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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 09:20:33 UTC

Update Date

2021-09-26 23:03:56 UTC

HMDB ID

HMDB0251748

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Eliprodil

Description

Eliprodil belongs to the class of organic compounds known as 4-benzylpiperidines. These are organic compounds containing a benzyl group attached to the 4-position of a piperidine. Eliprodil failed a Phase III clinical trial for the treatment of acute ischemic stroke in 1996, sponsored by Synthélabo Recherche. Eliprodil is a very strong basic compound (based on its pKa). Eliprodil (codenamed SL-82.0715) is an NMDA antagonist drug candidate which selectively inhibits the NR2B (GLUN2B) subtype NMDA receptor at submicromolar concentrations. Therefore, when NMDA receptors are activated, there is an increase in intracellular Ca2+ concentration. NMDA receptors are a key component in mediating glutamate-induced excitotoxicity, and it is believed that NMDA antagonists would be neuroprotective after a stroke or other traumatic brain injury. These neurons quickly lose ATP and become depolarized, which releases glutamate. This, in turn, causes an influx of Na+ and Ca2+. After a traumatic brain injury, neurons become deprived of glucose and oxygen. High Ca2+ causes fatal metabolic consequences, including neuronal cell death. This compound has been identified in human blood as reported by (PMID: 31557052 ). Eliprodil is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Eliprodil 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

HMDB0251748
     RDKit          3D
Eliprodil
 47 49  0  0  0  0  0  0  0  0999 V2000
    2.2612    1.4527   -1.3480 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8758    0.2677   -0.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0310   -0.4608    0.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7330   -0.7903   -0.4539 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1382    0.3155   -0.6777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5913   -0.1171   -0.7635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9834   -0.7290    0.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2766   -1.5164    0.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3171   -0.5759   -0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5243   -0.3252   -1.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4862    0.5530   -1.9376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2794    1.2129   -1.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2345    2.0841   -1.4512 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0779    0.9656    0.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1094    0.0825    0.7625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9134   -1.5180    1.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1501   -1.9060    0.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2386    0.5813   -0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4531    1.6270    0.3498 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7243    1.9103    0.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7840    1.1496    0.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3948    1.4924    0.9109 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.5786    0.0920   -0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3015   -0.1799   -0.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9200    2.0813   -1.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9775   -0.3240   -1.9318 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0668    0.7983   -1.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0474    1.0697    0.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6201   -0.8765   -1.5887 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.6363    0.7392   -2.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6953    1.4785    1.0373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9997   -0.0694    1.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4723   -0.9669    2.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3452   -2.4586    1.6145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2928   -2.6703   -0.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9639   -2.3983    0.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6463    2.2624    0.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9068    2.7536    1.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4042   -0.5272   -0.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1861   -1.0226   -1.6066 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  1  0
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  9 10  2  0
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  7 16  1  0
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  2 18  1  0
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 16 41  1  0
 17 42  1  0
 17 43  1  0
 19 44  1  0
 20 45  1  0
 23 46  1  0
 24 47  1  0
M  END


  Mrv1533004261515212D          

 24 26  0  0  0  0            999 V2000
    2.1434   -2.8875    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
    1.4289   -4.1250    0.0000 N   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
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -8.6625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   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
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 11 14  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
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 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 20 23  1  0  0  0  0
 16 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0251748

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(CN1CCC(CC2=CC=C(F)C=C2)CC1)C1=CC=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H23ClFNO/c21-18-5-3-17(4-6-18)20(24)14-23-11-9-16(10-12-23)13-15-1-7-19(22)8-2-15/h1-8,16,20,24H,9-14H2

> <INCHI_KEY>
GGUSQTSTQSHJAH-UHFFFAOYSA-N

> <FORMULA>
C20H23ClFNO

> <MOLECULAR_WEIGHT>
347.86

> <EXACT_MASS>
347.1452202

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
37.27493850793962

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(4-chlorophenyl)-2-{4-[(4-fluorophenyl)methyl]piperidin-1-yl}ethan-1-ol

> <ALOGPS_LOGP>
4.65

> <JCHEM_LOGP>
4.746812119333334

> <ALOGPS_LOGS>
-4.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.069307123116221

> <JCHEM_PKA_STRONGEST_BASIC>
8.884208366667853

> <JCHEM_POLAR_SURFACE_AREA>
23.47

> <JCHEM_REFRACTIVITY>
96.971

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.58e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
eliprodil

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0251748
     RDKit          3D
Eliprodil
 47 49  0  0  0  0  0  0  0  0999 V2000
    2.2612    1.4527   -1.3480 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8758    0.2677   -0.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0310   -0.4608    0.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7330   -0.7903   -0.4539 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1382    0.3155   -0.6777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5913   -0.1171   -0.7635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9834   -0.7290    0.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2766   -1.5164    0.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3171   -0.5759   -0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5243   -0.3252   -1.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4862    0.5530   -1.9376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2794    1.2129   -1.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2345    2.0841   -1.4512 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0779    0.9656    0.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1094    0.0825    0.7625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9134   -1.5180    1.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1501   -1.9060    0.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2386    0.5813   -0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4531    1.6270    0.3498 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7243    1.9103    0.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7840    1.1496    0.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3948    1.4924    0.9109 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.5786    0.0920   -0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3015   -0.1799   -0.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9200    2.0813   -1.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9775   -0.3240   -1.9318 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5327   -1.4242    0.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0668    0.7983   -1.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3452   -2.4586    1.6145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2928   -2.6703   -0.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6463    2.2624    0.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9068    2.7536    1.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4042   -0.5272   -0.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1861   -1.0226   -1.6066 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  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  7 16  1  0
 16 17  1  0
  2 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 17  4  1  0
 24 18  1  0
 15  9  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
 10 36  1  0
 11 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 19 44  1  0
 20 45  1  0
 23 46  1  0
 24 47  1  0
M  END

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       2.667  -7.700   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  F   UNK     0      -2.667  -0.000   0.000  0.00  0.00           F+0
HETATM   15  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   23 Cl   UNK     0       4.001 -16.170   0.000  0.00  0.00          Cl+0
HETATM   24  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14   11                                                            
CONECT   15    3   16                                                       
CONECT   16   15   17   24                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   20                                                            
CONECT   24   16                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0251748
HETATM    1  O1  UNL     1       2.261   1.453  -1.348  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.876   0.268  -0.991  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.031  -0.461   0.029  1.00  0.00           C  
HETATM    4  N1  UNL     1       0.733  -0.790  -0.454  1.00  0.00           N  
HETATM    5  C3  UNL     1      -0.138   0.316  -0.678  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.591  -0.117  -0.763  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.983  -0.729   0.540  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.277  -1.516   0.319  1.00  0.00           C  
HETATM    9  C7  UNL     1      -4.317  -0.576  -0.151  1.00  0.00           C  
HETATM   10  C8  UNL     1      -4.524  -0.325  -1.480  1.00  0.00           C  
HETATM   11  C9  UNL     1      -5.486   0.553  -1.938  1.00  0.00           C  
HETATM   12  C10 UNL     1      -6.279   1.213  -1.033  1.00  0.00           C  
HETATM   13  F1  UNL     1      -7.234   2.084  -1.451  1.00  0.00           F  
HETATM   14  C11 UNL     1      -6.078   0.966   0.324  1.00  0.00           C  
HETATM   15  C12 UNL     1      -5.109   0.083   0.763  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.913  -1.518   1.211  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.150  -1.906   0.227  1.00  0.00           C  
HETATM   18  C15 UNL     1       4.239   0.581  -0.508  1.00  0.00           C  
HETATM   19  C16 UNL     1       4.453   1.627   0.350  1.00  0.00           C  
HETATM   20  C17 UNL     1       5.724   1.910   0.788  1.00  0.00           C  
HETATM   21  C18 UNL     1       6.784   1.150   0.370  1.00  0.00           C  
HETATM   22 CL1  UNL     1       8.395   1.492   0.911  1.00  0.00          CL  
HETATM   23  C19 UNL     1       6.579   0.092  -0.496  1.00  0.00           C  
HETATM   24  C20 UNL     1       5.301  -0.180  -0.926  1.00  0.00           C  
HETATM   25  H1  UNL     1       2.920   2.081  -1.748  1.00  0.00           H  
HETATM   26  H2  UNL     1       2.977  -0.324  -1.932  1.00  0.00           H  
HETATM   27  H3  UNL     1       1.947   0.123   0.964  1.00  0.00           H  
HETATM   28  H4  UNL     1       2.533  -1.424   0.314  1.00  0.00           H  
HETATM   29  H5  UNL     1       0.067   0.798  -1.677  1.00  0.00           H  
HETATM   30  H6  UNL     1      -0.047   1.070   0.114  1.00  0.00           H  
HETATM   31  H7  UNL     1      -1.620  -0.877  -1.589  1.00  0.00           H  
HETATM   32  H8  UNL     1      -2.179   0.777  -1.046  1.00  0.00           H  
HETATM   33  H9  UNL     1      -2.219   0.144   1.222  1.00  0.00           H  
HETATM   34  H10 UNL     1      -3.129  -2.261  -0.495  1.00  0.00           H  
HETATM   35  H11 UNL     1      -3.592  -2.063   1.224  1.00  0.00           H  
HETATM   36  H12 UNL     1      -3.917  -0.833  -2.203  1.00  0.00           H  
HETATM   37  H13 UNL     1      -5.636   0.739  -2.981  1.00  0.00           H  
HETATM   38  H14 UNL     1      -6.695   1.478   1.037  1.00  0.00           H  
HETATM   39  H15 UNL     1      -5.000  -0.069   1.842  1.00  0.00           H  
HETATM   40  H16 UNL     1      -0.472  -0.967   2.093  1.00  0.00           H  
HETATM   41  H17 UNL     1      -1.345  -2.459   1.614  1.00  0.00           H  
HETATM   42  H18 UNL     1      -0.293  -2.670  -0.461  1.00  0.00           H  
HETATM   43  H19 UNL     1       0.964  -2.398   0.831  1.00  0.00           H  
HETATM   44  H20 UNL     1       3.646   2.262   0.713  1.00  0.00           H  
HETATM   45  H21 UNL     1       5.907   2.754   1.481  1.00  0.00           H  
HETATM   46  H22 UNL     1       7.404  -0.527  -0.842  1.00  0.00           H  
HETATM   47  H23 UNL     1       5.186  -1.023  -1.607  1.00  0.00           H  
CONECT    1    2   25
CONECT    2    3   18   26
CONECT    3    4   27   28
CONECT    4    5   17
CONECT    5    6   29   30
CONECT    6    7   31   32
CONECT    7    8   16   33
CONECT    8    9   34   35
CONECT    9   10   10   15
CONECT   10   11   36
CONECT   11   12   12   37
CONECT   12   13   14
CONECT   14   15   15   38
CONECT   15   39
CONECT   16   17   40   41
CONECT   17   42   43
CONECT   18   19   19   24
CONECT   19   20   44
CONECT   20   21   21   45
CONECT   21   22   23
CONECT   23   24   24   46
CONECT   24   47
END

HMDB0251748
     RDKit          3D
Eliprodil
 47 49  0  0  0  0  0  0  0  0999 V2000
    2.2612    1.4527   -1.3480 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8758    0.2677   -0.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0310   -0.4608    0.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7330   -0.7903   -0.4539 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1382    0.3155   -0.6777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5913   -0.1171   -0.7635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9834   -0.7290    0.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2766   -1.5164    0.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3171   -0.5759   -0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5243   -0.3252   -1.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4862    0.5530   -1.9376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2794    1.2129   -1.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2345    2.0841   -1.4512 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0779    0.9656    0.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1094    0.0825    0.7625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9134   -1.5180    1.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1501   -1.9060    0.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2386    0.5813   -0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4531    1.6270    0.3498 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7243    1.9103    0.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7840    1.1496    0.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3948    1.4924    0.9109 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.5786    0.0920   -0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3015   -0.1799   -0.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9200    2.0813   -1.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9775   -0.3240   -1.9318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9470    0.1228    0.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5327   -1.4242    0.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0668    0.7983   -1.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0474    1.0697    0.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6201   -0.8765   -1.5887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1786    0.7768   -1.0461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2190    0.1439    1.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1295   -2.2611   -0.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5922   -2.0627    1.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9171   -0.8327   -2.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6363    0.7392   -2.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6953    1.4785    1.0373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9997   -0.0694    1.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4723   -0.9669    2.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3452   -2.4586    1.6145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2928   -2.6703   -0.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9639   -2.3983    0.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6463    2.2624    0.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9068    2.7536    1.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4042   -0.5272   -0.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1861   -1.0226   -1.6066 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  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  7 16  1  0
 16 17  1  0
  2 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 17  4  1  0
 24 18  1  0
 15  9  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
 10 36  1  0
 11 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 19 44  1  0
 20 45  1  0
 23 46  1  0
 24 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(4-Chlorophenyl)-4-((4-fluorophenyl)methyl)-1-piperidineethanol	MeSH

Chemical Formula

C₂₀H₂₃ClFNO

Average Molecular Weight

347.86

Monoisotopic Molecular Weight

347.1452202

IUPAC Name

1-(4-chlorophenyl)-2-{4-[(4-fluorophenyl)methyl]piperidin-1-yl}ethan-1-ol

Traditional Name

eliprodil

CAS Registry Number

Not Available

SMILES

OC(CN1CCC(CC2=CC=C(F)C=C2)CC1)C1=CC=C(Cl)C=C1

InChI Identifier

InChI=1S/C20H23ClFNO/c21-18-5-3-17(4-6-18)20(24)14-23-11-9-16(10-12-23)13-15-1-7-19(22)8-2-15/h1-8,16,20,24H,9-14H2

InChI Key

GGUSQTSTQSHJAH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4-benzylpiperidines. These are organic compounds containing a benzyl group attached to the 4-position of a piperidine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Benzylpiperidines

Direct Parent

4-benzylpiperidines

Alternative Parents

Substituents

4-benzylpiperidine
Chlorobenzene
Fluorobenzene
Halobenzene
Aralkylamine
Aryl chloride
Aryl fluoride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Tertiary amine
Secondary alcohol
1,2-aminoalcohol
Tertiary aliphatic amine
Azacycle
Organooxygen compound
Organochloride
Organohalogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Alcohol
Organofluoride
Aromatic alcohol
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0251748)

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	4.65	ALOGPS
logP	4.75	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	14.07	ChemAxon
pKa (Strongest Basic)	8.88	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	23.47 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	96.97 m³·mol⁻¹	ChemAxon
Polarizability	37.27 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+H]+	183.611	30932474
DeepCCS	[M-H]-	181.253	30932474
DeepCCS	[M-2H]-	214.755	30932474
DeepCCS	[M+Na]+	190.107	30932474
AllCCS	[M+H]+	182.7	32859911
AllCCS	[M+H-H2O]+	179.8	32859911
AllCCS	[M+NH4]+	185.4	32859911
AllCCS	[M+Na]+	186.2	32859911
AllCCS	[M-H]-	184.4	32859911
AllCCS	[M+Na-2H]-	184.4	32859911
AllCCS	[M+HCOO]-	184.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	12.4927 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.47 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1634.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	274.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	184.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	185.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	215.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	507.0 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	571.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	144.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1092.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	433.7 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	1424.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	327.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	363.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	273.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	123.5 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	7.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Eliprodil	OC(CN1CCC(CC2=CC=C(F)C=C2)CC1)C1=CC=C(Cl)C=C1	3734.4	Standard polar	33892256
Eliprodil	OC(CN1CCC(CC2=CC=C(F)C=C2)CC1)C1=CC=C(Cl)C=C1	2636.7	Standard non polar	33892256
Eliprodil	OC(CN1CCC(CC2=CC=C(F)C=C2)CC1)C1=CC=C(Cl)C=C1	2720.3	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 - Eliprodil GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4j-3962000000-7e7ae77b4834c7d87418	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Eliprodil GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Eliprodil GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Eliprodil GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	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 - Eliprodil 10V, Positive-QTOF	splash10-001j-0019000000-8a9c412547507f84fb92	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eliprodil 20V, Positive-QTOF	splash10-001i-0589000000-8833cbdde4e2d4d2aac1	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eliprodil 40V, Positive-QTOF	splash10-06s7-4910000000-fa4e738c20f5865c6984	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eliprodil 10V, Negative-QTOF	splash10-0002-0109000000-6f5579a3c1c2c740f0e7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eliprodil 20V, Negative-QTOF	splash10-002e-0719000000-617ca80c98222432dba7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eliprodil 40V, Negative-QTOF	splash10-03du-1900000000-0faddc90824e9c93af7e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eliprodil 10V, Positive-QTOF	splash10-000t-0009000000-4edf7c0e55a75d399cd3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eliprodil 20V, Positive-QTOF	splash10-001i-0009000000-df84549c7af8b7ed95c6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eliprodil 40V, Positive-QTOF	splash10-0a4j-1910000000-8e625360274d30bfda02	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eliprodil 10V, Negative-QTOF	splash10-0002-0009000000-4c965720dacd8b23e800	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eliprodil 20V, Negative-QTOF	splash10-0002-0209000000-0d38af3d662550f51d4a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eliprodil 40V, Negative-QTOF	splash10-001l-9315000000-3ae3d86141295cb623ff	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

DB12869

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

Eliprodil

METLIN ID

Not Available

PubChem Compound

60703

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 Eliprodil (HMDB0251748)

MOL for HMDB0251748 (Eliprodil)

3D MOL for HMDB0251748 (Eliprodil)

3D SDF for HMDB0251748 (Eliprodil)

3D-SDF for HMDB0251748 (Eliprodil)

PDB for HMDB0251748 (Eliprodil)

3D PDB for HMDB0251748 (Eliprodil)

SMILES for HMDB0251748 (Eliprodil)

INCHI for HMDB0251748 (Eliprodil)

Structure for HMDB0251748 (Eliprodil)

3D Structure for HMDB0251748 (Eliprodil)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra