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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:01:50 UTC

Update Date

2021-09-26 22:51:06 UTC

HMDB ID

HMDB0243804

Secondary Accession Numbers

None

Metabolite Identification

Common Name

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

Description

1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one, also known as energy 1 (naphyrone) or NP-pentanone, belongs to the class of organic compounds known as butyrophenones. Butyrophenones are compounds containing 1-phenylbutan-1-one moiety. Based on a literature review a significant number of articles have been published on 1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). 1-(naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-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

HMDB0243804
     RDKit          3D
1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one
 44 46  0  0  0  0  0  0  0  0999 V2000
   -2.5527    2.9125   -1.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1201    1.7866   -0.4418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6603    0.6008   -1.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2177   -0.5512   -0.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0956   -0.1824    0.4963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3002    0.0013    1.7461 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2788   -0.0025    0.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6325   -0.2224   -1.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9465   -0.0251   -1.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9060    0.3823   -0.7236 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2244    0.5838   -1.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1749    0.9896   -0.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8338    1.2114    1.1621 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5164    1.0109    1.5162 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5662    0.6053    0.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2464    0.4028    0.9474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3377   -0.9195    0.4685 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4730   -1.3730   -0.3343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3526   -1.9715    0.7519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3379   -2.6418    1.6611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9987   -2.2015    1.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9106    3.7992   -1.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6011    3.2207   -1.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4858    2.5583   -2.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0055    1.5318    0.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3538    2.1833    0.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8649    0.9642   -1.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5034    0.2666   -1.8706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9627   -1.3965   -1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9328   -0.5464   -2.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2396   -0.1925   -2.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4776    0.4035   -2.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2004    1.1356   -0.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5685    1.5318    1.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2488    1.1846    2.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0018    0.5844    1.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0284   -0.5521   -0.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1988   -2.1882   -1.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0521   -2.7263    0.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8392   -1.1779    1.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3992   -2.2629    2.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4478   -3.7480    1.6410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2408   -2.1120    1.8832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6548   -2.8578    0.2854 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
 12 13  1  0
 13 14  2  0
 14 15  1  0
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  4 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 16  7  1  0
 21 17  1  0
 15 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  8 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 16 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
M  END


  Mrv1652309102123022D          

 21 23  0  0  0  0            999 V2000
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -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
    3.5724   -2.8875    0.0000 O   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
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5253   -5.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -6.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -6.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1904   -5.4349    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
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  7 16  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0243804

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCC(N1CCCC1)C(=O)C1=CC2=CC=CC=C2C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H23NO/c1-2-7-18(20-12-5-6-13-20)19(21)17-11-10-15-8-3-4-9-16(15)14-17/h3-4,8-11,14,18H,2,5-7,12-13H2,1H3

> <INCHI_KEY>
DTNUPBSOODGRKW-UHFFFAOYSA-N

> <FORMULA>
C19H23NO

> <MOLECULAR_WEIGHT>
281.399

> <EXACT_MASS>
281.177964365

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
32.99100262548516

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.65

> <JCHEM_LOGP>
4.353521348666668

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.8304624242913

> <JCHEM_PKA_STRONGEST_BASIC>
7.988808510465773

> <JCHEM_POLAR_SURFACE_AREA>
20.310000000000002

> <JCHEM_REFRACTIVITY>
87.4999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.77e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
naphyrone

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0243804
     RDKit          3D
1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one
 44 46  0  0  0  0  0  0  0  0999 V2000
   -2.5527    2.9125   -1.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1201    1.7866   -0.4418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6603    0.6008   -1.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2177   -0.5512   -0.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0956   -0.1824    0.4963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3002    0.0013    1.7461 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2788   -0.0025    0.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6325   -0.2224   -1.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9465   -0.0251   -1.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9060    0.3823   -0.7236 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2244    0.5838   -1.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1749    0.9896   -0.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8338    1.2114    1.1621 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5164    1.0109    1.5162 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5662    0.6053    0.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2464    0.4028    0.9474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3377   -0.9195    0.4685 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4730   -1.3730   -0.3343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3526   -1.9715    0.7519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3379   -2.6418    1.6611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9987   -2.2015    1.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9106    3.7992   -1.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6011    3.2207   -1.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4858    2.5583   -2.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0055    1.5318    0.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3538    2.1833    0.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8649    0.9642   -1.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5034    0.2666   -1.8706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9627   -1.3965   -1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9328   -0.5464   -2.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2396   -0.1925   -2.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4776    0.4035   -2.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2004    1.1356   -0.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5685    1.5318    1.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2488    1.1846    2.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0018    0.5844    1.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0284   -0.5521   -0.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1988   -2.1882   -1.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0521   -2.7263    0.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8392   -1.1779    1.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3992   -2.2629    2.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4478   -3.7480    1.6410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2408   -2.1120    1.8832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6548   -2.8578    0.2854 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
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  4 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 16  7  1  0
 21 17  1  0
 15 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  8 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 16 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  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       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       5.335  -9.240   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       6.581 -10.145   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.105 -11.610   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.565 -11.610   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.089 -10.145   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   17                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15    7                                                       
CONECT   17    4   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   17                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0243804
HETATM    1  C1  UNL     1      -2.553   2.913  -1.357  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.120   1.787  -0.442  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.660   0.601  -1.260  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.218  -0.551  -0.383  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.096  -0.182   0.496  1.00  0.00           C  
HETATM    6  O1  UNL     1      -0.300   0.001   1.746  1.00  0.00           O  
HETATM    7  C6  UNL     1       1.279  -0.003   0.049  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.632  -0.222  -1.273  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.946  -0.025  -1.639  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.906   0.382  -0.724  1.00  0.00           C  
HETATM   11  C10 UNL     1       5.224   0.584  -1.075  1.00  0.00           C  
HETATM   12  C11 UNL     1       6.175   0.990  -0.158  1.00  0.00           C  
HETATM   13  C12 UNL     1       5.834   1.211   1.162  1.00  0.00           C  
HETATM   14  C13 UNL     1       4.516   1.011   1.516  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.566   0.605   0.601  1.00  0.00           C  
HETATM   16  C15 UNL     1       2.246   0.403   0.947  1.00  0.00           C  
HETATM   17  N1  UNL     1      -2.338  -0.920   0.469  1.00  0.00           N  
HETATM   18  C16 UNL     1      -3.473  -1.373  -0.334  1.00  0.00           C  
HETATM   19  C17 UNL     1      -4.353  -1.971   0.752  1.00  0.00           C  
HETATM   20  C18 UNL     1      -3.338  -2.642   1.661  1.00  0.00           C  
HETATM   21  C19 UNL     1      -1.999  -2.202   1.110  1.00  0.00           C  
HETATM   22  H1  UNL     1      -1.911   3.799  -1.265  1.00  0.00           H  
HETATM   23  H2  UNL     1      -3.601   3.221  -1.198  1.00  0.00           H  
HETATM   24  H3  UNL     1      -2.486   2.558  -2.423  1.00  0.00           H  
HETATM   25  H4  UNL     1      -3.005   1.532   0.183  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.354   2.183   0.226  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.865   0.964  -1.928  1.00  0.00           H  
HETATM   28  H7  UNL     1      -2.503   0.267  -1.871  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.963  -1.396  -1.030  1.00  0.00           H  
HETATM   30  H9  UNL     1       0.933  -0.546  -2.027  1.00  0.00           H  
HETATM   31  H10 UNL     1       3.240  -0.192  -2.669  1.00  0.00           H  
HETATM   32  H11 UNL     1       5.478   0.404  -2.125  1.00  0.00           H  
HETATM   33  H12 UNL     1       7.200   1.136  -0.479  1.00  0.00           H  
HETATM   34  H13 UNL     1       6.569   1.532   1.899  1.00  0.00           H  
HETATM   35  H14 UNL     1       4.249   1.185   2.551  1.00  0.00           H  
HETATM   36  H15 UNL     1       2.002   0.584   1.996  1.00  0.00           H  
HETATM   37  H16 UNL     1      -4.028  -0.552  -0.786  1.00  0.00           H  
HETATM   38  H17 UNL     1      -3.199  -2.188  -1.026  1.00  0.00           H  
HETATM   39  H18 UNL     1      -5.052  -2.726   0.351  1.00  0.00           H  
HETATM   40  H19 UNL     1      -4.839  -1.178   1.332  1.00  0.00           H  
HETATM   41  H20 UNL     1      -3.399  -2.263   2.708  1.00  0.00           H  
HETATM   42  H21 UNL     1      -3.448  -3.748   1.641  1.00  0.00           H  
HETATM   43  H22 UNL     1      -1.241  -2.112   1.883  1.00  0.00           H  
HETATM   44  H23 UNL     1      -1.655  -2.858   0.285  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4   27   28
CONECT    4    5   17   29
CONECT    5    6    6    7
CONECT    7    8    8   16
CONECT    8    9   30
CONECT    9   10   10   31
CONECT   10   11   15
CONECT   11   12   12   32
CONECT   12   13   33
CONECT   13   14   14   34
CONECT   14   15   35
CONECT   15   16   16
CONECT   16   36
CONECT   17   18   21
CONECT   18   19   37   38
CONECT   19   20   39   40
CONECT   20   21   41   42
CONECT   21   43   44
END

HMDB0243804
     RDKit          3D
1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one
 44 46  0  0  0  0  0  0  0  0999 V2000
   -2.5527    2.9125   -1.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1201    1.7866   -0.4418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6603    0.6008   -1.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2177   -0.5512   -0.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0956   -0.1824    0.4963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3002    0.0013    1.7461 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2788   -0.0025    0.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6325   -0.2224   -1.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9465   -0.0251   -1.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9060    0.3823   -0.7236 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2244    0.5838   -1.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1749    0.9896   -0.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8338    1.2114    1.1621 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5164    1.0109    1.5162 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5662    0.6053    0.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2464    0.4028    0.9474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3377   -0.9195    0.4685 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4730   -1.3730   -0.3343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3526   -1.9715    0.7519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3379   -2.6418    1.6611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9987   -2.2015    1.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9106    3.7992   -1.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6011    3.2207   -1.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4858    2.5583   -2.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0055    1.5318    0.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3538    2.1833    0.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8649    0.9642   -1.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5034    0.2666   -1.8706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9627   -1.3965   -1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9328   -0.5464   -2.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2396   -0.1925   -2.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4776    0.4035   -2.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2004    1.1356   -0.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5685    1.5318    1.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2488    1.1846    2.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0018    0.5844    1.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0284   -0.5521   -0.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1988   -2.1882   -1.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0521   -2.7263    0.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8392   -1.1779    1.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3992   -2.2629    2.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4478   -3.7480    1.6410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2408   -2.1120    1.8832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6548   -2.8578    0.2854 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
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  4 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 16  7  1  0
 21 17  1  0
 15 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  8 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 16 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Naphthalen-2-yl-2-pyrrolidin-1-ylpentan-1-one	HMDB
Energy 1 (naphyrone)	HMDB
NP-Pentanone	HMDB
NRG-1 (Naphyrone) CPD	HMDB
Naphthylpyrovalerone	HMDB

Chemical Formula

C₁₉H₂₃NO

Average Molecular Weight

281.399

Monoisotopic Molecular Weight

281.177964365

IUPAC Name

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

Traditional Name

naphyrone

CAS Registry Number

Not Available

SMILES

CCCC(N1CCCC1)C(=O)C1=CC2=CC=CC=C2C=C1

InChI Identifier

InChI=1S/C19H23NO/c1-2-7-18(20-12-5-6-13-20)19(21)17-11-10-15-8-3-4-9-16(15)14-17/h3-4,8-11,14,18H,2,5-7,12-13H2,1H3

InChI Key

DTNUPBSOODGRKW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as butyrophenones. Butyrophenones are compounds containing 1-phenylbutan-1-one moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Butyrophenones

Direct Parent

Butyrophenones

Alternative Parents

Substituents

Butyrophenone
Naphthalene
Aryl ketone
Aryl alkyl ketone
N-alkylpyrrolidine
Alpha-aminoketone
Pyrrolidine
Ketone
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organoheterocyclic compound
Amine
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic nitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	4.65	ALOGPS
logP	4.35	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	17.83	ChemAxon
pKa (Strongest Basic)	7.99	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	87.5 m³·mol⁻¹	ChemAxon
Polarizability	32.99 Å³	ChemAxon
Number of Rings	3	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]+	170.958	30932474
DeepCCS	[M-H]-	168.6	30932474
DeepCCS	[M-2H]-	201.485	30932474
DeepCCS	[M+Na]+	177.051	30932474
AllCCS	[M+H]+	169.3	32859911
AllCCS	[M+H-H2O]+	165.7	32859911
AllCCS	[M+NH4]+	172.6	32859911
AllCCS	[M+Na]+	173.6	32859911
AllCCS	[M-H]-	177.2	32859911
AllCCS	[M+Na-2H]-	177.2	32859911
AllCCS	[M+HCOO]-	177.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	12.4579 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.14 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1738.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	252.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	191.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	178.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	152.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	558.8 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	558.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	220.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1000.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	478.9 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	1540.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	308.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	370.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	327.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	285.7 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	8.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one	CCCC(N1CCCC1)C(=O)C1=CC2=CC=CC=C2C=C1	3258.3	Standard polar	33892256
1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one	CCCC(N1CCCC1)C(=O)C1=CC2=CC=CC=C2C=C1	2328.3	Standard non polar	33892256
1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one	CCCC(N1CCCC1)C(=O)C1=CC2=CC=CC=C2C=C1	2283.2	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 - 1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-6920000000-e6c03fd92d9df2c9124b	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-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 - 1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one 10V, Positive-QTOF	splash10-001i-0090000000-1a9921b0b28c94184cc4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one 20V, Positive-QTOF	splash10-001i-2590000000-f93dad0477149e8ebf25	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one 40V, Positive-QTOF	splash10-0059-4900000000-a389df69b84c8b775fea	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one 10V, Negative-QTOF	splash10-001i-0090000000-a2d4cba31dc9278eeca1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one 20V, Negative-QTOF	splash10-01q9-0390000000-945ba73f9876a5900851	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one 40V, Negative-QTOF	splash10-05s0-6970000000-bc7c47fe76b5dfb5cf2d	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

9418039

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11243002

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

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MarkerDB ID

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Good Scents ID

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References

Synthesis Reference

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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 1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one (HMDB0243804)

MOL for HMDB0243804 (1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one)

3D MOL for HMDB0243804 (1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one)

3D SDF for HMDB0243804 (1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one)

3D-SDF for HMDB0243804 (1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one)

PDB for HMDB0243804 (1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one)

3D PDB for HMDB0243804 (1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one)

SMILES for HMDB0243804 (1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one)

INCHI for HMDB0243804 (1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one)

Structure for HMDB0243804 (1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one)

3D Structure for HMDB0243804 (1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra