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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:13:06 UTC

Update Date

2022-03-07 02:53:43 UTC

HMDB ID

HMDB0033486

Secondary Accession Numbers

HMDB33486

Metabolite Identification

Common Name

Pipermethystine

Description

Pipermethystine belongs to the class of organic compounds known as hydropyridines. Hydropyridines are compounds containing a hydrogenated pyridine ring (i.e. containing less than the maximum number of double bonds.). Pipermethystine has been detected, but not quantified in, beverages. This could make pipermethystine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Pipermethystine.

Structure

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

HMDB0033486
     RDKit          3D
Pipermethystine
 38 39  0  0  0  0  0  0  0  0999 V2000
    5.3923    1.5365   -1.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0506    0.7153   -0.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8568    0.6026    0.6290 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8468    0.0463   -0.2195 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4981   -0.7325    0.9079 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3855   -2.1623    0.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2085   -2.7391    0.4933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0154   -1.9513    0.7247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0963   -2.5182    0.6354 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0701   -0.5780    1.0444 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0061    0.2956    0.8295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1747    1.5210    1.1605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2966   -0.0555    0.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2292    1.1429    0.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5310    0.7930   -0.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8085    0.8401   -1.7629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0438    0.5051   -2.2763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0423    0.1079   -1.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7927    0.0536   -0.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5602    0.3901    0.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464   -0.1310    1.6276 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0702    2.5683   -1.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5025    1.5548   -1.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8717    1.1729   -2.4435 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3887   -0.6578    1.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087   -2.7680    0.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1606   -3.8048    0.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7942   -0.9152    0.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1536   -0.3961   -0.8111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4132    1.5127    1.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7533    1.9636   -0.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0098    1.1553   -2.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2719    0.5384   -3.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0280   -0.1640   -1.7741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5908   -0.2615    0.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3678    0.3435    1.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3203    0.9583    1.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3091   -0.4822    2.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 10 21  1  0
 21  5  1  0
 20 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
 21 38  1  0
M  END


  Mrv0541 05061307082D          

 21 22  0  0  0  0            999 V2000
    2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    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
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
 12  1  1  0  0  0  0
 13  5  2  0  0  0  0
 13  6  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 14 11  1  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 17 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 12  2  0  0  0  0
 19 15  2  0  0  0  0
 20 16  2  0  0  0  0
 21 12  1  0  0  0  0
 21 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033486

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OC1CN(C(=O)CCC2=CC=CC=C2)C(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H17NO4/c1-12(18)21-14-8-10-16(20)17(11-14)15(19)9-7-13-5-3-2-4-6-13/h2-6,8,10,14H,7,9,11H2,1H3

> <INCHI_KEY>
JLNNQCUATONMIT-UHFFFAOYSA-N

> <FORMULA>
C16H17NO4

> <MOLECULAR_WEIGHT>
287.3105

> <EXACT_MASS>
287.115758037

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
30.040892822318348

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-oxo-1-(3-phenylpropanoyl)-1,2,3,6-tetrahydropyridin-3-yl acetate

> <ALOGPS_LOGP>
1.78

> <JCHEM_LOGP>
1.6524289099999991

> <ALOGPS_LOGS>
-4.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.9963492336747

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8791062059603605

> <JCHEM_POLAR_SURFACE_AREA>
63.68000000000001

> <JCHEM_REFRACTIVITY>
77.19999999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.85e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-oxo-1-(3-phenylpropanoyl)-2,3-dihydropyridin-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033486
     RDKit          3D
Pipermethystine
 38 39  0  0  0  0  0  0  0  0999 V2000
    5.3923    1.5365   -1.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0506    0.7153   -0.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8568    0.6026    0.6290 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8468    0.0463   -0.2195 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4981   -0.7325    0.9079 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3855   -2.1623    0.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2085   -2.7391    0.4933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0154   -1.9513    0.7247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0963   -2.5182    0.6354 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0701   -0.5780    1.0444 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0061    0.2956    0.8295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1747    1.5210    1.1605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2966   -0.0555    0.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2292    1.1429    0.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5310    0.7930   -0.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8085    0.8401   -1.7629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0438    0.5051   -2.2763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0423    0.1079   -1.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7927    0.0536   -0.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5602    0.3901    0.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464   -0.1310    1.6276 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0702    2.5683   -1.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5025    1.5548   -1.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8717    1.1729   -2.4435 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3887   -0.6578    1.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087   -2.7680    0.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1606   -3.8048    0.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7942   -0.9152    0.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1536   -0.3961   -0.8111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4132    1.5127    1.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7533    1.9636   -0.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0098    1.1553   -2.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2719    0.5384   -3.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0280   -0.1640   -1.7741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5908   -0.2615    0.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3678    0.3435    1.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3203    0.9583    1.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3091   -0.4822    2.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 10 21  1  0
 21  5  1  0
 20 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
 21 38  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       4.001  13.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       6.668   6.930   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       2.667  10.780   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.336   6.930   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335  10.780   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3   13                                                       
CONECT    6    4   13                                                       
CONECT    7    9   13                                                       
CONECT    8   10   14                                                       
CONECT    9    7   15                                                       
CONECT   10    8   16                                                       
CONECT   11   14   17                                                       
CONECT   12    1   18   21                                                  
CONECT   13    5    6    7                                                  
CONECT   14    8   11   21                                                  
CONECT   15    9   17   19                                                  
CONECT   16   10   17   20                                                  
CONECT   17   11   15   16                                                  
CONECT   18   12                                                            
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0033486
HETATM    1  C1  UNL     1       5.392   1.537  -1.552  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.051   0.715  -0.339  1.00  0.00           C  
HETATM    3  O1  UNL     1       5.857   0.603   0.629  1.00  0.00           O  
HETATM    4  O2  UNL     1       3.847   0.046  -0.219  1.00  0.00           O  
HETATM    5  C3  UNL     1       3.498  -0.732   0.908  1.00  0.00           C  
HETATM    6  C4  UNL     1       3.386  -2.162   0.581  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.208  -2.739   0.493  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.015  -1.951   0.725  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.096  -2.518   0.635  1.00  0.00           O  
HETATM   10  N1  UNL     1       1.070  -0.578   1.044  1.00  0.00           N  
HETATM   11  C7  UNL     1       0.006   0.296   0.830  1.00  0.00           C  
HETATM   12  O4  UNL     1       0.175   1.521   1.161  1.00  0.00           O  
HETATM   13  C8  UNL     1      -1.297  -0.056   0.257  1.00  0.00           C  
HETATM   14  C9  UNL     1      -2.229   1.143   0.162  1.00  0.00           C  
HETATM   15  C10 UNL     1      -3.531   0.793  -0.409  1.00  0.00           C  
HETATM   16  C11 UNL     1      -3.808   0.840  -1.763  1.00  0.00           C  
HETATM   17  C12 UNL     1      -5.044   0.505  -2.276  1.00  0.00           C  
HETATM   18  C13 UNL     1      -6.042   0.108  -1.411  1.00  0.00           C  
HETATM   19  C14 UNL     1      -5.793   0.054  -0.072  1.00  0.00           C  
HETATM   20  C15 UNL     1      -4.560   0.390   0.416  1.00  0.00           C  
HETATM   21  C16 UNL     1       2.346  -0.131   1.628  1.00  0.00           C  
HETATM   22  H1  UNL     1       5.070   2.568  -1.369  1.00  0.00           H  
HETATM   23  H2  UNL     1       6.503   1.555  -1.667  1.00  0.00           H  
HETATM   24  H3  UNL     1       4.872   1.173  -2.444  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.389  -0.658   1.605  1.00  0.00           H  
HETATM   26  H5  UNL     1       4.309  -2.768   0.405  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.161  -3.805   0.247  1.00  0.00           H  
HETATM   28  H7  UNL     1      -1.794  -0.915   0.750  1.00  0.00           H  
HETATM   29  H8  UNL     1      -1.154  -0.396  -0.811  1.00  0.00           H  
HETATM   30  H9  UNL     1      -2.413   1.513   1.210  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.753   1.964  -0.371  1.00  0.00           H  
HETATM   32  H11 UNL     1      -3.010   1.155  -2.429  1.00  0.00           H  
HETATM   33  H12 UNL     1      -5.272   0.538  -3.335  1.00  0.00           H  
HETATM   34  H13 UNL     1      -7.028  -0.164  -1.774  1.00  0.00           H  
HETATM   35  H14 UNL     1      -6.591  -0.262   0.595  1.00  0.00           H  
HETATM   36  H15 UNL     1      -4.368   0.343   1.497  1.00  0.00           H  
HETATM   37  H16 UNL     1       2.320   0.958   1.616  1.00  0.00           H  
HETATM   38  H17 UNL     1       2.309  -0.482   2.690  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   21   25
CONECT    6    7    7   26
CONECT    7    8   27
CONECT    8    9    9   10
CONECT   10   11   21
CONECT   11   12   12   13
CONECT   13   14   28   29
CONECT   14   15   30   31
CONECT   15   16   16   20
CONECT   16   17   32
CONECT   17   18   18   33
CONECT   18   19   34
CONECT   19   20   20   35
CONECT   20   36
CONECT   21   37   38
END

HMDB0033486
     RDKit          3D
Pipermethystine
 38 39  0  0  0  0  0  0  0  0999 V2000
    5.3923    1.5365   -1.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0506    0.7153   -0.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8568    0.6026    0.6290 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8468    0.0463   -0.2195 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4981   -0.7325    0.9079 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3855   -2.1623    0.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2085   -2.7391    0.4933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0154   -1.9513    0.7247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0963   -2.5182    0.6354 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0701   -0.5780    1.0444 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0061    0.2956    0.8295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1747    1.5210    1.1605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2966   -0.0555    0.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2292    1.1429    0.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5310    0.7930   -0.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8085    0.8401   -1.7629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0438    0.5051   -2.2763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0423    0.1079   -1.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7927    0.0536   -0.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5602    0.3901    0.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464   -0.1310    1.6276 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0702    2.5683   -1.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5025    1.5548   -1.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8717    1.1729   -2.4435 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3887   -0.6578    1.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087   -2.7680    0.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1606   -3.8048    0.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7942   -0.9152    0.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1536   -0.3961   -0.8111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4132    1.5127    1.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7533    1.9636   -0.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0098    1.1553   -2.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2719    0.5384   -3.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0280   -0.1640   -1.7741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5908   -0.2615    0.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3678    0.3435    1.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3203    0.9583    1.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3091   -0.4822    2.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 10 21  1  0
 21  5  1  0
 20 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
 21 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Acetoxy-5,6-dihydro-1-(3-phenylpropanoyl)-2(1H)-pyridone	HMDB
6-oxo-1-(3-Phenylpropanoyl)-1,2,3,6-tetrahydropyridin-3-yl acetic acid	Generator
Pipermethystine	MeSH

Chemical Formula

C₁₆H₁₇NO₄

Average Molecular Weight

287.3105

Monoisotopic Molecular Weight

287.115758037

IUPAC Name

6-oxo-1-(3-phenylpropanoyl)-1,2,3,6-tetrahydropyridin-3-yl acetate

Traditional Name

6-oxo-1-(3-phenylpropanoyl)-2,3-dihydropyridin-3-yl acetate

CAS Registry Number

71627-22-0

SMILES

CC(=O)OC1CN(C(=O)CCC2=CC=CC=C2)C(=O)C=C1

InChI Identifier

InChI=1S/C16H17NO4/c1-12(18)21-14-8-10-16(20)17(11-14)15(19)9-7-13-5-3-2-4-6-13/h2-6,8,10,14H,7,9,11H2,1H3

InChI Key

JLNNQCUATONMIT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydropyridines. Hydropyridines are compounds containing a hydrogenated pyridine ring (i.E. Containing less than the maximum number of double bonds.).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Hydropyridines

Direct Parent

Hydropyridines

Alternative Parents

Substituents

Monocyclic benzene moiety
Hydropyridine
Carboxylic acid imide, n-substituted
Benzenoid
Carboxylic acid imide
Dicarboximide
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Azacycle
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033486)
Cytoplasm (HMDB: HMDB0033486)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033486)

Source

Exogenous

Food

Food (HMDB: HMDB0033486)

Beverage

Beverages (FooDB: FOOD00870)

Not Available

Nutrient (HMDB: HMDB0033486)

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
Water Solubility	0.028 g/L	ALOGPS
logP	1.78	ALOGPS
logP	1.65	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	15	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	63.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	77.2 m³·mol⁻¹	ChemAxon
Polarizability	30.04 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	166.571	31661259
DarkChem	[M-H]-	164.235	31661259
DeepCCS	[M+H]+	165.786	30932474
DeepCCS	[M-H]-	163.428	30932474
DeepCCS	[M-2H]-	196.314	30932474
DeepCCS	[M+Na]+	171.88	30932474
AllCCS	[M+H]+	167.8	32859911
AllCCS	[M+H-H2O]+	164.3	32859911
AllCCS	[M+NH4]+	171.0	32859911
AllCCS	[M+Na]+	171.9	32859911
AllCCS	[M-H]-	169.9	32859911
AllCCS	[M+Na-2H]-	169.8	32859911
AllCCS	[M+HCOO]-	169.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pipermethystine	CC(=O)OC1CN(C(=O)CCC2=CC=CC=C2)C(=O)C=C1	3702.2	Standard polar	33892256
Pipermethystine	CC(=O)OC1CN(C(=O)CCC2=CC=CC=C2)C(=O)C=C1	2260.1	Standard non polar	33892256
Pipermethystine	CC(=O)OC1CN(C(=O)CCC2=CC=CC=C2)C(=O)C=C1	2255.9	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 - Pipermethystine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9530000000-5c26d5c0e696f58befbf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pipermethystine 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 - Pipermethystine 10V, Negative-QTOF	splash10-000l-1190000000-fa1e9589a94f6b386586	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipermethystine 20V, Negative-QTOF	splash10-052f-6890000000-7a27ec94699e31f96d84	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipermethystine 40V, Negative-QTOF	splash10-0a4l-9500000000-09683c9534d40779281f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipermethystine 10V, Negative-QTOF	splash10-01r6-2590000000-d3e642a8cd07e26d79d4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipermethystine 20V, Negative-QTOF	splash10-0bt9-7930000000-2fb6964bc6a6b3b8faca	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipermethystine 40V, Negative-QTOF	splash10-0btc-9700000000-aafecfe1b3874010bdb8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipermethystine 10V, Positive-QTOF	splash10-002s-1390000000-538017a875af7cca90ad	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipermethystine 20V, Positive-QTOF	splash10-002b-8790000000-8c4e1c6f082794de78a2	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipermethystine 40V, Positive-QTOF	splash10-06sm-5900000000-baeccd6121337b6b636e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipermethystine 10V, Positive-QTOF	splash10-000i-1390000000-496a194fefc172f8556a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipermethystine 20V, Positive-QTOF	splash10-0a4l-5910000000-2a324b23e54d08116220	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipermethystine 40V, Positive-QTOF	splash10-0a4i-3900000000-f692d89bc981cebdfe39	2021-09-25	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

FDB011533

KNApSAcK ID

C00037653

Chemspider ID

168674

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pipermethystine

METLIN ID

Not Available

PubChem Compound

194391

PDB ID

Not Available

ChEBI ID

157726

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

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

Showing metabocard for Pipermethystine (HMDB0033486)

MOL for HMDB0033486 (Pipermethystine)

3D MOL for HMDB0033486 (Pipermethystine)

3D SDF for HMDB0033486 (Pipermethystine)

3D-SDF for HMDB0033486 (Pipermethystine)

PDB for HMDB0033486 (Pipermethystine)

3D PDB for HMDB0033486 (Pipermethystine)

SMILES for HMDB0033486 (Pipermethystine)

INCHI for HMDB0033486 (Pipermethystine)

Structure for HMDB0033486 (Pipermethystine)

3D Structure for HMDB0033486 (Pipermethystine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra