Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7) Show 7 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:04 UTC

HMDB ID

HMDB0015648

Secondary Accession Numbers

HMDB15648

Metabolite Identification

Common Name

Fesoterodine

Description

Fesoterodine, also known as toviaz, 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. Fesoterodine is a drug which is used for the treatment of overactive bladder (with symptoms of urinary frequency, urgency, or urge incontinence). Therefore, acting as a competitive muscarinic receptor antagonist, fesoterodine ultimately acts to decrease the detrusor pressure by its muscarinic antagonism, thereby decreasing bladder contraction and consequently, the urge to urinate. Fesoterodine is a very strong basic compound (based on its pKa). This results in the inhibition of bladder contraction, decrease in detrusor pressure, and an incomplete emptying of the bladder. The 5-hydroxymethyl metabolite, which exhibits an antimuscarinic activity. In-vivo the fesoteridine prodrug is broken down into its active metabolite, 5-hydroxymethyl tolterodine (5-HMT), by plasma esterases. It is an antimuscarinic prodrug used for treating overactive bladder syndrome. Mouse, Intravenous, NOAEL: 10 mg/kg. Fesoterodine is only found in individuals that have used or taken this drug. Mouse, Oral, LD50: ~ 316 mg/kg. Extensive metabolism via CYP2D6 and CYP3A4 into inactive metabolites. Both urinary bladder contraction and salivation are mediated via cholinergic muscarinic receptors.

Structure

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


  Mrv0541 02241212462D          

 30 31  0  0  1  0            999 V2000
    3.1895    1.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.6204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230   -0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7605    0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730    0.9059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230   -3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  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
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 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
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 15 25  1  6  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
M  END

HMDB0015648
     RDKit          3D
Fesoterodine
 67 68  0  0  0  0  0  0  0  0999 V2000
    4.4370   -3.7559   -0.6123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1528   -2.8693    0.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9396   -3.3641    1.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8143   -1.4852    0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4891   -0.5088    0.4924 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7202   -1.3321   -0.7303 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4058   -0.0639   -1.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0294    0.4767   -2.2546 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7252    1.7449   -2.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7778    2.4518   -1.9911 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4340    3.8172   -2.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1642    4.2019   -3.5586 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1638    1.8996   -0.8938 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4458    0.6316   -0.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7787    0.0410    0.7624 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4710   -0.6861    0.4070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4979    0.1706   -0.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7099   -0.5361   -0.6525 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6370    0.3301   -1.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1954    1.4488   -0.4312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7419   -0.2987   -2.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0262   -1.6504    0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0233   -2.6499   -0.4393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4335   -1.3778    1.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7555    1.0142    1.8256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2718    1.3951    2.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2032    2.3503    3.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9979    2.9916    3.8230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0734    2.6429    3.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9716    1.6800    2.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0030   -4.7627   -0.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5179   -3.7730   -0.8594 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9336   -3.2712   -1.4992 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0479   -2.7899    1.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0152   -3.0934    0.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0327   -4.4762    1.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9572   -2.9462    2.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7757   -0.0760   -2.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2254    2.1772   -3.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6678    4.5790   -1.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3578    3.8410   -2.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8853    3.7099   -4.3835 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4045    2.4670   -0.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4992   -0.7695    1.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2479   -1.5313   -0.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9798   -1.1261    1.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7928    1.0795    0.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0814    0.5692   -1.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0185    0.8708   -2.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7249    1.6027    0.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1827    2.4347   -0.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2975    1.2650   -0.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5392   -1.2732   -2.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0134    0.3525   -2.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6983   -0.3465   -1.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0869   -2.2889    0.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9679   -3.4983    0.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0635   -2.3536   -0.4095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6829   -3.1631   -1.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9544   -2.0808    2.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5407   -1.5661    1.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1722   -0.3555    1.8584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2126    0.9044    2.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0815    2.5839    4.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0797    3.7582    4.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0097    3.1722    3.2305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8612    1.4642    1.4806 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
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  2  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
 19 21  1  0
 18 22  1  0
 22 23  1  0
 22 24  1  0
 15 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 14  7  1  0
 30 25  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  8 38  1  0
  9 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 15 44  1  1
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 21 55  1  0
 22 56  1  0
 23 57  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  0
 24 61  1  0
 24 62  1  0
 26 63  1  0
 27 64  1  0
 28 65  1  0
 29 66  1  0
 30 67  1  0
M  END


  Mrv0541 02241212462D          

 30 31  0  0  1  0            999 V2000
    3.1895    1.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.6204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230   -0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7605    0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730    0.9059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230   -3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  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
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 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
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 15 25  1  6  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015648

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)N(CC[C@H](C1=CC=CC=C1)C1=C(OC(=O)C(C)C)C=CC(CO)=C1)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C26H37NO3/c1-18(2)26(29)30-25-13-12-21(17-28)16-24(25)23(22-10-8-7-9-11-22)14-15-27(19(3)4)20(5)6/h7-13,16,18-20,23,28H,14-15,17H2,1-6H3/t23-/m1/s1

> <INCHI_KEY>
DCCSDBARQIPTGU-HSZRJFAPSA-N

> <FORMULA>
C26H37NO3

> <MOLECULAR_WEIGHT>
411.5769

> <EXACT_MASS>
411.277344055

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
48.2894920536105

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(1R)-3-[bis(propan-2-yl)amino]-1-phenylpropyl]-4-(hydroxymethyl)phenyl 2-methylpropanoate

> <ALOGPS_LOGP>
5.45

> <JCHEM_LOGP>
5.698894813000001

> <ALOGPS_LOGS>
-5.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.983366375423817

> <JCHEM_PKA_STRONGEST_BASIC>
10.636868002290807

> <JCHEM_POLAR_SURFACE_AREA>
49.77

> <JCHEM_REFRACTIVITY>
124.08480000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.05e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fesoterodine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015648
     RDKit          3D
Fesoterodine
 67 68  0  0  0  0  0  0  0  0999 V2000
    4.4370   -3.7559   -0.6123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1528   -2.8693    0.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9396   -3.3641    1.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8143   -1.4852    0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4891   -0.5088    0.4924 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7202   -1.3321   -0.7303 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4058   -0.0639   -1.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0294    0.4767   -2.2546 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7252    1.7449   -2.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7778    2.4518   -1.9911 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4340    3.8172   -2.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1642    4.2019   -3.5586 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1638    1.8996   -0.8938 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4458    0.6316   -0.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7787    0.0410    0.7624 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4710   -0.6861    0.4070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4979    0.1706   -0.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7099   -0.5361   -0.6525 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6370    0.3301   -1.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1954    1.4488   -0.4312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7419   -0.2987   -2.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0262   -1.6504    0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0233   -2.6499   -0.4393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4335   -1.3778    1.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7555    1.0142    1.8256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2718    1.3951    2.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2032    2.3503    3.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9979    2.9916    3.8230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0734    2.6429    3.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9716    1.6800    2.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0030   -4.7627   -0.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5179   -3.7730   -0.8594 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9336   -3.2712   -1.4992 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0479   -2.7899    1.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0152   -3.0934    0.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0327   -4.4762    1.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9572   -2.9462    2.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7757   -0.0760   -2.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2254    2.1772   -3.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6678    4.5790   -1.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3578    3.8410   -2.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8853    3.7099   -4.3835 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4045    2.4670   -0.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4992   -0.7695    1.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2479   -1.5313   -0.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9798   -1.1261    1.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7928    1.0795    0.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0814    0.5692   -1.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0185    0.8708   -2.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7249    1.6027    0.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1827    2.4347   -0.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2975    1.2650   -0.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5392   -1.2732   -2.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0134    0.3525   -2.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6983   -0.3465   -1.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0869   -2.2889    0.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9679   -3.4983    0.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0635   -2.3536   -0.4095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6829   -3.1631   -1.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9544   -2.0808    2.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5407   -1.5661    1.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1722   -0.3555    1.8584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2126    0.9044    2.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0815    2.5839    4.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0797    3.7582    4.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0097    3.1722    3.2305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8612    1.4642    1.4806 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
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  2  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
 19 21  1  0
 18 22  1  0
 22 23  1  0
 22 24  1  0
 15 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 14  7  1  0
 30 25  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  8 38  1  0
  9 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 15 44  1  1
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 21 55  1  0
 22 56  1  0
 23 57  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  0
 24 61  1  0
 24 62  1  0
 26 63  1  0
 27 64  1  0
 28 65  1  0
 29 66  1  0
 30 67  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       5.954   3.025   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.184   1.691   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.954   0.357   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.644   1.691   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.874   3.025   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       2.874   0.357   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334   0.357   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.564  -0.976   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.976  -0.976   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.746   0.357   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.976   1.691   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.564   1.691   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.286   0.357   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.056   1.691   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.874  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.644  -3.644   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       5.184  -3.644   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       5.954  -4.977   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.494  -4.977   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.184  -6.311   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.954  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.184  -0.976   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.494  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.564  -3.644   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334  -4.977   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.564  -6.311   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.976  -6.311   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.746  -4.977   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.976  -3.644   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13   10   14                                                       
CONECT   14   13                                                            
CONECT   15    8   16   25                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   18   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   15   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

COMPND    HMDB0015648
HETATM    1  C1  UNL     1       4.437  -3.756  -0.612  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.153  -2.869   0.586  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.940  -3.364   1.363  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.814  -1.485   0.124  1.00  0.00           C  
HETATM    5  O1  UNL     1       4.489  -0.509   0.492  1.00  0.00           O  
HETATM    6  O2  UNL     1       2.720  -1.332  -0.730  1.00  0.00           O  
HETATM    7  C5  UNL     1       2.406  -0.064  -1.153  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.029   0.477  -2.255  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.725   1.745  -2.692  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.778   2.452  -1.991  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.434   3.817  -2.442  1.00  0.00           C  
HETATM   12  O3  UNL     1       2.164   4.202  -3.559  1.00  0.00           O  
HETATM   13  C10 UNL     1       1.164   1.900  -0.894  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.446   0.632  -0.429  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.779   0.041   0.762  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.471  -0.686   0.407  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.498   0.171  -0.283  1.00  0.00           C  
HETATM   18  N1  UNL     1      -2.710  -0.536  -0.652  1.00  0.00           N  
HETATM   19  C15 UNL     1      -3.637   0.330  -1.253  1.00  0.00           C  
HETATM   20  C16 UNL     1      -4.195   1.449  -0.431  1.00  0.00           C  
HETATM   21  C17 UNL     1      -4.742  -0.299  -2.049  1.00  0.00           C  
HETATM   22  C18 UNL     1      -3.026  -1.650   0.081  1.00  0.00           C  
HETATM   23  C19 UNL     1      -4.023  -2.650  -0.439  1.00  0.00           C  
HETATM   24  C20 UNL     1      -3.433  -1.378   1.532  1.00  0.00           C  
HETATM   25  C21 UNL     1       0.755   1.014   1.826  1.00  0.00           C  
HETATM   26  C22 UNL     1      -0.272   1.395   2.630  1.00  0.00           C  
HETATM   27  C23 UNL     1      -0.203   2.350   3.613  1.00  0.00           C  
HETATM   28  C24 UNL     1       0.998   2.992   3.823  1.00  0.00           C  
HETATM   29  C25 UNL     1       2.073   2.643   3.035  1.00  0.00           C  
HETATM   30  C26 UNL     1       1.972   1.680   2.056  1.00  0.00           C  
HETATM   31  H1  UNL     1       4.003  -4.763  -0.447  1.00  0.00           H  
HETATM   32  H2  UNL     1       5.518  -3.773  -0.859  1.00  0.00           H  
HETATM   33  H3  UNL     1       3.934  -3.271  -1.499  1.00  0.00           H  
HETATM   34  H4  UNL     1       5.048  -2.790   1.219  1.00  0.00           H  
HETATM   35  H5  UNL     1       2.015  -3.093   0.800  1.00  0.00           H  
HETATM   36  H6  UNL     1       3.033  -4.476   1.402  1.00  0.00           H  
HETATM   37  H7  UNL     1       2.957  -2.946   2.386  1.00  0.00           H  
HETATM   38  H8  UNL     1       3.776  -0.076  -2.810  1.00  0.00           H  
HETATM   39  H9  UNL     1       3.225   2.177  -3.575  1.00  0.00           H  
HETATM   40  H10 UNL     1       1.668   4.579  -1.647  1.00  0.00           H  
HETATM   41  H11 UNL     1       0.358   3.841  -2.736  1.00  0.00           H  
HETATM   42  H12 UNL     1       1.885   3.710  -4.383  1.00  0.00           H  
HETATM   43  H13 UNL     1       0.404   2.467  -0.333  1.00  0.00           H  
HETATM   44  H14 UNL     1       1.499  -0.769   1.119  1.00  0.00           H  
HETATM   45  H15 UNL     1      -0.248  -1.531  -0.271  1.00  0.00           H  
HETATM   46  H16 UNL     1      -0.980  -1.126   1.289  1.00  0.00           H  
HETATM   47  H17 UNL     1      -1.793   1.079   0.253  1.00  0.00           H  
HETATM   48  H18 UNL     1      -1.081   0.569  -1.268  1.00  0.00           H  
HETATM   49  H19 UNL     1      -3.018   0.871  -2.056  1.00  0.00           H  
HETATM   50  H20 UNL     1      -3.725   1.603   0.545  1.00  0.00           H  
HETATM   51  H21 UNL     1      -4.183   2.435  -0.949  1.00  0.00           H  
HETATM   52  H22 UNL     1      -5.298   1.265  -0.240  1.00  0.00           H  
HETATM   53  H23 UNL     1      -4.539  -1.273  -2.476  1.00  0.00           H  
HETATM   54  H24 UNL     1      -5.013   0.352  -2.945  1.00  0.00           H  
HETATM   55  H25 UNL     1      -5.698  -0.347  -1.463  1.00  0.00           H  
HETATM   56  H26 UNL     1      -2.087  -2.289   0.157  1.00  0.00           H  
HETATM   57  H27 UNL     1      -3.968  -3.498   0.326  1.00  0.00           H  
HETATM   58  H28 UNL     1      -5.063  -2.354  -0.409  1.00  0.00           H  
HETATM   59  H29 UNL     1      -3.683  -3.163  -1.366  1.00  0.00           H  
HETATM   60  H30 UNL     1      -2.954  -2.081   2.241  1.00  0.00           H  
HETATM   61  H31 UNL     1      -4.541  -1.566   1.660  1.00  0.00           H  
HETATM   62  H32 UNL     1      -3.172  -0.356   1.858  1.00  0.00           H  
HETATM   63  H33 UNL     1      -1.213   0.904   2.497  1.00  0.00           H  
HETATM   64  H34 UNL     1      -1.081   2.584   4.202  1.00  0.00           H  
HETATM   65  H35 UNL     1       1.080   3.758   4.602  1.00  0.00           H  
HETATM   66  H36 UNL     1       3.010   3.172   3.231  1.00  0.00           H  
HETATM   67  H37 UNL     1       2.861   1.464   1.481  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3    4   34
CONECT    3   35   36   37
CONECT    4    5    5    6
CONECT    6    7
CONECT    7    8    8   14
CONECT    8    9   38
CONECT    9   10   10   39
CONECT   10   11   13
CONECT   11   12   40   41
CONECT   12   42
CONECT   13   14   14   43
CONECT   14   15
CONECT   15   16   25   44
CONECT   16   17   45   46
CONECT   17   18   47   48
CONECT   18   19   22
CONECT   19   20   21   49
CONECT   20   50   51   52
CONECT   21   53   54   55
CONECT   22   23   24   56
CONECT   23   57   58   59
CONECT   24   60   61   62
CONECT   25   26   26   30
CONECT   26   27   63
CONECT   27   28   28   64
CONECT   28   29   65
CONECT   29   30   30   66
CONECT   30   67
END

HMDB0015648
     RDKit          3D
Fesoterodine
 67 68  0  0  0  0  0  0  0  0999 V2000
    4.4370   -3.7559   -0.6123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1528   -2.8693    0.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9396   -3.3641    1.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8143   -1.4852    0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4891   -0.5088    0.4924 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7202   -1.3321   -0.7303 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4058   -0.0639   -1.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0294    0.4767   -2.2546 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7252    1.7449   -2.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7778    2.4518   -1.9911 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4340    3.8172   -2.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1642    4.2019   -3.5586 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1638    1.8996   -0.8938 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4458    0.6316   -0.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7787    0.0410    0.7624 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4710   -0.6861    0.4070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4979    0.1706   -0.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7099   -0.5361   -0.6525 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6370    0.3301   -1.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1954    1.4488   -0.4312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7419   -0.2987   -2.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0262   -1.6504    0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0233   -2.6499   -0.4393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4335   -1.3778    1.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7555    1.0142    1.8256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2718    1.3951    2.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2032    2.3503    3.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9979    2.9916    3.8230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0734    2.6429    3.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9716    1.6800    2.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0030   -4.7627   -0.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5179   -3.7730   -0.8594 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9336   -3.2712   -1.4992 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0479   -2.7899    1.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0152   -3.0934    0.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0327   -4.4762    1.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9572   -2.9462    2.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7757   -0.0760   -2.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2254    2.1772   -3.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6678    4.5790   -1.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3578    3.8410   -2.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8853    3.7099   -4.3835 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4045    2.4670   -0.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4992   -0.7695    1.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2479   -1.5313   -0.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9798   -1.1261    1.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7928    1.0795    0.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0814    0.5692   -1.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0185    0.8708   -2.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7249    1.6027    0.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1827    2.4347   -0.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2975    1.2650   -0.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5392   -1.2732   -2.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0134    0.3525   -2.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6983   -0.3465   -1.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0869   -2.2889    0.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9679   -3.4983    0.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0635   -2.3536   -0.4095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6829   -3.1631   -1.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9544   -2.0808    2.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5407   -1.5661    1.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1722   -0.3555    1.8584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2126    0.9044    2.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0815    2.5839    4.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0797    3.7582    4.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0097    3.1722    3.2305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8612    1.4642    1.4806 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
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  2  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
 19 21  1  0
 18 22  1  0
 22 23  1  0
 22 24  1  0
 15 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 14  7  1  0
 30 25  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  8 38  1  0
  9 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 15 44  1  1
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 21 55  1  0
 22 56  1  0
 23 57  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  0
 24 61  1  0
 24 62  1  0
 26 63  1  0
 27 64  1  0
 28 65  1  0
 29 66  1  0
 30 67  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Fesoterodine fumarate	HMDB
Toviaz	HMDB

Chemical Formula

C₂₆H₃₇NO₃

Average Molecular Weight

411.5769

Monoisotopic Molecular Weight

411.277344055

IUPAC Name

2-[(1R)-3-[bis(propan-2-yl)amino]-1-phenylpropyl]-4-(hydroxymethyl)phenyl 2-methylpropanoate

Traditional Name

fesoterodine

CAS Registry Number

286930-03-8

SMILES

CC(C)N(CC[C@H](C1=CC=CC=C1)C1=C(OC(=O)C(C)C)C=CC(CO)=C1)C(C)C

InChI Identifier

InChI=1S/C26H37NO3/c1-18(2)26(29)30-25-13-12-21(17-28)16-24(25)23(22-10-8-7-9-11-22)14-15-27(19(3)4)20(5)6/h7-13,16,18-20,23,28H,14-15,17H2,1-6H3/t23-/m1/s1

InChI Key

DCCSDBARQIPTGU-HSZRJFAPSA-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
Phenol ester
Phenoxy compound
Benzyl alcohol
Aralkylamine
Amino acid or derivatives
Carboxylic acid ester
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Organic oxide
Organopnictogen compound
Alcohol
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Primary alcohol
Aromatic alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015648)

Source

Exogenous

Exogenous (HMDB: HMDB0015648)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

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
Water Solubility	0.002 g/L	ALOGPS
logP	5.45	ALOGPS
logP	5.7	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	14.98	ChemAxon
pKa (Strongest Basic)	10.64	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	124.08 m³·mol⁻¹	ChemAxon
Polarizability	48.29 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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
DarkChem	[M+H]+	197.412	31661259
DarkChem	[M-H]-	198.147	31661259
DeepCCS	[M+H]+	206.028	30932474
DeepCCS	[M-H]-	203.633	30932474
DeepCCS	[M-2H]-	236.87	30932474
DeepCCS	[M+Na]+	211.941	30932474
AllCCS	[M+H]+	204.3	32859911
AllCCS	[M+H-H2O]+	202.0	32859911
AllCCS	[M+NH4]+	206.5	32859911
AllCCS	[M+Na]+	207.1	32859911
AllCCS	[M-H]-	206.9	32859911
AllCCS	[M+Na-2H]-	208.0	32859911
AllCCS	[M+HCOO]-	209.4	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.	7.75 minutes	32390414
Predicted by Siyang on May 30, 2022	13.8306 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.83 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	39.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2123.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	224.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	211.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	156.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	103.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	529.3 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	485.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	92.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1131.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	548.5 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	1162.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	337.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	368.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	174.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	224.2 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	8.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fesoterodine	CC(C)N(CC[C@H](C1=CC=CC=C1)C1=C(OC(=O)C(C)C)C=CC(CO)=C1)C(C)C	3393.2	Standard polar	33892256
Fesoterodine	CC(C)N(CC[C@H](C1=CC=CC=C1)C1=C(OC(=O)C(C)C)C=CC(CO)=C1)C(C)C	2722.1	Standard non polar	33892256
Fesoterodine	CC(C)N(CC[C@H](C1=CC=CC=C1)C1=C(OC(=O)C(C)C)C=CC(CO)=C1)C(C)C	2822.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Fesoterodine,1TMS,isomer #1	CC(C)C(=O)OC1=CC=C(CO[Si](C)(C)C)C=C1[C@H](CCN(C(C)C)C(C)C)C1=CC=CC=C1	2855.4	Semi standard non polar	33892256
Fesoterodine,1TBDMS,isomer #1	CC(C)C(=O)OC1=CC=C(CO[Si](C)(C)C(C)(C)C)C=C1[C@H](CCN(C(C)C)C(C)C)C1=CC=CC=C1	3049.2	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB06702	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB06702	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06702

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5293755

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fesoterodine

METLIN ID

Not Available

PubChem Compound

6918558

PDB ID

Not Available

ChEBI ID

775715

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

Malhotra B, Dickins M, Alvey C, Jumadilova Z, Li X, Duczynski G, Gandelman K: Effects of the moderate CYP3A4 inhibitor, fluconazole, on the pharmacokinetics of fesoterodine in healthy subjects. Br J Clin Pharmacol. 2011 Aug;72(2):263-9. doi: 10.1111/j.1365-2125.2011.04007.x. [PubMed:21545485 ]
Malhotra B, Gandelman K, Sachse R, Wood N, Michel MC: The design and development of fesoterodine as a prodrug of 5-hydroxymethyl tolterodine (5-HMT), the active metabolite of tolterodine. Curr Med Chem. 2009;16(33):4481-9. [PubMed:19835561 ]

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

References

Malhotra B, Guan Z, Wood N, Gandelman K: Pharmacokinetic profile of fesoterodine. Int J Clin Pharmacol Ther. 2008 Nov;46(11):556-63. [PubMed:19000553 ]
Malhotra B, Dickins M, Alvey C, Jumadilova Z, Li X, Duczynski G, Gandelman K: Effects of the moderate CYP3A4 inhibitor, fluconazole, on the pharmacokinetics of fesoterodine in healthy subjects. Br J Clin Pharmacol. 2011 Aug;72(2):263-9. doi: 10.1111/j.1365-2125.2011.04007.x. [PubMed:21545485 ]
Malhotra B, Sachse R, Wood N: Evaluation of drug-drug interactions with fesoterodine. Eur J Clin Pharmacol. 2009 Jun;65(6):551-60. doi: 10.1007/s00228-009-0648-1. Epub 2009 Apr 4. [PubMed:19347334 ]
Malhotra BK, Wood N, Sachse R: Influence of age, gender, and race on pharmacokinetics, pharmacodynamics, and safety of fesoterodine. Int J Clin Pharmacol Ther. 2009 Sep;47(9):570-8. [PubMed:19761716 ]

Enzyme Details

2. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Malhotra B, Guan Z, Wood N, Gandelman K: Pharmacokinetic profile of fesoterodine. Int J Clin Pharmacol Ther. 2008 Nov;46(11):556-63. [PubMed:19000553 ]
Malhotra B, Dickins M, Alvey C, Jumadilova Z, Li X, Duczynski G, Gandelman K: Effects of the moderate CYP3A4 inhibitor, fluconazole, on the pharmacokinetics of fesoterodine in healthy subjects. Br J Clin Pharmacol. 2011 Aug;72(2):263-9. doi: 10.1111/j.1365-2125.2011.04007.x. [PubMed:21545485 ]
Malhotra B, Sachse R, Wood N: Evaluation of drug-drug interactions with fesoterodine. Eur J Clin Pharmacol. 2009 Jun;65(6):551-60. doi: 10.1007/s00228-009-0648-1. Epub 2009 Apr 4. [PubMed:19347334 ]
Malhotra BK, Wood N, Sachse R: Influence of age, gender, and race on pharmacokinetics, pharmacodynamics, and safety of fesoterodine. Int J Clin Pharmacol Ther. 2009 Sep;47(9):570-8. [PubMed:19761716 ]

Enzyme Details

3. Muscarinic acetylcholine receptor M3

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:: CHRM3
Uniprot ID:: P20309
Molecular weight:: 66127.4

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Nilvebrant L: Tolterodine and its active 5-hydroxymethyl metabolite: pure muscarinic receptor antagonists. Pharmacol Toxicol. 2002 May;90(5):260-7. [PubMed:12076307 ]

Enzyme Details

4. Muscarinic acetylcholine receptor M1

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:: CHRM1
Uniprot ID:: P11229
Molecular weight:: 51420.4

References

Nilvebrant L: Tolterodine and its active 5-hydroxymethyl metabolite: pure muscarinic receptor antagonists. Pharmacol Toxicol. 2002 May;90(5):260-7. [PubMed:12076307 ]

Enzyme Details

5. Muscarinic acetylcholine receptor M2

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition
Gene Name:: CHRM2
Uniprot ID:: P08172
Molecular weight:: 51714.6

References

Mansfield KJ, Chandran JJ, Vaux KJ, Millard RJ, Christopoulos A, Mitchelson FJ, Burcher E: Comparison of receptor binding characteristics of commonly used muscarinic antagonists in human bladder detrusor and mucosa. J Pharmacol Exp Ther. 2009 Mar;328(3):893-9. doi: 10.1124/jpet.108.145508. Epub 2008 Nov 24. [PubMed:19029429 ]

Enzyme Details

6. Muscarinic acetylcholine receptor M4

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is inhibition of adenylate cyclase
Gene Name:: CHRM4
Uniprot ID:: P08173
Molecular weight:: 53048.7

References

Mansfield KJ, Chandran JJ, Vaux KJ, Millard RJ, Christopoulos A, Mitchelson FJ, Burcher E: Comparison of receptor binding characteristics of commonly used muscarinic antagonists in human bladder detrusor and mucosa. J Pharmacol Exp Ther. 2009 Mar;328(3):893-9. doi: 10.1124/jpet.108.145508. Epub 2008 Nov 24. [PubMed:19029429 ]

Enzyme Details

7. Muscarinic acetylcholine receptor M5

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:: CHRM5
Uniprot ID:: P08912
Molecular weight:: 60073.2

References

Mansfield KJ, Chandran JJ, Vaux KJ, Millard RJ, Christopoulos A, Mitchelson FJ, Burcher E: Comparison of receptor binding characteristics of commonly used muscarinic antagonists in human bladder detrusor and mucosa. J Pharmacol Exp Ther. 2009 Mar;328(3):893-9. doi: 10.1124/jpet.108.145508. Epub 2008 Nov 24. [PubMed:19029429 ]

Showing metabocard for Fesoterodine (HMDB0015648)

MOL for HMDB0015648 (Fesoterodine)

3D MOL for HMDB0015648 (Fesoterodine)

3D SDF for HMDB0015648 (Fesoterodine)

3D-SDF for HMDB0015648 (Fesoterodine)

PDB for HMDB0015648 (Fesoterodine)

3D PDB for HMDB0015648 (Fesoterodine)

SMILES for HMDB0015648 (Fesoterodine)

INCHI for HMDB0015648 (Fesoterodine)

Structure for HMDB0015648 (Fesoterodine)

3D Structure for HMDB0015648 (Fesoterodine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

References

References

References

References

References

References

References