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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 11:48:08 UTC

Update Date

2021-09-24 11:48:08 UTC

HMDB ID

HMDB0304704

Secondary Accession Numbers

None

Metabolite Identification

Common Name

lupinine

Description

lupanine, also known as 2-oxosparteine, belongs to the class of organic compounds known as sparteine, lupanine, and related alkaloids. These are alkaloids with a structure based on either sparteine, lupanine, or derivatives thereof. These are tetracyclic compounds made of two fused quinolizidine ring systems. Based on a literature review a significant number of articles have been published on lupanine.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0304704
     RDKit          3D
lupinine
 42 45  0  0  0  0  0  0  0  0999 V2000
    3.2906    2.6740   -0.2564 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1118    1.4552   -0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2643    0.5113    0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0626   -0.7626   -0.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6097   -1.1544   -0.7945 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8253   -0.5817    0.3326 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4619   -1.1521    0.5118 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2706   -0.2341    1.4948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5685    1.0419    0.7109 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6726    1.6958    0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8291    0.8680    0.1823 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5778    0.7563   -0.4094 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8626    1.4069   -0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9168    0.4931    0.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0033   -0.6681   -0.5185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7102   -1.3921   -0.4630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5936   -0.6012   -0.7087 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3375   -1.2276   -0.7503 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3475    0.2829    1.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1906    1.0347   -0.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5571   -1.5913   -0.0614 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5691   -0.6598   -1.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4965   -2.2563   -0.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2628   -0.6523   -1.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4007   -0.7864    1.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5602   -2.1274    1.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1911   -0.6683    1.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4670    0.0389    2.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0211    1.7419    1.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4694    2.0251   -0.8499 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9078    2.6559    0.7473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1681    1.3106   -1.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6615    2.2556    0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3105    1.9194   -0.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5752    0.1080    1.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8683    1.0432    0.5204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1664   -0.1893   -1.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8589   -1.2841   -0.1963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7537   -2.2134   -1.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6847   -1.9607    0.5118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2299   -0.8376   -1.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4861   -2.3178   -0.9769 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 11  2  1  0
 17 12  1  0
 11  6  1  0
 18  7  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  1
  7 26  1  1
  8 27  1  0
  8 28  1  0
  9 29  1  1
 10 30  1  0
 10 31  1  0
 12 32  1  6
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 18 41  1  0
 18 42  1  0
M  END


  Mrv1652304022019483D          

 18 21  0  0  0  0            999 V2000
   -4.1083   -0.4995    0.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8435    0.9622    0.8507 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0216    1.0435    0.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9315   -1.1160   -0.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8262    1.2347   -0.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2630   -0.3454    0.8506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6242    1.4367    0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2083   -0.7705   -1.3774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2238    1.2217    0.1119 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6680   -1.5554    0.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4936    0.5394   -0.9899 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4916   -1.4644   -0.0654 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6259   -0.6863    0.5831 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9008    0.0901   -0.6110 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9460   -0.8609    1.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4823    0.7148    0.4738 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8095   -0.7751    0.5159 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9082   -1.3366    2.5253 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  4  1  0  0  0  0
  2  7  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
 13  4  1  6  0  0  0
 14  5  1  1  0  0  0
  6 15  1  0  0  0  0
  7 16  1  0  0  0  0
  8 11  1  0  0  0  0
  8 12  1  0  0  0  0
 11  9  1  1  0  0  0
  9 16  1  0  0  0  0
 12 10  1  1  0  0  0
 10 17  1  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 13 16  1  0  0  0  0
 14 17  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0304704

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1CCC[C@@H]2[C@H]3C[C@@H](CN12)[C@@H]1CCCCN1C3

> <INCHI_IDENTIFIER>
InChI=1S/C15H24N2O/c18-15-6-3-5-14-11-8-12(10-17(14)15)13-4-1-2-7-16(13)9-11/h11-14H,1-10H2/t11-,12-,13-,14+/m0/s1

> <INCHI_KEY>
JYIJIIVLEOETIQ-XDQVBPFNSA-N

> <FORMULA>
C15H24N2O

> <MOLECULAR_WEIGHT>
248.37

> <EXACT_MASS>
248.188863401

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
28.04615264402782

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-6-one

> <ALOGPS_LOGP>
2.34

> <JCHEM_LOGP>
1.0759273119999997

> <ALOGPS_LOGS>
-1.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.75154362875031

> <JCHEM_POLAR_SURFACE_AREA>
23.55

> <JCHEM_REFRACTIVITY>
71.4485

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.09e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-6-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0304704
     RDKit          3D
lupinine
 42 45  0  0  0  0  0  0  0  0999 V2000
    3.2906    2.6740   -0.2564 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1118    1.4552   -0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2643    0.5113    0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0626   -0.7626   -0.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6097   -1.1544   -0.7945 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8253   -0.5817    0.3326 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4619   -1.1521    0.5118 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2706   -0.2341    1.4948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5685    1.0419    0.7109 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6726    1.6958    0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8291    0.8680    0.1823 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5778    0.7563   -0.4094 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8626    1.4069   -0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9168    0.4931    0.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0033   -0.6681   -0.5185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7102   -1.3921   -0.4630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5936   -0.6012   -0.7087 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3375   -1.2276   -0.7503 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3475    0.2829    1.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1906    1.0347   -0.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5571   -1.5913   -0.0614 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5691   -0.6598   -1.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4965   -2.2563   -0.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2628   -0.6523   -1.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4007   -0.7864    1.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5602   -2.1274    1.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1911   -0.6683    1.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4670    0.0389    2.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0211    1.7419    1.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4694    2.0251   -0.8499 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9078    2.6559    0.7473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1681    1.3106   -1.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6615    2.2556    0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3105    1.9194   -0.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5752    0.1080    1.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8683    1.0432    0.5204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1664   -0.1893   -1.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8589   -1.2841   -0.1963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7537   -2.2134   -1.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6847   -1.9607    0.5118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2299   -0.8376   -1.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4861   -2.3178   -0.9769 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 11  2  1  0
 17 12  1  0
 11  6  1  0
 18  7  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  1
  7 26  1  1
  8 27  1  0
  8 28  1  0
  9 29  1  1
 10 30  1  0
 10 31  1  0
 12 32  1  6
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 18 41  1  0
 18 42  1  0
M  END

HEADER    PROTEIN                                 02-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-APR-20         0                                  
HETATM    1  C   UNK     0      -4.108  -0.500   0.656  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.844   0.962   0.851  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.022   1.044   0.369  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.932  -1.116  -0.063  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.826   1.235  -0.486  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.263  -0.345   0.851  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.624   1.437   0.053  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.208  -0.771  -1.377  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.224   1.222   0.112  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.668  -1.555   0.841  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.494   0.539  -0.990  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.492  -1.464  -0.065  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.626  -0.686   0.583  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.901   0.090  -0.611  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.946  -0.861   1.373  0.00  0.00           C+0
HETATM   16  N   UNK     0      -1.482   0.715   0.474  0.00  0.00           N+0
HETATM   17  N   UNK     0       1.810  -0.775   0.516  0.00  0.00           N+0
HETATM   18  O   UNK     0       2.908  -1.337   2.525  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    7                                                       
CONECT    3    5    6                                                       
CONECT    4    1   13                                                       
CONECT    5    3   14                                                       
CONECT    6    3   15                                                       
CONECT    7    2   16                                                       
CONECT    8   11   12                                                       
CONECT    9   11   16                                                       
CONECT   10   12   17                                                       
CONECT   11    8    9   14                                                  
CONECT   12    8   10   13                                                  
CONECT   13    4   12   16                                                  
CONECT   14    5   11   17                                                  
CONECT   15    6   17   18                                                  
CONECT   16    7    9   13                                                  
CONECT   17   10   14   15                                                  
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   42    0
END

COMPND    HMDB0304704
HETATM    1  O1  UNL     1       3.291   2.674  -0.256  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.112   1.455  -0.004  1.00  0.00           C  
HETATM    3  C2  UNL     1       4.264   0.511   0.122  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.063  -0.763  -0.634  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.610  -1.154  -0.795  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.825  -0.582   0.333  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.462  -1.152   0.512  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.271  -0.234   1.495  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.568   1.042   0.711  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.673   1.696   0.210  1.00  0.00           C  
HETATM   11  N1  UNL     1       1.829   0.868   0.182  1.00  0.00           N  
HETATM   12  C10 UNL     1      -1.578   0.756  -0.409  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.863   1.407  -0.056  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.917   0.493   0.482  1.00  0.00           C  
HETATM   15  C13 UNL     1      -4.003  -0.668  -0.518  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.710  -1.392  -0.463  1.00  0.00           C  
HETATM   17  N2  UNL     1      -1.594  -0.601  -0.709  1.00  0.00           N  
HETATM   18  C15 UNL     1      -0.338  -1.228  -0.750  1.00  0.00           C  
HETATM   19  H1  UNL     1       4.348   0.283   1.215  1.00  0.00           H  
HETATM   20  H2  UNL     1       5.191   1.035  -0.187  1.00  0.00           H  
HETATM   21  H3  UNL     1       4.557  -1.591  -0.061  1.00  0.00           H  
HETATM   22  H4  UNL     1       4.569  -0.660  -1.616  1.00  0.00           H  
HETATM   23  H5  UNL     1       2.496  -2.256  -0.888  1.00  0.00           H  
HETATM   24  H6  UNL     1       2.263  -0.652  -1.739  1.00  0.00           H  
HETATM   25  H7  UNL     1       2.401  -0.786   1.280  1.00  0.00           H  
HETATM   26  H8  UNL     1       0.560  -2.127   1.030  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.191  -0.668   1.874  1.00  0.00           H  
HETATM   28  H10 UNL     1       0.467   0.039   2.261  1.00  0.00           H  
HETATM   29  H11 UNL     1      -1.021   1.742   1.473  1.00  0.00           H  
HETATM   30  H12 UNL     1       0.469   2.025  -0.850  1.00  0.00           H  
HETATM   31  H13 UNL     1       0.908   2.656   0.747  1.00  0.00           H  
HETATM   32  H14 UNL     1      -1.168   1.311  -1.308  1.00  0.00           H  
HETATM   33  H15 UNL     1      -2.662   2.256   0.657  1.00  0.00           H  
HETATM   34  H16 UNL     1      -3.310   1.919  -0.958  1.00  0.00           H  
HETATM   35  H17 UNL     1      -3.575   0.108   1.459  1.00  0.00           H  
HETATM   36  H18 UNL     1      -4.868   1.043   0.520  1.00  0.00           H  
HETATM   37  H19 UNL     1      -4.166  -0.189  -1.512  1.00  0.00           H  
HETATM   38  H20 UNL     1      -4.859  -1.284  -0.196  1.00  0.00           H  
HETATM   39  H21 UNL     1      -2.754  -2.213  -1.240  1.00  0.00           H  
HETATM   40  H22 UNL     1      -2.685  -1.961   0.512  1.00  0.00           H  
HETATM   41  H23 UNL     1       0.230  -0.838  -1.641  1.00  0.00           H  
HETATM   42  H24 UNL     1      -0.486  -2.318  -0.977  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4   19   20
CONECT    4    5   21   22
CONECT    5    6   23   24
CONECT    6    7   11   25
CONECT    7    8   18   26
CONECT    8    9   27   28
CONECT    9   10   12   29
CONECT   10   11   30   31
CONECT   12   13   17   32
CONECT   13   14   33   34
CONECT   14   15   35   36
CONECT   15   16   37   38
CONECT   16   17   39   40
CONECT   17   18
CONECT   18   41   42
END

HMDB0304704
     RDKit          3D
lupinine
 42 45  0  0  0  0  0  0  0  0999 V2000
    3.2906    2.6740   -0.2564 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1118    1.4552   -0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2643    0.5113    0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0626   -0.7626   -0.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6097   -1.1544   -0.7945 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8253   -0.5817    0.3326 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4619   -1.1521    0.5118 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2706   -0.2341    1.4948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5685    1.0419    0.7109 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6726    1.6958    0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8291    0.8680    0.1823 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5778    0.7563   -0.4094 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8626    1.4069   -0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9168    0.4931    0.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0033   -0.6681   -0.5185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7102   -1.3921   -0.4630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5936   -0.6012   -0.7087 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3375   -1.2276   -0.7503 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3475    0.2829    1.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1906    1.0347   -0.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5571   -1.5913   -0.0614 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5691   -0.6598   -1.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4965   -2.2563   -0.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2628   -0.6523   -1.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4007   -0.7864    1.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5602   -2.1274    1.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1911   -0.6683    1.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4670    0.0389    2.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0211    1.7419    1.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4694    2.0251   -0.8499 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9078    2.6559    0.7473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1681    1.3106   -1.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6615    2.2556    0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3105    1.9194   -0.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5752    0.1080    1.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8683    1.0432    0.5204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1664   -0.1893   -1.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8589   -1.2841   -0.1963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7537   -2.2134   -1.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6847   -1.9607    0.5118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2299   -0.8376   -1.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4861   -2.3178   -0.9769 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 11  2  1  0
 17 12  1  0
 11  6  1  0
 18  7  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  1
  7 26  1  1
  8 27  1  0
  8 28  1  0
  9 29  1  1
 10 30  1  0
 10 31  1  0
 12 32  1  6
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 18 41  1  0
 18 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-2-Oxosparteine	ChEBI
(+)-Lupanine	ChEBI
(7alpha,7Aalpha,14alpha,14abeta)-dodecahydro-7,14-methano-2H,11H-dipyridol[1,2-a:1',2'-e][1,5]diazocin-11-one	ChEBI
2-Oxosparteine	ChEBI
D-Lupanine	ChEBI
(7a,7Aalpha,14a,14abeta)-dodecahydro-7,14-methano-2H,11H-dipyridol[1,2-a:1',2'-e][1,5]diazocin-11-one	Generator
(7Α,7aalpha,14α,14abeta)-dodecahydro-7,14-methano-2H,11H-dipyridol[1,2-a:1',2'-e][1,5]diazocin-11-one	Generator
Lupanine monohydrochloride, (7S-(7alpha,7aalpha,14alpha,14aalpha))-isomer	MeSH
Lupanine monohydrochloride, (7S-(7alpha,7abeta,14alpha,14aalpha))-isomer	MeSH
Lupanine monoperchlorate, (7S-(7alpha,7abeta,14alpha,14aalpha))-isomer	MeSH
Lupanine, (7S-(7alpha,7aalpha,14alpha,14aalpha))-isomer	MeSH
Lupanine monohydrobromide, (7S-(7alpha,7abeta,14alpha,14aalpha))-isomer	MeSH
Lupanine, (7S-(7alpha,7aalpha,14alpha,14abeta))-isomer	MeSH
alpha-Isolupanine	MeSH
Lupanine sulfate (1:1), (7S-(7alpha,7abeta,14alpha,14aalpha))-isomer	MeSH
Lupanine, (7R-(7alpha,7abeta,14alpha,14aalpha))-isomer	MeSH

Chemical Formula

C₁₅H₂₄N₂O

Average Molecular Weight

248.37

Monoisotopic Molecular Weight

248.188863401

IUPAC Name

(1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-6-one

Traditional Name

(1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-6-one

CAS Registry Number

Not Available

SMILES

O=C1CCC[C@@H]2[C@H]3C[C@@H](CN12)[C@@H]1CCCCN1C3

InChI Identifier

InChI=1S/C15H24N2O/c18-15-6-3-5-14-11-8-12(10-17(14)15)13-4-1-2-7-16(13)9-11/h11-14H,1-10H2/t11-,12-,13-,14+/m0/s1

InChI Key

JYIJIIVLEOETIQ-XDQVBPFNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sparteine, lupanine, and related alkaloids. These are alkaloids with a structure based on either sparteine, lupanine, or derivatives thereof. These are tetracyclic compounds made of two fused quinolizidine ring systems.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Lupin alkaloids

Sub Class

Sparteine, lupanine, and related alkaloids

Direct Parent

Sparteine, lupanine, and related alkaloids

Alternative Parents

Substituents

Sparteine-lupanine skeleton
Quinolizidinone
Quinolizidine
Delta-lactam
Piperidinone
Piperidine
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Lactam
Tertiary amine
Tertiary aliphatic amine
Azacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organic nitrogen compound
Amine
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Organopnictogen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

tertiary amine (CHEBI:28193 )
quinolizidine alkaloid (CHEBI:28193 )
delta-lactam (CHEBI:28193 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.34	ALOGPS
logP	1.08	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Basic)	9.75	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	23.55 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.45 m³·mol⁻¹	ChemAxon
Polarizability	28.05 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	162.789	32859911
AllCCS	[M+H-H2O]+	159.0	32859911
AllCCS	[M+Na]+	167.326	32859911
AllCCS	[M+NH4]+	166.312	32859911
AllCCS	[M-H]-	172.416	32859911
AllCCS	[M+Na-2H]-	172.163	32859911
AllCCS	[M+HCOO]-	172.016	32859911
DeepCCS	[M-2H]-	196.065	30932474
DeepCCS	[M+Na]+	171.127	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - lupinine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0l6r-1970000000-5de67a6c212c845443f5	2017-07-27	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - lupinine 10V, Positive-QTOF	splash10-0002-0090000000-fe13451db11c76943410	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - lupinine 20V, Positive-QTOF	splash10-0002-0190000000-fbadd8f52d75262ef4e5	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - lupinine 40V, Positive-QTOF	splash10-001i-9840000000-1b66617b54d497856ffa	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - lupinine 10V, Negative-QTOF	splash10-0002-0090000000-a9eead51b54a2d46cef1	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - lupinine 20V, Negative-QTOF	splash10-0002-1190000000-7294c8e93f3a81a70c27	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - lupinine 40V, Negative-QTOF	splash10-057l-7950000000-1a459fcc4a3863e2a0cf	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - lupinine 10V, Negative-QTOF	splash10-0002-0090000000-41e08c9382511812e9f6	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - lupinine 20V, Negative-QTOF	splash10-0002-0090000000-41e08c9382511812e9f6	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - lupinine 40V, Negative-QTOF	splash10-00mk-1690000000-08ceacb12268afa509c7	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - lupinine 10V, Positive-QTOF	splash10-0002-0090000000-f4af8f2053e468cbf165	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - lupinine 20V, Positive-QTOF	splash10-0002-0090000000-f4af8f2053e468cbf165	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - lupinine 40V, Positive-QTOF	splash10-0f6t-4930000000-d6d87ad724f819efe15c	2021-10-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB097315

KNApSAcK ID

C00002225

Chemspider ID

82596

KEGG Compound ID

Not Available

BioCyc ID

CPD-8917

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

28193

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for lupinine (HMDB0304704)

MOL for HMDB0304704 (lupinine)

3D MOL for HMDB0304704 (lupinine)

3D SDF for HMDB0304704 (lupinine)

3D-SDF for HMDB0304704 (lupinine)

PDB for HMDB0304704 (lupinine)

3D PDB for HMDB0304704 (lupinine)

SMILES for HMDB0304704 (lupinine)

INCHI for HMDB0304704 (lupinine)

Structure for HMDB0304704 (lupinine)

3D Structure for HMDB0304704 (lupinine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra

NMR Spectra