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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 01:21:02 UTC

Update Date

2021-09-26 22:58:20 UTC

HMDB ID

HMDB0248180

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Aloperine

Description

3,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-7-ene belongs to the class of organic compounds known as aloperine and related alkaloids. These are lupin Alkaloids with a structure based on the aloperine skeleton. Aloperine is a tetracyclic compound made up of a quinolizidine and a decahydroquinoline joined to form 3,15-diazatetracycloheptadecane. 3,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-7-ene is a very strong basic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Aloperine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Aloperine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0248180
     RDKit          3D
Aloperine
 41 44  0  0  0  0  0  0  0  0999 V2000
    0.6200    0.1650   -1.5122 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6710    0.0831   -0.7364 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8902    0.9387   -0.9058 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2913    1.4970    0.4156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1567    0.5433    1.5616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8628   -0.1061    1.6069 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7344   -0.8914    0.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5536   -1.8201    0.4219 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2245   -2.1620   -1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3900   -0.9190   -1.6314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6323   -0.5973   -0.8699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3732    0.5012   -1.5781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6791    1.6433   -0.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3752    1.1138    0.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4847    0.1186    1.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2887   -0.1882    0.4749 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6268   -1.2842    1.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4692    1.0575   -2.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7267    1.7677   -1.6125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6756    0.2439   -1.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7541    2.4454    0.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3840    1.7620    0.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9102   -0.2646    1.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3175    1.1171    2.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0791    0.5917    1.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6657   -1.4895    0.3083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8637   -2.7614    0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4197   -3.0404   -1.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2128   -2.3005   -1.5401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6113   -1.1686   -2.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2967   -1.4643   -0.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8112    0.9156   -2.4396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3442    0.1290   -2.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2941    2.3791   -1.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7060    2.0820   -0.2881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5368    1.9753    1.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3825    0.7235    0.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1124    0.5137    2.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0476   -0.8092    1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3467   -2.1283    1.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3040   -0.9124    2.1401 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
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 10  1  1  0
 16 11  1  0
  7  2  1  0
 17  8  1  0
  1 18  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  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 17 40  1  0
 17 41  1  0
M  END


  Mrv1533004241522152D          

 17 20  0  0  0  0            999 V2000
    6.8413   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8413    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1269    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4124    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8290    1.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0040    1.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6655    0.5156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8290   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4124   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1269   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0040   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4207   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4207    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7062    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7062   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0248180

> <DATABASE_NAME>
hmdb

> <SMILES>
C1CCN2CC3CC(C=C4CCCNC34)C2C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H24N2/c1-2-7-17-10-13-9-12(14(17)5-1)8-11-4-3-6-16-15(11)13/h8,12-16H,1-7,9-10H2

> <INCHI_KEY>
SKOLRLSBMUGVOY-UHFFFAOYSA-N

> <FORMULA>
C15H24N2

> <MOLECULAR_WEIGHT>
232.371

> <EXACT_MASS>
232.193948781

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
27.913017995896894

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-7-ene

> <ALOGPS_LOGP>
1.74

> <JCHEM_LOGP>
1.650376867999999

> <ALOGPS_LOGS>
-2.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_BASIC>
9.979754334663786

> <JCHEM_POLAR_SURFACE_AREA>
15.27

> <JCHEM_REFRACTIVITY>
71.8011

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.22e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-7-ene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0248180
     RDKit          3D
Aloperine
 41 44  0  0  0  0  0  0  0  0999 V2000
    0.6200    0.1650   -1.5122 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6710    0.0831   -0.7364 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8902    0.9387   -0.9058 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2913    1.4970    0.4156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1567    0.5433    1.5616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8628   -0.1061    1.6069 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7344   -0.8914    0.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5536   -1.8201    0.4219 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2245   -2.1620   -1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3900   -0.9190   -1.6314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6323   -0.5973   -0.8699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3732    0.5012   -1.5781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6791    1.6433   -0.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3752    1.1138    0.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4847    0.1186    1.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2887   -0.1882    0.4749 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6268   -1.2842    1.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4692    1.0575   -2.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7267    1.7677   -1.6125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6756    0.2439   -1.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7541    2.4454    0.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3840    1.7620    0.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9102   -0.2646    1.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3175    1.1171    2.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0791    0.5917    1.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6657   -1.4895    0.3083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8637   -2.7614    0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4197   -3.0404   -1.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2128   -2.3005   -1.5401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6113   -1.1686   -2.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2967   -1.4643   -0.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8112    0.9156   -2.4396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3442    0.1290   -2.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2941    2.3791   -1.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7060    2.0820   -0.2881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5368    1.9753    1.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3825    0.7235    0.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1124    0.5137    2.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0476   -0.8092    1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3467   -2.1283    1.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3040   -0.9124    2.1401 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
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 10  1  1  0
 16 11  1  0
  7  2  1  0
 17  8  1  0
  1 18  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  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 17 40  1  0
 17 41  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      12.770  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.770   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.437   2.310   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      10.103   1.540   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       9.014   2.629   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.474   2.629   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.709   0.962   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.014  -1.089   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.103  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.437  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.474  -1.089   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.385  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.385   1.540   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       5.052   2.310   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       3.718   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.718  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.052  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2   10                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9    1                                                       
CONECT   11    8   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12    6   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   40    0
END

COMPND    HMDB0248180
HETATM    1  C1  UNL     1       0.620   0.165  -1.512  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.671   0.083  -0.736  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.890   0.939  -0.906  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.291   1.497   0.416  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.157   0.543   1.562  1.00  0.00           C  
HETATM    6  N1  UNL     1       1.863  -0.106   1.607  1.00  0.00           N  
HETATM    7  C6  UNL     1       1.734  -0.891   0.401  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.554  -1.820   0.422  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.225  -2.162  -1.019  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.390  -0.919  -1.631  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.632  -0.597  -0.870  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.373   0.501  -1.578  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.679   1.643  -0.637  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.375   1.114   0.588  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.485   0.119   1.251  1.00  0.00           C  
HETATM   16  N2  UNL     1      -1.289  -0.188   0.475  1.00  0.00           N  
HETATM   17  C15 UNL     1      -0.627  -1.284   1.167  1.00  0.00           C  
HETATM   18  H1  UNL     1       0.469   1.057  -2.098  1.00  0.00           H  
HETATM   19  H2  UNL     1       2.727   1.768  -1.613  1.00  0.00           H  
HETATM   20  H3  UNL     1       3.676   0.244  -1.323  1.00  0.00           H  
HETATM   21  H4  UNL     1       2.754   2.445   0.584  1.00  0.00           H  
HETATM   22  H5  UNL     1       4.384   1.762   0.345  1.00  0.00           H  
HETATM   23  H6  UNL     1       3.910  -0.265   1.432  1.00  0.00           H  
HETATM   24  H7  UNL     1       3.318   1.117   2.496  1.00  0.00           H  
HETATM   25  H8  UNL     1       1.079   0.592   1.704  1.00  0.00           H  
HETATM   26  H9  UNL     1       2.666  -1.489   0.308  1.00  0.00           H  
HETATM   27  H10 UNL     1       0.864  -2.761   0.906  1.00  0.00           H  
HETATM   28  H11 UNL     1      -0.420  -3.040  -1.108  1.00  0.00           H  
HETATM   29  H12 UNL     1       1.213  -2.300  -1.540  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.611  -1.169  -2.690  1.00  0.00           H  
HETATM   31  H14 UNL     1      -2.297  -1.464  -0.800  1.00  0.00           H  
HETATM   32  H15 UNL     1      -1.811   0.916  -2.440  1.00  0.00           H  
HETATM   33  H16 UNL     1      -3.344   0.129  -2.008  1.00  0.00           H  
HETATM   34  H17 UNL     1      -3.294   2.379  -1.188  1.00  0.00           H  
HETATM   35  H18 UNL     1      -1.706   2.082  -0.288  1.00  0.00           H  
HETATM   36  H19 UNL     1      -3.537   1.975   1.272  1.00  0.00           H  
HETATM   37  H20 UNL     1      -4.383   0.723   0.343  1.00  0.00           H  
HETATM   38  H21 UNL     1      -2.112   0.514   2.234  1.00  0.00           H  
HETATM   39  H22 UNL     1      -3.048  -0.809   1.431  1.00  0.00           H  
HETATM   40  H23 UNL     1      -1.347  -2.128   1.297  1.00  0.00           H  
HETATM   41  H24 UNL     1      -0.304  -0.912   2.140  1.00  0.00           H  
CONECT    1    2    2   10   18
CONECT    2    3    7
CONECT    3    4   19   20
CONECT    4    5   21   22
CONECT    5    6   23   24
CONECT    6    7   25
CONECT    7    8   26
CONECT    8    9   17   27
CONECT    9   10   28   29
CONECT   10   11   30
CONECT   11   12   16   31
CONECT   12   13   32   33
CONECT   13   14   34   35
CONECT   14   15   36   37
CONECT   15   16   38   39
CONECT   16   17
CONECT   17   40   41
END

HMDB0248180
     RDKit          3D
Aloperine
 41 44  0  0  0  0  0  0  0  0999 V2000
    0.6200    0.1650   -1.5122 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6710    0.0831   -0.7364 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8902    0.9387   -0.9058 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2913    1.4970    0.4156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1567    0.5433    1.5616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8628   -0.1061    1.6069 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7344   -0.8914    0.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5536   -1.8201    0.4219 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2245   -2.1620   -1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3900   -0.9190   -1.6314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6323   -0.5973   -0.8699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3732    0.5012   -1.5781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6791    1.6433   -0.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3752    1.1138    0.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4847    0.1186    1.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2887   -0.1882    0.4749 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6268   -1.2842    1.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4692    1.0575   -2.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7267    1.7677   -1.6125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6756    0.2439   -1.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7541    2.4454    0.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3840    1.7620    0.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9102   -0.2646    1.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3175    1.1171    2.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0791    0.5917    1.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6657   -1.4895    0.3083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8637   -2.7614    0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4197   -3.0404   -1.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2128   -2.3005   -1.5401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6113   -1.1686   -2.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2967   -1.4643   -0.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8112    0.9156   -2.4396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3442    0.1290   -2.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2941    2.3791   -1.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7060    2.0820   -0.2881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5368    1.9753    1.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3825    0.7235    0.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1124    0.5137    2.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0476   -0.8092    1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3467   -2.1283    1.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3040   -0.9124    2.1401 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
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 10  1  1  0
 16 11  1  0
  7  2  1  0
 17  8  1  0
  1 18  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  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 17 40  1  0
 17 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-Epi-aloperine	MeSH
Alop1 compound	MeSH
Aloperine	MeSH

Chemical Formula

C₁₅H₂₄N₂

Average Molecular Weight

232.371

Monoisotopic Molecular Weight

232.193948781

IUPAC Name

3,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-7-ene

Traditional Name

3,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-7-ene

CAS Registry Number

Not Available

SMILES

C1CCN2CC3CC(C=C4CCCNC34)C2C1

InChI Identifier

InChI=1S/C15H24N2/c1-2-7-17-10-13-9-12(14(17)5-1)8-11-4-3-6-16-15(11)13/h8,12-16H,1-7,9-10H2

InChI Key

SKOLRLSBMUGVOY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aloperine and related alkaloids. These are lupin Alkaloids with a structure based on the aloperine skeleton. Aloperine is a tetracyclic compound made up of a quinolizidine and a decahydroquinoline joined to form 3,15-diazatetracycloheptadecane.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Lupin alkaloids

Sub Class

Aloperine and related alkaloids

Direct Parent

Aloperine and related alkaloids

Alternative Parents

Substituents

Aloperine skeleton
Quinolizidine
Piperidine
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

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	1.74	ALOGPS
logP	1.65	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Basic)	9.98	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	15.27 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.8 m³·mol⁻¹	ChemAxon
Polarizability	27.91 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
DeepCCS	[M-2H]-	191.15	30932474
DeepCCS	[M+Na]+	166.029	30932474
AllCCS	[M+H]+	158.9	32859911
AllCCS	[M+H-H2O]+	155.0	32859911
AllCCS	[M+NH4]+	162.5	32859911
AllCCS	[M+Na]+	163.5	32859911
AllCCS	[M-H]-	168.2	32859911
AllCCS	[M+Na-2H]-	168.0	32859911
AllCCS	[M+HCOO]-	168.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Aloperine	C1CCN2CC3CC(C=C4CCCNC34)C2C1	2543.1	Standard polar	33892256
Aloperine	C1CCN2CC3CC(C=C4CCCNC34)C2C1	1904.6	Standard non polar	33892256
Aloperine	C1CCN2CC3CC(C=C4CCCNC34)C2C1	1966.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Aloperine,1TMS,isomer #1	C[Si](C)(C)N1CCCC2=CC3CC(CN4CCCCC34)C21	2163.6	Semi standard non polar	33892256
Aloperine,1TMS,isomer #1	C[Si](C)(C)N1CCCC2=CC3CC(CN4CCCCC34)C21	2163.4	Standard non polar	33892256
Aloperine,1TMS,isomer #1	C[Si](C)(C)N1CCCC2=CC3CC(CN4CCCCC34)C21	2907.3	Standard polar	33892256
Aloperine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCCC2=CC3CC(CN4CCCCC34)C21	2347.9	Semi standard non polar	33892256
Aloperine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCCC2=CC3CC(CN4CCCCC34)C21	2463.1	Standard non polar	33892256
Aloperine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCCC2=CC3CC(CN4CCCCC34)C21	3120.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Aloperine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6t-5960000000-ba62aa087a68e6bfb1fc	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aloperine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - Aloperine 10V, Positive-QTOF	splash10-001i-0090000000-fb536913fc328181cf07	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aloperine 20V, Positive-QTOF	splash10-001i-0090000000-fb536913fc328181cf07	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aloperine 40V, Positive-QTOF	splash10-000t-9860000000-60e95b8e591e242abe11	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aloperine 10V, Negative-QTOF	splash10-001i-0090000000-685a3de85451b66117d2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aloperine 20V, Negative-QTOF	splash10-001i-0090000000-685a3de85451b66117d2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aloperine 40V, Negative-QTOF	splash10-004i-0290000000-3c8e933852654c0dc5c1	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3772951

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Aloperine (HMDB0248180)

MOL for HMDB0248180 (Aloperine)

3D MOL for HMDB0248180 (Aloperine)

3D SDF for HMDB0248180 (Aloperine)

3D-SDF for HMDB0248180 (Aloperine)

PDB for HMDB0248180 (Aloperine)

3D PDB for HMDB0248180 (Aloperine)

SMILES for HMDB0248180 (Aloperine)

INCHI for HMDB0248180 (Aloperine)

Structure for HMDB0248180 (Aloperine)

3D Structure for HMDB0248180 (Aloperine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra