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Showing metabocard for Rasagiline (HMDB0015454)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
enzymes (3) Show 3 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2023-02-21 17:18:30 UTC
HMDB IDHMDB0015454
Secondary Accession Numbers
  • HMDB15454
Metabolite Identification
Common NameRasagiline
DescriptionRasagiline is only found in individuals that have used or taken this drug. It is an irreversible inhibitor of monoamine oxidase and is used as a monotherapy in early Parkinson's disease or as an adjunct therapy in more advanced cases.The precise mechanisms of action of rasagiline is unknown. One mechanism is believed to be related to its MAO-B inhibitory activity, which causes an increase in extracellular levels of dopamine in the striatum. The elevated dopamine level and subsequent increased dopaminergic activity are likely to mediate rasagiline's beneficial effects seen in models of dopaminergic motor dysfunction.
Structure
Data?1676999910
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0015454 (Rasagiline)

1367
  Mrv0541 02231215242D          

 13 14  0  0  1  0            999 V2000
    4.1159    0.0242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -0.7600    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3412   -1.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -2.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.0114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.5989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9232    0.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.0114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1795    0.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4359    1.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  1  9  1  0  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  3  4  1  0  0  0  0
  4  6  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  8  2  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  2  0  0  0  0
 12 13  3  0  0  0  0
M  END
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3D MOL for HMDB0015454 (Rasagiline)

HMDB0015454
     RDKit          3D
Rasagiline
 26 27  0  0  0  0  0  0  0  0999 V2000
    4.5108    0.6367   -0.3758 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6005   -0.1083   -0.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4847   -1.0384    0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3489   -0.2609    0.4667 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1411   -0.9337    0.8077 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2647   -1.7718   -0.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4997   -0.6334   -1.4017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3232    0.2731   -0.5247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3217    1.1816   -0.7841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9382    1.8992    0.2098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5502    1.7118    1.5272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5553    0.8097    1.7973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9439    0.0959    0.8004 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2992    1.2909   -0.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8535   -1.6789    1.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3701   -1.6475   -0.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4796    0.6918    0.8012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1666   -1.5176    1.7423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5090   -2.4598   -0.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2489   -2.2587   -0.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4660   -0.1343   -1.5538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0163   -0.9666   -2.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6024    1.3133   -1.8407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7095    2.5923   -0.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0166    2.2552    2.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2394    0.6585    2.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  5  1  0
 13  8  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  5 18  1  1
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  9 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  0
M  END
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3D SDF for HMDB0015454 (Rasagiline)

1367
  Mrv0541 02231215242D          

 13 14  0  0  1  0            999 V2000
    4.1159    0.0242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -0.7600    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3412   -1.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -2.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.0114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.5989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9232    0.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.0114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1795    0.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4359    1.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  1  9  1  0  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  3  4  1  0  0  0  0
  4  6  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  8  2  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  2  0  0  0  0
 12 13  3  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015454

> <DATABASE_NAME>
hmdb

> <SMILES>
C#CCN[C@@H]1CCC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C12H13N/c1-2-9-13-12-8-7-10-5-3-4-6-11(10)12/h1,3-6,12-13H,7-9H2/t12-/m1/s1

> <INCHI_KEY>
RUOKEQAAGRXIBM-GFCCVEGCSA-N

> <FORMULA>
C12H13N

> <MOLECULAR_WEIGHT>
171.2383

> <EXACT_MASS>
171.104799421

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
20.245577692260497

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R)-N-(prop-2-yn-1-yl)-2,3-dihydro-1H-inden-1-amine

> <ALOGPS_LOGP>
2.26

> <JCHEM_LOGP>
2.3039019329999997

> <ALOGPS_LOGS>
-3.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.687241073617077

> <JCHEM_POLAR_SURFACE_AREA>
12.03

> <JCHEM_REFRACTIVITY>
54.46700000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.49e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
rasagiline

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0015454 (Rasagiline)

HMDB0015454
     RDKit          3D
Rasagiline
 26 27  0  0  0  0  0  0  0  0999 V2000
    4.5108    0.6367   -0.3758 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6005   -0.1083   -0.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4847   -1.0384    0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3489   -0.2609    0.4667 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1411   -0.9337    0.8077 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2647   -1.7718   -0.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4997   -0.6334   -1.4017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3232    0.2731   -0.5247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3217    1.1816   -0.7841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9382    1.8992    0.2098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5502    1.7118    1.5272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5553    0.8097    1.7973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9439    0.0959    0.8004 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2992    1.2909   -0.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8535   -1.6789    1.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3701   -1.6475   -0.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4796    0.6918    0.8012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1666   -1.5176    1.7423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5090   -2.4598   -0.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2489   -2.2587   -0.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4660   -0.1343   -1.5538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0163   -0.9666   -2.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6024    1.3133   -1.8407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7095    2.5923   -0.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0166    2.2552    2.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2394    0.6585    2.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  5  1  0
 13  8  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  5 18  1  1
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  9 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  0
M  END
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PDB for HMDB0015454 (Rasagiline)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1367                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       7.683   0.045   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       7.205  -1.419   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.104  -2.658   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.205  -3.897   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.748  -1.888   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.748  -3.428   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.414  -1.118   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414  -4.198   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.190   0.363   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.080  -1.888   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.080  -3.428   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.668   1.827   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.147   3.290   0.000  0.00  0.00           C+0
CONECT    1    2    9                                                       
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3    6                                                       
CONECT    5    2    6    7                                                  
CONECT    6    4    5    8                                                  
CONECT    7    5   10                                                       
CONECT    8    6   11                                                       
CONECT    9    1   12                                                       
CONECT   10    7   11                                                       
CONECT   11    8   10                                                       
CONECT   12    9   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END
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3D PDB for HMDB0015454 (Rasagiline)

COMPND    HMDB0015454
HETATM    1  C1  UNL     1       4.511   0.637  -0.376  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.601  -0.108  -0.122  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.485  -1.038   0.197  1.00  0.00           C  
HETATM    4  N1  UNL     1       1.349  -0.261   0.467  1.00  0.00           N  
HETATM    5  C4  UNL     1       0.141  -0.934   0.808  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.265  -1.772  -0.393  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.500  -0.633  -1.402  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.323   0.273  -0.525  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.322   1.182  -0.784  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.938   1.899   0.210  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.550   1.712   1.527  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.555   0.810   1.797  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.944   0.096   0.800  1.00  0.00           C  
HETATM   14  H1  UNL     1       5.299   1.291  -0.596  1.00  0.00           H  
HETATM   15  H2  UNL     1       2.853  -1.679   1.013  1.00  0.00           H  
HETATM   16  H3  UNL     1       2.370  -1.647  -0.733  1.00  0.00           H  
HETATM   17  H4  UNL     1       1.480   0.692   0.801  1.00  0.00           H  
HETATM   18  H5  UNL     1       0.167  -1.518   1.742  1.00  0.00           H  
HETATM   19  H6  UNL     1       0.509  -2.460  -0.732  1.00  0.00           H  
HETATM   20  H7  UNL     1      -1.249  -2.259  -0.195  1.00  0.00           H  
HETATM   21  H8  UNL     1       0.466  -0.134  -1.554  1.00  0.00           H  
HETATM   22  H9  UNL     1      -1.016  -0.967  -2.296  1.00  0.00           H  
HETATM   23  H10 UNL     1      -2.602   1.313  -1.841  1.00  0.00           H  
HETATM   24  H11 UNL     1      -3.709   2.592  -0.058  1.00  0.00           H  
HETATM   25  H12 UNL     1      -3.017   2.255   2.332  1.00  0.00           H  
HETATM   26  H13 UNL     1      -1.239   0.658   2.831  1.00  0.00           H  
CONECT    1    2    2    2   14
CONECT    2    3
CONECT    3    4   15   16
CONECT    4    5   17
CONECT    5    6   13   18
CONECT    6    7   19   20
CONECT    7    8   21   22
CONECT    8    9    9   13
CONECT    9   10   23
CONECT   10   11   11   24
CONECT   11   12   25
CONECT   12   13   13   26
END
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SMILES for HMDB0015454 (Rasagiline)

C#CCN[C@@H]1CCC2=CC=CC=C12
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INCHI for HMDB0015454 (Rasagiline)

InChI=1S/C12H13N/c1-2-9-13-12-8-7-10-5-3-4-6-11(10)12/h1,3-6,12-13H,7-9H2/t12-/m1/s1
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View in JSmolView Stereo Labels
Synonyms
ValueSource
(1R)-N-Propargylindan-1-amineChEBI
(R)-Indan-1-yl-prop-2-ynyl-amineChEBI
(R)-N-2-Propynyl-1-indanamineChEBI
RASChEBI
AzilectKegg
2,3-Dihydro-N-2-propynyl-1H-inden-1-amine-(1R)-hydrochlorideHMDB
N-2-Propynyl-1-indanamineHMDB
N-Propargyl-1-aminoindan mesylateHMDB
TVP 101HMDB
TVP-101HMDB
Rasagiline hydrochlorideHMDB
Chemical FormulaC12H13N
Average Molecular Weight171.2383
Monoisotopic Molecular Weight171.104799421
IUPAC Name(1R)-N-(prop-2-yn-1-yl)-2,3-dihydro-1H-inden-1-amine
Traditional Namerasagiline
CAS Registry Number136236-51-6
SMILES
C#CCN[C@@H]1CCC2=CC=CC=C12
InChI Identifier
InChI=1S/C12H13N/c1-2-9-13-12-8-7-10-5-3-4-6-11(10)12/h1,3-6,12-13H,7-9H2/t12-/m1/s1
InChI KeyRUOKEQAAGRXIBM-GFCCVEGCSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indanes. Indanes are compounds containing an indane moiety, which consists of a cyclopentane fused to a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassIndanes
Sub ClassNot Available
Direct ParentIndanes
Alternative Parents
Substituents
  • Indane
  • Aralkylamine
  • Acetylide
  • Secondary amine
  • Secondary aliphatic amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.025 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.025 g/LALOGPS
logP2.26ALOGPS
logP2.3ChemAxon
logS-3.8ALOGPS
pKa (Strongest Basic)8.69ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity54.47 m³·mol⁻¹ChemAxon
Polarizability20.25 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+140.7731661259
DarkChem[M-H]-140.49231661259
DeepCCS[M-2H]-169.59230932474
DeepCCS[M+Na]+145.1330932474
AllCCS[M+H]+139.132859911
AllCCS[M+H-H2O]+134.932859911
AllCCS[M+NH4]+143.132859911
AllCCS[M+Na]+144.332859911
AllCCS[M-H]-142.032859911
AllCCS[M+Na-2H]-142.532859911
AllCCS[M+HCOO]-143.132859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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, 2022.4.09 minutes32390414
Predicted by Siyang on May 30, 202210.2297 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.92 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid29.2 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1161.8 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid307.0 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid130.8 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid183.2 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid92.5 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid340.9 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid364.1 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)107.9 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid851.2 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid323.4 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid984.5 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid227.6 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid248.7 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate395.5 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA238.9 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water39.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
RasagilineC#CCN[C@@H]1CCC2=CC=CC=C122316.3Standard polar33892256
RasagilineC#CCN[C@@H]1CCC2=CC=CC=C121489.5Standard non polar33892256
RasagilineC#CCN[C@@H]1CCC2=CC=CC=C121453.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Rasagiline,1TMS,isomer #1C#CCN([C@@H]1CCC2=CC=CC=C21)[Si](C)(C)C1625.2Semi standard non polar33892256
Rasagiline,1TMS,isomer #1C#CCN([C@@H]1CCC2=CC=CC=C21)[Si](C)(C)C1704.9Standard non polar33892256
Rasagiline,1TMS,isomer #1C#CCN([C@@H]1CCC2=CC=CC=C21)[Si](C)(C)C2034.7Standard polar33892256
Rasagiline,1TBDMS,isomer #1C#CCN([C@@H]1CCC2=CC=CC=C21)[Si](C)(C)C(C)(C)C1865.9Semi standard non polar33892256
Rasagiline,1TBDMS,isomer #1C#CCN([C@@H]1CCC2=CC=CC=C21)[Si](C)(C)C(C)(C)C1964.7Standard non polar33892256
Rasagiline,1TBDMS,isomer #1C#CCN([C@@H]1CCC2=CC=CC=C21)[Si](C)(C)C(C)(C)C2180.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Rasagiline GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-2900000000-dbab21c92cfad0a2ad812017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Rasagiline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Rasagiline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rasagiline 10V, Positive-QTOFsplash10-00di-0900000000-bfc14f766c80568f4dad2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rasagiline 20V, Positive-QTOFsplash10-00xr-1900000000-3f0164be3683c15d6ad72016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rasagiline 40V, Positive-QTOFsplash10-014i-6900000000-5fec88fbd60af5d19c272016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rasagiline 10V, Negative-QTOFsplash10-00di-0900000000-12d5b712c3b9fed38bfc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rasagiline 20V, Negative-QTOFsplash10-00di-1900000000-41bf3edb6e2e4ffe36e32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rasagiline 40V, Negative-QTOFsplash10-0udi-9400000000-b6459f6f4228c902516e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rasagiline 10V, Positive-QTOFsplash10-01b9-0900000000-eb00c42ba63b4672a60e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rasagiline 20V, Positive-QTOFsplash10-014l-2900000000-6babe278cbb9510eb5512021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rasagiline 40V, Positive-QTOFsplash10-000f-9400000000-eebf913854197187a5e02021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rasagiline 10V, Negative-QTOFsplash10-00di-2900000000-84302f309d95873f62f42021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rasagiline 20V, Negative-QTOFsplash10-0v4i-5900000000-9671b1f95762e81388a82021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rasagiline 40V, Negative-QTOFsplash10-014i-6900000000-6a17bf25152fba7644122021-10-11Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01367 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01367 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01367
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2314553
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRasagiline
METLIN IDNot Available
PubChem Compound3052776
PDB IDNot Available
ChEBI ID63620
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Leegwater-Kim J, Bortan E: The role of rasagiline in the treatment of Parkinson's disease. Clin Interv Aging. 2010 May 25;5:149-56. [PubMed:20517484 ]
  2. Chen JJ, Swope DM, Dashtipour K: Comprehensive review of rasagiline, a second-generation monoamine oxidase inhibitor, for the treatment of Parkinson's disease. Clin Ther. 2007 Sep;29(9):1825-49. [PubMed:18035186 ]
  3. Weinreb O, Amit T, Bar-Am O, Youdim MB: Rasagiline: a novel anti-Parkinsonian monoamine oxidase-B inhibitor with neuroprotective activity. Prog Neurobiol. 2010 Nov;92(3):330-44. doi: 10.1016/j.pneurobio.2010.06.008. Epub 2010 Jun 19. [PubMed:20600573 ]

Enzymes

Enzyme Details
1. Amine oxidase [flavin-containing] B
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
References
  1. Naoi M, Maruyama W: Functional mechanism of neuroprotection by inhibitors of type B monoamine oxidase in Parkinson's disease. Expert Rev Neurother. 2009 Aug;9(8):1233-50. doi: 10.1586/ern.09.68. [PubMed:19673610 ]
  2. Uzun M, Alp R, Uzlu E, Alp S, Citil M, Topcu B, Erdogan HM: Investigation of oral selegiline and rasagiline administration on QT interval in conscious rabbits. Eur Rev Med Pharmacol Sci. 2009 Mar-Apr;13(2):95-8. [PubMed:19499843 ]
  3. Youdim MB, Weinstock M: Molecular basis of neuroprotective activities of rasagiline and the anti-Alzheimer drug TV3326 [(N-propargyl-(3R)aminoindan-5-YL)-ethyl methyl carbamate]. Cell Mol Neurobiol. 2001 Dec;21(6):555-73. [PubMed:12043833 ]
  4. Chau KY, Cooper JM, Schapira AH: Rasagiline protects against alpha-synuclein induced sensitivity to oxidative stress in dopaminergic cells. Neurochem Int. 2010 Nov;57(5):525-9. doi: 10.1016/j.neuint.2010.06.017. Epub 2010 Jul 17. [PubMed:20624440 ]
  5. Weinreb O, Amit T, Bar-Am O, Youdim MB: Rasagiline: a novel anti-Parkinsonian monoamine oxidase-B inhibitor with neuroprotective activity. Prog Neurobiol. 2010 Nov;92(3):330-44. doi: 10.1016/j.pneurobio.2010.06.008. Epub 2010 Jun 19. [PubMed:20600573 ]
  6. Youdim MB, Bar Am O, Yogev-Falach M, Weinreb O, Maruyama W, Naoi M, Amit T: Rasagiline: neurodegeneration, neuroprotection, and mitochondrial permeability transition. J Neurosci Res. 2005 Jan 1-15;79(1-2):172-9. [PubMed:15573406 ]
  7. Leegwater-Kim J, Bortan E: The role of rasagiline in the treatment of Parkinson's disease. Clin Interv Aging. 2010 May 25;5:149-56. [PubMed:20517484 ]
  8. Chen JJ, Swope DM, Dashtipour K: Comprehensive review of rasagiline, a second-generation monoamine oxidase inhibitor, for the treatment of Parkinson's disease. Clin Ther. 2007 Sep;29(9):1825-49. [PubMed:18035186 ]
  9. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Enzyme Details
2. Cytochrome P450 1A2
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
References
  1. Lecht S, Haroutiunian S, Hoffman A, Lazarovici P: Rasagiline - a novel MAO B inhibitor in Parkinson's disease therapy. Ther Clin Risk Manag. 2007 Jun;3(3):467-74. [PubMed:18488080 ]
  2. Leegwater-Kim J, Bortan E: The role of rasagiline in the treatment of Parkinson's disease. Clin Interv Aging. 2010 May 25;5:149-56. [PubMed:20517484 ]
  3. Chen JJ, Swope DM, Dashtipour K: Comprehensive review of rasagiline, a second-generation monoamine oxidase inhibitor, for the treatment of Parkinson's disease. Clin Ther. 2007 Sep;29(9):1825-49. [PubMed:18035186 ]
  4. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Enzyme Details
3. Apoptosis regulator Bcl-2
General function:
Involved in regulation of apoptosis
Specific function:
Suppresses apoptosis in a variety of cell systems including factor-dependent lymphohematopoietic and neural cells. Regulates cell death by controlling the mitochondrial membrane permeability. Appears to function in a feedback loop system with caspases. Inhibits caspase activity either by preventing the release of cytochrome c from the mitochondria and/or by binding to the apoptosis-activating factor (APAF-1)
Gene Name:
BCL2
Uniprot ID:
P10415
Molecular weight:
26265.7
References
  1. Youdim MB, Weinstock M: Molecular basis of neuroprotective activities of rasagiline and the anti-Alzheimer drug TV3326 [(N-propargyl-(3R)aminoindan-5-YL)-ethyl methyl carbamate]. Cell Mol Neurobiol. 2001 Dec;21(6):555-73. [PubMed:12043833 ]
  2. Akao Y, Maruyama W, Yi H, Shamoto-Nagai M, Youdim MB, Naoi M: An anti-Parkinson's disease drug, N-propargyl-1(R)-aminoindan (rasagiline), enhances expression of anti-apoptotic bcl-2 in human dopaminergic SH-SY5Y cells. Neurosci Lett. 2002 Jun 28;326(2):105-8. [PubMed:12057839 ]
  3. Maruyama W, Akao Y, Carrillo MC, Kitani K, Youdium MB, Naoi M: Neuroprotection by propargylamines in Parkinson's disease: suppression of apoptosis and induction of prosurvival genes. Neurotoxicol Teratol. 2002 Sep-Oct;24(5):675-82. [PubMed:12200198 ]
  4. Youdim MB, Amit T, Falach-Yogev M, Bar Am O, Maruyama W, Naoi M: The essentiality of Bcl-2, PKC and proteasome-ubiquitin complex activations in the neuroprotective-antiapoptotic action of the anti-Parkinson drug, rasagiline. Biochem Pharmacol. 2003 Oct 15;66(8):1635-41. [PubMed:14555244 ]
  5. Bar-Am O, Weinreb O, Amit T, Youdim MB: Regulation of Bcl-2 family proteins, neurotrophic factors, and APP processing in the neurorescue activity of propargylamine. FASEB J. 2005 Nov;19(13):1899-901. Epub 2005 Sep 7. [PubMed:16148027 ]