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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-15 18:09:04 UTC

Update Date

2019-07-23 07:14:43 UTC

HMDB ID

HMDB0060625

Secondary Accession Numbers

HMDB60625

Metabolite Identification

Common Name

N-despropyl ropinirole

Description

N-despropyl ropinirole is a metabolite of ropinirole. Ropinirole (INN; trade names Requip, Ropark, Adartrel) is a non-ergoline dopamine agonist. It is manufactured by GlaxoSmithKline (GSK), Cipla and Sun Pharmaceutical. It is used in the treatment of Parkinson's disease. Ropinirole is one of three medications approved by the FDA to treat Restless Leg Syndrome, the other two being pramipexole (Mirapex) and gabapentin enacarbil (Horizant). The discovery of the drug's utility in RLS has been used as a successful example of drug repurposing. (Wikipedia)

Structure

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

HMDB0060625
     RDKit          3D
N-despropyl ropinirole
 34 35  0  0  0  0  0  0  0  0999 V2000
   -5.1167    0.5916   -0.8285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2095   -0.6289   -0.9707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8627   -0.2361   -0.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8877   -1.2963   -0.4528 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6676   -0.8163    0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0345    0.2539   -0.6476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2633    0.6443    0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2361    1.8081    0.8538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3496    2.2043    1.5618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5057    1.4852    1.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5353    0.3231    0.7703 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4344   -0.0945    0.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7185   -1.3392   -0.6793 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1490   -1.6408   -0.3358 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8091   -2.6307   -0.7635 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5743   -0.6258    0.5276 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0313    0.3254   -0.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6256    1.4077   -0.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3926    1.0122   -1.8217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6780   -1.4643   -0.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1392   -0.9623   -2.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0083    0.1142    0.6264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4966    0.5927   -1.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6489   -1.5082   -1.4653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9630   -0.3001    1.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0240   -1.6012    0.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2763   -0.0813   -1.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6030    1.1758   -0.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3051    2.3970    0.8792 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3219    3.1108    2.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4067    1.7522    2.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7097   -1.2021   -1.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1355   -2.2039   -0.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5417   -0.5664    0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 12  7  1  0
 16 11  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 13 32  1  0
 13 33  1  0
 16 34  1  0
M  END


  Mrv0541 06151311092D          

 16 17  0  0  0  0            999 V2000
   -1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    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
    4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7439   -4.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5644   -4.6057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9769   -5.3202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8999   -3.8520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 11 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060625

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCNCCC1=CC=CC2=C1CC(=O)N2

> <INCHI_IDENTIFIER>
InChI=1S/C13H18N2O/c1-2-7-14-8-6-10-4-3-5-12-11(10)9-13(16)15-12/h3-5,14H,2,6-9H2,1H3,(H,15,16)

> <INCHI_KEY>
VKDWFHAQOZYATG-UHFFFAOYSA-N

> <FORMULA>
C13H18N2O

> <MOLECULAR_WEIGHT>
218.2948

> <EXACT_MASS>
218.141913208

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
25.10415214664915

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[2-(propylamino)ethyl]-2,3-dihydro-1H-indol-2-one

> <ALOGPS_LOGP>
1.54

> <JCHEM_LOGP>
1.7983905713333332

> <ALOGPS_LOGS>
-2.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.551428781010287

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.236038387325838

> <JCHEM_PKA_STRONGEST_BASIC>
10.256573735861421

> <JCHEM_POLAR_SURFACE_AREA>
41.13

> <JCHEM_REFRACTIVITY>
66.86050000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.12e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[2-(propylamino)ethyl]-1,3-dihydroindol-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060625
     RDKit          3D
N-despropyl ropinirole
 34 35  0  0  0  0  0  0  0  0999 V2000
   -5.1167    0.5916   -0.8285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2095   -0.6289   -0.9707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8627   -0.2361   -0.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8877   -1.2963   -0.4528 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6676   -0.8163    0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0345    0.2539   -0.6476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2633    0.6443    0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2361    1.8081    0.8538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3496    2.2043    1.5618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5057    1.4852    1.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5353    0.3231    0.7703 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4344   -0.0945    0.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7185   -1.3392   -0.6793 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1490   -1.6408   -0.3358 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8091   -2.6307   -0.7635 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5743   -0.6258    0.5276 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0313    0.3254   -0.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6256    1.4077   -0.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3926    1.0122   -1.8217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6780   -1.4643   -0.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1392   -0.9623   -2.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0083    0.1142    0.6264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4966    0.5927   -1.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6489   -1.5082   -1.4653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9630   -0.3001    1.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0240   -1.6012    0.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2763   -0.0813   -1.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6030    1.1758   -0.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3051    2.3970    0.8792 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3219    3.1108    2.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4067    1.7522    2.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7097   -1.2021   -1.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1355   -2.2039   -0.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5417   -0.5664    0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 12  7  1  0
 16 11  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 13 32  1  0
 13 33  1  0
 16 34  1  0
M  END

HEADER    PROTEIN                                 15-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JUN-13         0                                  
HETATM    1  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -6.160   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       1.334  -6.930   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.989  -8.436   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.520  -8.597   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.290  -9.931   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0       9.146  -7.190   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   11                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0060625
HETATM    1  C1  UNL     1      -5.117   0.592  -0.829  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.209  -0.629  -0.971  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.863  -0.236  -0.396  1.00  0.00           C  
HETATM    4  N1  UNL     1      -1.888  -1.296  -0.453  1.00  0.00           N  
HETATM    5  C4  UNL     1      -0.668  -0.816   0.145  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.034   0.254  -0.648  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.263   0.644   0.084  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.236   1.808   0.854  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.350   2.204   1.562  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.506   1.485   1.539  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.535   0.323   0.770  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.434  -0.094   0.053  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.719  -1.339  -0.679  1.00  0.00           C  
HETATM   14  C13 UNL     1       4.149  -1.641  -0.336  1.00  0.00           C  
HETATM   15  O1  UNL     1       4.809  -2.631  -0.763  1.00  0.00           O  
HETATM   16  N2  UNL     1       4.574  -0.626   0.528  1.00  0.00           N  
HETATM   17  H1  UNL     1      -6.031   0.325  -0.280  1.00  0.00           H  
HETATM   18  H2  UNL     1      -4.626   1.408  -0.255  1.00  0.00           H  
HETATM   19  H3  UNL     1      -5.393   1.012  -1.822  1.00  0.00           H  
HETATM   20  H4  UNL     1      -4.678  -1.464  -0.386  1.00  0.00           H  
HETATM   21  H5  UNL     1      -4.139  -0.962  -2.025  1.00  0.00           H  
HETATM   22  H6  UNL     1      -3.008   0.114   0.626  1.00  0.00           H  
HETATM   23  H7  UNL     1      -2.497   0.593  -1.064  1.00  0.00           H  
HETATM   24  H8  UNL     1      -1.649  -1.508  -1.465  1.00  0.00           H  
HETATM   25  H9  UNL     1      -0.963  -0.300   1.115  1.00  0.00           H  
HETATM   26  H10 UNL     1       0.024  -1.601   0.433  1.00  0.00           H  
HETATM   27  H11 UNL     1       0.276  -0.081  -1.680  1.00  0.00           H  
HETATM   28  H12 UNL     1      -0.603   1.176  -0.709  1.00  0.00           H  
HETATM   29  H13 UNL     1       0.305   2.397   0.879  1.00  0.00           H  
HETATM   30  H14 UNL     1       2.322   3.111   2.159  1.00  0.00           H  
HETATM   31  H15 UNL     1       4.407   1.752   2.076  1.00  0.00           H  
HETATM   32  H16 UNL     1       2.710  -1.202  -1.780  1.00  0.00           H  
HETATM   33  H17 UNL     1       2.135  -2.204  -0.354  1.00  0.00           H  
HETATM   34  H18 UNL     1       5.542  -0.566   0.948  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4   22   23
CONECT    4    5   24
CONECT    5    6   25   26
CONECT    6    7   27   28
CONECT    7    8    8   12
CONECT    8    9   29
CONECT    9   10   10   30
CONECT   10   11   31
CONECT   11   12   12   16
CONECT   12   13
CONECT   13   14   32   33
CONECT   14   15   15   16
CONECT   16   34
END

HMDB0060625
     RDKit          3D
N-despropyl ropinirole
 34 35  0  0  0  0  0  0  0  0999 V2000
   -5.1167    0.5916   -0.8285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2095   -0.6289   -0.9707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8627   -0.2361   -0.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8877   -1.2963   -0.4528 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6676   -0.8163    0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0345    0.2539   -0.6476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2633    0.6443    0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2361    1.8081    0.8538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3496    2.2043    1.5618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5057    1.4852    1.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5353    0.3231    0.7703 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4344   -0.0945    0.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7185   -1.3392   -0.6793 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1490   -1.6408   -0.3358 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8091   -2.6307   -0.7635 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5743   -0.6258    0.5276 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0313    0.3254   -0.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6256    1.4077   -0.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3926    1.0122   -1.8217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6780   -1.4643   -0.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1392   -0.9623   -2.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0083    0.1142    0.6264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4966    0.5927   -1.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6489   -1.5082   -1.4653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9630   -0.3001    1.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0240   -1.6012    0.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2763   -0.0813   -1.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6030    1.1758   -0.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3051    2.3970    0.8792 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3219    3.1108    2.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4067    1.7522    2.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7097   -1.2021   -1.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1355   -2.2039   -0.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5417   -0.5664    0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 12  7  1  0
 16 11  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 13 32  1  0
 13 33  1  0
 16 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₃H₁₈N₂O

Average Molecular Weight

218.2948

Monoisotopic Molecular Weight

218.141913208

IUPAC Name

4-[2-(propylamino)ethyl]-2,3-dihydro-1H-indol-2-one

Traditional Name

4-[2-(propylamino)ethyl]-1,3-dihydroindol-2-one

CAS Registry Number

Not Available

SMILES

CCCNCCC1=CC=CC2=C1CC(=O)N2

InChI Identifier

InChI=1S/C13H18N2O/c1-2-7-14-8-6-10-4-3-5-12-11(10)9-13(16)15-12/h3-5,14H,2,6-9H2,1H3,(H,15,16)

InChI Key

VKDWFHAQOZYATG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolines

Direct Parent

Indolines

Alternative Parents

Substituents

Dihydroindole
Phenethylamine
Aralkylamine
Benzenoid
Amino acid or derivatives
Carboxamide group
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Secondary aliphatic amine
Secondary amine
Azacycle
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Amine
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060625)

Organ

Kidney (HMDB: HMDB0060625)
Liver (HMDB: HMDB0060625)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060625)

Cellular substructure

Cytoplasm (HMDB: HMDB0060625)

Source

Endogenous

Endogenous (HMDB: HMDB0060625)

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
Water Solubility	0.41 g/L	ALOGPS
logP	1.54	ALOGPS
logP	1.8	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	13.24	ChemAxon
pKa (Strongest Basic)	10.26	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	41.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	66.86 m³·mol⁻¹	ChemAxon
Polarizability	25.1 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]+	151.255	31661259
DarkChem	[M-H]-	147.995	31661259
DeepCCS	[M+H]+	153.468	30932474
DeepCCS	[M-H]-	149.852	30932474
DeepCCS	[M-2H]-	186.594	30932474
DeepCCS	[M+Na]+	162.287	30932474
AllCCS	[M+H]+	151.2	32859911
AllCCS	[M+H-H2O]+	147.4	32859911
AllCCS	[M+NH4]+	154.7	32859911
AllCCS	[M+Na]+	155.7	32859911
AllCCS	[M-H]-	156.0	32859911
AllCCS	[M+Na-2H]-	156.3	32859911
AllCCS	[M+HCOO]-	156.8	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.	3.16 minutes	32390414
Predicted by Siyang on May 30, 2022	9.3299 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.13 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	714.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	223.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	114.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	47.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	236.0 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	298.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	575.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	646.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	165.2 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	846.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	178.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	195.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	452.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	460.5 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	93.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-despropyl ropinirole	CCCNCCC1=CC=CC2=C1CC(=O)N2	3088.7	Standard polar	33892256
N-despropyl ropinirole	CCCNCCC1=CC=CC2=C1CC(=O)N2	2234.8	Standard non polar	33892256
N-despropyl ropinirole	CCCNCCC1=CC=CC2=C1CC(=O)N2	2206.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-despropyl ropinirole,1TMS,isomer #1	CCCN(CCC1=CC=CC2=C1CC(=O)N2)[Si](C)(C)C	2239.8	Semi standard non polar	33892256
N-despropyl ropinirole,1TMS,isomer #1	CCCN(CCC1=CC=CC2=C1CC(=O)N2)[Si](C)(C)C	2189.5	Standard non polar	33892256
N-despropyl ropinirole,1TMS,isomer #1	CCCN(CCC1=CC=CC2=C1CC(=O)N2)[Si](C)(C)C	3016.7	Standard polar	33892256
N-despropyl ropinirole,1TMS,isomer #2	CCCNCCC1=CC=CC2=C1CC(=O)N2[Si](C)(C)C	2030.3	Semi standard non polar	33892256
N-despropyl ropinirole,1TMS,isomer #2	CCCNCCC1=CC=CC2=C1CC(=O)N2[Si](C)(C)C	2076.3	Standard non polar	33892256
N-despropyl ropinirole,1TMS,isomer #2	CCCNCCC1=CC=CC2=C1CC(=O)N2[Si](C)(C)C	2477.3	Standard polar	33892256
N-despropyl ropinirole,2TMS,isomer #1	CCCN(CCC1=CC=CC2=C1CC(=O)N2[Si](C)(C)C)[Si](C)(C)C	2126.4	Semi standard non polar	33892256
N-despropyl ropinirole,2TMS,isomer #1	CCCN(CCC1=CC=CC2=C1CC(=O)N2[Si](C)(C)C)[Si](C)(C)C	2239.1	Standard non polar	33892256
N-despropyl ropinirole,2TMS,isomer #1	CCCN(CCC1=CC=CC2=C1CC(=O)N2[Si](C)(C)C)[Si](C)(C)C	2472.7	Standard polar	33892256
N-despropyl ropinirole,1TBDMS,isomer #1	CCCN(CCC1=CC=CC2=C1CC(=O)N2)[Si](C)(C)C(C)(C)C	2465.5	Semi standard non polar	33892256
N-despropyl ropinirole,1TBDMS,isomer #1	CCCN(CCC1=CC=CC2=C1CC(=O)N2)[Si](C)(C)C(C)(C)C	2457.4	Standard non polar	33892256
N-despropyl ropinirole,1TBDMS,isomer #1	CCCN(CCC1=CC=CC2=C1CC(=O)N2)[Si](C)(C)C(C)(C)C	3111.3	Standard polar	33892256
N-despropyl ropinirole,1TBDMS,isomer #2	CCCNCCC1=CC=CC2=C1CC(=O)N2[Si](C)(C)C(C)(C)C	2251.4	Semi standard non polar	33892256
N-despropyl ropinirole,1TBDMS,isomer #2	CCCNCCC1=CC=CC2=C1CC(=O)N2[Si](C)(C)C(C)(C)C	2344.0	Standard non polar	33892256
N-despropyl ropinirole,1TBDMS,isomer #2	CCCNCCC1=CC=CC2=C1CC(=O)N2[Si](C)(C)C(C)(C)C	2576.2	Standard polar	33892256
N-despropyl ropinirole,2TBDMS,isomer #1	CCCN(CCC1=CC=CC2=C1CC(=O)N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2596.6	Semi standard non polar	33892256
N-despropyl ropinirole,2TBDMS,isomer #1	CCCN(CCC1=CC=CC2=C1CC(=O)N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2711.3	Standard non polar	33892256
N-despropyl ropinirole,2TBDMS,isomer #1	CCCN(CCC1=CC=CC2=C1CC(=O)N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2647.4	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10398490

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for N-despropyl ropinirole (HMDB0060625)

MOL for HMDB0060625 (N-despropyl ropinirole)

3D MOL for HMDB0060625 (N-despropyl ropinirole)

3D SDF for HMDB0060625 (N-despropyl ropinirole)

3D-SDF for HMDB0060625 (N-despropyl ropinirole)

PDB for HMDB0060625 (N-despropyl ropinirole)

3D PDB for HMDB0060625 (N-despropyl ropinirole)

SMILES for HMDB0060625 (N-despropyl ropinirole)

INCHI for HMDB0060625 (N-despropyl ropinirole)

Structure for HMDB0060625 (N-despropyl ropinirole)

3D Structure for HMDB0060625 (N-despropyl ropinirole)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized