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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:56 UTC

Update Date

2022-03-07 02:52:29 UTC

HMDB ID

HMDB0030290

Secondary Accession Numbers

HMDB30290

Metabolite Identification

Common Name

Cuscohygrine

Description

Cuscohygrine is found in fruits. Cuscohygrine is an alkaloid from the root of Cyphomandra betacea (tree tomato) Cuscohygrine is a pyrrolidine alkaloid found in coca. It can be extracted from plants of the family Solanaceae as well, including Atropa belladonna (deadly nightshade), Datura inoxia and Datura stramonium (jimson weed). Cuscohygrine usually comes with other, more potent alkaloids like atropine or cocaine. Cuscohygrine is an oil, which can be distilled without decomposition only in vacuum. It is easily soluble in water and forms an optically inactive crystalline hydrate C13H24N2O-3H2O, which melts at 40-41¬∞C

Structure

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

HMDB0030290
     RDKit          3D
Cuscohygrine
 40 41  0  0  0  0  0  0  0  0999 V2000
   -3.7803    1.2575    1.1011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6312   -0.2019    1.0733 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6698   -0.7100    0.2086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0346   -0.5945   -1.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6184   -1.0476   -0.8857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3737   -0.6130    0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3140    0.4633    0.6309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0186    0.0141    0.0719 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0716   -1.1075   -0.3811 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1782    0.8811    0.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3725    0.2429   -0.5582 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5156    1.2444   -0.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7020    0.3623   -0.8011 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2416   -1.0281   -0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9002   -0.8806    0.1079 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0516   -0.7827    1.5143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7349    1.7010    0.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7631    1.4782    1.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0161    1.6802    1.7921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5670   -0.0524    0.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9500   -1.7551    0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0811    0.4671   -1.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5578   -1.2666   -1.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5622   -2.1421   -1.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8833   -0.5405   -1.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9664   -1.5041    1.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2172    0.7214    1.7090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7149    1.3671    0.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9337    1.7871   -0.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3803    1.3214    1.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1309   -0.0347   -1.6054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3879    2.0296   -1.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5370    1.6477    0.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5326    0.6931   -0.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0057    0.4704   -1.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9440   -1.4422    0.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251   -1.6629   -1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7890    0.1653    1.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4476   -1.6172    1.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1075   -1.0116    1.8450 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  2  0
  8 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
  6  2  1  0
 15 11  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  7 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
 16 38  1  0
 16 39  1  0
 16 40  1  0
M  END

  Mrv0541 05061305082D          

 16 17  0  0  0  0            999 V2000
    2.6434   -1.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1934    2.9251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -2.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3608    1.8301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7629   -1.4073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9128    1.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -2.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7733    2.5446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -0.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810    1.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665    1.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810    0.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4280   -1.4073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5803    2.3731    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665   -0.0974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
 11  5  1  0  0  0  0
 11  9  1  0  0  0  0
 12  6  1  0  0  0  0
 12 10  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14  1  1  0  0  0  0
 14  7  1  0  0  0  0
 14 11  1  0  0  0  0
 15  2  1  0  0  0  0
 15  8  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030290

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCCC1CC(=O)CC1CCCN1C

> <INCHI_IDENTIFIER>
InChI=1S/C13H24N2O/c1-14-7-3-5-11(14)9-13(16)10-12-6-4-8-15(12)2/h11-12H,3-10H2,1-2H3

> <INCHI_KEY>
ZEBIACKKLGVLFZ-UHFFFAOYSA-N

> <FORMULA>
C13H24N2O

> <MOLECULAR_WEIGHT>
224.3425

> <EXACT_MASS>
224.1888634

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.199997698697345

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3-bis(1-methylpyrrolidin-2-yl)propan-2-one

> <ALOGPS_LOGP>
1.53

> <JCHEM_LOGP>
1.2944313309999997

> <ALOGPS_LOGS>
-1.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.665844592918024

> <JCHEM_PKA_STRONGEST_BASIC>
9.130722930961912

> <JCHEM_POLAR_SURFACE_AREA>
23.55

> <JCHEM_REFRACTIVITY>
66.874

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.92e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cuscohygrine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0030290
     RDKit          3D
Cuscohygrine
 40 41  0  0  0  0  0  0  0  0999 V2000
   -3.7803    1.2575    1.1011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6312   -0.2019    1.0733 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6698   -0.7100    0.2086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0346   -0.5945   -1.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6184   -1.0476   -0.8857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3737   -0.6130    0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3140    0.4633    0.6309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0186    0.0141    0.0719 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0716   -1.1075   -0.3811 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1782    0.8811    0.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3725    0.2429   -0.5582 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5156    1.2444   -0.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7020    0.3623   -0.8011 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2416   -1.0281   -0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9002   -0.8806    0.1079 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0516   -0.7827    1.5143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7349    1.7010    0.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7631    1.4782    1.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0161    1.6802    1.7921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5670   -0.0524    0.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9500   -1.7551    0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0811    0.4671   -1.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5578   -1.2666   -1.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5622   -2.1421   -1.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8833   -0.5405   -1.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9664   -1.5041    1.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2172    0.7214    1.7090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7149    1.3671    0.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9337    1.7871   -0.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3803    1.3214    1.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1309   -0.0347   -1.6054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3879    2.0296   -1.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5370    1.6477    0.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5326    0.6931   -0.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0057    0.4704   -1.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9440   -1.4422    0.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251   -1.6629   -1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7890    0.1653    1.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4476   -1.6172    1.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1075   -1.0116    1.8450 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  2  0
  8 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
  6  2  1  0
 15 11  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  7 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
 16 38  1  0
 16 39  1  0
 16 40  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.934  -2.151   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.961   5.460   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.415  -4.092   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.540   3.416   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.891  -2.627   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.571   2.272   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.875  -4.092   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.310   4.750   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.645  -0.182   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.311   2.128   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.645  -1.722   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.977   2.898   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.311   0.588   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       6.399  -2.627   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       4.817   4.430   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       4.977  -0.182   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   15                                                            
CONECT    3    5    7                                                       
CONECT    4    6    8                                                       
CONECT    5    3   11                                                       
CONECT    6    4   12                                                       
CONECT    7    3   14                                                       
CONECT    8    4   15                                                       
CONECT    9   11   13                                                       
CONECT   10   12   13                                                       
CONECT   11    5    9   14                                                  
CONECT   12    6   10   15                                                  
CONECT   13    9   10   16                                                  
CONECT   14    1    7   11                                                  
CONECT   15    2    8   12                                                  
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0030290
HETATM    1  C1  UNL     1      -3.780   1.257   1.101  1.00  0.00           C  
HETATM    2  N1  UNL     1      -3.631  -0.202   1.073  1.00  0.00           N  
HETATM    3  C2  UNL     1      -4.670  -0.710   0.209  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.035  -0.594  -1.161  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.618  -1.048  -0.886  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.374  -0.613   0.540  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.314   0.463   0.631  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.019   0.014   0.072  1.00  0.00           C  
HETATM    9  O1  UNL     1       0.072  -1.108  -0.381  1.00  0.00           O  
HETATM   10  C8  UNL     1       1.178   0.881   0.042  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.372   0.243  -0.558  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.516   1.244  -0.521  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.702   0.362  -0.801  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.242  -1.028  -0.480  1.00  0.00           C  
HETATM   15  N2  UNL     1       2.900  -0.881   0.108  1.00  0.00           N  
HETATM   16  C13 UNL     1       3.052  -0.783   1.514  1.00  0.00           C  
HETATM   17  H1  UNL     1      -3.735   1.701   0.101  1.00  0.00           H  
HETATM   18  H2  UNL     1      -4.763   1.478   1.565  1.00  0.00           H  
HETATM   19  H3  UNL     1      -3.016   1.680   1.792  1.00  0.00           H  
HETATM   20  H4  UNL     1      -5.567  -0.052   0.291  1.00  0.00           H  
HETATM   21  H5  UNL     1      -4.950  -1.755   0.443  1.00  0.00           H  
HETATM   22  H6  UNL     1      -4.081   0.467  -1.486  1.00  0.00           H  
HETATM   23  H7  UNL     1      -4.558  -1.267  -1.870  1.00  0.00           H  
HETATM   24  H8  UNL     1      -2.562  -2.142  -1.018  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.883  -0.540  -1.541  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.966  -1.504   1.074  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.217   0.721   1.709  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.715   1.367   0.097  1.00  0.00           H  
HETATM   29  H13 UNL     1       0.934   1.787  -0.589  1.00  0.00           H  
HETATM   30  H14 UNL     1       1.380   1.321   1.055  1.00  0.00           H  
HETATM   31  H15 UNL     1       2.131  -0.035  -1.605  1.00  0.00           H  
HETATM   32  H16 UNL     1       3.388   2.030  -1.292  1.00  0.00           H  
HETATM   33  H17 UNL     1       3.537   1.648   0.513  1.00  0.00           H  
HETATM   34  H18 UNL     1       5.533   0.693  -0.128  1.00  0.00           H  
HETATM   35  H19 UNL     1       5.006   0.470  -1.866  1.00  0.00           H  
HETATM   36  H20 UNL     1       4.944  -1.442   0.293  1.00  0.00           H  
HETATM   37  H21 UNL     1       4.225  -1.663  -1.366  1.00  0.00           H  
HETATM   38  H22 UNL     1       2.789   0.165   1.972  1.00  0.00           H  
HETATM   39  H23 UNL     1       2.448  -1.617   1.978  1.00  0.00           H  
HETATM   40  H24 UNL     1       4.108  -1.012   1.845  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    6
CONECT    3    4   20   21
CONECT    4    5   22   23
CONECT    5    6   24   25
CONECT    6    7   26
CONECT    7    8   27   28
CONECT    8    9    9   10
CONECT   10   11   29   30
CONECT   11   12   15   31
CONECT   12   13   32   33
CONECT   13   14   34   35
CONECT   14   15   36   37
CONECT   15   16
CONECT   16   38   39   40
END

HMDB0030290
     RDKit          3D
Cuscohygrine
 40 41  0  0  0  0  0  0  0  0999 V2000
   -3.7803    1.2575    1.1011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6312   -0.2019    1.0733 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6698   -0.7100    0.2086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0346   -0.5945   -1.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6184   -1.0476   -0.8857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3737   -0.6130    0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3140    0.4633    0.6309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0186    0.0141    0.0719 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0716   -1.1075   -0.3811 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1782    0.8811    0.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3725    0.2429   -0.5582 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5156    1.2444   -0.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7020    0.3623   -0.8011 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2416   -1.0281   -0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9002   -0.8806    0.1079 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0516   -0.7827    1.5143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7349    1.7010    0.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7631    1.4782    1.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0161    1.6802    1.7921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5670   -0.0524    0.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9500   -1.7551    0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0811    0.4671   -1.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5578   -1.2666   -1.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5622   -2.1421   -1.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8833   -0.5405   -1.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9664   -1.5041    1.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2172    0.7214    1.7090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7149    1.3671    0.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9337    1.7871   -0.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3803    1.3214    1.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1309   -0.0347   -1.6054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3879    2.0296   -1.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5370    1.6477    0.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5326    0.6931   -0.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0057    0.4704   -1.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9440   -1.4422    0.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251   -1.6629   -1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7890    0.1653    1.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4476   -1.6172    1.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1075   -1.0116    1.8450 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  2  0
  8 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
  6  2  1  0
 15 11  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  7 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
 16 38  1  0
 16 39  1  0
 16 40  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Cuskhygrine	Kegg
1,3-Bis(1-methyl-2-pyrrolidinyl)-2-propanone, 9ci	HMDB
Bellaradine	HMDB
Hellaradine	HMDB
meso-Cuscohygrine	MeSH, HMDB

Chemical Formula

C₁₃H₂₄N₂O

Average Molecular Weight

224.3425

Monoisotopic Molecular Weight

224.1888634

IUPAC Name

1,3-bis(1-methylpyrrolidin-2-yl)propan-2-one

Traditional Name

cuscohygrine

CAS Registry Number

454-14-8

SMILES

CN1CCCC1CC(=O)CC1CCCN1C

InChI Identifier

InChI=1S/C13H24N2O/c1-14-7-3-5-11(14)9-13(16)10-12-6-4-8-15(12)2/h11-12H,3-10H2,1-2H3

InChI Key

ZEBIACKKLGVLFZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Not Available

Sub Class

Not Available

Direct Parent

Alkaloids and derivatives

Alternative Parents

Substituents

Alkaloid or derivatives
Beta-aminoketone
N-alkylpyrrolidine
Pyrrolidine
Ketone
Tertiary amine
Tertiary aliphatic amine
Organoheterocyclic compound
Azacycle
Organopnictogen compound
Organic nitrogen compound
Amine
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Pyrrolidine alkaloids (C06521 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030290)
Cytoplasm (HMDB: HMDB0030290)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030290)

Source

Endogenous

Endogenous (HMDB: HMDB0030290)

Plant

Plant (HMDB: HMDB0030290)

Exogenous

Food

Food (HMDB: HMDB0030290)

Vegetable

Tuber

Potato (FooDB: FOOD00175)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0030290)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	40 - 41 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	75760 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	19.2 g/L	ALOGPS
logP	1.53	ALOGPS
logP	1.29	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	17.67	ChemAxon
pKa (Strongest Basic)	9.13	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	23.55 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	66.87 m³·mol⁻¹	ChemAxon
Polarizability	26.2 Å³	ChemAxon
Number of Rings	2	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
DarkChem	[M+H]+	154.053	31661259
DarkChem	[M-H]-	150.168	31661259
DeepCCS	[M+H]+	150.47	30932474
DeepCCS	[M-H]-	147.624	30932474
DeepCCS	[M-2H]-	184.047	30932474
DeepCCS	[M+Na]+	159.622	30932474
AllCCS	[M+H]+	154.7	32859911
AllCCS	[M+H-H2O]+	150.7	32859911
AllCCS	[M+NH4]+	158.5	32859911
AllCCS	[M+Na]+	159.6	32859911
AllCCS	[M-H]-	162.1	32859911
AllCCS	[M+Na-2H]-	162.7	32859911
AllCCS	[M+HCOO]-	163.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cuscohygrine	CN1CCCC1CC(=O)CC1CCCN1C	2273.4	Standard polar	33892256
Cuscohygrine	CN1CCCC1CC(=O)CC1CCCN1C	1690.3	Standard non polar	33892256
Cuscohygrine	CN1CCCC1CC(=O)CC1CCCN1C	1665.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cuscohygrine,1TMS,isomer #1	CN1CCCC1C=C(CC1CCCN1C)O[Si](C)(C)C	1880.4	Semi standard non polar	33892256
Cuscohygrine,1TMS,isomer #1	CN1CCCC1C=C(CC1CCCN1C)O[Si](C)(C)C	1830.8	Standard non polar	33892256
Cuscohygrine,1TBDMS,isomer #1	CN1CCCC1C=C(CC1CCCN1C)O[Si](C)(C)C(C)(C)C	2109.2	Semi standard non polar	33892256
Cuscohygrine,1TBDMS,isomer #1	CN1CCCC1C=C(CC1CCCN1C)O[Si](C)(C)C(C)(C)C	2015.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cuscohygrine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9100000000-75be6ca05d59d8989e68	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cuscohygrine 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 - Cuscohygrine 10V, Positive-QTOF	splash10-004i-0090000000-e8b79af0fea5809bc617	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cuscohygrine 20V, Positive-QTOF	splash10-003r-9240000000-3e2623086deae7e63825	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cuscohygrine 40V, Positive-QTOF	splash10-001i-9200000000-57da29ea842732ed14cf	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cuscohygrine 10V, Negative-QTOF	splash10-00di-0090000000-64350ede9395a0a40a03	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cuscohygrine 20V, Negative-QTOF	splash10-00di-3190000000-2ba7b0efaad7a48e641e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cuscohygrine 40V, Negative-QTOF	splash10-0006-9620000000-d97b0dced81144a61a60	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cuscohygrine 10V, Positive-QTOF	splash10-004i-0090000000-4867679bcafa330885bb	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cuscohygrine 20V, Positive-QTOF	splash10-004i-3290000000-95209dfd7768afc9364b	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cuscohygrine 40V, Positive-QTOF	splash10-001j-9100000000-66b8d9220ff45d5ce772	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cuscohygrine 10V, Negative-QTOF	splash10-00di-0090000000-c52a79615d7e06621850	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cuscohygrine 20V, Negative-QTOF	splash10-00dl-8890000000-9ab44af63a1aa791ab75	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cuscohygrine 40V, Negative-QTOF	splash10-0006-9400000000-2df947e50483f7c1ae79	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cuscohygrine

METLIN ID

Not Available

PubChem Compound

441070

PDB ID

Not Available

ChEBI ID

27920

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1818751

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Cuscohygrine (HMDB0030290)

MOL for HMDB0030290 (Cuscohygrine)

3D MOL for HMDB0030290 (Cuscohygrine)

3D SDF for HMDB0030290 (Cuscohygrine)

3D-SDF for HMDB0030290 (Cuscohygrine)

PDB for HMDB0030290 (Cuscohygrine)

3D PDB for HMDB0030290 (Cuscohygrine)

SMILES for HMDB0030290 (Cuscohygrine)

INCHI for HMDB0030290 (Cuscohygrine)

Structure for HMDB0030290 (Cuscohygrine)

3D Structure for HMDB0030290 (Cuscohygrine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra