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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 11:53:33 UTC

Update Date

2021-09-26 23:06:40 UTC

HMDB ID

HMDB0253446

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Indalpine

Description

Indalpine belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Indalpine is a very strong basic compound (based on its pKa). It was initially marketed by Pharmuka. Indalpine was one of the first selective serotonin reuptake inhibitors to reach the American market. However, after the emergence of widespread concern regarding adverse effects caused by SSRIs, and reported hematological effects caused by Indalpine, it was abruptly withdrawn from the US market. This compound has been identified in human blood as reported by (PMID: 31557052 ). Indalpine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Indalpine 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

HMDB0253446
     RDKit          3D
Indalpine
 37 39  0  0  0  0  0  0  0  0999 V2000
   -4.1265   -1.4408    1.3838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8761   -1.9795    1.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9826   -1.2856    0.3795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3538   -0.0701   -0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6962    0.8602   -0.9558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2975    0.6523   -1.4324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5974    0.9542   -0.2303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0505    0.7674   -0.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8974    1.0770    0.5935 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8832   -0.1025    1.5118 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4715   -1.2777    0.9413 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5216   -1.2643   -0.4948 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2870   -0.6324   -1.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5306    1.9270   -1.2029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6759    1.6645   -0.5647 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6036    0.4732    0.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5054   -0.2326    0.8624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8098   -2.0139    1.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5874   -2.9520    1.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9895   -1.6512    0.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1411   -0.3860   -1.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0194    1.3812   -2.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2841    0.3257    0.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4246    2.0371   -0.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2621    1.4982   -1.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4393    1.9470    1.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9465    1.3095    0.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4495    0.1734    2.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8215   -0.3589    1.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3801   -1.5435    1.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4185   -0.8174   -0.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5086   -2.3391   -0.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4410   -1.3225   -0.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4101   -0.6239   -2.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2794    2.8046   -1.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5236    2.2590   -0.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4963    0.1826    1.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  5 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17  1  1  0
 16  4  1  0
 13  8  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 17 37  1  0
M  END


  Mrv0541 05281410052D          

 17 19  0  0  0  0            999 V2000
    3.3522    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3522    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -0.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8837    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -1.0567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -1.4983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1189   -2.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6537    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -0.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6880   -2.4545    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1903    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 12  5  1  0  0  0  0
 12  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  6  1  0  0  0  0
 13 11  2  0  0  0  0
 14  3  2  0  0  0  0
 14 13  1  0  0  0  0
 15  4  2  0  0  0  0
 15 14  1  0  0  0  0
 16  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 17 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253446

> <DATABASE_NAME>
hmdb

> <SMILES>
C(CC1=CNC2=CC=CC=C12)C1CCNCC1

> <INCHI_IDENTIFIER>
InChI=1S/C15H20N2/c1-2-4-15-14(3-1)13(11-17-15)6-5-12-7-9-16-10-8-12/h1-4,11-12,16-17H,5-10H2

> <INCHI_KEY>
SADQVAVFGNTEOD-UHFFFAOYSA-N

> <FORMULA>
C15H20N2

> <MOLECULAR_WEIGHT>
228.3327

> <EXACT_MASS>
228.16264865

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
27.586915814128364

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[2-(piperidin-4-yl)ethyl]-1H-indole

> <ALOGPS_LOGP>
3.58

> <JCHEM_LOGP>
3.0662100519999993

> <ALOGPS_LOGS>
-4.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.31878029195073

> <JCHEM_PKA_STRONGEST_BASIC>
10.355899821464133

> <JCHEM_POLAR_SURFACE_AREA>
27.82

> <JCHEM_REFRACTIVITY>
71.76750000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
indalpine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0253446
     RDKit          3D
Indalpine
 37 39  0  0  0  0  0  0  0  0999 V2000
   -4.1265   -1.4408    1.3838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8761   -1.9795    1.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9826   -1.2856    0.3795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3538   -0.0701   -0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6962    0.8602   -0.9558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2975    0.6523   -1.4324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5974    0.9542   -0.2303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0505    0.7674   -0.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8974    1.0770    0.5935 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8832   -0.1025    1.5118 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4715   -1.2777    0.9413 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5216   -1.2643   -0.4948 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2870   -0.6324   -1.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5306    1.9270   -1.2029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6759    1.6645   -0.5647 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6036    0.4732    0.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5054   -0.2326    0.8624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8098   -2.0139    1.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5874   -2.9520    1.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9895   -1.6512    0.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1411   -0.3860   -1.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0194    1.3812   -2.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2841    0.3257    0.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4246    2.0371   -0.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2621    1.4982   -1.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4393    1.9470    1.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9465    1.3095    0.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4495    0.1734    2.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8215   -0.3589    1.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3801   -1.5435    1.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4185   -0.8174   -0.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5086   -2.3391   -0.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4410   -1.3225   -0.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4101   -0.6239   -2.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2794    2.8046   -1.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5236    2.2590   -0.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4963    0.1826    1.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  5 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17  1  1  0
 16  4  1  0
 13  8  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 17 37  1  0
M  END

HEADER    PROTEIN                                 28-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-MAY-14         0                                  
HETATM    1  C   UNK     0       6.257   2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.257   3.613   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.143  -0.188   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.839  -1.973   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.698  -2.797   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.315  -3.437   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.222  -4.261   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.332  -1.652   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -1.284  -4.582   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1   14                                                       
CONECT    4    2   15                                                       
CONECT    5    6   12                                                       
CONECT    6    5   13                                                       
CONECT    7    9   12                                                       
CONECT    8   10   12                                                       
CONECT    9    7   16                                                       
CONECT   10    8   16                                                       
CONECT   11   13   17                                                       
CONECT   12    5    7    8                                                  
CONECT   13    6   11   14                                                  
CONECT   14    3   13   15                                                  
CONECT   15    4   14   17                                                  
CONECT   16    9   10                                                       
CONECT   17   11   15                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0253446
HETATM    1  C1  UNL     1      -4.127  -1.441   1.384  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.876  -1.979   1.153  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.983  -1.286   0.380  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.354  -0.070  -0.149  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.696   0.860  -0.956  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.297   0.652  -1.432  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.597   0.954  -0.230  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.051   0.767  -0.615  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.897   1.077   0.593  1.00  0.00           C  
HETATM   10  C10 UNL     1       2.883  -0.103   1.512  1.00  0.00           C  
HETATM   11  N1  UNL     1       3.471  -1.278   0.941  1.00  0.00           N  
HETATM   12  C11 UNL     1       3.522  -1.264  -0.495  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.287  -0.632  -1.100  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.531   1.927  -1.203  1.00  0.00           C  
HETATM   15  N2  UNL     1      -3.676   1.664  -0.565  1.00  0.00           N  
HETATM   16  C14 UNL     1      -3.604   0.473   0.078  1.00  0.00           C  
HETATM   17  C15 UNL     1      -4.505  -0.233   0.862  1.00  0.00           C  
HETATM   18  H1  UNL     1      -4.810  -2.014   2.000  1.00  0.00           H  
HETATM   19  H2  UNL     1      -2.587  -2.952   1.580  1.00  0.00           H  
HETATM   20  H3  UNL     1      -0.989  -1.651   0.161  1.00  0.00           H  
HETATM   21  H4  UNL     1      -0.141  -0.386  -1.727  1.00  0.00           H  
HETATM   22  H5  UNL     1      -0.019   1.381  -2.216  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.284   0.326   0.618  1.00  0.00           H  
HETATM   24  H7  UNL     1       0.425   2.037  -0.005  1.00  0.00           H  
HETATM   25  H8  UNL     1       2.262   1.498  -1.429  1.00  0.00           H  
HETATM   26  H9  UNL     1       2.439   1.947   1.095  1.00  0.00           H  
HETATM   27  H10 UNL     1       3.947   1.310   0.321  1.00  0.00           H  
HETATM   28  H11 UNL     1       3.450   0.173   2.442  1.00  0.00           H  
HETATM   29  H12 UNL     1       1.822  -0.359   1.764  1.00  0.00           H  
HETATM   30  H13 UNL     1       4.380  -1.544   1.335  1.00  0.00           H  
HETATM   31  H14 UNL     1       4.419  -0.817  -0.922  1.00  0.00           H  
HETATM   32  H15 UNL     1       3.509  -2.339  -0.832  1.00  0.00           H  
HETATM   33  H16 UNL     1       1.441  -1.322  -0.848  1.00  0.00           H  
HETATM   34  H17 UNL     1       2.410  -0.624  -2.200  1.00  0.00           H  
HETATM   35  H18 UNL     1      -2.279   2.805  -1.807  1.00  0.00           H  
HETATM   36  H19 UNL     1      -4.524   2.259  -0.538  1.00  0.00           H  
HETATM   37  H20 UNL     1      -5.496   0.183   1.051  1.00  0.00           H  
CONECT    1    2    2   17   18
CONECT    2    3   19
CONECT    3    4    4   20
CONECT    4    5   16
CONECT    5    6   14   14
CONECT    6    7   21   22
CONECT    7    8   23   24
CONECT    8    9   13   25
CONECT    9   10   26   27
CONECT   10   11   28   29
CONECT   11   12   30
CONECT   12   13   31   32
CONECT   13   33   34
CONECT   14   15   35
CONECT   15   16   36
CONECT   16   17   17
CONECT   17   37
END

HMDB0253446
     RDKit          3D
Indalpine
 37 39  0  0  0  0  0  0  0  0999 V2000
   -4.1265   -1.4408    1.3838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8761   -1.9795    1.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9826   -1.2856    0.3795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3538   -0.0701   -0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6962    0.8602   -0.9558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2975    0.6523   -1.4324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5974    0.9542   -0.2303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0505    0.7674   -0.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8974    1.0770    0.5935 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8832   -0.1025    1.5118 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4715   -1.2777    0.9413 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5216   -1.2643   -0.4948 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2870   -0.6324   -1.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5306    1.9270   -1.2029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6759    1.6645   -0.5647 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6036    0.4732    0.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5054   -0.2326    0.8624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8098   -2.0139    1.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5874   -2.9520    1.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9895   -1.6512    0.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1411   -0.3860   -1.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0194    1.3812   -2.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2841    0.3257    0.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4246    2.0371   -0.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2621    1.4982   -1.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4393    1.9470    1.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9465    1.3095    0.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4495    0.1734    2.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8215   -0.3589    1.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3801   -1.5435    1.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4185   -0.8174   -0.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5086   -2.3391   -0.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4410   -1.3225   -0.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4101   -0.6239   -2.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2794    2.8046   -1.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5236    2.2590   -0.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4963    0.1826    1.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  5 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17  1  1  0
 16  4  1  0
 13  8  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 17 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Upstene	ChEMBL, MeSH
4-(2-(3-Indolyl)ethyl)piperidine	MeSH
Indalpine monohydrochloride	MeSH
(3-Indolyl-2-ethyl)piperidine	MeSH

Chemical Formula

C₁₅H₂₀N₂

Average Molecular Weight

228.3327

Monoisotopic Molecular Weight

228.16264865

IUPAC Name

3-[2-(piperidin-4-yl)ethyl]-1H-indole

Traditional Name

indalpine

CAS Registry Number

Not Available

SMILES

C(CC1=CNC2=CC=CC=C12)C1CCNCC1

InChI Identifier

InChI=1S/C15H20N2/c1-2-4-15-14(3-1)13(11-17-15)6-5-12-7-9-16-10-8-12/h1-4,11-12,16-17H,5-10H2

InChI Key

SADQVAVFGNTEOD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Aralkylamine
Piperidine
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Secondary aliphatic amine
Secondary amine
Azacycle
Organopnictogen compound
Organic nitrogen compound
Amine
Organonitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

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	3.58	ALOGPS
logP	3.07	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	17.32	ChemAxon
pKa (Strongest Basic)	10.36	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	27.82 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	71.77 m³·mol⁻¹	ChemAxon
Polarizability	27.59 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	181.365	30932474
DeepCCS	[M+Na]+	156.224	30932474
AllCCS	[M+H]+	156.0	32859911
AllCCS	[M+H-H2O]+	151.9	32859911
AllCCS	[M+NH4]+	159.7	32859911
AllCCS	[M+Na]+	160.8	32859911
AllCCS	[M-H]-	163.1	32859911
AllCCS	[M+Na-2H]-	163.1	32859911
AllCCS	[M+HCOO]-	163.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Indalpine	C(CC1=CNC2=CC=CC=C12)C1CCNCC1	3047.8	Standard polar	33892256
Indalpine	C(CC1=CNC2=CC=CC=C12)C1CCNCC1	2219.7	Standard non polar	33892256
Indalpine	C(CC1=CNC2=CC=CC=C12)C1CCNCC1	2314.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Indalpine,1TMS,isomer #1	C[Si](C)(C)N1C=C(CCC2CCNCC2)C2=CC=CC=C21	2300.9	Semi standard non polar	33892256
Indalpine,1TMS,isomer #1	C[Si](C)(C)N1C=C(CCC2CCNCC2)C2=CC=CC=C21	2305.9	Standard non polar	33892256
Indalpine,1TMS,isomer #1	C[Si](C)(C)N1C=C(CCC2CCNCC2)C2=CC=CC=C21	2827.9	Standard polar	33892256
Indalpine,1TMS,isomer #2	C[Si](C)(C)N1CCC(CCC2=C[NH]C3=CC=CC=C23)CC1	2392.2	Semi standard non polar	33892256
Indalpine,1TMS,isomer #2	C[Si](C)(C)N1CCC(CCC2=C[NH]C3=CC=CC=C23)CC1	2329.6	Standard non polar	33892256
Indalpine,1TMS,isomer #2	C[Si](C)(C)N1CCC(CCC2=C[NH]C3=CC=CC=C23)CC1	2893.1	Standard polar	33892256
Indalpine,2TMS,isomer #1	C[Si](C)(C)N1CCC(CCC2=CN([Si](C)(C)C)C3=CC=CC=C23)CC1	2436.7	Semi standard non polar	33892256
Indalpine,2TMS,isomer #1	C[Si](C)(C)N1CCC(CCC2=CN([Si](C)(C)C)C3=CC=CC=C23)CC1	2451.2	Standard non polar	33892256
Indalpine,2TMS,isomer #1	C[Si](C)(C)N1CCC(CCC2=CN([Si](C)(C)C)C3=CC=CC=C23)CC1	2758.4	Standard polar	33892256
Indalpine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=C(CCC2CCNCC2)C2=CC=CC=C21	2538.5	Semi standard non polar	33892256
Indalpine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=C(CCC2CCNCC2)C2=CC=CC=C21	2509.6	Standard non polar	33892256
Indalpine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=C(CCC2CCNCC2)C2=CC=CC=C21	2932.9	Standard polar	33892256
Indalpine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CCC(CCC2=C[NH]C3=CC=CC=C23)CC1	2634.4	Semi standard non polar	33892256
Indalpine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CCC(CCC2=C[NH]C3=CC=CC=C23)CC1	2564.2	Standard non polar	33892256
Indalpine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CCC(CCC2=C[NH]C3=CC=CC=C23)CC1	3062.4	Standard polar	33892256
Indalpine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCC(CCC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)CC1	2866.8	Semi standard non polar	33892256
Indalpine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCC(CCC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)CC1	2885.0	Standard non polar	33892256
Indalpine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCC(CCC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)CC1	2960.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Indalpine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9620000000-1fa89594f786498151e6	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indalpine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indalpine 10V, Positive-QTOF	splash10-004i-1290000000-b248ffb328e2836bd99c	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indalpine 20V, Positive-QTOF	splash10-003s-7950000000-b27bdff651cc77b76281	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indalpine 40V, Positive-QTOF	splash10-001j-9600000000-aad09d3214ad763cd449	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indalpine 10V, Negative-QTOF	splash10-004i-0090000000-498b4e7749ec084279f6	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indalpine 20V, Negative-QTOF	splash10-004i-1090000000-c0d866ae216c098619de	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indalpine 40V, Negative-QTOF	splash10-02tc-9530000000-5caa0b5ad446f65ac628	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indalpine 10V, Positive-QTOF	splash10-004i-0090000000-edeaa3b4b0d2bc5c95b5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indalpine 20V, Positive-QTOF	splash10-004i-2290000000-3f48068e72f8fedb2b34	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indalpine 40V, Positive-QTOF	splash10-052f-8910000000-e3509262d9062650999e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indalpine 10V, Negative-QTOF	splash10-004i-0090000000-f1bfa23995955ad58c1e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indalpine 20V, Negative-QTOF	splash10-004i-0090000000-132b77007b9dee368c04	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indalpine 40V, Negative-QTOF	splash10-016u-1920000000-1cba1b5d9977dc57e7f7	2021-10-12	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

DB08953

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

Indalpine

METLIN ID

Not Available

PubChem Compound

44668

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

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 Indalpine (HMDB0253446)

MOL for HMDB0253446 (Indalpine)

3D MOL for HMDB0253446 (Indalpine)

3D SDF for HMDB0253446 (Indalpine)

3D-SDF for HMDB0253446 (Indalpine)

PDB for HMDB0253446 (Indalpine)

3D PDB for HMDB0253446 (Indalpine)

SMILES for HMDB0253446 (Indalpine)

INCHI for HMDB0253446 (Indalpine)

Structure for HMDB0253446 (Indalpine)

3D Structure for HMDB0253446 (Indalpine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra