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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:48:18 UTC

Update Date

2022-03-07 02:55:23 UTC

HMDB ID

HMDB0037554

Secondary Accession Numbers

HMDB37554

Metabolite Identification

Common Name

(±)-Rollipyrrole

Description

(±)-Rollipyrrole belongs to the class of organic compounds known as pyrrolines. Pyrrolines are compounds containing a pyrroline ring, which is a five-member unsaturated aliphatic ring with one nitrogen atom and four carbon atoms (±)-Rollipyrrole has been detected, but not quantified in, alcoholic beverages and fruits. This could make (±)-rollipyrrole a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (±)-Rollipyrrole.

Structure

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

HMDB0037554
     RDKit          3D
(±)-Rollipyrrole
 41 42  0  0  0  0  0  0  0  0999 V2000
   -2.0526    0.7251    2.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5094   -0.3632    1.7179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3848   -0.6973    0.2998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8411   -1.7899   -0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5848   -2.8815    0.4559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4526   -1.8364   -1.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7409   -2.7583   -2.5160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7062   -0.6642   -1.8887 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8173    0.1553   -0.7330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5020    0.7353   -0.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6190    0.1115   -0.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7789   -1.2736   -0.2095 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1388   -1.5503    0.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6336   -2.7049    0.1443 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8432   -0.2559    0.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2725   -0.2181    0.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9210    1.0946    0.6762 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9598    0.6794    0.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2067    2.1335    0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7465    1.1709   -1.0672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2968    1.9494   -2.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1628    0.9383    3.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5389    1.4625    1.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0178   -1.0680    2.3616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8108   -3.6016    0.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1820   -2.4759    1.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2747   -3.4165   -0.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1662   -0.4445   -2.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4318    1.8301   -0.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0224   -1.9558   -0.3787 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8761   -0.8380   -0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4436   -0.7793    1.5036 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8580    1.5334    1.6982 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0424    0.8997    0.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7361    1.8211   -0.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2220    2.6737    0.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7839    2.4449    1.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5814    2.5782   -0.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3753    2.4947   -1.9377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2457    1.4082   -3.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0986    2.7337   -2.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
 18 19  1  0
  9 20  1  0
 20 21  1  0
  9  3  1  0
 18 11  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  5 25  1  0
  5 26  1  0
  5 27  1  0
  8 28  1  0
 10 29  1  0
 12 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 21 39  1  0
 21 40  1  0
 21 41  1  0
M  END

  Mrv0541 02241208532D          

 21 22  0  0  0  0            999 V2000
   -1.7820   -0.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7820   -0.9222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9980   -1.1767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5151   -0.5096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9980    0.1548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4491    0.3901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4491   -1.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2030   -1.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7422   -1.9609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3101   -0.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3225    0.5426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0819   -0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7573   -0.7186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4135   -0.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1465    0.5551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8260    1.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1479    1.9609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6211    1.2304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9649   -1.0639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1987   -1.3706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2030   -0.4627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  3  9  1  0  0  0  0
  4  5  1  0  0  0  0
  4 10  2  0  0  0  0
  7  8  1  0  0  0  0
 10 12  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  2  0  0  0  0
 11 16  1  0  0  0  0
 12 13  1  0  0  0  0
 12 19  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 21  2  0  0  0  0
 15 18  1  0  0  0  0
 16 17  2  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037554

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1=C(C)\C(NC1=O)=C\C1(NC(=O)C(C)=C1C=C)OC

> <INCHI_IDENTIFIER>
InChI=1S/C16H20N2O3/c1-6-11-9(3)13(17-15(11)20)8-16(21-5)12(7-2)10(4)14(19)18-16/h7-8H,2,6H2,1,3-5H3,(H,17,20)(H,18,19)/b13-8-

> <INCHI_KEY>
RDWKBPHIFOCLKH-JYRVWZFOSA-N

> <FORMULA>
C16H20N2O3

> <MOLECULAR_WEIGHT>
288.3416

> <EXACT_MASS>
288.147392516

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.47194258949761

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-ethenyl-5-{[(2Z)-4-ethyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-5-methoxy-3-methyl-2,5-dihydro-1H-pyrrol-2-one

> <ALOGPS_LOGP>
1.63

> <JCHEM_LOGP>
1.3690724290000003

> <ALOGPS_LOGS>
-3.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.514716156243063

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.648328681402516

> <JCHEM_PKA_STRONGEST_BASIC>
1.0478581231670316

> <JCHEM_POLAR_SURFACE_AREA>
67.43

> <JCHEM_REFRACTIVITY>
82.75699999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-ethenyl-5-{[(2Z)-4-ethyl-3-methyl-5-oxo-1H-pyrrol-2-ylidene]methyl}-5-methoxy-3-methyl-1H-pyrrol-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037554
     RDKit          3D
(±)-Rollipyrrole
 41 42  0  0  0  0  0  0  0  0999 V2000
   -2.0526    0.7251    2.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5094   -0.3632    1.7179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3848   -0.6973    0.2998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8411   -1.7899   -0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5848   -2.8815    0.4559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4526   -1.8364   -1.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7409   -2.7583   -2.5160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7062   -0.6642   -1.8887 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8173    0.1553   -0.7330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5020    0.7353   -0.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6190    0.1115   -0.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7789   -1.2736   -0.2095 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1388   -1.5503    0.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6336   -2.7049    0.1443 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8432   -0.2559    0.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2725   -0.2181    0.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9210    1.0946    0.6762 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9598    0.6794    0.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2067    2.1335    0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7465    1.1709   -1.0672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2968    1.9494   -2.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1628    0.9383    3.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5389    1.4625    1.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0178   -1.0680    2.3616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8108   -3.6016    0.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1820   -2.4759    1.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2747   -3.4165   -0.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1662   -0.4445   -2.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4318    1.8301   -0.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0224   -1.9558   -0.3787 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8761   -0.8380   -0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4436   -0.7793    1.5036 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8580    1.5334    1.6982 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0424    0.8997    0.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7361    1.8211   -0.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2220    2.6737    0.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7839    2.4449    1.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5814    2.5782   -0.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3753    2.4947   -1.9377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2457    1.4082   -3.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0986    2.7337   -2.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
 18 19  1  0
  9 20  1  0
 20 21  1  0
  9  3  1  0
 18 11  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  5 25  1  0
  5 26  1  0
  5 27  1  0
  8 28  1  0
 10 29  1  0
 12 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 21 39  1  0
 21 40  1  0
 21 41  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.326  -0.181   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.326  -1.721   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.863  -2.197   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.962  -0.951   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -1.863   0.289   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0      -4.572   0.728   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -4.572  -2.628   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.979  -2.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.385  -3.660   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.579  -0.949   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.469   1.013   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.020  -0.461   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       3.280  -1.341   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       4.505  -0.414   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.007   1.036   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.542   2.243   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.143   3.660   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.893   2.297   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.801  -1.986   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.371  -2.558   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.979  -0.864   0.000  0.00  0.00           O+0
CONECT    1    2    5    6                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5   10                                                  
CONECT    5    1    4                                                       
CONECT    6    1                                                            
CONECT    7    2    8                                                       
CONECT    8    7                                                            
CONECT    9    3                                                            
CONECT   10    4   12                                                       
CONECT   11   12   15   16                                                  
CONECT   12   10   11   13   19                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   11   14   18                                                  
CONECT   16   11   17                                                       
CONECT   17   16                                                            
CONECT   18   15                                                            
CONECT   19   12   20                                                       
CONECT   20   19                                                            
CONECT   21   14                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0037554
HETATM    1  C1  UNL     1      -2.053   0.725   2.270  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.509  -0.363   1.718  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.385  -0.697   0.300  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.841  -1.790  -0.273  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.585  -2.881   0.456  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.453  -1.836  -1.676  1.00  0.00           C  
HETATM    7  O1  UNL     1      -2.741  -2.758  -2.516  1.00  0.00           O  
HETATM    8  N1  UNL     1      -1.706  -0.664  -1.889  1.00  0.00           N  
HETATM    9  C7  UNL     1      -1.817   0.155  -0.733  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.502   0.735  -0.438  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.619   0.112  -0.212  1.00  0.00           C  
HETATM   12  N2  UNL     1       0.779  -1.274  -0.209  1.00  0.00           N  
HETATM   13  C10 UNL     1       2.139  -1.550   0.067  1.00  0.00           C  
HETATM   14  O2  UNL     1       2.634  -2.705   0.144  1.00  0.00           O  
HETATM   15  C11 UNL     1       2.843  -0.256   0.242  1.00  0.00           C  
HETATM   16  C12 UNL     1       4.273  -0.218   0.533  1.00  0.00           C  
HETATM   17  C13 UNL     1       4.921   1.095   0.676  1.00  0.00           C  
HETATM   18  C14 UNL     1       1.960   0.679   0.079  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.207   2.134   0.166  1.00  0.00           C  
HETATM   20  O3  UNL     1      -2.747   1.171  -1.067  1.00  0.00           O  
HETATM   21  C16 UNL     1      -2.297   1.949  -2.087  1.00  0.00           C  
HETATM   22  H1  UNL     1      -2.163   0.938   3.320  1.00  0.00           H  
HETATM   23  H2  UNL     1      -1.539   1.462   1.675  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.018  -1.068   2.362  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.811  -3.602   0.805  1.00  0.00           H  
HETATM   26  H5  UNL     1      -4.182  -2.476   1.288  1.00  0.00           H  
HETATM   27  H6  UNL     1      -4.275  -3.417  -0.219  1.00  0.00           H  
HETATM   28  H7  UNL     1      -1.166  -0.445  -2.754  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.432   1.830  -0.388  1.00  0.00           H  
HETATM   30  H9  UNL     1       0.022  -1.956  -0.379  1.00  0.00           H  
HETATM   31  H10 UNL     1       4.876  -0.838  -0.199  1.00  0.00           H  
HETATM   32  H11 UNL     1       4.444  -0.779   1.504  1.00  0.00           H  
HETATM   33  H12 UNL     1       4.858   1.533   1.698  1.00  0.00           H  
HETATM   34  H13 UNL     1       6.042   0.900   0.576  1.00  0.00           H  
HETATM   35  H14 UNL     1       4.736   1.821  -0.139  1.00  0.00           H  
HETATM   36  H15 UNL     1       1.222   2.674   0.323  1.00  0.00           H  
HETATM   37  H16 UNL     1       2.784   2.445   1.064  1.00  0.00           H  
HETATM   38  H17 UNL     1       2.581   2.578  -0.784  1.00  0.00           H  
HETATM   39  H18 UNL     1      -1.375   2.495  -1.938  1.00  0.00           H  
HETATM   40  H19 UNL     1      -2.246   1.408  -3.062  1.00  0.00           H  
HETATM   41  H20 UNL     1      -3.099   2.734  -2.264  1.00  0.00           H  
CONECT    1    2    2   22   23
CONECT    2    3   24
CONECT    3    4    4    9
CONECT    4    5    6
CONECT    5   25   26   27
CONECT    6    7    7    8
CONECT    8    9   28
CONECT    9   10   20
CONECT   10   11   11   29
CONECT   11   12   18
CONECT   12   13   30
CONECT   13   14   14   15
CONECT   15   16   18   18
CONECT   16   17   31   32
CONECT   17   33   34   35
CONECT   18   19
CONECT   19   36   37   38
CONECT   20   21
CONECT   21   39   40   41
END

HMDB0037554
     RDKit          3D
(±)-Rollipyrrole
 41 42  0  0  0  0  0  0  0  0999 V2000
   -2.0526    0.7251    2.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5094   -0.3632    1.7179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3848   -0.6973    0.2998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8411   -1.7899   -0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5848   -2.8815    0.4559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4526   -1.8364   -1.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7409   -2.7583   -2.5160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7062   -0.6642   -1.8887 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8173    0.1553   -0.7330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5020    0.7353   -0.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6190    0.1115   -0.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7789   -1.2736   -0.2095 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1388   -1.5503    0.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6336   -2.7049    0.1443 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8432   -0.2559    0.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2725   -0.2181    0.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9210    1.0946    0.6762 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9598    0.6794    0.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2067    2.1335    0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7465    1.1709   -1.0672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2968    1.9494   -2.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1628    0.9383    3.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5389    1.4625    1.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0178   -1.0680    2.3616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8108   -3.6016    0.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1820   -2.4759    1.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2747   -3.4165   -0.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1662   -0.4445   -2.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4318    1.8301   -0.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0224   -1.9558   -0.3787 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8761   -0.8380   -0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4436   -0.7793    1.5036 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8580    1.5334    1.6982 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0424    0.8997    0.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7361    1.8211   -0.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2220    2.6737    0.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7839    2.4449    1.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5814    2.5782   -0.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3753    2.4947   -1.9377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2457    1.4082   -3.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0986    2.7337   -2.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
 18 19  1  0
  9 20  1  0
 20 21  1  0
  9  3  1  0
 18 11  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  5 25  1  0
  5 26  1  0
  5 27  1  0
  8 28  1  0
 10 29  1  0
 12 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 21 39  1  0
 21 40  1  0
 21 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₂₀N₂O₃

Average Molecular Weight

288.3416

Monoisotopic Molecular Weight

288.147392516

IUPAC Name

4-ethenyl-5-{[(2Z)-4-ethyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-5-methoxy-3-methyl-2,5-dihydro-1H-pyrrol-2-one

Traditional Name

4-ethenyl-5-{[(2Z)-4-ethyl-3-methyl-5-oxo-1H-pyrrol-2-ylidene]methyl}-5-methoxy-3-methyl-1H-pyrrol-2-one

CAS Registry Number

Not Available

SMILES

CCC1=C(C)\C(NC1=O)=C\C1(NC(=O)C(C)=C1C=C)OC

InChI Identifier

InChI=1S/C16H20N2O3/c1-6-11-9(3)13(17-15(11)20)8-16(21-5)12(7-2)10(4)14(19)18-16/h7-8H,2,6H2,1,3-5H3,(H,17,20)(H,18,19)/b13-8-

InChI Key

RDWKBPHIFOCLKH-JYRVWZFOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolines. Pyrrolines are compounds containing a pyrroline ring, which is a five-member unsaturated aliphatic ring with one nitrogen atom and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolines

Sub Class

Not Available

Direct Parent

Pyrrolines

Alternative Parents

Substituents

Pyrroline
Secondary carboxylic acid amide
Lactam
Carboxamide group
Azacycle
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0037554)
Cytoplasm (HMDB: HMDB0037554)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037554)

Source

Exogenous

Exogenous (HMDB: HMDB0037554)

Food

Food (HMDB: HMDB0037554)

Fruit

Fruits (FooDB: FOOD00871)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Endogenous

Plant

Plant (HMDB: HMDB0037554)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0037554)

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	0.27 g/L	ALOGPS
logP	1.63	ALOGPS
logP	1.37	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	10.65	ChemAxon
pKa (Strongest Basic)	1.05	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	67.43 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	82.76 m³·mol⁻¹	ChemAxon
Polarizability	31.47 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
DeepCCS	[M+H]+	176.595	30932474
DeepCCS	[M-H]-	174.237	30932474
DeepCCS	[M-2H]-	207.475	30932474
DeepCCS	[M+Na]+	182.702	30932474
AllCCS	[M+H]+	168.4	32859911
AllCCS	[M+H-H2O]+	164.8	32859911
AllCCS	[M+NH4]+	171.7	32859911
AllCCS	[M+Na]+	172.6	32859911
AllCCS	[M-H]-	173.6	32859911
AllCCS	[M+Na-2H]-	173.8	32859911
AllCCS	[M+HCOO]-	174.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(??)-Rollipyrrole	CCC1=C(C)\C(NC1=O)=C\C1(NC(=O)C(C)=C1C=C)OC	3706.2	Standard polar	33892256
(??)-Rollipyrrole	CCC1=C(C)\C(NC1=O)=C\C1(NC(=O)C(C)=C1C=C)OC	2221.5	Standard non polar	33892256
(??)-Rollipyrrole	CCC1=C(C)\C(NC1=O)=C\C1(NC(=O)C(C)=C1C=C)OC	2619.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(±)-Rollipyrrole,1TMS,isomer #1	C=CC1=C(C)C(=O)NC1(/C=C1/C(C)=C(CC)C(=O)N1[Si](C)(C)C)OC	2548.9	Semi standard non polar	33892256
(±)-Rollipyrrole,1TMS,isomer #1	C=CC1=C(C)C(=O)NC1(/C=C1/C(C)=C(CC)C(=O)N1[Si](C)(C)C)OC	2368.2	Standard non polar	33892256
(±)-Rollipyrrole,1TMS,isomer #2	C=CC1=C(C)C(=O)N([Si](C)(C)C)C1(/C=C1\NC(=O)C(CC)=C1C)OC	2561.7	Semi standard non polar	33892256
(±)-Rollipyrrole,1TMS,isomer #2	C=CC1=C(C)C(=O)N([Si](C)(C)C)C1(/C=C1\NC(=O)C(CC)=C1C)OC	2452.5	Standard non polar	33892256
(±)-Rollipyrrole,2TMS,isomer #1	C=CC1=C(C)C(=O)N([Si](C)(C)C)C1(/C=C1/C(C)=C(CC)C(=O)N1[Si](C)(C)C)OC	2504.1	Semi standard non polar	33892256
(±)-Rollipyrrole,2TMS,isomer #1	C=CC1=C(C)C(=O)N([Si](C)(C)C)C1(/C=C1/C(C)=C(CC)C(=O)N1[Si](C)(C)C)OC	2423.4	Standard non polar	33892256
(±)-Rollipyrrole,1TBDMS,isomer #1	C=CC1=C(C)C(=O)NC1(/C=C1/C(C)=C(CC)C(=O)N1[Si](C)(C)C(C)(C)C)OC	2744.6	Semi standard non polar	33892256
(±)-Rollipyrrole,1TBDMS,isomer #1	C=CC1=C(C)C(=O)NC1(/C=C1/C(C)=C(CC)C(=O)N1[Si](C)(C)C(C)(C)C)OC	2553.0	Standard non polar	33892256
(±)-Rollipyrrole,1TBDMS,isomer #2	C=CC1=C(C)C(=O)N([Si](C)(C)C(C)(C)C)C1(/C=C1\NC(=O)C(CC)=C1C)OC	2765.3	Semi standard non polar	33892256
(±)-Rollipyrrole,1TBDMS,isomer #2	C=CC1=C(C)C(=O)N([Si](C)(C)C(C)(C)C)C1(/C=C1\NC(=O)C(CC)=C1C)OC	2660.5	Standard non polar	33892256
(±)-Rollipyrrole,2TBDMS,isomer #1	C=CC1=C(C)C(=O)N([Si](C)(C)C(C)(C)C)C1(/C=C1/C(C)=C(CC)C(=O)N1[Si](C)(C)C(C)(C)C)OC	2903.2	Semi standard non polar	33892256
(±)-Rollipyrrole,2TBDMS,isomer #1	C=CC1=C(C)C(=O)N([Si](C)(C)C(C)(C)C)C1(/C=C1/C(C)=C(CC)C(=O)N1[Si](C)(C)C(C)(C)C)OC	2805.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-Rollipyrrole GC-MS (Non-derivatized) - 70eV, Positive	splash10-074i-2490000000-efdcb67d9f6d97b189ef	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-Rollipyrrole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-Rollipyrrole 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 - (±)-Rollipyrrole 10V, Positive-QTOF	splash10-000i-0190000000-735f6170bbb1e6caa8d7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Rollipyrrole 20V, Positive-QTOF	splash10-0fk9-2940000000-1fd74fd7d32ec474a35f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Rollipyrrole 40V, Positive-QTOF	splash10-014i-9500000000-3857381b54f362689698	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Rollipyrrole 10V, Negative-QTOF	splash10-000i-0090000000-41925e38c236e679bc4f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Rollipyrrole 20V, Negative-QTOF	splash10-00kr-1590000000-f40f780a0382716947a3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Rollipyrrole 40V, Negative-QTOF	splash10-0006-9340000000-d46b8cdd131549103505	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Rollipyrrole 10V, Positive-QTOF	splash10-000i-0090000000-b69bf0ebe4b822db3161	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Rollipyrrole 20V, Positive-QTOF	splash10-05fr-0970000000-22f24c80c15cd2f2823c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Rollipyrrole 40V, Positive-QTOF	splash10-00y0-7940000000-478cd09d647013f3ff66	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Rollipyrrole 10V, Negative-QTOF	splash10-000i-0190000000-1accb3b5da66a0d69445	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Rollipyrrole 20V, Negative-QTOF	splash10-05g3-2790000000-b335f759c3143c3676cf	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Rollipyrrole 40V, Negative-QTOF	splash10-000i-1900000000-25b4af1a578828f9c6b9	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

FDB016636

KNApSAcK ID

Not Available

Chemspider ID

35014429

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101133764

PDB ID

Not Available

ChEBI ID

169694

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 (±)-Rollipyrrole (HMDB0037554)

MOL for HMDB0037554 ((±)-Rollipyrrole)

3D MOL for HMDB0037554 ((±)-Rollipyrrole)

3D SDF for HMDB0037554 ((±)-Rollipyrrole)

3D-SDF for HMDB0037554 ((±)-Rollipyrrole)

PDB for HMDB0037554 ((±)-Rollipyrrole)

3D PDB for HMDB0037554 ((±)-Rollipyrrole)

SMILES for HMDB0037554 ((±)-Rollipyrrole)

INCHI for HMDB0037554 ((±)-Rollipyrrole)

Structure for HMDB0037554 ((±)-Rollipyrrole)

3D Structure for HMDB0037554 ((±)-Rollipyrrole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra