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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-11-21 17:40:50 UTC

Update Date

2022-03-07 03:18:14 UTC

HMDB ID

HMDB0240236

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Quifenadine

Description

Quifenadine belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. In humans, quifenadine is involved in the quifenadine h1-antihistamine action pathway. Quifenadine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Quifenadine.

Structure

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

HMDB0240236
     RDKit          3D
Quifenadine
 45 48  0  0  0  0  0  0  0  0999 V2000
   -0.1463   -0.4495    1.6107 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4250   -0.2314    0.3507 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1946   -1.4207   -0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1646   -1.9098    0.8365 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -3.0158    0.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7286   -3.6866   -0.6652 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7691   -3.1916   -1.5144 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0029   -2.0814   -1.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3014    0.9751    0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4611    1.6401    1.7022 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2557    2.7381    1.8592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9479    3.2372    0.7957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8206    2.6014   -0.4368 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0101    1.4868   -0.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6490    0.1339   -0.6170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2639    1.4742   -0.2697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7660    1.3632   -0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3164    0.8065   -1.5271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4965   -0.4187   -1.9193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6718   -0.8460   -0.7970 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5545   -0.9982    0.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0922    0.3112    0.8454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1596   -1.2796    2.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3499   -1.4259    1.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6798   -3.3908    1.2346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3352   -4.5400   -0.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6237   -3.7259   -2.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2500   -1.6955   -1.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8960    1.2244    2.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3093    3.1901    2.8592 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5697    4.1066    0.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3887    3.0343   -1.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9346    1.0172   -1.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1592    0.2797   -1.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9339    1.7951    0.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9712    2.2793   -0.9727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2147    2.3379    0.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3619    0.4839   -1.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3286    1.5563   -2.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1750   -1.2643   -2.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9292   -0.1589   -2.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4476   -1.5737   -0.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1334   -1.6405    1.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2117    0.2709    0.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6778    0.6016    1.8228 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  2  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  2 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
  8  3  1  0
 14  9  1  0
 20 15  1  0
 22 17  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 21 42  1  0
 21 43  1  0
 22 44  1  0
 22 45  1  0
M  END

      
  Mrv1652311211718402D          

 22 25  0  0  0  0            999 V2000
   -3.0578    1.5508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0578    0.7258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3433    1.9633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7723    1.9633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3433    1.1383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6289    1.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9143    1.9634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9143    2.7883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6287    3.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3433    2.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7722    0.3134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7722   -0.5116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0579   -0.9242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3433   -0.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3433    0.3133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7723    2.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2012    2.7883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2013    1.9634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4868    3.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4868    1.5508    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6984    2.1760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2140    2.5681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  3  6  2  0  0  0  0
 10  3  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  2 11  2  0  0  0  0
 15  2  1  0  0  0  0
 17 18  1  0  0  0  0
  4 16  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 19 22  1  0  0  0  0
 16 19  1  0  0  0  0
 19 17  1  0  0  0  0
 18 20  1  0  0  0  0
  4 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0240236

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(C1CC2CCN1CC2)(C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H23NO/c22-20(17-7-3-1-4-8-17,18-9-5-2-6-10-18)19-15-16-11-13-21(19)14-12-16/h1-10,16,19,22H,11-15H2

> <INCHI_KEY>
JNZMANQLHCNXTA-UHFFFAOYSA-N

> <FORMULA>
C20H23NO

> <MOLECULAR_WEIGHT>
293.41

> <EXACT_MASS>
293.177964365

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
33.28513388006366

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{1-azabicyclo[2.2.2]octan-2-yl}diphenylmethanol

> <ALOGPS_LOGP>
3.77

> <JCHEM_LOGP>
3.5174492816666674

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.871921181271166

> <JCHEM_PKA_STRONGEST_BASIC>
9.358786597659332

> <JCHEM_POLAR_SURFACE_AREA>
23.47

> <JCHEM_REFRACTIVITY>
89.89559999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.17e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-azabicyclo[2.2.2]octan-2-yldiphenylmethanol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0240236
     RDKit          3D
Quifenadine
 45 48  0  0  0  0  0  0  0  0999 V2000
   -0.1463   -0.4495    1.6107 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4250   -0.2314    0.3507 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1946   -1.4207   -0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1646   -1.9098    0.8365 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -3.0158    0.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7286   -3.6866   -0.6652 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7691   -3.1916   -1.5144 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0029   -2.0814   -1.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3014    0.9751    0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4611    1.6401    1.7022 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2557    2.7381    1.8592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9479    3.2372    0.7957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8206    2.6014   -0.4368 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0101    1.4868   -0.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6490    0.1339   -0.6170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2639    1.4742   -0.2697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7660    1.3632   -0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3164    0.8065   -1.5271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4965   -0.4187   -1.9193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6718   -0.8460   -0.7970 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5545   -0.9982    0.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0922    0.3112    0.8454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1596   -1.2796    2.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3499   -1.4259    1.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6798   -3.3908    1.2346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3352   -4.5400   -0.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6237   -3.7259   -2.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2500   -1.6955   -1.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8960    1.2244    2.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3093    3.1901    2.8592 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5697    4.1066    0.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3887    3.0343   -1.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9346    1.0172   -1.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1592    0.2797   -1.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9339    1.7951    0.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9712    2.2793   -0.9727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2147    2.3379    0.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3619    0.4839   -1.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3286    1.5563   -2.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1750   -1.2643   -2.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9292   -0.1589   -2.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4476   -1.5737   -0.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1334   -1.6405    1.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2117    0.2709    0.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6778    0.6016    1.8228 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  2  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  2 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
  8  3  1  0
 14  9  1  0
 20 15  1  0
 22 17  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 21 42  1  0
 21 43  1  0
 22 44  1  0
 22 45  1  0
M  END

HEADER    PROTEIN                                 21-NOV-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-NOV-17         0                                  
HETATM    1  C   UNK     0      -5.708   2.895   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.708   1.355   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.374   3.665   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.042   3.665   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.374   2.125   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -3.041   2.895   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.707   3.665   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.707   5.205   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.040   5.975   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.374   5.205   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.041   0.585   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -7.041  -0.955   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.708  -1.725   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.374  -0.955   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.374   0.585   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -7.042   5.205   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -9.709   5.205   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -9.709   3.665   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.375   5.975   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      -8.375   2.895   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      -8.770   4.062   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -7.866   4.794   0.000  0.00  0.00           C+0
CONECT    1    2    3    4    5                                             
CONECT    2    1   11   15                                                  
CONECT    3    1    6   10                                                  
CONECT    4    1   16   20                                                  
CONECT    5    1                                                            
CONECT    6    7    3                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    3                                                       
CONECT   11   12    2                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    2                                                       
CONECT   16    4   19                                                       
CONECT   17   18   19                                                       
CONECT   18   17   20                                                       
CONECT   19   22   16   17                                                  
CONECT   20   21   18    4                                                  
CONECT   21   20   22                                                       
CONECT   22   21   19                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0240236
HETATM    1  O1  UNL     1      -0.146  -0.450   1.611  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.425  -0.231   0.351  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.195  -1.421  -0.037  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.165  -1.910   0.836  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.922  -3.016   0.544  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.729  -3.687  -0.665  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.769  -3.192  -1.514  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.003  -2.081  -1.230  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.301   0.975   0.504  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.461   1.640   1.702  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.256   2.738   1.859  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.948   3.237   0.796  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.821   2.601  -0.437  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.010   1.487  -0.583  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.649   0.134  -0.617  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.264   1.474  -0.270  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.766   1.363  -0.223  1.00  0.00           C  
HETATM   18  C17 UNL     1      -3.316   0.806  -1.527  1.00  0.00           C  
HETATM   19  C18 UNL     1      -2.497  -0.419  -1.919  1.00  0.00           C  
HETATM   20  N1  UNL     1      -1.672  -0.846  -0.797  1.00  0.00           N  
HETATM   21  C19 UNL     1      -2.554  -0.998   0.332  1.00  0.00           C  
HETATM   22  C20 UNL     1      -3.092   0.311   0.845  1.00  0.00           C  
HETATM   23  H1  UNL     1       0.160  -1.280   2.030  1.00  0.00           H  
HETATM   24  H2  UNL     1       2.350  -1.426   1.782  1.00  0.00           H  
HETATM   25  H3  UNL     1       3.680  -3.391   1.235  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.335  -4.540  -0.855  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.624  -3.726  -2.463  1.00  0.00           H  
HETATM   28  H6  UNL     1       0.250  -1.696  -1.900  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.896   1.224   2.549  1.00  0.00           H  
HETATM   30  H8  UNL     1       2.309   3.190   2.859  1.00  0.00           H  
HETATM   31  H9  UNL     1       3.570   4.107   0.944  1.00  0.00           H  
HETATM   32  H10 UNL     1       3.389   3.034  -1.248  1.00  0.00           H  
HETATM   33  H11 UNL     1       1.935   1.017  -1.557  1.00  0.00           H  
HETATM   34  H12 UNL     1      -0.159   0.280  -1.617  1.00  0.00           H  
HETATM   35  H13 UNL     1      -0.934   1.795   0.742  1.00  0.00           H  
HETATM   36  H14 UNL     1      -0.971   2.279  -0.973  1.00  0.00           H  
HETATM   37  H15 UNL     1      -3.215   2.338   0.011  1.00  0.00           H  
HETATM   38  H16 UNL     1      -4.362   0.484  -1.300  1.00  0.00           H  
HETATM   39  H17 UNL     1      -3.329   1.556  -2.325  1.00  0.00           H  
HETATM   40  H18 UNL     1      -3.175  -1.264  -2.205  1.00  0.00           H  
HETATM   41  H19 UNL     1      -1.929  -0.159  -2.809  1.00  0.00           H  
HETATM   42  H20 UNL     1      -3.448  -1.574  -0.058  1.00  0.00           H  
HETATM   43  H21 UNL     1      -2.133  -1.641   1.130  1.00  0.00           H  
HETATM   44  H22 UNL     1      -4.212   0.271   0.987  1.00  0.00           H  
HETATM   45  H23 UNL     1      -2.678   0.602   1.823  1.00  0.00           H  
CONECT    1    2   23
CONECT    2    3    9   15
CONECT    3    4    4    8
CONECT    4    5   24
CONECT    5    6    6   25
CONECT    6    7   26
CONECT    7    8    8   27
CONECT    8   28
CONECT    9   10   10   14
CONECT   10   11   29
CONECT   11   12   12   30
CONECT   12   13   31
CONECT   13   14   14   32
CONECT   14   33
CONECT   15   16   20   34
CONECT   16   17   35   36
CONECT   17   18   22   37
CONECT   18   19   38   39
CONECT   19   20   40   41
CONECT   20   21
CONECT   21   22   42   43
CONECT   22   44   45
END

HMDB0240236
     RDKit          3D
Quifenadine
 45 48  0  0  0  0  0  0  0  0999 V2000
   -0.1463   -0.4495    1.6107 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4250   -0.2314    0.3507 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1946   -1.4207   -0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1646   -1.9098    0.8365 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -3.0158    0.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7286   -3.6866   -0.6652 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7691   -3.1916   -1.5144 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0029   -2.0814   -1.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3014    0.9751    0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4611    1.6401    1.7022 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2557    2.7381    1.8592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9479    3.2372    0.7957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8206    2.6014   -0.4368 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0101    1.4868   -0.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6490    0.1339   -0.6170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2639    1.4742   -0.2697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7660    1.3632   -0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3164    0.8065   -1.5271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4965   -0.4187   -1.9193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6718   -0.8460   -0.7970 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5545   -0.9982    0.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0922    0.3112    0.8454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1596   -1.2796    2.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3499   -1.4259    1.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6798   -3.3908    1.2346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3352   -4.5400   -0.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6237   -3.7259   -2.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2500   -1.6955   -1.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8960    1.2244    2.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3093    3.1901    2.8592 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5697    4.1066    0.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3887    3.0343   -1.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9346    1.0172   -1.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1592    0.2797   -1.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9339    1.7951    0.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9712    2.2793   -0.9727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2147    2.3379    0.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3619    0.4839   -1.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3286    1.5563   -2.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1750   -1.2643   -2.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9292   -0.1589   -2.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4476   -1.5737   -0.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1334   -1.6405    1.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2117    0.2709    0.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6778    0.6016    1.8228 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  2  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  2 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
  8  3  1  0
 14  9  1  0
 20 15  1  0
 22 17  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 21 42  1  0
 21 43  1  0
 22 44  1  0
 22 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Α,α-diphenyl-3-quinuclidinemethanol	HMDB
alpha,alpha-Diphenyl-3-quinuclidinemethanol	HMDB
Diphenyl-3-quinuclidylcarbinol	HMDB
Quifenadine	HMDB

Chemical Formula

C₂₀H₂₃NO

Average Molecular Weight

293.41

Monoisotopic Molecular Weight

293.177964365

IUPAC Name

{1-azabicyclo[2.2.2]octan-2-yl}diphenylmethanol

Traditional Name

1-azabicyclo[2.2.2]octan-2-yldiphenylmethanol

CAS Registry Number

10447-39-9

SMILES

OC(C1CC2CCN1CC2)(C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C20H23NO/c22-20(17-7-3-1-4-8-17,18-9-5-2-6-10-18)19-15-16-11-13-21(19)14-12-16/h1-10,16,19,22H,11-15H2

InChI Key

JNZMANQLHCNXTA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Quinuclidine
Aralkylamine
Piperidine
Tertiary alcohol
Tertiary aliphatic amine
Tertiary amine
1,2-aminoalcohol
Organoheterocyclic compound
Azacycle
Aromatic alcohol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0240236)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Quifenadine H1-Antihistamine Action (PathBank: SMP0060743)

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	3.77	ALOGPS
logP	3.52	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	12.87	ChemAxon
pKa (Strongest Basic)	9.36	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	3	ChemAxon
Refractivity	89.9 m³·mol⁻¹	ChemAxon
Polarizability	33.29 Å³	ChemAxon
Number of Rings	4	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
AllCCS	[M-H]-	179.405	31661259
AllCCS	[M+H]+	172.105	31661259
DeepCCS	[M+H]+	165.926	30932474
DeepCCS	[M-H]-	163.568	30932474
DeepCCS	[M-2H]-	196.454	30932474
DeepCCS	[M+Na]+	172.019	30932474
AllCCS	[M+H]+	172.1	32859911
AllCCS	[M+H-H2O]+	168.6	32859911
AllCCS	[M+NH4]+	175.3	32859911
AllCCS	[M+Na]+	176.3	32859911
AllCCS	[M-H]-	179.4	32859911
AllCCS	[M+Na-2H]-	179.0	32859911
AllCCS	[M+HCOO]-	178.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.93 minutes	32390414
Predicted by Siyang on May 30, 2022	10.4774 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.03 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	996.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	223.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	167.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	183.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	99.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	364.7 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	382.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	563.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	787.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	277.8 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	850.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	212.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	285.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	450.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	432.2 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	78.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Quifenadine	OC(C1CC2CCN1CC2)(C1=CC=CC=C1)C1=CC=CC=C1	2791.3	Standard polar	33892256
Quifenadine	OC(C1CC2CCN1CC2)(C1=CC=CC=C1)C1=CC=CC=C1	2297.7	Standard non polar	33892256
Quifenadine	OC(C1CC2CCN1CC2)(C1=CC=CC=C1)C1=CC=CC=C1	2361.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Quifenadine,1TMS,isomer #1	C[Si](C)(C)OC(C1=CC=CC=C1)(C1=CC=CC=C1)C1CC2CCN1CC2	2432.9	Semi standard non polar	33892256
Quifenadine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(C1=CC=CC=C1)(C1=CC=CC=C1)C1CC2CCN1CC2	2669.3	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 - Quifenadine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Quifenadine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Quifenadine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Quifenadine GC-MS ("Quifenadine,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	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 - Quifenadine 10V, Positive-QTOF	splash10-0006-0190000000-256fa29ee83a48fb7eeb	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quifenadine 20V, Positive-QTOF	splash10-0036-0980000000-b7e02cfd3848711fd415	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quifenadine 40V, Positive-QTOF	splash10-08fr-3900000000-6776e6b0e1ea3161e72c	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quifenadine 10V, Negative-QTOF	splash10-0006-0090000000-0ae6164e56a923d4a348	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quifenadine 20V, Negative-QTOF	splash10-0006-1190000000-683090136635d8db9f23	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quifenadine 40V, Negative-QTOF	splash10-08i0-4930000000-bb3852505004a55484e5	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quifenadine 10V, Negative-QTOF	splash10-0006-0090000000-17a2775e8d18d2b59e53	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quifenadine 20V, Negative-QTOF	splash10-0006-0490000000-b01fba61a2444ab31cb1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quifenadine 40V, Negative-QTOF	splash10-0a4i-0940000000-c0b9e9dfa089487f14a4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quifenadine 10V, Positive-QTOF	splash10-0006-0090000000-235438a9e84c80482884	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quifenadine 20V, Positive-QTOF	splash10-0006-0190000000-6bb1a66dbb898613e4cd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quifenadine 40V, Positive-QTOF	splash10-03di-0900000000-7c4da14f6ad13d15d47d	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Quifenadine H1-Antihistamine Action		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2308316

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Quifenadine

METLIN ID

Not Available

PubChem Compound

3045613

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

Makarov L, Balykova L, Soldatova O, Komolyatova V, Serebruany V: The antiarrhythmic properties of quifenadine, H1-histamine receptor blocker in children with premature beats: a randomized controlled pilot trial. Am J Ther. 2010 Jul-Aug;17(4):396-401. doi: 10.1097/MJT.0b013e3181a86987. [PubMed:19487925 ]

Showing metabocard for Quifenadine (HMDB0240236)

MOL for HMDB0240236 (Quifenadine)

3D MOL for HMDB0240236 (Quifenadine)

3D SDF for HMDB0240236 (Quifenadine)

3D-SDF for HMDB0240236 (Quifenadine)

PDB for HMDB0240236 (Quifenadine)

3D PDB for HMDB0240236 (Quifenadine)

SMILES for HMDB0240236 (Quifenadine)

INCHI for HMDB0240236 (Quifenadine)

Structure for HMDB0240236 (Quifenadine)

3D Structure for HMDB0240236 (Quifenadine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra