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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-10-17 09:48:25 UTC

Update Date

2020-04-22 23:33:43 UTC

HMDB ID

HMDB0005030

Secondary Accession Numbers

HMDB05030

Metabolite Identification

Common Name

Fexofenadine

Description

Fexofenadine is an antihistamine drug used in the treatment of hayfever and similar allergy symptoms. It was developed as a successor of and alternative to terfenadine, an antihistamine with potentially fatal contraindications. Fexofenadine, like other second-generation antihistamines, does not readily enter the brain from the blood, and so causes less drowsiness than first generation histamine receptor antagonists; Fexofenadine hydrochloride (brand names include Allegra and Telfast) is an antihistamine drug used in the treatment of hayfever and similar allergy symptoms. It was developed as a successor of and alternative to terfenadine, an antihistamine with potentially fatal contraindications. Fexofenadine, like other second generation antihistamines, does not readily enter the brain from the blood, and so causes less drowsiness than first-generation histamine-receptor antagonists.

Structure

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

  Mrv1652309201717592D          

 37 40  0  0  0  0            999 V2000
    8.3812  -11.1373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3812  -11.9623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0957  -12.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8102  -11.9623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8102  -11.1373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0957  -10.7248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2392  -11.9623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2392  -11.1373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5247  -10.7248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9538  -12.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6681  -11.9623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6681  -11.1373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.8102  -10.3123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   12.6450   -7.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.0734   -9.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
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  7 10  2  0  0  0  0
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  9 20  1  0  0  0  0
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 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 32 36  1  0  0  0  0
 32 37  1  0  0  0  0
M  END

HMDB0005030
     RDKit          3D
Fexofenadine
 76 79  0  0  0  0  0  0  0  0999 V2000
    6.9635    1.7697    1.5857 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3776    0.6451    0.6623 C   0  0  0  0  0  0  0  0  0  0  0  0
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 37 76  1  0
M  END

  Mrv1652309201717592D          

 37 40  0  0  0  0            999 V2000
    8.3812  -11.1373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3812  -11.9623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0957  -12.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  7 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  8 13  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
  9 20  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 25 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 32 36  1  0  0  0  0
 32 37  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005030

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)(C(O)=O)C1=CC=C(C=C1)C(O)CCCN1CCC(CC1)C(O)(C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C32H39NO4/c1-31(2,30(35)36)25-17-15-24(16-18-25)29(34)14-9-21-33-22-19-28(20-23-33)32(37,26-10-5-3-6-11-26)27-12-7-4-8-13-27/h3-8,10-13,15-18,28-29,34,37H,9,14,19-23H2,1-2H3,(H,35,36)

> <INCHI_KEY>
RWTNPBWLLIMQHL-UHFFFAOYSA-N

> <FORMULA>
C32H39NO4

> <MOLECULAR_WEIGHT>
501.6564

> <EXACT_MASS>
501.287908741

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
57.42211230747313

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(4-{1-hydroxy-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]butyl}phenyl)-2-methylpropanoic acid

> <ALOGPS_LOGP>
5.02

> <JCHEM_LOGP>
2.9385009869991623

> <ALOGPS_LOGS>
-5.28

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.19564234596055

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.04043821405387

> <JCHEM_PKA_STRONGEST_BASIC>
9.010501448307204

> <JCHEM_POLAR_SURFACE_AREA>
80.99999999999999

> <JCHEM_REFRACTIVITY>
147.98460000000009

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.66e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fexofenadine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005030
     RDKit          3D
Fexofenadine
 76 79  0  0  0  0  0  0  0  0999 V2000
    6.9635    1.7697    1.5857 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3776    0.6451    0.6623 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9752   -0.4491    1.5504 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4766    1.0664   -0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6393    0.5279   -0.2242 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3396    2.0622   -1.2151 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2181    0.0658   -0.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6990    0.5941   -1.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6083   -0.0281   -1.8300 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -1.1638   -1.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8771   -1.7709   -2.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9109   -3.1392   -2.1302 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5636   -1.2278   -1.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4036   -1.5231   -0.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1385   -1.1849    0.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3005    0.1394    0.6295 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8482    0.7028   -0.5434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2160    0.1007   -0.8671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1119    0.0081    0.3085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3918    0.7418   -0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0373    2.0899   -0.3055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1468    0.1921   -1.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1345    1.0180   -1.6977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9053    0.5949   -2.7622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7217   -0.6556   -3.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7446   -1.4770   -2.7690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9707   -1.0330   -1.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2599    0.7791    1.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6647   -0.4174    1.7152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4696   -0.4467    2.8204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8942    0.7025    3.4116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4982    1.9034    2.8757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6864    1.9459    1.7603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5579    0.3964    1.6307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1001    0.5157    1.7887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5435   -1.6854   -0.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6190   -1.0822    0.4451 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9220    2.2070    1.9780 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3375    2.5388    1.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3957    1.2992    2.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4360   -0.5843    2.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0322   -0.2009    1.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0176   -1.4284    1.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8666    2.9302   -1.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1372    1.4869   -1.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2381    0.4455   -2.7516 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8843   -1.4005   -3.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8726   -3.6161   -1.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7522   -0.0956   -1.5832 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7717   -1.4699   -2.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7086   -2.5936    0.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2288   -0.9597    0.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6493   -1.8725    0.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2657   -1.5619    1.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9498    1.8203   -0.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2600    0.5765   -1.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9921   -0.8821   -1.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6418    0.7354   -1.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4152   -1.0757    0.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3333    2.3328   -1.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3436    2.0110   -1.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6811    1.2293   -3.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2899   -1.0469   -4.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5396   -2.4535   -3.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2314   -1.6889   -1.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3430   -1.3603    1.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7709   -1.4116    3.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5251    0.6236    4.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8505    2.8023    3.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3655    2.8973    1.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9677   -0.2645    2.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0138    1.4017    1.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7803    1.5560    2.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7577   -0.1276    2.6265 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1081   -2.5592    0.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0190   -1.5178    1.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  2  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 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
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 20 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 19 34  1  0
 34 35  1  0
 10 36  1  0
 36 37  2  0
 37  7  1  0
 35 16  1  0
 27 22  1  0
 33 28  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  3 41  1  0
  3 42  1  0
  3 43  1  0
  6 44  1  0
  8 45  1  0
  9 46  1  0
 11 47  1  0
 12 48  1  0
 13 49  1  0
 13 50  1  0
 14 51  1  0
 14 52  1  0
 15 53  1  0
 15 54  1  0
 17 55  1  0
 17 56  1  0
 18 57  1  0
 18 58  1  0
 19 59  1  0
 21 60  1  0
 23 61  1  0
 24 62  1  0
 25 63  1  0
 26 64  1  0
 27 65  1  0
 29 66  1  0
 30 67  1  0
 31 68  1  0
 32 69  1  0
 33 70  1  0
 34 71  1  0
 34 72  1  0
 35 73  1  0
 35 74  1  0
 36 75  1  0
 37 76  1  0
M  END

HEADER    PROTEIN                                 20-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-SEP-17         0                                  
HETATM    1  C   UNK     0      15.645 -20.790   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.645 -22.330   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.979 -23.100   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.312 -22.330   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      18.312 -20.790   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.979 -20.020   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.980 -22.330   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.980 -20.790   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.646 -20.020   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.314 -23.100   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.647 -22.330   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.647 -20.790   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.314 -20.020   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.646 -18.479   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.982 -17.708   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.982 -16.168   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      19.648 -15.398   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      18.312 -16.169   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.312 -17.709   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      18.312 -19.250   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      19.648 -13.859   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      20.983 -13.089   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      22.298 -13.848   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      23.604 -13.095   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      24.915 -13.851   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      23.604 -11.549   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      24.915 -15.399   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      26.248 -16.169   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      27.582 -15.399   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      27.582 -13.852   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      26.249 -13.081   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      28.915 -16.169   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      30.229 -15.410   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      31.536 -16.164   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      30.230 -13.860   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      27.826 -17.258   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      30.004 -17.258   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    1                                                       
CONECT    7    8   10                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8    5   14   20                                             
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14    9   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20    9                                                            
CONECT   21   17   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24   27   31                                                  
CONECT   26   24                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30   25                                                       
CONECT   32   29   33   36   37                                             
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   32                                                            
CONECT   37   32                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

COMPND    HMDB0243728
HETATM    1  C1  UNL     1       8.632   0.628   1.233  1.00  0.00           C  
HETATM    2  C2  UNL     1       8.015   0.282  -0.107  1.00  0.00           C  
HETATM    3  C3  UNL     1       8.724  -0.936  -0.661  1.00  0.00           C  
HETATM    4  C4  UNL     1       8.160   1.445  -1.004  1.00  0.00           C  
HETATM    5  O1  UNL     1       8.774   1.368  -2.089  1.00  0.00           O  
HETATM    6  O2  UNL     1       7.605   2.657  -0.642  1.00  0.00           O  
HETATM    7  C5  UNL     1       6.560   0.036   0.050  1.00  0.00           C  
HETATM    8  C6  UNL     1       5.777   0.087  -1.106  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.406  -0.146  -0.976  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.829  -0.420   0.243  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.315  -0.657   0.296  1.00  0.00           C  
HETATM   12  O3  UNL     1       1.838   0.453  -0.436  1.00  0.00           O  
HETATM   13  C10 UNL     1       2.080  -1.942  -0.422  1.00  0.00           C  
HETATM   14  C11 UNL     1       0.697  -2.450  -0.492  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.317  -1.587  -1.157  1.00  0.00           C  
HETATM   16  N1  UNL     1      -0.560  -0.356  -0.486  1.00  0.00           N  
HETATM   17  C13 UNL     1      -1.227  -0.537   0.770  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.580   0.200   0.833  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.354  -0.217  -0.370  1.00  0.00           C  
HETATM   20  C16 UNL     1      -4.786   0.111  -0.430  1.00  0.00           C  
HETATM   21  O4  UNL     1      -5.287  -0.409  -1.666  1.00  0.00           O  
HETATM   22  C17 UNL     1      -5.501  -0.622   0.677  1.00  0.00           C  
HETATM   23  C18 UNL     1      -5.536  -0.044   1.930  1.00  0.00           C  
HETATM   24  C19 UNL     1      -6.187  -0.731   2.923  1.00  0.00           C  
HETATM   25  C20 UNL     1      -6.805  -1.969   2.723  1.00  0.00           C  
HETATM   26  C21 UNL     1      -6.751  -2.521   1.454  1.00  0.00           C  
HETATM   27  C22 UNL     1      -6.100  -1.835   0.456  1.00  0.00           C  
HETATM   28  C23 UNL     1      -5.215   1.502  -0.357  1.00  0.00           C  
HETATM   29  C24 UNL     1      -4.456   2.620  -0.509  1.00  0.00           C  
HETATM   30  C25 UNL     1      -5.031   3.856  -0.404  1.00  0.00           C  
HETATM   31  C26 UNL     1      -6.376   4.024  -0.145  1.00  0.00           C  
HETATM   32  C27 UNL     1      -7.177   2.911   0.015  1.00  0.00           C  
HETATM   33  C28 UNL     1      -6.585   1.677  -0.093  1.00  0.00           C  
HETATM   34  C29 UNL     1      -2.614   0.107  -1.669  1.00  0.00           C  
HETATM   35  C30 UNL     1      -1.230   0.615  -1.337  1.00  0.00           C  
HETATM   36  C31 UNL     1       4.595  -0.472   1.384  1.00  0.00           C  
HETATM   37  C32 UNL     1       5.967  -0.239   1.256  1.00  0.00           C  
HETATM   38  H1  UNL     1       9.657   1.042   1.073  1.00  0.00           H  
HETATM   39  H2  UNL     1       8.690  -0.304   1.821  1.00  0.00           H  
HETATM   40  H3  UNL     1       8.069   1.432   1.739  1.00  0.00           H  
HETATM   41  H4  UNL     1       8.148  -1.342  -1.501  1.00  0.00           H  
HETATM   42  H5  UNL     1       8.707  -1.721   0.138  1.00  0.00           H  
HETATM   43  H6  UNL     1       9.728  -0.671  -0.987  1.00  0.00           H  
HETATM   44  H7  UNL     1       8.003   3.297   0.021  1.00  0.00           H  
HETATM   45  H8  UNL     1       6.195   0.300  -2.080  1.00  0.00           H  
HETATM   46  H9  UNL     1       3.835  -0.102  -1.888  1.00  0.00           H  
HETATM   47  H10 UNL     1       2.013  -0.624   1.342  1.00  0.00           H  
HETATM   48  H11 UNL     1       1.948   0.311  -1.406  1.00  0.00           H  
HETATM   49  H12 UNL     1       2.457  -1.793  -1.476  1.00  0.00           H  
HETATM   50  H13 UNL     1       2.747  -2.755   0.028  1.00  0.00           H  
HETATM   51  H14 UNL     1       0.687  -3.489  -0.970  1.00  0.00           H  
HETATM   52  H15 UNL     1       0.379  -2.688   0.577  1.00  0.00           H  
HETATM   53  H16 UNL     1       0.076  -1.401  -2.207  1.00  0.00           H  
HETATM   54  H17 UNL     1      -1.262  -2.206  -1.251  1.00  0.00           H  
HETATM   55  H18 UNL     1      -0.611  -0.234   1.619  1.00  0.00           H  
HETATM   56  H19 UNL     1      -1.487  -1.623   0.941  1.00  0.00           H  
HETATM   57  H20 UNL     1      -2.323   1.246   0.936  1.00  0.00           H  
HETATM   58  H21 UNL     1      -3.066  -0.239   1.734  1.00  0.00           H  
HETATM   59  H22 UNL     1      -3.308  -1.361  -0.331  1.00  0.00           H  
HETATM   60  H23 UNL     1      -4.804  -1.256  -1.802  1.00  0.00           H  
HETATM   61  H24 UNL     1      -5.090   0.913   2.176  1.00  0.00           H  
HETATM   62  H25 UNL     1      -6.209  -0.266   3.912  1.00  0.00           H  
HETATM   63  H26 UNL     1      -7.303  -2.468   3.532  1.00  0.00           H  
HETATM   64  H27 UNL     1      -7.230  -3.480   1.298  1.00  0.00           H  
HETATM   65  H28 UNL     1      -6.071  -2.288  -0.528  1.00  0.00           H  
HETATM   66  H29 UNL     1      -3.392   2.489  -0.721  1.00  0.00           H  
HETATM   67  H30 UNL     1      -4.413   4.740  -0.527  1.00  0.00           H  
HETATM   68  H31 UNL     1      -6.846   5.009  -0.059  1.00  0.00           H  
HETATM   69  H32 UNL     1      -8.247   2.994   0.220  1.00  0.00           H  
HETATM   70  H33 UNL     1      -7.241   0.824   0.037  1.00  0.00           H  
HETATM   71  H34 UNL     1      -2.433  -0.824  -2.286  1.00  0.00           H  
HETATM   72  H35 UNL     1      -3.166   0.769  -2.334  1.00  0.00           H  
HETATM   73  H36 UNL     1      -1.192   1.596  -0.870  1.00  0.00           H  
HETATM   74  H37 UNL     1      -0.666   0.645  -2.295  1.00  0.00           H  
HETATM   75  H38 UNL     1       4.142  -0.685   2.324  1.00  0.00           H  
HETATM   76  H39 UNL     1       6.582  -0.275   2.140  1.00  0.00           H  
CONECT    1    2   38   39   40
CONECT    2    3    4    7
CONECT    3   41   42   43
CONECT    4    5    5    6
CONECT    6   44
CONECT    7    8    8   37
CONECT    8    9   45
CONECT    9   10   10   46
CONECT   10   11   36
CONECT   11   12   13   47
CONECT   12   48
CONECT   13   14   49   50
CONECT   14   15   51   52
CONECT   15   16   53   54
CONECT   16   17   35
CONECT   17   18   55   56
CONECT   18   19   57   58
CONECT   19   20   34   59
CONECT   20   21   22   28
CONECT   21   60
CONECT   22   23   23   27
CONECT   23   24   61
CONECT   24   25   25   62
CONECT   25   26   63
CONECT   26   27   27   64
CONECT   27   65
CONECT   28   29   29   33
CONECT   29   30   66
CONECT   30   31   31   67
CONECT   31   32   68
CONECT   32   33   33   69
CONECT   33   70
CONECT   34   35   71   72
CONECT   35   73   74
CONECT   36   37   37   75
CONECT   37   76
END

HMDB0005030
     RDKit          3D
Fexofenadine
 76 79  0  0  0  0  0  0  0  0999 V2000
    6.9635    1.7697    1.5857 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3776    0.6451    0.6623 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9752   -0.4491    1.5504 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4766    1.0664   -0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6393    0.5279   -0.2242 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3396    2.0622   -1.2151 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2181    0.0658   -0.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6990    0.5941   -1.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6083   -0.0281   -1.8300 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -1.1638   -1.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8771   -1.7709   -2.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9109   -3.1392   -2.1302 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5636   -1.2278   -1.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4036   -1.5231   -0.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1385   -1.1849    0.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3005    0.1394    0.6295 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8482    0.7028   -0.5434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2160    0.1007   -0.8671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1119    0.0081    0.3085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3918    0.7418   -0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0373    2.0899   -0.3055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1468    0.1921   -1.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1345    1.0180   -1.6977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9053    0.5949   -2.7622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7217   -0.6556   -3.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7446   -1.4770   -2.7690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9707   -1.0330   -1.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2599    0.7791    1.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6647   -0.4174    1.7152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4696   -0.4467    2.8204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8942    0.7025    3.4116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4982    1.9034    2.8757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6864    1.9459    1.7603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5579    0.3964    1.6307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1001    0.5157    1.7887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5435   -1.6854   -0.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6190   -1.0822    0.4451 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9220    2.2070    1.9780 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3375    2.5388    1.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3957    1.2992    2.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4360   -0.5843    2.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0322   -0.2009    1.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0176   -1.4284    1.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8666    2.9302   -1.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1372    1.4869   -1.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2381    0.4455   -2.7516 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8843   -1.4005   -3.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8726   -3.6161   -1.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7522   -0.0956   -1.5832 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7717   -1.4699   -2.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7086   -2.5936    0.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2288   -0.9597    0.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6493   -1.8725    0.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2657   -1.5619    1.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9498    1.8203   -0.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2600    0.5765   -1.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9921   -0.8821   -1.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6418    0.7354   -1.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4152   -1.0757    0.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3333    2.3328   -1.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3436    2.0110   -1.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6811    1.2293   -3.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2899   -1.0469   -4.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5396   -2.4535   -3.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2314   -1.6889   -1.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3430   -1.3603    1.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7709   -1.4116    3.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5251    0.6236    4.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8505    2.8023    3.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3655    2.8973    1.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9677   -0.2645    2.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0138    1.4017    1.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7803    1.5560    2.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7577   -0.1276    2.6265 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1081   -2.5592    0.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0190   -1.5178    1.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  2  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 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
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 20 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 19 34  1  0
 34 35  1  0
 10 36  1  0
 36 37  2  0
 37  7  1  0
 35 16  1  0
 27 22  1  0
 33 28  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  3 41  1  0
  3 42  1  0
  3 43  1  0
  6 44  1  0
  8 45  1  0
  9 46  1  0
 11 47  1  0
 12 48  1  0
 13 49  1  0
 13 50  1  0
 14 51  1  0
 14 52  1  0
 15 53  1  0
 15 54  1  0
 17 55  1  0
 17 56  1  0
 18 57  1  0
 18 58  1  0
 19 59  1  0
 21 60  1  0
 23 61  1  0
 24 62  1  0
 25 63  1  0
 26 64  1  0
 27 65  1  0
 29 66  1  0
 30 67  1  0
 31 68  1  0
 32 69  1  0
 33 70  1  0
 34 71  1  0
 34 72  1  0
 35 73  1  0
 35 74  1  0
 36 75  1  0
 37 76  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-alpha,alpha-dimethylbenzeneacetic acid	ChEBI
Carboxyterfenadine	ChEBI
Terfenadine acid metabolite	ChEBI
Terfenadine carboxylate	ChEBI
Terfenadine-COOH	ChEBI
Telfast	Kegg
4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-a,a-dimethylbenzeneacetate	Generator
4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-a,a-dimethylbenzeneacetic acid	Generator
4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-alpha,alpha-dimethylbenzeneacetate	Generator
4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-α,α-dimethylbenzeneacetate	Generator
4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-α,α-dimethylbenzeneacetic acid	Generator
Terfenadine carboxylic acid	Generator
Allegra	HMDB, MeSH
Fexofenadine hydrochloride	HMDB, MeSH
Aventis pharma brand OF fexofenadine hydrochloride	MeSH, HMDB
MDL 16,455a	MeSH, HMDB
alpha-(4-(1-Carboxy-1-methylethyl)phenyl)-4-hydroxydiphenylmethyl-1-piperidinebutanol	MeSH, HMDB
Aventis behring brand OF fexofenadine hydrochloride	MeSH, HMDB
Aventis brand OF fexofenadine hydrochloride	MeSH, HMDB
Hoechst brand OF fexofenadine hydrochloride	MeSH, HMDB

Chemical Formula

C₃₂H₃₉NO₄

Average Molecular Weight

501.6564

Monoisotopic Molecular Weight

501.287908741

IUPAC Name

2-(4-{1-hydroxy-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]butyl}phenyl)-2-methylpropanoic acid

Traditional Name

fexofenadine

CAS Registry Number

83799-24-0

SMILES

CC(C)(C(O)=O)C1=CC=C(C=C1)C(O)CCCN1CCC(CC1)C(O)(C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C32H39NO4/c1-31(2,30(35)36)25-17-15-24(16-18-25)29(34)14-9-21-33-22-19-28(20-23-33)32(37,26-10-5-3-6-11-26)27-12-7-4-8-13-27/h3-8,10-13,15-18,28-29,34,37H,9,14,19-23H2,1-2H3,(H,35,36)

InChI Key

RWTNPBWLLIMQHL-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
Phenylbutylamine
Phenylpropane
Aralkylamine
Piperidine
Tertiary alcohol
Amino acid or derivatives
Secondary alcohol
Amino acid
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Organic oxide
Amine
Carbonyl group
Aromatic alcohol
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

piperidines (CHEBI:5050 )
tertiary amine (CHEBI:5050 )

Ontology

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0005030)

Cellular substructure

Organ

Tissue

Epithelium

Epidermis (HMDB: HMDB0005030)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0005030)
Feces (PMID: 27543620)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0005030)

Source

Exogenous

Exogenous (HMDB: HMDB0005030)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0005030)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Fexofenadine H1-Antihistamine Action (HMDB: HMDB0005030)
Fexofenadine H1-Antihistamine Action (PathBank: SMP0060218)

Role

Industrial application

H1-receptor antagonist (HMDB: HMDB0005030)
Anti-allergic agent (HMDB: HMDB0005030)

Pharmaceutical industry

Anti-allergic (HMDB: HMDB0005030)

Biological role

Drug metabolite (HMDB: HMDB0005030)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	142.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	226.9	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0027 g/L	ALOGPS
logP	5.02	ALOGPS
logP	2.94	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.04	ChemAxon
pKa (Strongest Basic)	9.01	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	81 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	147.98 m³·mol⁻¹	ChemAxon
Polarizability	57.42 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	217.202	31661259
DarkChem	[M-H]-	210.183	31661259
DeepCCS	[M+H]+	211.232	30932474
DeepCCS	[M-H]-	208.837	30932474
DeepCCS	[M-2H]-	241.72	30932474
DeepCCS	[M+Na]+	217.145	30932474
AllCCS	[M+H]+	224.2	32859911
AllCCS	[M+H-H2O]+	222.5	32859911
AllCCS	[M+NH4]+	225.7	32859911
AllCCS	[M+Na]+	226.1	32859911
AllCCS	[M-H]-	214.9	32859911
AllCCS	[M+Na-2H]-	216.7	32859911
AllCCS	[M+HCOO]-	219.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fexofenadine	CC(C)(C(O)=O)C1=CC=C(C=C1)C(O)CCCN1CCC(CC1)C(O)(C1=CC=CC=C1)C1=CC=CC=C1	4396.4	Standard polar	33892256
Fexofenadine	CC(C)(C(O)=O)C1=CC=C(C=C1)C(O)CCCN1CCC(CC1)C(O)(C1=CC=CC=C1)C1=CC=CC=C1	3456.4	Standard non polar	33892256
Fexofenadine	CC(C)(C(O)=O)C1=CC=C(C=C1)C(O)CCCN1CCC(CC1)C(O)(C1=CC=CC=C1)C1=CC=CC=C1	4047.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Fexofenadine,1TMS,isomer #1	CC(C)(C(=O)O[Si](C)(C)C)C1=CC=C(C(O)CCCN2CCC(C(O)(C3=CC=CC=C3)C3=CC=CC=C3)CC2)C=C1	4130.8	Semi standard non polar	33892256
Fexofenadine,1TMS,isomer #2	CC(C)(C(=O)O)C1=CC=C(C(CCCN2CCC(C(O)(C3=CC=CC=C3)C3=CC=CC=C3)CC2)O[Si](C)(C)C)C=C1	4068.8	Semi standard non polar	33892256
Fexofenadine,1TMS,isomer #3	CC(C)(C(=O)O)C1=CC=C(C(O)CCCN2CCC(C(O[Si](C)(C)C)(C3=CC=CC=C3)C3=CC=CC=C3)CC2)C=C1	4125.1	Semi standard non polar	33892256
Fexofenadine,2TMS,isomer #1	CC(C)(C(=O)O[Si](C)(C)C)C1=CC=C(C(CCCN2CCC(C(O)(C3=CC=CC=C3)C3=CC=CC=C3)CC2)O[Si](C)(C)C)C=C1	3929.6	Semi standard non polar	33892256
Fexofenadine,2TMS,isomer #2	CC(C)(C(=O)O[Si](C)(C)C)C1=CC=C(C(O)CCCN2CCC(C(O[Si](C)(C)C)(C3=CC=CC=C3)C3=CC=CC=C3)CC2)C=C1	3979.0	Semi standard non polar	33892256
Fexofenadine,2TMS,isomer #3	CC(C)(C(=O)O)C1=CC=C(C(CCCN2CCC(C(O[Si](C)(C)C)(C3=CC=CC=C3)C3=CC=CC=C3)CC2)O[Si](C)(C)C)C=C1	3904.9	Semi standard non polar	33892256
Fexofenadine,3TMS,isomer #1	CC(C)(C(=O)O[Si](C)(C)C)C1=CC=C(C(CCCN2CCC(C(O[Si](C)(C)C)(C3=CC=CC=C3)C3=CC=CC=C3)CC2)O[Si](C)(C)C)C=C1	3783.0	Semi standard non polar	33892256
Fexofenadine,1TBDMS,isomer #1	CC(C)(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=C(C(O)CCCN2CCC(C(O)(C3=CC=CC=C3)C3=CC=CC=C3)CC2)C=C1	4355.1	Semi standard non polar	33892256
Fexofenadine,1TBDMS,isomer #2	CC(C)(C(=O)O)C1=CC=C(C(CCCN2CCC(C(O)(C3=CC=CC=C3)C3=CC=CC=C3)CC2)O[Si](C)(C)C(C)(C)C)C=C1	4287.8	Semi standard non polar	33892256
Fexofenadine,1TBDMS,isomer #3	CC(C)(C(=O)O)C1=CC=C(C(O)CCCN2CCC(C(O[Si](C)(C)C(C)(C)C)(C3=CC=CC=C3)C3=CC=CC=C3)CC2)C=C1	4357.0	Semi standard non polar	33892256
Fexofenadine,2TBDMS,isomer #1	CC(C)(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=C(C(CCCN2CCC(C(O)(C3=CC=CC=C3)C3=CC=CC=C3)CC2)O[Si](C)(C)C(C)(C)C)C=C1	4324.2	Semi standard non polar	33892256
Fexofenadine,2TBDMS,isomer #2	CC(C)(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=C(C(O)CCCN2CCC(C(O[Si](C)(C)C(C)(C)C)(C3=CC=CC=C3)C3=CC=CC=C3)CC2)C=C1	4417.8	Semi standard non polar	33892256
Fexofenadine,2TBDMS,isomer #3	CC(C)(C(=O)O)C1=CC=C(C(CCCN2CCC(C(O[Si](C)(C)C(C)(C)C)(C3=CC=CC=C3)C3=CC=CC=C3)CC2)O[Si](C)(C)C(C)(C)C)C=C1	4339.3	Semi standard non polar	33892256
Fexofenadine,3TBDMS,isomer #1	CC(C)(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=C(C(CCCN2CCC(C(O[Si](C)(C)C(C)(C)C)(C3=CC=CC=C3)C3=CC=CC=C3)CC2)O[Si](C)(C)C(C)(C)C)C=C1	4409.8	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 - Fexofenadine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-0912400000-d47ca5514638bcd48093	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fexofenadine GC-MS (2 TMS) - 70eV, Positive	splash10-001i-1931153000-7fd2e3b3cc17ae068da6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fexofenadine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fexofenadine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fexofenadine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fexofenadine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fexofenadine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fexofenadine GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fexofenadine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fexofenadine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fexofenadine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fexofenadine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fexofenadine GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fexofenadine GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fexofenadine GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fexofenadine LC-ESI-QFT , negative-QTOF	splash10-0a6r-0005900000-17ae091cc3d9ba9c62f3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fexofenadine LC-ESI-QFT , negative-QTOF	splash10-0a6r-0396000000-be2d6fedab983b50c280	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fexofenadine LC-ESI-QFT , negative-QTOF	splash10-0a4i-1970000000-c78b1c745afc54f58e01	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fexofenadine LC-ESI-QFT , negative-QTOF	splash10-0a4r-0920000000-9ad3dc88e743866c23ca	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fexofenadine LC-ESI-QFT , negative-QTOF	splash10-0btj-0900000000-66a31911b29382b93745	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fexofenadine LC-ESI-QFT , negative-QTOF	splash10-0a4i-1900000000-ce2d00bbddc284806cb0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fexofenadine LC-ESI-QFT , positive-QTOF	splash10-0udi-0000090000-2622c1f2ddb4bff3f93d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fexofenadine LC-ESI-QFT , positive-QTOF	splash10-0159-0000910000-0afa1079fbe9a822e35c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fexofenadine LC-ESI-QFT , positive-QTOF	splash10-00xr-1920200000-1163d721ce08480aea71	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fexofenadine LC-ESI-QFT , positive-QTOF	splash10-00di-1910000000-c593678096415da5efb2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fexofenadine LC-ESI-QFT , positive-QTOF	splash10-002f-2900000000-01de1f32826ab5569301	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fexofenadine LC-ESI-QFT , positive-QTOF	splash10-002f-3900000000-72f624b2d6e05d29cb72	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fexofenadine 30V, Negative-QTOF	splash10-0a6r-0296000000-08bc8f52b1adac426d92	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fexofenadine 45V, Negative-QTOF	splash10-0a4i-1970000000-7a763967a0e22ba5aee4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fexofenadine 15V, Negative-QTOF	splash10-0a6r-0004900000-264e1e3683f099cd4d18	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fexofenadine 45V, Positive-QTOF	splash10-00xr-1920200000-f89d210776b04ca1a4f1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fexofenadine 30V, Positive-QTOF	splash10-0159-0000910000-e86af4100fbcd4806c84	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fexofenadine 15V, Positive-QTOF	splash10-0udi-0000090000-9d409ff3e4f83806f5ac	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fexofenadine 10V, Positive-QTOF	splash10-0f89-0001930000-b9b7ff78564293a249b0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fexofenadine 20V, Positive-QTOF	splash10-0541-0212900000-ab3069ba65212a7da302	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fexofenadine 40V, Positive-QTOF	splash10-000g-1985500000-f990cf713f3191736f10	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fexofenadine 10V, Negative-QTOF	splash10-0udi-0100690000-e140f2c9a1bcece115e3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fexofenadine 20V, Negative-QTOF	splash10-0zj0-4223930000-8c8b81776964fc2cb368	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fexofenadine 40V, Negative-QTOF	splash10-004u-9651000000-b823e5714fa6afb8f50f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fexofenadine 10V, Positive-QTOF	splash10-0ue9-0000980000-811ef09a2d84417ca55c	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Brain
Epidermis
Kidney
Liver

Pathways

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

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

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

3231

KEGG Compound ID

C06999

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fexofenadine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

5050

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Carr, Albert A.; Dolfini, Joseph E.; Wright, George J. Piperidine derivatives with antihistamine action. Ger. Offen. (1980), 39 pp. CODEN: GWXXBX DE 3007498 19801023 CAN 94:156758 AN 1981:156758

Material Safety Data Sheet (MSDS)

Not Available

General References

Cvetkovic M, Leake B, Fromm MF, Wilkinson GR, Kim RB: OATP and P-glycoprotein transporters mediate the cellular uptake and excretion of fexofenadine. Drug Metab Dispos. 1999 Aug;27(8):866-71. [PubMed:10421612 ]
Tashiro M, Sakurada Y, Iwabuchi K, Mochizuki H, Kato M, Aoki M, Funaki Y, Itoh M, Iwata R, Wong DF, Yanai K: Central effects of fexofenadine and cetirizine: measurement of psychomotor performance, subjective sleepiness, and brain histamine H1-receptor occupancy using 11C-doxepin positron emission tomography. J Clin Pharmacol. 2004 Aug;44(8):890-900. [PubMed:15286093 ]
Simons FE, Silver NA, Gu X, Simons KJ: Clinical pharmacology of H1-antihistamines in the skin. J Allergy Clin Immunol. 2002 Nov;110(5):777-83. [PubMed:12417888 ]
Purohit A, Duvernelle C, Melac M, Pauli G, Frossard N: Twenty-four hours of activity of cetirizine and fexofenadine in the skin. Ann Allergy Asthma Immunol. 2001 Apr;86(4):387-92. [PubMed:11345280 ]
Inoue T, Katoh N, Kishimoto S, Matsunaga K: Inhibitory effects of oral prednisolone and fexofenadine on skin responses by prick tests with histamine and compound 48/80. J Dermatol Sci. 2002 Dec;30(3):180-4. [PubMed:12443840 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

Enzyme Details

2. Histamine H1 receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:: HRH1
Uniprot ID:: P35367
Molecular weight:: 55783.6

Showing metabocard for Fexofenadine (HMDB0005030)

MOL for HMDB0005030 (Fexofenadine)

3D MOL for HMDB0005030 (Fexofenadine)

3D SDF for HMDB0005030 (Fexofenadine)

3D-SDF for HMDB0005030 (Fexofenadine)

PDB for HMDB0005030 (Fexofenadine)

3D PDB for HMDB0005030 (Fexofenadine)

SMILES for HMDB0005030 (Fexofenadine)

INCHI for HMDB0005030 (Fexofenadine)

Structure for HMDB0005030 (Fexofenadine)

3D Structure for HMDB0005030 (Fexofenadine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes