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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:41 UTC

HMDB ID

HMDB0014639

Secondary Accession Numbers

HMDB14639

Metabolite Identification

Common Name

Darifenacin

Description

Darifenacin, also known as enablex or emselex, 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. Darifenacin is a drug which is used for the treatment of overactive bladder with symptoms of urge urinary incontinence, urgency and frequency. Darifenacin is a very strong basic compound (based on its pKa). Darifenacin is a potentially toxic compound.

Structure

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

496
  Mrv0541 02231214432D          

 32 36  0  0  1  0            999 V2000
    3.2716    1.3928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5908   -1.4435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2378    0.0455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3609    1.8109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9320    0.3230    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1116    0.2368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3446    1.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4841   -0.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1515    0.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9523   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2910    0.1505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1978   -0.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0253    1.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6667    0.0455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8061    0.8179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5303   -1.0687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9555   -0.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9514   -0.9193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3812   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856    0.7317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6165   -1.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1350   -0.6894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0377   -1.7398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0957    0.0455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3812   -1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3703   -2.2247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8102   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8102   -1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5908   -0.1157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0957   -1.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0723   -0.7796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  2  0  0  0  0
  2 29  1  0  0  0  0
  2 32  1  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  0  0  0  0
  3 10  1  0  0  0  0
  4 13  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  6 13  1  0  0  0  0
  7  9  1  0  0  0  0
 10 14  1  0  0  0  0
 11 15  2  0  0  0  0
 11 17  1  0  0  0  0
 12 16  2  0  0  0  0
 12 18  1  0  0  0  0
 14 19  1  0  0  0  0
 15 20  1  0  0  0  0
 16 21  1  0  0  0  0
 17 22  2  0  0  0  0
 18 23  2  0  0  0  0
 19 24  2  0  0  0  0
 19 25  1  0  0  0  0
 20 26  2  0  0  0  0
 21 27  2  0  0  0  0
 22 26  1  0  0  0  0
 23 27  1  0  0  0  0
 24 28  1  0  0  0  0
 25 31  2  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 29 31  1  0  0  0  0
 30 32  1  0  0  0  0
M  END

HMDB0014639
     RDKit          3D
Darifenacin
 62 66  0  0  0  0  0  0  0  0999 V2000
   -2.4607   -3.1355    1.5736 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6037   -1.7498    1.7988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9819   -1.3293    2.9054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2978   -0.7905    0.6966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4773    0.6250    1.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0659    1.5493    0.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2442    2.8701    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8298    3.3519    1.7241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2484    2.4863    2.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0767    1.1550    2.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4193   -1.0522   -0.2920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6951   -0.7634    0.1946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8083   -0.9671   -0.6005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5910   -1.4599   -1.8694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3319   -1.7464   -2.3526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2170   -1.5375   -1.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9702   -1.0895    0.0787 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1821   -1.0316    1.0610 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9127    0.2489    0.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2643    0.8933   -0.2705 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9656    1.7922   -1.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0065    1.3582   -2.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1584    0.6142   -1.4883 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1770   -0.7574   -1.5561 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2177   -1.5134   -1.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3109   -0.9006   -0.5041 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3230    0.4615   -0.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2690    1.2138   -0.9025 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6221    0.8207    0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4703   -0.4292    0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4825   -1.4395    0.0462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5148   -0.1055   -0.9638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9306   -3.8652    2.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8854   -3.5463    0.7961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4065    1.1812   -0.7268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7106    3.5562   -0.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9876    4.4006    1.9177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9263    2.8712    3.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6089    0.5144    3.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8517   -0.3802    1.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8114   -0.7412   -0.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4650   -1.6241   -2.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1447   -2.1350   -3.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2186   -1.7517   -1.8921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9821   -2.1298   -0.3473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8504   -1.9319    0.9054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1400   -1.1173    2.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7036    0.9042    1.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9971    0.1816    0.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    2.6008   -0.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1937    2.3594   -1.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5737    0.8761   -2.9271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4568    2.3151   -2.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3390   -1.2609   -2.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2087   -2.6116   -1.1503 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3034    2.2884   -0.8230 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4606    1.0092    1.3337 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1367    1.6391   -0.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1478   -0.5674    0.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0828   -0.4489   -0.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3444    0.4093   -1.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0538   -0.6375   -1.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  4 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 20 32  1  0
 10  5  1  0
 16 11  1  0
 32 17  1  0
 28 23  1  0
 31 26  1  0
  1 33  1  0
  1 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 12 40  1  0
 13 41  1  0
 14 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  6
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  0
 22 53  1  0
 24 54  1  0
 25 55  1  0
 28 56  1  0
 29 57  1  0
 29 58  1  0
 30 59  1  0
 30 60  1  0
 32 61  1  0
 32 62  1  0
M  END

496
  Mrv0541 02231214432D          

 32 36  0  0  1  0            999 V2000
    3.2716    1.3928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5908   -1.4435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2378    0.0455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3609    1.8109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9320    0.3230    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1116    0.2368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3446    1.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4841   -0.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1515    0.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9523   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2910    0.1505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1978   -0.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0253    1.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6667    0.0455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8061    0.8179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5303   -1.0687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9555   -0.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9514   -0.9193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3812   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856    0.7317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6165   -1.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1350   -0.6894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0377   -1.7398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0957    0.0455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3812   -1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3703   -2.2247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8102   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8102   -1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5908   -0.1157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0957   -1.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0723   -0.7796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  2  0  0  0  0
  2 29  1  0  0  0  0
  2 32  1  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  0  0  0  0
  3 10  1  0  0  0  0
  4 13  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  6 13  1  0  0  0  0
  7  9  1  0  0  0  0
 10 14  1  0  0  0  0
 11 15  2  0  0  0  0
 11 17  1  0  0  0  0
 12 16  2  0  0  0  0
 12 18  1  0  0  0  0
 14 19  1  0  0  0  0
 15 20  1  0  0  0  0
 16 21  1  0  0  0  0
 17 22  2  0  0  0  0
 18 23  2  0  0  0  0
 19 24  2  0  0  0  0
 19 25  1  0  0  0  0
 20 26  2  0  0  0  0
 21 27  2  0  0  0  0
 22 26  1  0  0  0  0
 23 27  1  0  0  0  0
 24 28  1  0  0  0  0
 25 31  2  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 29 31  1  0  0  0  0
 30 32  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014639

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(=O)C([C@@H]1CCN(CCC2=CC3=C(OCC3)C=C2)C1)(C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H30N2O2/c29-27(31)28(23-7-3-1-4-8-23,24-9-5-2-6-10-24)25-14-17-30(20-25)16-13-21-11-12-26-22(19-21)15-18-32-26/h1-12,19,25H,13-18,20H2,(H2,29,31)/t25-/m1/s1

> <INCHI_KEY>
HXGBXQDTNZMWGS-RUZDIDTESA-N

> <FORMULA>
C28H30N2O2

> <MOLECULAR_WEIGHT>
426.55

> <EXACT_MASS>
426.230728214

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
48.541763093099924

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(3S)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-yl]-2,2-diphenylacetamide

> <ALOGPS_LOGP>
4.35

> <JCHEM_LOGP>
4.540284133666668

> <ALOGPS_LOGS>
-6.16

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.212146603505996

> <JCHEM_PKA_STRONGEST_BASIC>
10.108034786798411

> <JCHEM_POLAR_SURFACE_AREA>
55.56

> <JCHEM_REFRACTIVITY>
128.37470000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.98e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
darifenacin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014639
     RDKit          3D
Darifenacin
 62 66  0  0  0  0  0  0  0  0999 V2000
   -2.4607   -3.1355    1.5736 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6037   -1.7498    1.7988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9819   -1.3293    2.9054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2978   -0.7905    0.6966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4773    0.6250    1.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0659    1.5493    0.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2442    2.8701    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8298    3.3519    1.7241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2484    2.4863    2.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0767    1.1550    2.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4193   -1.0522   -0.2920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6951   -0.7634    0.1946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8083   -0.9671   -0.6005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5910   -1.4599   -1.8694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3319   -1.7464   -2.3526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2170   -1.5375   -1.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9702   -1.0895    0.0787 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1821   -1.0316    1.0610 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9127    0.2489    0.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2643    0.8933   -0.2705 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9656    1.7922   -1.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0065    1.3582   -2.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1584    0.6142   -1.4883 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1770   -0.7574   -1.5561 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2177   -1.5134   -1.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3109   -0.9006   -0.5041 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3230    0.4615   -0.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2690    1.2138   -0.9025 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6221    0.8207    0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4703   -0.4292    0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4825   -1.4395    0.0462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5148   -0.1055   -0.9638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9306   -3.8652    2.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8854   -3.5463    0.7961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4065    1.1812   -0.7268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7106    3.5562   -0.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9876    4.4006    1.9177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9263    2.8712    3.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6089    0.5144    3.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8517   -0.3802    1.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8114   -0.7412   -0.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4650   -1.6241   -2.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1447   -2.1350   -3.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2186   -1.7517   -1.8921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9821   -2.1298   -0.3473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8504   -1.9319    0.9054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1400   -1.1173    2.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7036    0.9042    1.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9971    0.1816    0.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    2.6008   -0.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1937    2.3594   -1.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5737    0.8761   -2.9271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4568    2.3151   -2.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3390   -1.2609   -2.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2087   -2.6116   -1.1503 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3034    2.2884   -0.8230 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4606    1.0092    1.3337 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1367    1.6391   -0.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1478   -0.5674    0.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0828   -0.4489   -0.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3444    0.4093   -1.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0538   -0.6375   -1.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  4 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 20 32  1  0
 10  5  1  0
 16 11  1  0
 32 17  1  0
 28 23  1  0
 31 26  1  0
  1 33  1  0
  1 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 12 40  1  0
 13 41  1  0
 14 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  6
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  0
 22 53  1  0
 24 54  1  0
 25 55  1  0
 28 56  1  0
 29 57  1  0
 29 58  1  0
 30 59  1  0
 30 60  1  0
 32 61  1  0
 32 62  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 496                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       6.107   2.600   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      19.769  -2.695   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      11.644   0.085   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       8.140   3.380   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       9.206   0.603   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.675   0.442   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.977   1.937   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.237  -0.542   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.483   1.616   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.978  -0.685   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.143   0.281   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.836  -1.090   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.514   1.974   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.311   0.085   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.238   1.527   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.590  -1.995   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.517  -1.126   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.243  -1.716   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.645  -0.685   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.706   1.366   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.751  -3.527   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.985  -1.287   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.404  -3.248   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.979   0.085   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.645  -2.225   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.080  -0.041   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.158  -4.153   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      18.312  -0.685   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      18.312  -2.225   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      19.769  -0.216   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.979  -2.995   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      20.668  -1.455   0.000  0.00  0.00           C+0
CONECT    1   13                                                            
CONECT    2   29   32                                                       
CONECT    3    8    9   10                                                  
CONECT    4   13                                                            
CONECT    5    6    7    8                                                  
CONECT    6    5   11   12   13                                             
CONECT    7    5    9                                                       
CONECT    8    3    5                                                       
CONECT    9    3    7                                                       
CONECT   10    3   14                                                       
CONECT   11    6   15   17                                                  
CONECT   12    6   16   18                                                  
CONECT   13    1    4    6                                                  
CONECT   14   10   19                                                       
CONECT   15   11   20                                                       
CONECT   16   12   21                                                       
CONECT   17   11   22                                                       
CONECT   18   12   23                                                       
CONECT   19   14   24   25                                                  
CONECT   20   15   26                                                       
CONECT   21   16   27                                                       
CONECT   22   17   26                                                       
CONECT   23   18   27                                                       
CONECT   24   19   28                                                       
CONECT   25   19   31                                                       
CONECT   26   20   22                                                       
CONECT   27   21   23                                                       
CONECT   28   24   29   30                                                  
CONECT   29    2   28   31                                                  
CONECT   30   28   32                                                       
CONECT   31   25   29                                                       
CONECT   32    2   30                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

COMPND    HMDB0014639
HETATM    1  N1  UNL     1      -2.461  -3.136   1.574  1.00  0.00           N  
HETATM    2  C1  UNL     1      -2.604  -1.750   1.799  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.982  -1.329   2.905  1.00  0.00           O  
HETATM    4  C2  UNL     1      -2.298  -0.790   0.697  1.00  0.00           C  
HETATM    5  C3  UNL     1      -2.477   0.625   1.091  1.00  0.00           C  
HETATM    6  C4  UNL     1      -3.066   1.549   0.220  1.00  0.00           C  
HETATM    7  C5  UNL     1      -3.244   2.870   0.508  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.830   3.352   1.724  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.248   2.486   2.612  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.077   1.155   2.302  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.419  -1.052  -0.292  1.00  0.00           C  
HETATM   12  C10 UNL     1      -4.695  -0.763   0.195  1.00  0.00           C  
HETATM   13  C11 UNL     1      -5.808  -0.967  -0.600  1.00  0.00           C  
HETATM   14  C12 UNL     1      -5.591  -1.460  -1.869  1.00  0.00           C  
HETATM   15  C13 UNL     1      -4.332  -1.746  -2.353  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.217  -1.538  -1.545  1.00  0.00           C  
HETATM   17  C15 UNL     1      -0.970  -1.090   0.079  1.00  0.00           C  
HETATM   18  C16 UNL     1       0.182  -1.032   1.061  1.00  0.00           C  
HETATM   19  C17 UNL     1       0.913   0.249   0.814  1.00  0.00           C  
HETATM   20  N2  UNL     1       0.264   0.893  -0.271  1.00  0.00           N  
HETATM   21  C18 UNL     1       0.966   1.792  -1.067  1.00  0.00           C  
HETATM   22  C19 UNL     1       2.007   1.358  -2.011  1.00  0.00           C  
HETATM   23  C20 UNL     1       3.158   0.614  -1.488  1.00  0.00           C  
HETATM   24  C21 UNL     1       3.177  -0.757  -1.556  1.00  0.00           C  
HETATM   25  C22 UNL     1       4.218  -1.513  -1.082  1.00  0.00           C  
HETATM   26  C23 UNL     1       5.311  -0.901  -0.504  1.00  0.00           C  
HETATM   27  C24 UNL     1       5.323   0.462  -0.421  1.00  0.00           C  
HETATM   28  C25 UNL     1       4.269   1.214  -0.903  1.00  0.00           C  
HETATM   29  C26 UNL     1       6.622   0.821   0.250  1.00  0.00           C  
HETATM   30  C27 UNL     1       7.470  -0.429   0.127  1.00  0.00           C  
HETATM   31  O2  UNL     1       6.482  -1.440   0.046  1.00  0.00           O  
HETATM   32  C28 UNL     1      -0.515  -0.106  -0.964  1.00  0.00           C  
HETATM   33  H1  UNL     1      -2.931  -3.865   2.182  1.00  0.00           H  
HETATM   34  H2  UNL     1      -1.885  -3.546   0.796  1.00  0.00           H  
HETATM   35  H3  UNL     1      -3.406   1.181  -0.727  1.00  0.00           H  
HETATM   36  H4  UNL     1      -3.711   3.556  -0.209  1.00  0.00           H  
HETATM   37  H5  UNL     1      -2.988   4.401   1.918  1.00  0.00           H  
HETATM   38  H6  UNL     1      -1.926   2.871   3.568  1.00  0.00           H  
HETATM   39  H7  UNL     1      -1.609   0.514   3.037  1.00  0.00           H  
HETATM   40  H8  UNL     1      -4.852  -0.380   1.189  1.00  0.00           H  
HETATM   41  H9  UNL     1      -6.811  -0.741  -0.219  1.00  0.00           H  
HETATM   42  H10 UNL     1      -6.465  -1.624  -2.503  1.00  0.00           H  
HETATM   43  H11 UNL     1      -4.145  -2.135  -3.348  1.00  0.00           H  
HETATM   44  H12 UNL     1      -2.219  -1.752  -1.892  1.00  0.00           H  
HETATM   45  H13 UNL     1      -0.982  -2.130  -0.347  1.00  0.00           H  
HETATM   46  H14 UNL     1       0.850  -1.932   0.905  1.00  0.00           H  
HETATM   47  H15 UNL     1      -0.140  -1.117   2.110  1.00  0.00           H  
HETATM   48  H16 UNL     1       0.704   0.904   1.724  1.00  0.00           H  
HETATM   49  H17 UNL     1       1.997   0.182   0.794  1.00  0.00           H  
HETATM   50  H18 UNL     1       1.378   2.601  -0.405  1.00  0.00           H  
HETATM   51  H19 UNL     1       0.194   2.359  -1.685  1.00  0.00           H  
HETATM   52  H20 UNL     1       1.574   0.876  -2.927  1.00  0.00           H  
HETATM   53  H21 UNL     1       2.457   2.315  -2.442  1.00  0.00           H  
HETATM   54  H22 UNL     1       2.339  -1.261  -2.002  1.00  0.00           H  
HETATM   55  H23 UNL     1       4.209  -2.612  -1.150  1.00  0.00           H  
HETATM   56  H24 UNL     1       4.303   2.288  -0.823  1.00  0.00           H  
HETATM   57  H25 UNL     1       6.461   1.009   1.334  1.00  0.00           H  
HETATM   58  H26 UNL     1       7.137   1.639  -0.247  1.00  0.00           H  
HETATM   59  H27 UNL     1       8.148  -0.567   0.992  1.00  0.00           H  
HETATM   60  H28 UNL     1       8.083  -0.449  -0.783  1.00  0.00           H  
HETATM   61  H29 UNL     1      -1.344   0.409  -1.463  1.00  0.00           H  
HETATM   62  H30 UNL     1       0.054  -0.637  -1.749  1.00  0.00           H  
CONECT    1    2   33   34
CONECT    2    3    3    4
CONECT    4    5   11   17
CONECT    5    6    6   10
CONECT    6    7   35
CONECT    7    8    8   36
CONECT    8    9   37
CONECT    9   10   10   38
CONECT   10   39
CONECT   11   12   12   16
CONECT   12   13   40
CONECT   13   14   14   41
CONECT   14   15   42
CONECT   15   16   16   43
CONECT   16   44
CONECT   17   18   32   45
CONECT   18   19   46   47
CONECT   19   20   48   49
CONECT   20   21   32
CONECT   21   22   50   51
CONECT   22   23   52   53
CONECT   23   24   24   28
CONECT   24   25   54
CONECT   25   26   26   55
CONECT   26   27   31
CONECT   27   28   28   29
CONECT   28   56
CONECT   29   30   57   58
CONECT   30   31   59   60
CONECT   32   61   62
END

HMDB0014639
     RDKit          3D
Darifenacin
 62 66  0  0  0  0  0  0  0  0999 V2000
   -2.4607   -3.1355    1.5736 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6037   -1.7498    1.7988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9819   -1.3293    2.9054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2978   -0.7905    0.6966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4773    0.6250    1.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0659    1.5493    0.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2442    2.8701    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8298    3.3519    1.7241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2484    2.4863    2.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0767    1.1550    2.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4193   -1.0522   -0.2920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6951   -0.7634    0.1946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8083   -0.9671   -0.6005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5910   -1.4599   -1.8694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3319   -1.7464   -2.3526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2170   -1.5375   -1.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9702   -1.0895    0.0787 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1821   -1.0316    1.0610 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9127    0.2489    0.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2643    0.8933   -0.2705 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9656    1.7922   -1.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0065    1.3582   -2.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1584    0.6142   -1.4883 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1770   -0.7574   -1.5561 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2177   -1.5134   -1.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3109   -0.9006   -0.5041 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3230    0.4615   -0.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2690    1.2138   -0.9025 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6221    0.8207    0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4703   -0.4292    0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4825   -1.4395    0.0462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5148   -0.1055   -0.9638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9306   -3.8652    2.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8854   -3.5463    0.7961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4065    1.1812   -0.7268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7106    3.5562   -0.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9876    4.4006    1.9177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9263    2.8712    3.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6089    0.5144    3.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8517   -0.3802    1.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8114   -0.7412   -0.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4650   -1.6241   -2.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1447   -2.1350   -3.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2186   -1.7517   -1.8921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9821   -2.1298   -0.3473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8504   -1.9319    0.9054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1400   -1.1173    2.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7036    0.9042    1.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9971    0.1816    0.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    2.6008   -0.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1937    2.3594   -1.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5737    0.8761   -2.9271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4568    2.3151   -2.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3390   -1.2609   -2.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2087   -2.6116   -1.1503 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3034    2.2884   -0.8230 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4606    1.0092    1.3337 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1367    1.6391   -0.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1478   -0.5674    0.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0828   -0.4489   -0.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3444    0.4093   -1.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0538   -0.6375   -1.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  4 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 20 32  1  0
 10  5  1  0
 16 11  1  0
 32 17  1  0
 28 23  1  0
 31 26  1  0
  1 33  1  0
  1 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 12 40  1  0
 13 41  1  0
 14 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  6
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  0
 22 53  1  0
 24 54  1  0
 25 55  1  0
 28 56  1  0
 29 57  1  0
 29 58  1  0
 30 59  1  0
 30 60  1  0
 32 61  1  0
 32 62  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(S)-1-(2-(2,3-Dihydro-5-benzofuranyl)ethyl)-alpha,alpha-diphenyl-3-pyrrolidineacetamide	ChEBI
(S)-1-(2-(2,3-Dihydro-5-benzofuranyl)ethyl)-a,a-diphenyl-3-pyrrolidineacetamide	Generator
(S)-1-(2-(2,3-Dihydro-5-benzofuranyl)ethyl)-α,α-diphenyl-3-pyrrolidineacetamide	Generator
Enablex	HMDB
Darifenacin hydrochloride	HMDB
Darifenicin	HMDB
Darifenacin hydrobromide	HMDB
Emselex	HMDB
Darifenacine	HMDB

Chemical Formula

C₂₈H₃₀N₂O₂

Average Molecular Weight

426.55

Monoisotopic Molecular Weight

426.230728214

IUPAC Name

2-[(3S)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-yl]-2,2-diphenylacetamide

Traditional Name

darifenacin

CAS Registry Number

133099-04-4

SMILES

NC(=O)C([C@@H]1CCN(CCC2=CC3=C(OCC3)C=C2)C1)(C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C28H30N2O2/c29-27(31)28(23-7-3-1-4-8-23,24-9-5-2-6-10-24)25-14-17-30(20-25)16-13-21-11-12-26-22(19-21)15-18-32-26/h1-12,19,25H,13-18,20H2,(H2,29,31)/t25-/m1/s1

InChI Key

HXGBXQDTNZMWGS-RUZDIDTESA-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
Phenylacetamide
Phenethylamine
Coumaran
Alkyl aryl ether
Aralkylamine
N-alkylpyrrolidine
Pyrrolidine
Amino acid or derivatives
Carboxamide group
Primary carboxylic acid amide
Tertiary amine
Tertiary aliphatic amine
Ether
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Azacycle
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Amine
Carbonyl group
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:391960 )
1-benzofurans (CHEBI:391960 )
pyrrolidines (CHEBI:391960 )

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: HMDB0014639)

Source

Exogenous

Exogenous (HMDB: HMDB0014639)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Antimuscarinic (HMDB: HMDB0014639)

Pharmaceutical industry

Antispasmodic drug (HMDB: HMDB0014639)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0003 g/L	Not Available
LogP	4.5	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0003 g/L	ALOGPS
logP	4.35	ALOGPS
logP	4.54	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	16.21	ChemAxon
pKa (Strongest Basic)	10.11	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.56 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	128.37 m³·mol⁻¹	ChemAxon
Polarizability	48.54 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	200.839	31661259
DarkChem	[M-H]-	195.613	31661259
DeepCCS	[M+H]+	198.247	30932474
DeepCCS	[M-H]-	195.851	30932474
DeepCCS	[M-2H]-	228.735	30932474
DeepCCS	[M+Na]+	204.159	30932474
AllCCS	[M+H]+	206.2	32859911
AllCCS	[M+H-H2O]+	204.0	32859911
AllCCS	[M+NH4]+	208.3	32859911
AllCCS	[M+Na]+	208.9	32859911
AllCCS	[M-H]-	204.7	32859911
AllCCS	[M+Na-2H]-	204.9	32859911
AllCCS	[M+HCOO]-	205.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Darifenacin	NC(=O)C([C@@H]1CCN(CCC2=CC3=C(OCC3)C=C2)C1)(C1=CC=CC=C1)C1=CC=CC=C1	4286.0	Standard polar	33892256
Darifenacin	NC(=O)C([C@@H]1CCN(CCC2=CC3=C(OCC3)C=C2)C1)(C1=CC=CC=C1)C1=CC=CC=C1	3585.3	Standard non polar	33892256
Darifenacin	NC(=O)C([C@@H]1CCN(CCC2=CC3=C(OCC3)C=C2)C1)(C1=CC=CC=C1)C1=CC=CC=C1	3643.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Darifenacin,1TMS,isomer #1	C[Si](C)(C)NC(=O)C(C1=CC=CC=C1)(C1=CC=CC=C1)[C@@H]1CCN(CCC2=CC=C3OCCC3=C2)C1	3669.9	Semi standard non polar	33892256
Darifenacin,1TMS,isomer #1	C[Si](C)(C)NC(=O)C(C1=CC=CC=C1)(C1=CC=CC=C1)[C@@H]1CCN(CCC2=CC=C3OCCC3=C2)C1	3317.7	Standard non polar	33892256
Darifenacin,1TMS,isomer #1	C[Si](C)(C)NC(=O)C(C1=CC=CC=C1)(C1=CC=CC=C1)[C@@H]1CCN(CCC2=CC=C3OCCC3=C2)C1	4505.3	Standard polar	33892256
Darifenacin,2TMS,isomer #1	C[Si](C)(C)N(C(=O)C(C1=CC=CC=C1)(C1=CC=CC=C1)[C@@H]1CCN(CCC2=CC=C3OCCC3=C2)C1)[Si](C)(C)C	3694.3	Semi standard non polar	33892256
Darifenacin,2TMS,isomer #1	C[Si](C)(C)N(C(=O)C(C1=CC=CC=C1)(C1=CC=CC=C1)[C@@H]1CCN(CCC2=CC=C3OCCC3=C2)C1)[Si](C)(C)C	3479.4	Standard non polar	33892256
Darifenacin,2TMS,isomer #1	C[Si](C)(C)N(C(=O)C(C1=CC=CC=C1)(C1=CC=CC=C1)[C@@H]1CCN(CCC2=CC=C3OCCC3=C2)C1)[Si](C)(C)C	4331.1	Standard polar	33892256
Darifenacin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C(C1=CC=CC=C1)(C1=CC=CC=C1)[C@@H]1CCN(CCC2=CC=C3OCCC3=C2)C1	3891.0	Semi standard non polar	33892256
Darifenacin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C(C1=CC=CC=C1)(C1=CC=CC=C1)[C@@H]1CCN(CCC2=CC=C3OCCC3=C2)C1	3572.7	Standard non polar	33892256
Darifenacin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C(C1=CC=CC=C1)(C1=CC=CC=C1)[C@@H]1CCN(CCC2=CC=C3OCCC3=C2)C1	4565.2	Standard polar	33892256
Darifenacin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C(C1=CC=CC=C1)(C1=CC=CC=C1)[C@@H]1CCN(CCC2=CC=C3OCCC3=C2)C1)[Si](C)(C)C(C)(C)C	4129.2	Semi standard non polar	33892256
Darifenacin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C(C1=CC=CC=C1)(C1=CC=CC=C1)[C@@H]1CCN(CCC2=CC=C3OCCC3=C2)C1)[Si](C)(C)C(C)(C)C	3877.8	Standard non polar	33892256
Darifenacin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C(C1=CC=CC=C1)(C1=CC=CC=C1)[C@@H]1CCN(CCC2=CC=C3OCCC3=C2)C1)[Si](C)(C)C(C)(C)C	4368.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Darifenacin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00lv-2491000000-40c43db64189724fe0c2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Darifenacin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Darifenacin 10V, Positive-QTOF	splash10-004i-0101900000-1979d23256753a983573	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Darifenacin 20V, Positive-QTOF	splash10-03gj-0756900000-6e69c78743e94527add2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Darifenacin 40V, Positive-QTOF	splash10-0uxs-2910000000-ec1acf0e02b7c0a392f3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Darifenacin 10V, Negative-QTOF	splash10-004i-0001900000-e8c519b1d7f130de607a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Darifenacin 20V, Negative-QTOF	splash10-004i-4285900000-73144c3d58ba99d76581	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Darifenacin 40V, Negative-QTOF	splash10-0006-9030000000-5dfb7a1ae0753d3d4c11	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Darifenacin 10V, Negative-QTOF	splash10-005c-4005900000-8a58ca84e09117fd29e5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Darifenacin 20V, Negative-QTOF	splash10-0006-9004100000-2c811675031a777fbc67	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Darifenacin 40V, Negative-QTOF	splash10-0006-9212000000-514c545cfeaf92ef3a8e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Darifenacin 10V, Positive-QTOF	splash10-004i-0002900000-3905ca525d1dcc4e15f3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Darifenacin 20V, Positive-QTOF	splash10-004i-0104900000-359dc4da59d626f0edf4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Darifenacin 40V, Positive-QTOF	splash10-0002-0932000000-13b487199d725fb1e357	2021-09-22	Wishart Lab	View Spectrum

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 DB00496	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00496	21059682	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

DB00496

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

392054

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Darifenacin

METLIN ID

Not Available

PubChem Compound

444031

PDB ID

Not Available

ChEBI ID

391960

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

Not Available

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

Skerjanec A: The clinical pharmacokinetics of darifenacin. Clin Pharmacokinet. 2006;45(4):325-50. [PubMed:16584282 ]

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

Skerjanec A: The clinical pharmacokinetics of darifenacin. Clin Pharmacokinet. 2006;45(4):325-50. [PubMed:16584282 ]

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

Bharucha AE, Ravi K, Zinsmeister AR: Comparison of selective M3 and nonselective muscarinic receptor antagonists on gastrointestinal transit and bowel habits in humans. Am J Physiol Gastrointest Liver Physiol. 2010 Jul;299(1):G215-9. doi: 10.1152/ajpgi.00072.2010. Epub 2010 Apr 15. [PubMed:20395537 ]
Bozkurt TE, Sahin-Erdemli I: M(1) and M(3) muscarinic receptors are involved in the release of urinary bladder-derived relaxant factor. Pharmacol Res. 2009 May;59(5):300-5. doi: 10.1016/j.phrs.2009.01.013. Epub 2009 Feb 5. [PubMed:19416629 ]
Jha S, Parsons M: Treatment of overactive bladder in the aging population: focus on darifenacin. Clin Interv Aging. 2006;1(4):309-16. [PubMed:18046909 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

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

Jha S, Parsons M: Treatment of overactive bladder in the aging population: focus on darifenacin. Clin Interv Aging. 2006;1(4):309-16. [PubMed:18046909 ]
Moriya H, Takagi Y, Nakanishi T, Hayashi M, Tani T, Hirotsu I: Affinity profiles of various muscarinic antagonists for cloned human muscarinic acetylcholine receptor (mAChR) subtypes and mAChRs in rat heart and submandibular gland. Life Sci. 1999;64(25):2351-8. [PubMed:10374898 ]

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

Jha S, Parsons M: Treatment of overactive bladder in the aging population: focus on darifenacin. Clin Interv Aging. 2006;1(4):309-16. [PubMed:18046909 ]
Moriya H, Takagi Y, Nakanishi T, Hayashi M, Tani T, Hirotsu I: Affinity profiles of various muscarinic antagonists for cloned human muscarinic acetylcholine receptor (mAChR) subtypes and mAChRs in rat heart and submandibular gland. Life Sci. 1999;64(25):2351-8. [PubMed:10374898 ]

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

Jha S, Parsons M: Treatment of overactive bladder in the aging population: focus on darifenacin. Clin Interv Aging. 2006;1(4):309-16. [PubMed:18046909 ]
Moriya H, Takagi Y, Nakanishi T, Hayashi M, Tani T, Hirotsu I: Affinity profiles of various muscarinic antagonists for cloned human muscarinic acetylcholine receptor (mAChR) subtypes and mAChRs in rat heart and submandibular gland. Life Sci. 1999;64(25):2351-8. [PubMed:10374898 ]

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

Moriya H, Takagi Y, Nakanishi T, Hayashi M, Tani T, Hirotsu I: Affinity profiles of various muscarinic antagonists for cloned human muscarinic acetylcholine receptor (mAChR) subtypes and mAChRs in rat heart and submandibular gland. Life Sci. 1999;64(25):2351-8. [PubMed:10374898 ]
Jha S, Parsons M: Treatment of overactive bladder in the aging population: focus on darifenacin. Clin Interv Aging. 2006;1(4):309-16. [PubMed:18046909 ]

Showing metabocard for Darifenacin (HMDB0014639)

MOL for HMDB0014639 (Darifenacin)

3D MOL for HMDB0014639 (Darifenacin)

3D SDF for HMDB0014639 (Darifenacin)

3D-SDF for HMDB0014639 (Darifenacin)

PDB for HMDB0014639 (Darifenacin)

3D PDB for HMDB0014639 (Darifenacin)

SMILES for HMDB0014639 (Darifenacin)

INCHI for HMDB0014639 (Darifenacin)

Structure for HMDB0014639 (Darifenacin)

3D Structure for HMDB0014639 (Darifenacin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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