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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:47:07 UTC

Update Date

2021-09-26 22:52:31 UTC

HMDB ID

HMDB0244638

Secondary Accession Numbers

None

Metabolite Identification

Common Name

alpha-Pyrrolidinovalerophenone

Description

alpha-Pyrrolidinovalerophenone, also known as flakka or alpha-PVP, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Based on a literature review a significant number of articles have been published on alpha-Pyrrolidinovalerophenone. This compound has been identified in human blood as reported by (PMID: 31557052 ). Alpha-pyrrolidinovalerophenone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically alpha-Pyrrolidinovalerophenone 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

HMDB0244638
     RDKit          3D
alpha-Pyrrolidinovalerophenone
 38 39  0  0  0  0  0  0  0  0999 V2000
   -1.0740    2.5887   -2.4837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6996    1.1834   -1.9901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7454    1.2531   -0.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3951   -0.0735    0.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9463   -0.5390   -0.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0694   -1.5327   -0.9992 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2057   -0.0082    0.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2242    1.0038    1.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4208    1.5527    1.6845 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6225    1.0895    1.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6217    0.0731    0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4352   -0.4570   -0.1499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4254   -1.0540   -0.2292 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6699   -0.5606    0.3215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5373   -1.7437    0.6249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4841   -2.7656    1.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1995   -2.2709    0.4838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0243    2.6343   -3.5820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1513    2.7104   -2.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4778    3.3597   -1.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286    0.5062   -2.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019    0.8929   -2.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0496    2.0050   -0.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7706    1.5661   -0.2006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4757    0.0453    1.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3499    1.4373    1.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4196    2.3613    2.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5422    1.5293    1.6120 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5719   -0.2873   -0.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4700   -1.2682   -0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4431   -0.0212    1.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2264    0.0820   -0.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1948   -1.4660    1.4912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1426   -2.1032   -0.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4973   -2.7896    2.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7918   -3.7572    0.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4936   -2.1020    1.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8038   -3.0741   -0.2014 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  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  4 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 12  7  1  0
 17 13  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
M  END

  Mrv1652309102123472D          

 17 18  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8109   -4.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -4.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -4.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760   -4.1974    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  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
  4 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
 13 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0244638

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCC(N1CCCC1)C(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H21NO/c1-2-8-14(16-11-6-7-12-16)15(17)13-9-4-3-5-10-13/h3-5,9-10,14H,2,6-8,11-12H2,1H3

> <INCHI_KEY>
YDIIDRWHPFMLGR-UHFFFAOYSA-N

> <FORMULA>
C15H21NO

> <MOLECULAR_WEIGHT>
231.339

> <EXACT_MASS>
231.1623143

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.057576051441913

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-phenyl-2-(pyrrolidin-1-yl)pentan-1-one

> <ALOGPS_LOGP>
3.53

> <JCHEM_LOGP>
3.364044592

> <ALOGPS_LOGS>
-2.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.90663861027398

> <JCHEM_PKA_STRONGEST_BASIC>
7.892197412012619

> <JCHEM_POLAR_SURFACE_AREA>
20.310000000000002

> <JCHEM_REFRACTIVITY>
71.04970000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-pyrrolidinopentiophenone

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0244638
     RDKit          3D
alpha-Pyrrolidinovalerophenone
 38 39  0  0  0  0  0  0  0  0999 V2000
   -1.0740    2.5887   -2.4837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6996    1.1834   -1.9901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7454    1.2531   -0.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3951   -0.0735    0.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9463   -0.5390   -0.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0694   -1.5327   -0.9992 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2057   -0.0082    0.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2242    1.0038    1.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4208    1.5527    1.6845 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6225    1.0895    1.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6217    0.0731    0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4352   -0.4570   -0.1499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4254   -1.0540   -0.2292 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6699   -0.5606    0.3215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5373   -1.7437    0.6249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4841   -2.7656    1.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1995   -2.2709    0.4838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0243    2.6343   -3.5820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1513    2.7104   -2.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4778    3.3597   -1.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286    0.5062   -2.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019    0.8929   -2.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0496    2.0050   -0.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7706    1.5661   -0.2006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4757    0.0453    1.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3499    1.4373    1.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4196    2.3613    2.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5422    1.5293    1.6120 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5719   -0.2873   -0.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4700   -1.2682   -0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4431   -0.0212    1.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2264    0.0820   -0.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1948   -1.4660    1.4912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1426   -2.1032   -0.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4973   -2.7896    2.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7918   -3.7572    0.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4936   -2.1020    1.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8038   -3.0741   -0.2014 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  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  4 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 12  7  1  0
 17 13  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
M  END

HEADER    PROTEIN                                 10-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-21         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       4.001  -6.930   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       5.247  -7.835   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.771  -9.300   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.231  -9.300   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.755  -7.835   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13    4   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   13                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0244638
HETATM    1  C1  UNL     1      -1.074   2.589  -2.484  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.700   1.183  -1.990  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.745   1.253  -0.482  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.395  -0.073   0.159  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.946  -0.539  -0.185  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.069  -1.533  -0.999  1.00  0.00           O  
HETATM    7  C6  UNL     1       2.206  -0.008   0.289  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.224   1.004   1.212  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.421   1.553   1.684  1.00  0.00           C  
HETATM   10  C9  UNL     1       4.622   1.089   1.233  1.00  0.00           C  
HETATM   11  C10 UNL     1       4.622   0.073   0.306  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.435  -0.457  -0.150  1.00  0.00           C  
HETATM   13  N1  UNL     1      -1.425  -1.054  -0.229  1.00  0.00           N  
HETATM   14  C12 UNL     1      -2.670  -0.561   0.321  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.537  -1.744   0.625  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.484  -2.766   1.061  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.200  -2.271   0.484  1.00  0.00           C  
HETATM   18  H1  UNL     1      -1.024   2.634  -3.582  1.00  0.00           H  
HETATM   19  H2  UNL     1      -2.151   2.710  -2.205  1.00  0.00           H  
HETATM   20  H3  UNL     1      -0.478   3.360  -1.976  1.00  0.00           H  
HETATM   21  H4  UNL     1      -1.429   0.506  -2.434  1.00  0.00           H  
HETATM   22  H5  UNL     1       0.302   0.893  -2.316  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.050   2.005  -0.127  1.00  0.00           H  
HETATM   24  H7  UNL     1      -1.771   1.566  -0.201  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.476   0.045   1.246  1.00  0.00           H  
HETATM   26  H9  UNL     1       1.350   1.437   1.644  1.00  0.00           H  
HETATM   27  H10 UNL     1       3.420   2.361   2.422  1.00  0.00           H  
HETATM   28  H11 UNL     1       5.542   1.529   1.612  1.00  0.00           H  
HETATM   29  H12 UNL     1       5.572  -0.287  -0.047  1.00  0.00           H  
HETATM   30  H13 UNL     1       3.470  -1.268  -0.891  1.00  0.00           H  
HETATM   31  H14 UNL     1      -2.443  -0.021   1.263  1.00  0.00           H  
HETATM   32  H15 UNL     1      -3.226   0.082  -0.385  1.00  0.00           H  
HETATM   33  H16 UNL     1      -4.195  -1.466   1.491  1.00  0.00           H  
HETATM   34  H17 UNL     1      -4.143  -2.103  -0.211  1.00  0.00           H  
HETATM   35  H18 UNL     1      -2.497  -2.790   2.166  1.00  0.00           H  
HETATM   36  H19 UNL     1      -2.792  -3.757   0.681  1.00  0.00           H  
HETATM   37  H20 UNL     1      -0.494  -2.102   1.322  1.00  0.00           H  
HETATM   38  H21 UNL     1      -0.804  -3.074  -0.201  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   21   22
CONECT    3    4   23   24
CONECT    4    5   13   25
CONECT    5    6    6    7
CONECT    7    8    8   12
CONECT    8    9   26
CONECT    9   10   10   27
CONECT   10   11   28
CONECT   11   12   12   29
CONECT   12   30
CONECT   13   14   17
CONECT   14   15   31   32
CONECT   15   16   33   34
CONECT   16   17   35   36
CONECT   17   37   38
END

HMDB0244638
     RDKit          3D
alpha-Pyrrolidinovalerophenone
 38 39  0  0  0  0  0  0  0  0999 V2000
   -1.0740    2.5887   -2.4837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6996    1.1834   -1.9901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7454    1.2531   -0.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3951   -0.0735    0.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9463   -0.5390   -0.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0694   -1.5327   -0.9992 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2057   -0.0082    0.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2242    1.0038    1.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4208    1.5527    1.6845 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6225    1.0895    1.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6217    0.0731    0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4352   -0.4570   -0.1499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4254   -1.0540   -0.2292 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6699   -0.5606    0.3215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5373   -1.7437    0.6249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4841   -2.7656    1.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1995   -2.2709    0.4838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0243    2.6343   -3.5820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1513    2.7104   -2.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4778    3.3597   -1.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286    0.5062   -2.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019    0.8929   -2.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0496    2.0050   -0.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7706    1.5661   -0.2006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4757    0.0453    1.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3499    1.4373    1.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4196    2.3613    2.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5422    1.5293    1.6120 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5719   -0.2873   -0.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4700   -1.2682   -0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4431   -0.0212    1.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2264    0.0820   -0.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1948   -1.4660    1.4912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1426   -2.1032   -0.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4973   -2.7896    2.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7918   -3.7572    0.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4936   -2.1020    1.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8038   -3.0741   -0.2014 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  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  4 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 12  7  1  0
 17 13  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
a-Pyrrolidinovalerophenone	Generator
Α-pyrrolidinovalerophenone	Generator
alpha-Pyrrolidinopentiophenone	HMDB
Flakka	HMDB
1-Phenyl-2-(1-pyrrolidinyl)-1-pentanone	HMDB
alpha-PVP	HMDB
1-Phenyl-2-pyrrolidin-1-ylpentan-1-one	MeSH

Chemical Formula

C₁₅H₂₁NO

Average Molecular Weight

231.339

Monoisotopic Molecular Weight

231.1623143

IUPAC Name

1-phenyl-2-(pyrrolidin-1-yl)pentan-1-one

Traditional Name

α-pyrrolidinopentiophenone

CAS Registry Number

Not Available

SMILES

CCCC(N1CCCC1)C(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C15H21NO/c1-2-8-14(16-11-6-7-12-16)15(17)13-9-4-3-5-10-13/h3-5,9-10,14H,2,6-8,11-12H2,1H3

InChI Key

YDIIDRWHPFMLGR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Butyrophenone
Benzoyl
Aryl alkyl ketone
Monocyclic benzene moiety
Benzenoid
N-alkylpyrrolidine
Alpha-aminoketone
Pyrrolidine
Tertiary amine
Tertiary aliphatic amine
Organoheterocyclic compound
Azacycle
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	3.53	ALOGPS
logP	3.36	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	17.91	ChemAxon
pKa (Strongest Basic)	7.89	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	20.31 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	71.05 m³·mol⁻¹	ChemAxon
Polarizability	27.06 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
DeepCCS	[M+H]+	158.052	30932474
DeepCCS	[M-H]-	155.694	30932474
DeepCCS	[M-2H]-	188.888	30932474
DeepCCS	[M+Na]+	164.145	30932474
AllCCS	[M+H]+	154.8	32859911
AllCCS	[M+H-H2O]+	150.8	32859911
AllCCS	[M+NH4]+	158.5	32859911
AllCCS	[M+Na]+	159.6	32859911
AllCCS	[M-H]-	161.7	32859911
AllCCS	[M+Na-2H]-	162.0	32859911
AllCCS	[M+HCOO]-	162.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
alpha-Pyrrolidinovalerophenone	CCCC(N1CCCC1)C(=O)C1=CC=CC=C1	2358.3	Standard polar	33892256
alpha-Pyrrolidinovalerophenone	CCCC(N1CCCC1)C(=O)C1=CC=CC=C1	1795.3	Standard non polar	33892256
alpha-Pyrrolidinovalerophenone	CCCC(N1CCCC1)C(=O)C1=CC=CC=C1	1752.7	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 - alpha-Pyrrolidinovalerophenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-6900000000-1cb777475f42901440ff	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Pyrrolidinovalerophenone 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 - alpha-Pyrrolidinovalerophenone 10V, Positive-QTOF	splash10-001i-0090000000-5cfd05ea747f651278e3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Pyrrolidinovalerophenone 20V, Positive-QTOF	splash10-001l-5950000000-d267ed1b2962e224cda7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Pyrrolidinovalerophenone 40V, Positive-QTOF	splash10-0059-9400000000-9fb0aab775f67957987f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Pyrrolidinovalerophenone 10V, Negative-QTOF	splash10-001i-0090000000-cf41a937501d1092930e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Pyrrolidinovalerophenone 20V, Negative-QTOF	splash10-001i-1590000000-d177117ba0f1cbb8bba5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Pyrrolidinovalerophenone 40V, Negative-QTOF	splash10-00or-9620000000-ec5b8309097474d4591b	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9324063

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11148955

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 alpha-Pyrrolidinovalerophenone (HMDB0244638)

MOL for HMDB0244638 (alpha-Pyrrolidinovalerophenone)

3D MOL for HMDB0244638 (alpha-Pyrrolidinovalerophenone)

3D SDF for HMDB0244638 (alpha-Pyrrolidinovalerophenone)

3D-SDF for HMDB0244638 (alpha-Pyrrolidinovalerophenone)

PDB for HMDB0244638 (alpha-Pyrrolidinovalerophenone)

3D PDB for HMDB0244638 (alpha-Pyrrolidinovalerophenone)

SMILES for HMDB0244638 (alpha-Pyrrolidinovalerophenone)

INCHI for HMDB0244638 (alpha-Pyrrolidinovalerophenone)

Structure for HMDB0244638 (alpha-Pyrrolidinovalerophenone)

3D Structure for HMDB0244638 (alpha-Pyrrolidinovalerophenone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra