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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:52:07 UTC

Update Date

2021-09-26 22:56:11 UTC

HMDB ID

HMDB0246856

Secondary Accession Numbers

None

Metabolite Identification

Common Name

5,6-Didehydrospartein-2-one

Description

Lupanine, 5,6-didehydro-, also known as 5,6-dehydro-lupanine, 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. Lupanine, 5,6-didehydro- is a very strong basic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). 5,6-didehydrospartein-2-one is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 5,6-Didehydrospartein-2-one 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

HMDB0246856
     RDKit          3D
5,6-Didehydrospartein-2-one
 40 43  0  0  0  0  0  0  0  0999 V2000
    3.4100    2.4911   -0.3409 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2229    1.3177    0.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3031    0.6061    0.7452 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2918   -0.8648    0.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9775   -1.4465    0.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9332   -0.7247   -0.1055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6016   -1.3716   -0.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1469   -0.7006   -1.6977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2532    0.7049   -1.3255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8214    1.4745   -0.6151 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9709    0.6874   -0.2358 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5296    0.6949   -0.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7245    0.7417   -1.4444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9638    0.7258   -0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0203   -0.3174    0.4401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7078   -0.6793    1.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5922   -0.5323    0.1970 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3714   -1.0277    0.7137 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087    0.8799    1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2802    0.9963    0.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9865   -1.1455   -0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7431   -1.3510    1.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8685   -2.5183    0.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6913   -2.4404   -0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0229   -0.6248   -2.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7196   -1.1995   -2.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4918    1.2292   -2.2881 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3796    1.9695    0.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2171    2.3068   -1.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5463    1.6013    0.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6920   -0.1457   -2.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6783    1.6830   -2.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0974    1.7539   -0.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8295    0.5820   -1.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5228   -1.2295    0.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6921    0.0341    1.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7664   -1.7409    1.3901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5311   -0.0986    2.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5753   -1.9761    1.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1283   -0.3448    1.4402 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  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
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 18 39  1  0
 18 40  1  0
M  END


  Mrv1533004161505402D          

 18 21  0  0  0  0            999 V2000
    6.1269   -1.2375    0.0000 O   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
    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 C   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
    4.6655    0.3094    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
    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 N   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
    1.9917    0.8250    0.0000 C   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 N   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
  1  2  2  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  2  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
  2 11  1  0  0  0  0
  6 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 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
 17 18  1  0  0  0  0
  7 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0246856

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1CCC=C2C3CC(CN12)C1CCCCN1C3

> <INCHI_IDENTIFIER>
InChI=1S/C15H22N2O/c18-15-6-3-5-14-11-8-12(10-17(14)15)13-4-1-2-7-16(13)9-11/h5,11-13H,1-4,6-10H2

> <INCHI_KEY>
GSQQGCZVTAUICD-UHFFFAOYSA-N

> <FORMULA>
C15H22N2O

> <MOLECULAR_WEIGHT>
246.354

> <EXACT_MASS>
246.173213336

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
27.846000910986778

> <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-en-6-one

> <ALOGPS_LOGP>
2.82

> <JCHEM_LOGP>
0.7436707089999994

> <ALOGPS_LOGS>
-1.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.628128143686018

> <JCHEM_POLAR_SURFACE_AREA>
23.550000000000004

> <JCHEM_REFRACTIVITY>
72.94189999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.53e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-2-en-6-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0246856
     RDKit          3D
5,6-Didehydrospartein-2-one
 40 43  0  0  0  0  0  0  0  0999 V2000
    3.4100    2.4911   -0.3409 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2229    1.3177    0.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3031    0.6061    0.7452 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2918   -0.8648    0.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9775   -1.4465    0.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9332   -0.7247   -0.1055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6016   -1.3716   -0.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1469   -0.7006   -1.6977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2532    0.7049   -1.3255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8214    1.4745   -0.6151 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9709    0.6874   -0.2358 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5296    0.6949   -0.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7245    0.7417   -1.4444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9638    0.7258   -0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0203   -0.3174    0.4401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7078   -0.6793    1.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5922   -0.5323    0.1970 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3714   -1.0277    0.7137 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087    0.8799    1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2802    0.9963    0.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9865   -1.1455   -0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7431   -1.3510    1.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8685   -2.5183    0.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6913   -2.4404   -0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0229   -0.6248   -2.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7196   -1.1995   -2.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4918    1.2292   -2.2881 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3796    1.9695    0.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2171    2.3068   -1.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5463    1.6013    0.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6920   -0.1457   -2.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6783    1.6830   -2.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0974    1.7539   -0.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8295    0.5820   -1.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5228   -1.2295    0.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6921    0.0341    1.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7664   -1.7409    1.3901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5311   -0.0986    2.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5753   -1.9761    1.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1283   -0.3448    1.4402 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  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
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 18 39  1  0
 18 40  1  0
M  END

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  O   UNK     0      11.437  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      11.437  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.770   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.770   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.437   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.103   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.014   2.629   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.709   0.577   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.474  -1.089   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.014  -1.089   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      10.103  -0.000   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       6.385  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.052  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.718   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.718   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.052   2.310   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       6.385   1.540   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       7.474   2.629   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    2    6                                                  
CONECT   12    9   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17    7                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   42    0
END

COMPND    HMDB0246856
HETATM    1  O1  UNL     1       3.410   2.491  -0.341  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.223   1.318   0.033  1.00  0.00           C  
HETATM    3  C2  UNL     1       4.303   0.606   0.745  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.292  -0.865   0.536  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.978  -1.446   0.243  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.933  -0.725  -0.105  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.602  -1.372  -0.397  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.147  -0.701  -1.698  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.253   0.705  -1.325  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.821   1.474  -0.615  1.00  0.00           C  
HETATM   11  N1  UNL     1       1.971   0.687  -0.236  1.00  0.00           N  
HETATM   12  C10 UNL     1      -1.530   0.695  -0.514  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.725   0.742  -1.444  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.964   0.726  -0.602  1.00  0.00           C  
HETATM   15  C13 UNL     1      -4.020  -0.317   0.440  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.708  -0.679   1.065  1.00  0.00           C  
HETATM   17  N2  UNL     1      -1.592  -0.532   0.197  1.00  0.00           N  
HETATM   18  C15 UNL     1      -0.371  -1.028   0.714  1.00  0.00           C  
HETATM   19  H1  UNL     1       4.309   0.880   1.833  1.00  0.00           H  
HETATM   20  H2  UNL     1       5.280   0.996   0.336  1.00  0.00           H  
HETATM   21  H3  UNL     1       4.986  -1.146  -0.304  1.00  0.00           H  
HETATM   22  H4  UNL     1       4.743  -1.351   1.443  1.00  0.00           H  
HETATM   23  H5  UNL     1       2.869  -2.518   0.318  1.00  0.00           H  
HETATM   24  H6  UNL     1       0.691  -2.440  -0.592  1.00  0.00           H  
HETATM   25  H7  UNL     1       1.023  -0.625  -2.386  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.720  -1.199  -2.134  1.00  0.00           H  
HETATM   27  H9  UNL     1      -0.492   1.229  -2.288  1.00  0.00           H  
HETATM   28  H10 UNL     1       0.380   1.969   0.273  1.00  0.00           H  
HETATM   29  H11 UNL     1       1.217   2.307  -1.257  1.00  0.00           H  
HETATM   30  H12 UNL     1      -1.546   1.601   0.120  1.00  0.00           H  
HETATM   31  H13 UNL     1      -2.692  -0.146  -2.124  1.00  0.00           H  
HETATM   32  H14 UNL     1      -2.678   1.683  -2.011  1.00  0.00           H  
HETATM   33  H15 UNL     1      -4.097   1.754  -0.183  1.00  0.00           H  
HETATM   34  H16 UNL     1      -4.829   0.582  -1.299  1.00  0.00           H  
HETATM   35  H17 UNL     1      -4.523  -1.230   0.023  1.00  0.00           H  
HETATM   36  H18 UNL     1      -4.692   0.034   1.259  1.00  0.00           H  
HETATM   37  H19 UNL     1      -2.766  -1.741   1.390  1.00  0.00           H  
HETATM   38  H20 UNL     1      -2.531  -0.099   2.016  1.00  0.00           H  
HETATM   39  H21 UNL     1      -0.575  -1.976   1.253  1.00  0.00           H  
HETATM   40  H22 UNL     1       0.128  -0.345   1.440  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    6   23
CONECT    6    7   11
CONECT    7    8   18   24
CONECT    8    9   25   26
CONECT    9   10   12   27
CONECT   10   11   28   29
CONECT   12   13   17   30
CONECT   13   14   31   32
CONECT   14   15   33   34
CONECT   15   16   35   36
CONECT   16   17   37   38
CONECT   17   18
CONECT   18   39   40
END

HMDB0246856
     RDKit          3D
5,6-Didehydrospartein-2-one
 40 43  0  0  0  0  0  0  0  0999 V2000
    3.4100    2.4911   -0.3409 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2229    1.3177    0.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3031    0.6061    0.7452 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2918   -0.8648    0.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9775   -1.4465    0.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9332   -0.7247   -0.1055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6016   -1.3716   -0.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1469   -0.7006   -1.6977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2532    0.7049   -1.3255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8214    1.4745   -0.6151 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9709    0.6874   -0.2358 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5296    0.6949   -0.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7245    0.7417   -1.4444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9638    0.7258   -0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0203   -0.3174    0.4401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7078   -0.6793    1.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5922   -0.5323    0.1970 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3714   -1.0277    0.7137 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087    0.8799    1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2802    0.9963    0.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9865   -1.1455   -0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7431   -1.3510    1.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8685   -2.5183    0.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6913   -2.4404   -0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0229   -0.6248   -2.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7196   -1.1995   -2.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4918    1.2292   -2.2881 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3796    1.9695    0.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2171    2.3068   -1.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5463    1.6013    0.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6920   -0.1457   -2.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6783    1.6830   -2.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0974    1.7539   -0.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8295    0.5820   -1.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5228   -1.2295    0.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6921    0.0341    1.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7664   -1.7409    1.3901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5311   -0.0986    2.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5753   -1.9761    1.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1283   -0.3448    1.4402 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  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
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 18 39  1  0
 18 40  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5,6-Dehydro-lupanine	MeSH
5,6-Dehydrolupanine	MeSH

Chemical Formula

C₁₅H₂₂N₂O

Average Molecular Weight

246.354

Monoisotopic Molecular Weight

246.173213336

IUPAC Name

7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-2-en-6-one

Traditional Name

7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-2-en-6-one

CAS Registry Number

Not Available

SMILES

O=C1CCC=C2C3CC(CN12)C1CCCCN1C3

InChI Identifier

InChI=1S/C15H22N2O/c18-15-6-3-5-14-11-8-12(10-17(14)15)13-4-1-2-7-16(13)9-11/h5,11-13H,1-4,6-10H2

InChI Key

GSQQGCZVTAUICD-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 carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Lactam
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Amine
Organic nitrogen compound
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	2.82	ALOGPS
logP	0.74	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Basic)	9.63	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	72.94 m³·mol⁻¹	ChemAxon
Polarizability	27.85 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]-	188.592	30932474
DeepCCS	[M+Na]+	163.552	30932474
AllCCS	[M+H]+	161.1	32859911
AllCCS	[M+H-H2O]+	157.3	32859911
AllCCS	[M+NH4]+	164.7	32859911
AllCCS	[M+Na]+	165.7	32859911
AllCCS	[M-H]-	171.4	32859911
AllCCS	[M+Na-2H]-	171.1	32859911
AllCCS	[M+HCOO]-	171.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5,6-Didehydrospartein-2-one	O=C1CCC=C2C3CC(CN12)C1CCCCN1C3	3310.9	Standard polar	33892256
5,6-Didehydrospartein-2-one	O=C1CCC=C2C3CC(CN12)C1CCCCN1C3	2162.6	Standard non polar	33892256
5,6-Didehydrospartein-2-one	O=C1CCC=C2C3CC(CN12)C1CCCCN1C3	2200.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5,6-Didehydrospartein-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gb9-3890000000-3c268a593292488561ca	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,6-Didehydrospartein-2-one 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 - 5,6-Didehydrospartein-2-one 10V, Positive-QTOF	splash10-0002-0090000000-b34e970da2cd14a1e2c2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Didehydrospartein-2-one 20V, Positive-QTOF	splash10-0002-0090000000-b34e970da2cd14a1e2c2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Didehydrospartein-2-one 40V, Positive-QTOF	splash10-0udj-3930000000-c7548c954e2c1852476e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Didehydrospartein-2-one 10V, Negative-QTOF	splash10-0002-0090000000-4a0996a0879be85733ed	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Didehydrospartein-2-one 20V, Negative-QTOF	splash10-0002-0090000000-4a0996a0879be85733ed	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Didehydrospartein-2-one 40V, Negative-QTOF	splash10-0005-1950000000-d874f1ca0d1c8c032a29	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	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

520559

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-Didehydrospartein-2-one (HMDB0246856)

MOL for HMDB0246856 (5,6-Didehydrospartein-2-one)

3D MOL for HMDB0246856 (5,6-Didehydrospartein-2-one)

3D SDF for HMDB0246856 (5,6-Didehydrospartein-2-one)

3D-SDF for HMDB0246856 (5,6-Didehydrospartein-2-one)

PDB for HMDB0246856 (5,6-Didehydrospartein-2-one)

3D PDB for HMDB0246856 (5,6-Didehydrospartein-2-one)

SMILES for HMDB0246856 (5,6-Didehydrospartein-2-one)

INCHI for HMDB0246856 (5,6-Didehydrospartein-2-one)

Structure for HMDB0246856 (5,6-Didehydrospartein-2-one)

3D Structure for HMDB0246856 (5,6-Didehydrospartein-2-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra