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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 18:12:02 UTC

Update Date

2021-09-26 23:13:34 UTC

HMDB ID

HMDB0257294

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Rolipram

Description

Rolipram, also known as ZK 62711, belongs to the class of organic compounds known as phenylpyrrolidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrolidine ring through a CC or CN bond. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. Based on a literature review a significant number of articles have been published on Rolipram. This compound has been identified in human blood as reported by (PMID: 31557052 ). Rolipram is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Rolipram 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

HMDB0257294
     RDKit          3D
Rolipram
 41 43  0  0  0  0  0  0  0  0999 V2000
   -1.3193   -4.0100   -1.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4980   -2.6523   -0.8908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4379   -1.8165   -0.5735 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8308   -2.3932   -0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9193   -1.6236   -0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7659   -0.2758    0.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9608    0.5182    0.3788 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0749    0.3566   -0.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2581    0.6202    0.1710 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0367    0.4107    1.4138 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9524    0.5669    2.4551 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6216   -0.0401    1.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4929    0.2858   -0.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6152   -0.4691   -0.3356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8723    0.0451   -0.4180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3100    1.3457   -0.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3960    1.4089    0.8306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6854    1.6965    0.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2224    2.5536   -1.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0256    1.7670   -1.5177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2445   -4.4564   -1.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5239   -4.1375   -1.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0056   -4.5512   -0.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9772   -3.4465   -0.6869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9011   -2.1177   -0.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7232    1.5810    0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1203   -0.6889   -0.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9694    1.0734   -1.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9015    0.8746    2.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1924    0.3442    2.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6190   -1.1570    1.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3594    1.3464    0.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5339    2.0812    0.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4719    0.4416    1.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2120    2.2228    1.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4094    2.2606    0.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1731    0.7820   -0.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9457    3.5617   -0.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9790    2.5324   -1.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3673    2.3125   -2.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4285    0.8464   -2.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 14  3  1  0
 20 16  1  0
 12  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
M  END


  Mrv1572004111621162D          

 20 22  0  0  0  0            999 V2000
   -1.4054   -2.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3254   -3.2532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1504   -3.2532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0705   -2.4686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4054   -2.4686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4054    0.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4054   -0.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0235    0.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0235    1.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3583    1.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6909    0.4912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6909    1.3162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7379   -1.9837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6909   -1.1587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0235   -0.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2784    2.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1034    2.5858    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2064    3.2532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6909   -1.9837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7379   -1.1587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  7  6  2  0  0  0  0
 11  6  1  0  0  0  0
 11  8  2  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13  4  1  0  0  0  0
 13  5  1  0  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 15 14  2  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 17 16  2  0  0  0  0
 18 16  1  0  0  0  0
 19  1  1  0  0  0  0
 19 14  1  0  0  0  0
 20 13  1  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0257294

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC2CCCC2)C=C(C=C1)C1CN=C(O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H21NO3/c1-19-14-7-6-11(12-9-16(18)17-10-12)8-15(14)20-13-4-2-3-5-13/h6-8,12-13H,2-5,9-10H2,1H3,(H,17,18)

> <INCHI_KEY>
HJORMJIFDVBMOB-UHFFFAOYSA-N

> <FORMULA>
C16H21NO3

> <MOLECULAR_WEIGHT>
275.348

> <EXACT_MASS>
275.15214354

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
30.0709506176893

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[3-(cyclopentyloxy)-4-methoxyphenyl]-3,4-dihydro-2H-pyrrol-5-ol

> <ALOGPS_LOGP>
3.16

> <JCHEM_LOGP>
2.0514844136217043

> <ALOGPS_LOGS>
-4.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.828053424212124

> <JCHEM_PKA_STRONGEST_BASIC>
6.084459879851206

> <JCHEM_POLAR_SURFACE_AREA>
51.05000000000001

> <JCHEM_REFRACTIVITY>
76.6858

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.39e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
rolipramum

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0257294
     RDKit          3D
Rolipram
 41 43  0  0  0  0  0  0  0  0999 V2000
   -1.3193   -4.0100   -1.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4980   -2.6523   -0.8908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4379   -1.8165   -0.5735 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8308   -2.3932   -0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9193   -1.6236   -0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7659   -0.2758    0.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9608    0.5182    0.3788 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0749    0.3566   -0.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2581    0.6202    0.1710 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0367    0.4107    1.4138 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9524    0.5669    2.4551 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6216   -0.0401    1.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4929    0.2858   -0.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6152   -0.4691   -0.3356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8723    0.0451   -0.4180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3100    1.3457   -0.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3960    1.4089    0.8306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6854    1.6965    0.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2224    2.5536   -1.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0256    1.7670   -1.5177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2445   -4.4564   -1.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5239   -4.1375   -1.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0056   -4.5512   -0.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9772   -3.4465   -0.6869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9011   -2.1177   -0.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7232    1.5810    0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1203   -0.6889   -0.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9694    1.0734   -1.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9015    0.8746    2.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1924    0.3442    2.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6190   -1.1570    1.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3594    1.3464    0.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5339    2.0812    0.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4719    0.4416    1.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2120    2.2228    1.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4094    2.2606    0.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1731    0.7820   -0.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9457    3.5617   -0.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9790    2.5324   -1.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3673    2.3125   -2.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4285    0.8464   -2.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 14  3  1  0
 20 16  1  0
 12  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
M  END

HEADER    PROTEIN                                 11-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-APR-16         0                                  
HETATM    1  C   UNK     0      -2.623  -4.473   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.607  -6.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.147  -6.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.132  -4.608   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.623  -4.608   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.623   0.147   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.623  -1.393   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.044   0.147   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.044   3.362   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.535   3.362   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.290   0.917   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.290   2.457   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.377  -3.703   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.290  -2.163   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.044  -1.393   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.520   4.827   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -2.060   4.827   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       0.385   6.073   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.290  -3.703   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.377  -2.163   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2   13                                                       
CONECT    5    3   13                                                       
CONECT    6    7   11                                                       
CONECT    7    6   14                                                       
CONECT    8   11   15                                                       
CONECT    9   12   16                                                       
CONECT   10   12   17                                                       
CONECT   11    6    8   12                                                  
CONECT   12    9   10   11                                                  
CONECT   13    4    5   20                                                  
CONECT   14    7   15   19                                                  
CONECT   15    8   14   20                                                  
CONECT   16    9   17   18                                                  
CONECT   17   10   16                                                       
CONECT   18   16                                                            
CONECT   19    1   14                                                       
CONECT   20   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0257294
HETATM    1  C1  UNL     1      -1.319  -4.010  -1.132  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.498  -2.652  -0.891  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.438  -1.817  -0.574  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.831  -2.393  -0.502  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.919  -1.624  -0.193  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.766  -0.276   0.049  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.961   0.518   0.379  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.075   0.357  -0.635  1.00  0.00           C  
HETATM    9  N1  UNL     1       5.258   0.620   0.171  1.00  0.00           N  
HETATM   10  C8  UNL     1       5.037   0.411   1.414  1.00  0.00           C  
HETATM   11  O2  UNL     1       5.952   0.567   2.455  1.00  0.00           O  
HETATM   12  C9  UNL     1       3.622  -0.040   1.628  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.493   0.286  -0.026  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.615  -0.469  -0.336  1.00  0.00           C  
HETATM   15  O3  UNL     1      -1.872   0.045  -0.418  1.00  0.00           O  
HETATM   16  C12 UNL     1      -2.310   1.346  -0.226  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.396   1.409   0.831  1.00  0.00           C  
HETATM   18  C14 UNL     1      -4.685   1.696   0.135  1.00  0.00           C  
HETATM   19  C15 UNL     1      -4.222   2.554  -1.048  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.026   1.767  -1.518  1.00  0.00           C  
HETATM   21  H1  UNL     1      -2.244  -4.456  -1.563  1.00  0.00           H  
HETATM   22  H2  UNL     1      -0.524  -4.137  -1.901  1.00  0.00           H  
HETATM   23  H3  UNL     1      -1.006  -4.551  -0.204  1.00  0.00           H  
HETATM   24  H4  UNL     1       0.977  -3.446  -0.687  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.901  -2.118  -0.147  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.723   1.581   0.560  1.00  0.00           H  
HETATM   27  H7  UNL     1       4.120  -0.689  -0.941  1.00  0.00           H  
HETATM   28  H8  UNL     1       3.969   1.073  -1.470  1.00  0.00           H  
HETATM   29  H9  UNL     1       6.901   0.875   2.245  1.00  0.00           H  
HETATM   30  H10 UNL     1       3.192   0.344   2.557  1.00  0.00           H  
HETATM   31  H11 UNL     1       3.619  -1.157   1.574  1.00  0.00           H  
HETATM   32  H12 UNL     1       0.359   1.346   0.162  1.00  0.00           H  
HETATM   33  H13 UNL     1      -1.534   2.081   0.045  1.00  0.00           H  
HETATM   34  H14 UNL     1      -3.472   0.442   1.392  1.00  0.00           H  
HETATM   35  H15 UNL     1      -3.212   2.223   1.571  1.00  0.00           H  
HETATM   36  H16 UNL     1      -5.409   2.261   0.736  1.00  0.00           H  
HETATM   37  H17 UNL     1      -5.173   0.782  -0.275  1.00  0.00           H  
HETATM   38  H18 UNL     1      -3.946   3.562  -0.722  1.00  0.00           H  
HETATM   39  H19 UNL     1      -4.979   2.532  -1.859  1.00  0.00           H  
HETATM   40  H20 UNL     1      -2.367   2.313  -2.196  1.00  0.00           H  
HETATM   41  H21 UNL     1      -3.428   0.846  -2.028  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4   14
CONECT    4    5   24
CONECT    5    6    6   25
CONECT    6    7   13
CONECT    7    8   12   26
CONECT    8    9   27   28
CONECT    9   10   10
CONECT   10   11   12
CONECT   11   29
CONECT   12   30   31
CONECT   13   14   14   32
CONECT   14   15
CONECT   15   16
CONECT   16   17   20   33
CONECT   17   18   34   35
CONECT   18   19   36   37
CONECT   19   20   38   39
CONECT   20   40   41
END

HMDB0257294
     RDKit          3D
Rolipram
 41 43  0  0  0  0  0  0  0  0999 V2000
   -1.3193   -4.0100   -1.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4980   -2.6523   -0.8908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4379   -1.8165   -0.5735 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8308   -2.3932   -0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9193   -1.6236   -0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7659   -0.2758    0.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9608    0.5182    0.3788 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0749    0.3566   -0.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2581    0.6202    0.1710 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0367    0.4107    1.4138 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9524    0.5669    2.4551 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6216   -0.0401    1.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4929    0.2858   -0.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6152   -0.4691   -0.3356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8723    0.0451   -0.4180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3100    1.3457   -0.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3960    1.4089    0.8306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6854    1.6965    0.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2224    2.5536   -1.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0256    1.7670   -1.5177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2445   -4.4564   -1.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5239   -4.1375   -1.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0056   -4.5512   -0.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9772   -3.4465   -0.6869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9011   -2.1177   -0.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7232    1.5810    0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1203   -0.6889   -0.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9694    1.0734   -1.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9015    0.8746    2.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1924    0.3442    2.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6190   -1.1570    1.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3594    1.3464    0.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5339    2.0812    0.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4719    0.4416    1.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2120    2.2228    1.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4094    2.2606    0.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1731    0.7820   -0.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9457    3.5617   -0.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9790    2.5324   -1.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3673    2.3125   -2.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4285    0.8464   -2.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 14  3  1  0
 20 16  1  0
 12  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(3-(Cyclopentyloxy)-4-methoxyphenyl)-2-pyrrolidinone	ChEBI
Rolipramum	ChEBI
ZK 62711	ChEBI
Rolipram	MeSH

Chemical Formula

C₁₆H₂₁NO₃

Average Molecular Weight

275.348

Monoisotopic Molecular Weight

275.15214354

IUPAC Name

3-[3-(cyclopentyloxy)-4-methoxyphenyl]-3,4-dihydro-2H-pyrrol-5-ol

Traditional Name

rolipramum

CAS Registry Number

Not Available

SMILES

COC1=C(OC2CCCC2)C=C(C=C1)C1CN=C(O)C1

InChI Identifier

InChI=1S/C16H21NO3/c1-19-14-7-6-11(12-9-16(18)17-10-12)8-15(14)20-13-4-2-3-5-13/h6-8,12-13H,2-5,9-10H2,1H3,(H,17,18)

InChI Key

HJORMJIFDVBMOB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyrrolidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrolidine ring through a CC or CN bond. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolidines

Sub Class

Phenylpyrrolidines

Direct Parent

Phenylpyrrolidines

Alternative Parents

Substituents

3-phenylpyrrolidine
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
2-pyrrolidone
Pyrrolidone
Pyrrole
Carboxamide group
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Ether
Azacycle
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Carbonyl group
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrrolidin-2-ones (CHEBI:104872 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0257294)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.16	ALOGPS
logP	2.05	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	3.83	ChemAxon
pKa (Strongest Basic)	6.08	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	51.05 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	76.69 m³·mol⁻¹	ChemAxon
Polarizability	30.07 Å³	ChemAxon
Number of Rings	3	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]+	167.091	30932474
DeepCCS	[M-H]-	164.733	30932474
DeepCCS	[M-2H]-	197.619	30932474
DeepCCS	[M+Na]+	173.185	30932474
AllCCS	[M+H]+	166.2	32859911
AllCCS	[M+H-H2O]+	162.7	32859911
AllCCS	[M+NH4]+	169.5	32859911
AllCCS	[M+Na]+	170.5	32859911
AllCCS	[M-H]-	169.5	32859911
AllCCS	[M+Na-2H]-	169.5	32859911
AllCCS	[M+HCOO]-	169.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.64 minutes	32390414
Predicted by Siyang on May 30, 2022	11.9454 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.81 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1845.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	252.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	171.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	176.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	254.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	497.8 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	502.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	135.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1054.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	438.3 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	1258.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	335.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	355.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	311.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	209.4 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	12.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Rolipram	COC1=C(OC2CCCC2)C=C(C=C1)C1CN=C(O)C1	3327.3	Standard polar	33892256
Rolipram	COC1=C(OC2CCCC2)C=C(C=C1)C1CN=C(O)C1	2272.4	Standard non polar	33892256
Rolipram	COC1=C(OC2CCCC2)C=C(C=C1)C1CN=C(O)C1	2318.4	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 - Rolipram GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zfr-2390000000-82a63560b02f568a09b2	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rolipram GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rolipram GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rolipram GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rolipram LC-ESI-qTof , Positive-QTOF	splash10-0f89-3910000000-38dfbb97597c517723c3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rolipram , positive-QTOF	splash10-004i-0090000000-560244a4d0d6418f226c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rolipram , positive-QTOF	splash10-004i-0090000000-9507b0584062362f343b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rolipram , positive-QTOF	splash10-0a6u-0590000000-63d3f57e5eff4592ddd0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rolipram , positive-QTOF	splash10-004i-1690000000-748a69ba652840c85f95	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rolipram , positive-QTOF	splash10-004i-0590000000-1ce7657ef60958653797	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rolipram , positive-QTOF	splash10-0f89-3910000000-38dfbb97597c517723c3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rolipram 35V, Positive-QTOF	splash10-0bwc-0930000000-2e82d6327e2160443665	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rolipram 10V, Positive-QTOF	splash10-004i-3090000000-19f67be09f1f3fafa536	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rolipram 20V, Positive-QTOF	splash10-016r-5390000000-151e38f8b148dfd1f327	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rolipram 40V, Positive-QTOF	splash10-0aor-9100000000-1ac3fa59c900d8edef9f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rolipram 10V, Negative-QTOF	splash10-00di-1090000000-bba4d18bee682d468b31	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rolipram 20V, Negative-QTOF	splash10-05g0-4290000000-51ede755aa6fb15c5252	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rolipram 40V, Negative-QTOF	splash10-000i-9300000000-91caa1154cffdaecaafe	2016-08-04	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

DB01954

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4913

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Rolipram

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

104872

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Rolipram (HMDB0257294)

MOL for HMDB0257294 (Rolipram)

3D MOL for HMDB0257294 (Rolipram)

3D SDF for HMDB0257294 (Rolipram)

3D-SDF for HMDB0257294 (Rolipram)

PDB for HMDB0257294 (Rolipram)

3D PDB for HMDB0257294 (Rolipram)

SMILES for HMDB0257294 (Rolipram)

INCHI for HMDB0257294 (Rolipram)

Structure for HMDB0257294 (Rolipram)

3D Structure for HMDB0257294 (Rolipram)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra