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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 11:49:16 UTC

Update Date

2021-09-26 23:06:33 UTC

HMDB ID

HMDB0253384

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Ifenprodil

Description

Ifenprodil, also known as vadilex, 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. Based on a literature review a significant number of articles have been published on Ifenprodil. This compound has been identified in human blood as reported by (PMID: 31557052 ). Ifenprodil is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Ifenprodil 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

HMDB0253384
     RDKit          3D
Ifenprodil
 51 53  0  0  0  0  0  0  0  0999 V2000
    2.4455   -1.6870    1.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7099   -0.4710    0.7977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3293   -0.1043   -0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0876   -1.1049   -1.4307 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7895    0.1519   -0.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4714    0.3557    0.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8405    0.5878    0.7504 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5839    0.6268   -0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9629    0.8617   -0.3932 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9044    0.4231   -1.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466    0.1927   -1.5969 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3059   -0.6313    0.7735 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2655   -1.6457   -0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1943   -1.1626   -1.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2430   -0.2260   -0.6220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6405   -0.8104   -0.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6588    0.1430   -0.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0074    0.1225    1.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9509    0.9859    1.6297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5642    1.8962    0.8061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2236    1.9303   -0.5397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2677    1.0509   -1.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9313    0.1923    0.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4509    0.5780    0.8357 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6143   -1.5236    2.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4255   -1.8540    0.8613 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7956   -2.5954    1.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9100    0.3599    1.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8720    0.8237   -0.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1362   -0.7135   -2.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9307    0.3358    1.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3920    0.7509    1.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3627    1.7770   -0.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4888    0.4534   -2.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0207    0.0337   -2.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9095   -2.3039    0.6463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4283   -2.3702   -0.4885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6729   -2.0947   -1.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5702   -0.6922   -1.8954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2334    0.6835   -1.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8596   -1.1884   -1.7285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6500   -1.6961   -0.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5435   -0.5825    1.7809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2336    0.9796    2.6734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3038    2.5804    1.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7175    2.6557   -1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0393    1.1192   -2.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5167    1.0896    1.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1411   -0.5994    1.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2576    1.2387   -0.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3073    1.0774    1.8130 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 15 23  1  0
 23 24  1  0
 11  5  1  0
 24 12  1  0
 22 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  4 30  1  0
  6 31  1  0
  7 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 24 51  1  0
M  END


  Mrv0541 05281411122D          

 24 26  0  0  0  0            999 V2000
   -4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    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
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0012    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0012    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7157    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    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
   -2.8578    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5723    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    3.7125    0.0000 C   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
   -4.2868    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7157    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5723    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578    5.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 16  1  1  0  0  0  0
 17  5  2  0  0  0  0
 17  6  1  0  0  0  0
 17 15  1  0  0  0  0
 18 11  1  0  0  0  0
 18 12  1  0  0  0  0
 18 15  1  0  0  0  0
 19  7  2  0  0  0  0
 19  8  1  0  0  0  0
 20  9  2  0  0  0  0
 20 10  1  0  0  0  0
 21 16  1  0  0  0  0
 21 19  1  0  0  0  0
 22 13  1  0  0  0  0
 22 14  1  0  0  0  0
 22 16  1  0  0  0  0
 23 20  1  0  0  0  0
 24 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253384

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C(O)C1=CC=C(O)C=C1)N1CCC(CC2=CC=CC=C2)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C21H27NO2/c1-16(21(24)19-7-9-20(23)10-8-19)22-13-11-18(12-14-22)15-17-5-3-2-4-6-17/h2-10,16,18,21,23-24H,11-15H2,1H3

> <INCHI_KEY>
UYNVMODNBIQBMV-UHFFFAOYSA-N

> <FORMULA>
C21H27NO2

> <MOLECULAR_WEIGHT>
325.4446

> <EXACT_MASS>
325.204179113

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
37.52432476297191

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[2-(4-benzylpiperidin-1-yl)-1-hydroxypropyl]phenol

> <ALOGPS_LOGP>
3.98

> <JCHEM_LOGP>
3.5710014461647885

> <ALOGPS_LOGS>
-3.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.022389337135788

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.66631038886235

> <JCHEM_PKA_STRONGEST_BASIC>
9.025073855378915

> <JCHEM_POLAR_SURFACE_AREA>
43.7

> <JCHEM_REFRACTIVITY>
98.3495

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ifenprodil

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253384
     RDKit          3D
Ifenprodil
 51 53  0  0  0  0  0  0  0  0999 V2000
    2.4455   -1.6870    1.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7099   -0.4710    0.7977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3293   -0.1043   -0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0876   -1.1049   -1.4307 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7895    0.1519   -0.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4714    0.3557    0.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8405    0.5878    0.7504 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5839    0.6268   -0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9629    0.8617   -0.3932 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9044    0.4231   -1.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466    0.1927   -1.5969 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3059   -0.6313    0.7735 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2655   -1.6457   -0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1943   -1.1626   -1.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2430   -0.2260   -0.6220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6405   -0.8104   -0.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6588    0.1430   -0.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0074    0.1225    1.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9509    0.9859    1.6297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5642    1.8962    0.8061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2236    1.9303   -0.5397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2677    1.0509   -1.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9313    0.1923    0.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4509    0.5780    0.8357 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6143   -1.5236    2.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4255   -1.8540    0.8613 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7956   -2.5954    1.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9100    0.3599    1.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8720    0.8237   -0.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1362   -0.7135   -2.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9307    0.3358    1.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3920    0.7509    1.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3627    1.7770   -0.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4888    0.4534   -2.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0207    0.0337   -2.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9095   -2.3039    0.6463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4283   -2.3702   -0.4885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6729   -2.0947   -1.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5702   -0.6922   -1.8954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2334    0.6835   -1.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8596   -1.1884   -1.7285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6500   -1.6961   -0.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5435   -0.5825    1.7809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2336    0.9796    2.6734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3038    2.5804    1.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7175    2.6557   -1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0393    1.1192   -2.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5167    1.0896    1.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1411   -0.5994    1.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2576    1.2387   -0.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3073    1.0774    1.8130 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 15 23  1  0
 23 24  1  0
 11  5  1  0
 24 12  1  0
 22 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  4 30  1  0
  6 31  1  0
  7 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 24 51  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      -8.002  10.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.002  15.400   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.336  13.090   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.336  16.170   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -10.669  13.860   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001  11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.668  11.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.002  13.860   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -10.669  15.400   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.668  13.090   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      -5.335  10.780   0.000  0.00  0.00           N+0
HETATM   23  O   UNK     0     -12.003  16.170   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -5.335  13.860   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3   17                                                       
CONECT    6    4   17                                                       
CONECT    7    9   19                                                       
CONECT    8   10   19                                                       
CONECT    9    7   20                                                       
CONECT   10    8   20                                                       
CONECT   11   13   18                                                       
CONECT   12   14   18                                                       
CONECT   13   11   22                                                       
CONECT   14   12   22                                                       
CONECT   15   17   18                                                       
CONECT   16    1   21   22                                                  
CONECT   17    5    6   15                                                  
CONECT   18   11   12   15                                                  
CONECT   19    7    8   21                                                  
CONECT   20    9   10   23                                                  
CONECT   21   16   19   24                                                  
CONECT   22   13   14   16                                                  
CONECT   23   20                                                            
CONECT   24   21                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0253384
HETATM    1  C1  UNL     1       2.445  -1.687   1.331  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.710  -0.471   0.798  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.329  -0.104  -0.514  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.088  -1.105  -1.431  1.00  0.00           O  
HETATM    5  C4  UNL     1       3.789   0.152  -0.430  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.471   0.356   0.748  1.00  0.00           C  
HETATM    7  C6  UNL     1       5.840   0.588   0.750  1.00  0.00           C  
HETATM    8  C7  UNL     1       6.584   0.627  -0.410  1.00  0.00           C  
HETATM    9  O2  UNL     1       7.963   0.862  -0.393  1.00  0.00           O  
HETATM   10  C8  UNL     1       5.904   0.423  -1.593  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.547   0.193  -1.597  1.00  0.00           C  
HETATM   12  N1  UNL     1       0.306  -0.631   0.773  1.00  0.00           N  
HETATM   13  C10 UNL     1      -0.265  -1.646  -0.021  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.194  -1.163  -1.112  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.243  -0.226  -0.622  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.641  -0.810  -0.720  1.00  0.00           C  
HETATM   17  C14 UNL     1      -4.659   0.143  -0.227  1.00  0.00           C  
HETATM   18  C15 UNL     1      -5.007   0.122   1.103  1.00  0.00           C  
HETATM   19  C16 UNL     1      -5.951   0.986   1.630  1.00  0.00           C  
HETATM   20  C17 UNL     1      -6.564   1.896   0.806  1.00  0.00           C  
HETATM   21  C18 UNL     1      -6.224   1.930  -0.540  1.00  0.00           C  
HETATM   22  C19 UNL     1      -5.268   1.051  -1.058  1.00  0.00           C  
HETATM   23  C20 UNL     1      -1.931   0.192   0.791  1.00  0.00           C  
HETATM   24  C21 UNL     1      -0.451   0.578   0.836  1.00  0.00           C  
HETATM   25  H1  UNL     1       2.614  -1.524   2.411  1.00  0.00           H  
HETATM   26  H2  UNL     1       3.425  -1.854   0.861  1.00  0.00           H  
HETATM   27  H3  UNL     1       1.796  -2.595   1.284  1.00  0.00           H  
HETATM   28  H4  UNL     1       1.910   0.360   1.546  1.00  0.00           H  
HETATM   29  H5  UNL     1       1.872   0.824  -0.947  1.00  0.00           H  
HETATM   30  H6  UNL     1       2.136  -0.714  -2.338  1.00  0.00           H  
HETATM   31  H7  UNL     1       3.931   0.336   1.680  1.00  0.00           H  
HETATM   32  H8  UNL     1       6.392   0.751   1.683  1.00  0.00           H  
HETATM   33  H9  UNL     1       8.363   1.777  -0.448  1.00  0.00           H  
HETATM   34  H10 UNL     1       6.489   0.453  -2.512  1.00  0.00           H  
HETATM   35  H11 UNL     1       4.021   0.034  -2.534  1.00  0.00           H  
HETATM   36  H12 UNL     1      -0.910  -2.304   0.646  1.00  0.00           H  
HETATM   37  H13 UNL     1       0.428  -2.370  -0.489  1.00  0.00           H  
HETATM   38  H14 UNL     1      -1.673  -2.095  -1.533  1.00  0.00           H  
HETATM   39  H15 UNL     1      -0.570  -0.692  -1.895  1.00  0.00           H  
HETATM   40  H16 UNL     1      -2.233   0.684  -1.257  1.00  0.00           H  
HETATM   41  H17 UNL     1      -3.860  -1.188  -1.728  1.00  0.00           H  
HETATM   42  H18 UNL     1      -3.650  -1.696  -0.048  1.00  0.00           H  
HETATM   43  H19 UNL     1      -4.543  -0.582   1.781  1.00  0.00           H  
HETATM   44  H20 UNL     1      -6.234   0.980   2.673  1.00  0.00           H  
HETATM   45  H21 UNL     1      -7.304   2.580   1.195  1.00  0.00           H  
HETATM   46  H22 UNL     1      -6.718   2.656  -1.177  1.00  0.00           H  
HETATM   47  H23 UNL     1      -5.039   1.119  -2.113  1.00  0.00           H  
HETATM   48  H24 UNL     1      -2.517   1.090   1.041  1.00  0.00           H  
HETATM   49  H25 UNL     1      -2.141  -0.599   1.522  1.00  0.00           H  
HETATM   50  H26 UNL     1      -0.258   1.239  -0.017  1.00  0.00           H  
HETATM   51  H27 UNL     1      -0.307   1.077   1.813  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   12   28
CONECT    3    4    5   29
CONECT    4   30
CONECT    5    6    6   11
CONECT    6    7   31
CONECT    7    8    8   32
CONECT    8    9   10
CONECT    9   33
CONECT   10   11   11   34
CONECT   11   35
CONECT   12   13   24
CONECT   13   14   36   37
CONECT   14   15   38   39
CONECT   15   16   23   40
CONECT   16   17   41   42
CONECT   17   18   18   22
CONECT   18   19   43
CONECT   19   20   20   44
CONECT   20   21   45
CONECT   21   22   22   46
CONECT   22   47
CONECT   23   24   48   49
CONECT   24   50   51
END

HMDB0253384
     RDKit          3D
Ifenprodil
 51 53  0  0  0  0  0  0  0  0999 V2000
    2.4455   -1.6870    1.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7099   -0.4710    0.7977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3293   -0.1043   -0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0876   -1.1049   -1.4307 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7895    0.1519   -0.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4714    0.3557    0.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8405    0.5878    0.7504 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5839    0.6268   -0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9629    0.8617   -0.3932 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9044    0.4231   -1.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466    0.1927   -1.5969 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3059   -0.6313    0.7735 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2655   -1.6457   -0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1943   -1.1626   -1.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2430   -0.2260   -0.6220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6405   -0.8104   -0.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6588    0.1430   -0.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0074    0.1225    1.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9509    0.9859    1.6297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5642    1.8962    0.8061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2236    1.9303   -0.5397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2677    1.0509   -1.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9313    0.1923    0.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4509    0.5780    0.8357 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6143   -1.5236    2.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4255   -1.8540    0.8613 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7956   -2.5954    1.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9100    0.3599    1.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8720    0.8237   -0.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1362   -0.7135   -2.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9307    0.3358    1.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3920    0.7509    1.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3627    1.7770   -0.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4888    0.4534   -2.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0207    0.0337   -2.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9095   -2.3039    0.6463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4283   -2.3702   -0.4885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6729   -2.0947   -1.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5702   -0.6922   -1.8954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2334    0.6835   -1.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8596   -1.1884   -1.7285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6500   -1.6961   -0.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5435   -0.5825    1.7809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2336    0.9796    2.6734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3038    2.5804    1.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7175    2.6557   -1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0393    1.1192   -2.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5167    1.0896    1.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1411   -0.5994    1.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2576    1.2387   -0.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3073    1.0774    1.8130 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 15 23  1  0
 23 24  1  0
 11  5  1  0
 24 12  1  0
 22 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  4 30  1  0
  6 31  1  0
  7 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 24 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(4-Benzylpiperidino)-1-(4-hydroxyphenyl)-2-methyl-1-ethanol	MeSH
4-Benzyl-alpha-(p-hydroxyphenyl)-beta-methyl-1-piperidineethanol	MeSH
Vadilex	MeSH
alpha-(4-Hydroxyphenyl)-beta-methyl-4-(phenylmethyl)-1-piperidine ethanol	MeSH
Ifenprodil hydrochloride	MeSH
Ifenprodil hydrochloride, (+-)-isomer	MeSH
Ifenprodil tartrate	MeSH
Ifenprodil tartrate (1:1), (r,s)-(+-)-(R-(r,r))-isomer	MeSH
Ifenprodil tartrate (1:1), (R-(r,r))-isomer	MeSH
Ifenprodil tartrate (2:1), (R-(r,r))-isomer	MeSH
Ifenprodil, (r,s)-(+-)-isomer	MeSH
Ifenprodil, tartrate(R-(r,r))-isomer	MeSH
RC 61-91IFENPRODIL tartrATE	ChEMBL
RC 61-91IFENPRODIL tartric acid	Generator

Chemical Formula

C₂₁H₂₇NO₂

Average Molecular Weight

325.4446

Monoisotopic Molecular Weight

325.204179113

IUPAC Name

4-[2-(4-benzylpiperidin-1-yl)-1-hydroxypropyl]phenol

Traditional Name

ifenprodil

CAS Registry Number

Not Available

SMILES

CC(C(O)C1=CC=C(O)C=C1)N1CCC(CC2=CC=CC=C2)CC1

InChI Identifier

InChI=1S/C21H27NO2/c1-16(21(24)19-7-9-20(23)10-8-19)22-13-11-18(12-14-22)15-17-5-3-2-4-6-17/h2-10,16,18,21,23-24H,11-15H2,1H3

InChI Key

UYNVMODNBIQBMV-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
Phenylpropane
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Monocyclic benzene moiety
Benzenoid
1,2-aminoalcohol
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Amine
Alcohol
Aromatic alcohol
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)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.98	ALOGPS
logP	3.57	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	9.67	ChemAxon
pKa (Strongest Basic)	9.03	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	43.7 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	98.35 m³·mol⁻¹	ChemAxon
Polarizability	37.52 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	177.521	30932474
DeepCCS	[M-H]-	175.163	30932474
DeepCCS	[M-2H]-	209.007	30932474
DeepCCS	[M+Na]+	184.234	30932474
AllCCS	[M+H]+	183.9	32859911
AllCCS	[M+H-H2O]+	180.9	32859911
AllCCS	[M+NH4]+	186.7	32859911
AllCCS	[M+Na]+	187.6	32859911
AllCCS	[M-H]-	183.9	32859911
AllCCS	[M+Na-2H]-	184.1	32859911
AllCCS	[M+HCOO]-	184.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ifenprodil	CC(C(O)C1=CC=C(O)C=C1)N1CCC(CC2=CC=CC=C2)CC1	3487.0	Standard polar	33892256
Ifenprodil	CC(C(O)C1=CC=C(O)C=C1)N1CCC(CC2=CC=CC=C2)CC1	2571.3	Standard non polar	33892256
Ifenprodil	CC(C(O)C1=CC=C(O)C=C1)N1CCC(CC2=CC=CC=C2)CC1	2828.2	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 - Ifenprodil GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fk9-3940000000-b41acd48bed1c2d4f4b7	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ifenprodil GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ifenprodil GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ifenprodil GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ifenprodil GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ifenprodil GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ifenprodil GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ifenprodil GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ifenprodil , positive-QTOF	splash10-004i-0319000000-a8642bda70c1638039bd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ifenprodil 35V, Positive-QTOF	splash10-056r-0709000000-0a5023758c8c64a175de	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ifenprodil 10V, Positive-QTOF	splash10-0a6r-0019000000-88a13d2c606a609ce078	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ifenprodil 20V, Positive-QTOF	splash10-0pb9-3496000000-679c639538aa49c0a2a8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ifenprodil 40V, Positive-QTOF	splash10-075d-9820000000-256d6b1ee22b07f5438c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ifenprodil 10V, Negative-QTOF	splash10-00di-0009000000-9792b49642ef56c70723	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ifenprodil 20V, Negative-QTOF	splash10-05fr-0429000000-63b16c23780ec9b0cd74	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ifenprodil 40V, Negative-QTOF	splash10-00dl-4900000000-11a2c3711ad90f5a7e0f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ifenprodil 10V, Positive-QTOF	splash10-004i-0009000000-261e6fd14ce1c606bcf1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ifenprodil 20V, Positive-QTOF	splash10-0a59-2349000000-c040e7d5f75de86f1eb4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ifenprodil 40V, Positive-QTOF	splash10-0006-9510000000-b5c0ae7350c429fd3645	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ifenprodil 10V, Negative-QTOF	splash10-00di-0009000000-c92e2470b1dd5bc174f1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ifenprodil 20V, Negative-QTOF	splash10-00di-1519000000-6182dcba2a5afc6c6e31	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ifenprodil 40V, Negative-QTOF	splash10-0006-7941000000-788a5231c023a49bf275	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

DB08954

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3561

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ifenprodil

METLIN ID

Not Available

PubChem Compound

3689

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 Ifenprodil (HMDB0253384)

MOL for HMDB0253384 (Ifenprodil)

3D MOL for HMDB0253384 (Ifenprodil)

3D SDF for HMDB0253384 (Ifenprodil)

3D-SDF for HMDB0253384 (Ifenprodil)

PDB for HMDB0253384 (Ifenprodil)

3D PDB for HMDB0253384 (Ifenprodil)

SMILES for HMDB0253384 (Ifenprodil)

INCHI for HMDB0253384 (Ifenprodil)

Structure for HMDB0253384 (Ifenprodil)

3D Structure for HMDB0253384 (Ifenprodil)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra