MiMeDB: Showing metabocard for lupanine (MMDBc0054552)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:17:34 UTC

Update Date

2022-08-12 20:09:01 UTC

Metabolite ID

MMDBc0054552

Metabolite Identification

Common Name

lupanine

Description

lupinine, also known as 2-oxosparteine or alpha-isolupanine, 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. lupinine is found, on average, in the highest concentration within milk (cow). lupinine has also been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make lupinine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on lupinine.

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>
MMDBc0054552

> <DATABASE_NAME>
MIME

> <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

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	HMDB
Lupanine monohydrochloride, (7S-(7alpha,7abeta,14alpha,14aalpha))-isomer	HMDB
Lupanine monoperchlorate, (7S-(7alpha,7abeta,14alpha,14aalpha))-isomer	HMDB
Lupanine, (7S-(7alpha,7aalpha,14alpha,14aalpha))-isomer	HMDB
Lupanine monohydrobromide, (7S-(7alpha,7abeta,14alpha,14aalpha))-isomer	HMDB
Lupanine, (7S-(7alpha,7aalpha,14alpha,14abeta))-isomer	HMDB
alpha-Isolupanine	HMDB
Lupanine sulfate (1:1), (7S-(7alpha,7abeta,14alpha,14aalpha))-isomer	HMDB
Lupanine, (7R-(7alpha,7abeta,14alpha,14aalpha))-isomer	HMDB

Molecular Formula

C₁₅H₂₄N₂O

Average Mass

248.37

Monoisotopic Mass

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	6.09 g/L	ALOGPS
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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0l6r-1970000000-5de67a6c212c845443f5	2017-07-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090000000-fe13451db11c76943410	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0190000000-fbadd8f52d75262ef4e5	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9840000000-1b66617b54d497856ffa	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-a9eead51b54a2d46cef1	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-1190000000-7294c8e93f3a81a70c27	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057l-7950000000-1a459fcc4a3863e2a0cf	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-41e08c9382511812e9f6	2021-10-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0090000000-41e08c9382511812e9f6	2021-10-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00mk-1690000000-08ceacb12268afa509c7	2021-10-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090000000-f4af8f2053e468cbf165	2021-10-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0090000000-f4af8f2053e468cbf165	2021-10-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f6t-4930000000-d6d87ad724f819efe15c	2021-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human feces; Human

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	31557052

External Links

HMDB ID

HMDB0304704

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

Lupinine

METLIN ID

Not Available

PubChem Compound

91471

PDB ID

Not Available

ChEBI ID

28193

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for lupanine (MMDBc0054552)

MOL for #<Metabolite:0x00005634c2ab5a20>

3D MOL for #<Metabolite:0x00005634c2ab5a20>

3D SDF for #<Metabolite:0x00005634c2ab5a20>

3D-SDF for #<Metabolite:0x00005634c2ab5a20>

PDB for #<Metabolite:0x00005634c2ab5a20>

3D PDB for #<Metabolite:0x00005634c2ab5a20>

SMILES for #<Metabolite:0x00005634c2ab5a20>

INCHI for #<Metabolite:0x00005634c2ab5a20>

Structure for #<Metabolite:0x00005634c2ab5a20>

3D Structure for #<Metabolite:0x00005634c2ab5a20>