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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:47:18 UTC

Update Date

2021-09-26 22:56:04 UTC

HMDB ID

HMDB0246775

Secondary Accession Numbers

None

Metabolite Identification

Common Name

5,6-Didehydrosparteine

Description

5,6-Didehydrosparteine 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 small amount of articles have been published on 5,6-Didehydrosparteine. This compound has been identified in human blood as reported by (PMID: 31557052 ). 5,6-didehydrosparteine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 5,6-Didehydrosparteine 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

HMDB0246775
     RDKit          3D
5,6-Didehydrosparteine
 41 44  0  0  0  0  0  0  0  0999 V2000
    2.8291   -1.5430   -0.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7512   -0.8530    0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4182   -1.4822    0.3265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1513   -0.7412    1.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4199    0.6679    1.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8518    1.4096    0.6911 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8113    0.5651    0.0414 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9128    1.1944   -0.6551 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1910    0.5265   -0.1890 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1612   -0.9509   -0.5029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4326    0.6830   -0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7515    1.1785    0.5574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7366    1.2694   -0.5910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9628   -0.1534   -1.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7160   -0.8683   -1.4051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5360   -0.4808   -0.7868 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4912   -1.4042   -0.8457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7730   -2.6286   -0.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5976   -2.5283    0.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6220   -0.7076    2.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0907   -1.1986    1.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8046    1.2109    1.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6273    2.2494    0.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3431    1.8567    1.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8040    0.9791   -1.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9908    2.2754   -0.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2593    0.6674    0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0707    0.9764   -0.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9094   -1.4556    0.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3893   -1.0639   -1.5829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1076    1.5321   -0.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0687    0.4137    1.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5817    2.1516    1.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7086    1.6404   -0.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3164    1.8737   -1.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4362   -0.6856   -0.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6840   -0.1364   -1.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8862   -1.9718   -1.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5886   -0.8053   -2.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0965   -1.2308   -1.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9382   -2.4313   -1.0027 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
  5 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  3  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 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


  Mrv1533004171508592D          

 17 20  0  0  0  0            999 V2000
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5834   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4084   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7469    0.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5834    1.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4084    1.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7062    1.2375    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
    3.4207   -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
    1.9917    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  6 15  1  0  0  0  0
 10 15  1  0  0  0  0
  8 16  1  0  0  0  0
  4 16  1  0  0  0  0
 16 17  1  0  0  0  0
  1 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0246775

> <DATABASE_NAME>
hmdb

> <SMILES>
C1CCN2CC3CC(CN4CCCC=C34)C2C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H24N2/c1-3-7-16-11-13-9-12(14(16)5-1)10-17-8-4-2-6-15(13)17/h5,12-13,15H,1-4,6-11H2

> <INCHI_KEY>
YIHBNZCJQJSZJP-UHFFFAOYSA-N

> <FORMULA>
C15H24N2

> <MOLECULAR_WEIGHT>
232.371

> <EXACT_MASS>
232.193948781

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
27.717841881926503

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-2-ene

> <ALOGPS_LOGP>
3.37

> <JCHEM_LOGP>
1.6955708739999995

> <ALOGPS_LOGS>
-1.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_BASIC>
9.232244647775442

> <JCHEM_POLAR_SURFACE_AREA>
6.48

> <JCHEM_REFRACTIVITY>
73.31640000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-2-ene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0246775
     RDKit          3D
5,6-Didehydrosparteine
 41 44  0  0  0  0  0  0  0  0999 V2000
    2.8291   -1.5430   -0.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7512   -0.8530    0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4182   -1.4822    0.3265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1513   -0.7412    1.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4199    0.6679    1.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8518    1.4096    0.6911 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8113    0.5651    0.0414 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9128    1.1944   -0.6551 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1910    0.5265   -0.1890 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1612   -0.9509   -0.5029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4326    0.6830   -0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7515    1.1785    0.5574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7366    1.2694   -0.5910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9628   -0.1534   -1.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7160   -0.8683   -1.4051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5360   -0.4808   -0.7868 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4912   -1.4042   -0.8457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7730   -2.6286   -0.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5976   -2.5283    0.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6220   -0.7076    2.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0907   -1.1986    1.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8046    1.2109    1.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6273    2.2494    0.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3431    1.8567    1.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8040    0.9791   -1.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9908    2.2754   -0.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2593    0.6674    0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0707    0.9764   -0.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9094   -1.4556    0.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3893   -1.0639   -1.5829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1076    1.5321   -0.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0687    0.4137    1.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5817    2.1516    1.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7086    1.6404   -0.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3164    1.8737   -1.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4362   -0.6856   -0.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6840   -0.1364   -1.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8862   -1.9718   -1.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5886   -0.8053   -2.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0965   -1.2308   -1.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9382   -2.4313   -1.0027 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
  5 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  3  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 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                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.089  -1.089   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.629  -1.089   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.394   0.578   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.089   2.629   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.629   2.629   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.718   1.540   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       5.052   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.385   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.385  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.052  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.718   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
CONECT    1    2   17                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    6   10                                                  
CONECT   16    8    4   17                                                  
CONECT   17   16    1                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   40    0
END

COMPND    HMDB0246775
HETATM    1  C1  UNL     1       2.829  -1.543  -0.213  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.751  -0.853   0.037  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.418  -1.482   0.326  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.151  -0.741   1.510  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.420   0.668   1.077  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.852   1.410   0.691  1.00  0.00           C  
HETATM    7  N1  UNL     1       1.811   0.565   0.041  1.00  0.00           N  
HETATM    8  C7  UNL     1       2.913   1.194  -0.655  1.00  0.00           C  
HETATM    9  C8  UNL     1       4.191   0.527  -0.189  1.00  0.00           C  
HETATM   10  C9  UNL     1       4.161  -0.951  -0.503  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.433   0.683  -0.052  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.751   1.178   0.557  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.737   1.269  -0.591  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.963  -0.153  -1.058  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.716  -0.868  -1.405  1.00  0.00           C  
HETATM   16  N2  UNL     1      -1.536  -0.481  -0.787  1.00  0.00           N  
HETATM   17  C15 UNL     1      -0.491  -1.404  -0.846  1.00  0.00           C  
HETATM   18  H1  UNL     1       2.773  -2.629  -0.214  1.00  0.00           H  
HETATM   19  H2  UNL     1       0.598  -2.528   0.664  1.00  0.00           H  
HETATM   20  H3  UNL     1       0.622  -0.708   2.304  1.00  0.00           H  
HETATM   21  H4  UNL     1      -1.091  -1.199   1.812  1.00  0.00           H  
HETATM   22  H5  UNL     1      -0.805   1.211   1.988  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.627   2.249   0.000  1.00  0.00           H  
HETATM   24  H7  UNL     1       1.343   1.857   1.589  1.00  0.00           H  
HETATM   25  H8  UNL     1       2.804   0.979  -1.749  1.00  0.00           H  
HETATM   26  H9  UNL     1       2.991   2.275  -0.464  1.00  0.00           H  
HETATM   27  H10 UNL     1       4.259   0.667   0.916  1.00  0.00           H  
HETATM   28  H11 UNL     1       5.071   0.976  -0.649  1.00  0.00           H  
HETATM   29  H12 UNL     1       4.909  -1.456   0.131  1.00  0.00           H  
HETATM   30  H13 UNL     1       4.389  -1.064  -1.583  1.00  0.00           H  
HETATM   31  H14 UNL     1      -1.108   1.532  -0.724  1.00  0.00           H  
HETATM   32  H15 UNL     1      -3.069   0.414   1.293  1.00  0.00           H  
HETATM   33  H16 UNL     1      -2.582   2.152   1.049  1.00  0.00           H  
HETATM   34  H17 UNL     1      -4.709   1.640  -0.207  1.00  0.00           H  
HETATM   35  H18 UNL     1      -3.316   1.874  -1.394  1.00  0.00           H  
HETATM   36  H19 UNL     1      -4.436  -0.686  -0.185  1.00  0.00           H  
HETATM   37  H20 UNL     1      -4.684  -0.136  -1.889  1.00  0.00           H  
HETATM   38  H21 UNL     1      -2.886  -1.972  -1.228  1.00  0.00           H  
HETATM   39  H22 UNL     1      -2.589  -0.805  -2.527  1.00  0.00           H  
HETATM   40  H23 UNL     1       0.097  -1.231  -1.795  1.00  0.00           H  
HETATM   41  H24 UNL     1      -0.938  -2.431  -1.003  1.00  0.00           H  
CONECT    1    2    2   10   18
CONECT    2    3    7
CONECT    3    4   17   19
CONECT    4    5   20   21
CONECT    5    6   11   22
CONECT    6    7   23   24
CONECT    7    8
CONECT    8    9   25   26
CONECT    9   10   27   28
CONECT   10   29   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

HMDB0246775
     RDKit          3D
5,6-Didehydrosparteine
 41 44  0  0  0  0  0  0  0  0999 V2000
    2.8291   -1.5430   -0.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7512   -0.8530    0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4182   -1.4822    0.3265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1513   -0.7412    1.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4199    0.6679    1.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8518    1.4096    0.6911 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8113    0.5651    0.0414 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9128    1.1944   -0.6551 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1910    0.5265   -0.1890 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1612   -0.9509   -0.5029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4326    0.6830   -0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7515    1.1785    0.5574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7366    1.2694   -0.5910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9628   -0.1534   -1.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7160   -0.8683   -1.4051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5360   -0.4808   -0.7868 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4912   -1.4042   -0.8457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7730   -2.6286   -0.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5976   -2.5283    0.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6220   -0.7076    2.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0907   -1.1986    1.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8046    1.2109    1.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6273    2.2494    0.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3431    1.8567    1.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8040    0.9791   -1.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9908    2.2754   -0.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2593    0.6674    0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0707    0.9764   -0.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9094   -1.4556    0.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3893   -1.0639   -1.5829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1076    1.5321   -0.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0687    0.4137    1.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5817    2.1516    1.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7086    1.6404   -0.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3164    1.8737   -1.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4362   -0.6856   -0.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6840   -0.1364   -1.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8862   -1.9718   -1.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5886   -0.8053   -2.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0965   -1.2308   -1.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9382   -2.4313   -1.0027 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
  5 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  3  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 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 NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄N₂

Average Molecular Weight

232.371

Monoisotopic Molecular Weight

232.193948781

IUPAC Name

7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-2-ene

Traditional Name

7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-2-ene

CAS Registry Number

Not Available

SMILES

C1CCN2CC3CC(CN4CCCC=C34)C2C1

InChI Identifier

InChI=1S/C15H24N2/c1-3-7-16-11-13-9-12(14(16)5-1)10-17-8-4-2-6-15(13)17/h5,12-13,15H,1-4,6-11H2

InChI Key

YIHBNZCJQJSZJP-UHFFFAOYSA-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
Quinolizidine
Tetrahydropyridine
Piperidine
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Enamine
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)

Source

Exogenous

Exogenous (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	3.37	ALOGPS
logP	1.7	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Basic)	9.23	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	6.48 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	73.32 m³·mol⁻¹	ChemAxon
Polarizability	27.72 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]-	190.718	30932474
DeepCCS	[M+Na]+	165.555	30932474
AllCCS	[M+H]+	158.6	32859911
AllCCS	[M+H-H2O]+	154.6	32859911
AllCCS	[M+NH4]+	162.3	32859911
AllCCS	[M+Na]+	163.3	32859911
AllCCS	[M-H]-	170.4	32859911
AllCCS	[M+Na-2H]-	170.3	32859911
AllCCS	[M+HCOO]-	170.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	9.1241 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.75 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	554.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	210.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	136.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	171.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	80.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	227.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	280.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	796.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	631.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	60.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	817.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	170.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	216.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	837.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	544.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	281.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5,6-Didehydrosparteine	C1CCN2CC3CC(CN4CCCC=C34)C2C1	2460.5	Standard polar	33892256
5,6-Didehydrosparteine	C1CCN2CC3CC(CN4CCCC=C34)C2C1	1885.6	Standard non polar	33892256
5,6-Didehydrosparteine	C1CCN2CC3CC(CN4CCCC=C34)C2C1	1930.9	Semi standard non polar	33892256

Spectra

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

14169655

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13994061

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 5,6-Didehydrosparteine (HMDB0246775)

MOL for HMDB0246775 (5,6-Didehydrosparteine)

3D MOL for HMDB0246775 (5,6-Didehydrosparteine)

3D SDF for HMDB0246775 (5,6-Didehydrosparteine)

3D-SDF for HMDB0246775 (5,6-Didehydrosparteine)

PDB for HMDB0246775 (5,6-Didehydrosparteine)

3D PDB for HMDB0246775 (5,6-Didehydrosparteine)

SMILES for HMDB0246775 (5,6-Didehydrosparteine)

INCHI for HMDB0246775 (5,6-Didehydrosparteine)

Structure for HMDB0246775 (5,6-Didehydrosparteine)

3D Structure for HMDB0246775 (5,6-Didehydrosparteine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized