETATM   23  H11 UNL     1      -2.340   1.866   1.738  1.00  0.00           H  
HETATM   24  H12 UNL     1      -2.183   0.120   2.268  1.00  0.00           H  
CONECT    1    2    2   12   13
CONECT    2    3   14
CONECT    3    4   15   16
CONECT    4    5   11   17
CONECT    5    6    6   10
CONECT    6    7   18
CONECT    7    8    8   19
CONECT    8    9   20
CONECT    9   10   10
CONECT   10   21
CONECT   11   12   22
CONECT   12   23   24
END
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SMILES for NP0000034 (Anatabine)

C1N[C@@H](CC=C1)C1=CN=CC=C1
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INCHI for NP0000034 (Anatabine)

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
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View in JSmol
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, simulated)varshavi.d26@gmail.comNot AvailableNot Available2021-08-12View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, simulated)varshavi.d26@gmail.comNot AvailableNot Available2021-08-12View Spectrum
Species
Species of Origin
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
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
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