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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 02:51:35 UTC

HMDB ID

HMDB0014349

Secondary Accession Numbers

HMDB14349

Metabolite Identification

Common Name

Dofetilide

Description

Dofetilide, also known as tikosyn or 1-mspmpe, belongs to the class of organic compounds known as sulfanilides. These are organic aromatic compounds containing a sulfanilide moiety, with the general structure RS(=O)(=O)NC1=CC=CC=C1. Dofetilide is a drug which is used for the maintenance of normal sinus rhythm (delay in time to recurrence of atrial fibrillation/atrial flutter [af/afl]) in patients with atrial fibrillation/atrial flutter of greater than one week duration who have been converted to normal sinus rhythm. Dofetilide is a very strong basic compound (based on its pKa). A tertiary amino compound that is N-ethyl-N-methylethanamine substituted by a 4-phenoxy and a 4-phenyl group at the terminal carbon atoms respectively.

Structure

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

204
  Mrv0541 02231214312D          

 29 30  0  0  1  0            999 V2000
    5.9370    5.1564    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -5.1564    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3495    4.4419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5245    5.8708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -4.4419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -5.8708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    4.7439    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -4.7439    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    5.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -5.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  2  0  0  0  0
  1  5  2  0  0  0  0
  1  9  1  0  0  0  0
  1 28  1  0  0  0  0
  2  6  2  0  0  0  0
  2  7  2  0  0  0  0
  2 10  1  0  0  0  0
  2 29  1  0  0  0  0
  3 15  1  0  0  0  0
  3 22  1  0  0  0  0
  8 11  1  0  0  0  0
  8 13  1  0  0  0  0
  8 16  1  0  0  0  0
  9 19  1  0  0  0  0
 10 23  1  0  0  0  0
 11 12  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 17  2  0  0  0  0
 14 18  1  0  0  0  0
 17 20  1  0  0  0  0
 18 21  2  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 22 24  2  0  0  0  0
 22 25  1  0  0  0  0
 23 26  2  0  0  0  0
 23 27  1  0  0  0  0
 24 26  1  0  0  0  0
 25 27  2  0  0  0  0
M  END

HMDB0014349
     RDKit          3D
Dofetilide
 56 57  0  0  0  0  0  0  0  0999 V2000
    0.0472   -1.9704   -1.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2733   -1.0467   -0.2180 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3628    0.2311   -0.3713 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8641    0.1477   -0.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4603    1.4169   -0.3521 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8345    1.5395   -0.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6138    0.4383    0.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0019    0.5369    0.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6319    1.7340    0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0042    1.9682    0.1078 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0184    1.3564    1.3270 S   0  0  0  0  0  6  0  0  0  0  0  0
    9.0270   -0.4160    1.2756 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4170    1.8991    1.1969 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5222    1.7360    2.7003 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8202    2.8343   -0.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4604    2.7562   -0.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6760   -0.9632    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4358   -0.3176   -1.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8882   -0.2381   -0.8018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7502   -1.2598   -1.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1072   -1.1882   -0.8830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6288   -0.0589   -0.2428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0264    0.0342    0.0427 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9171   -1.2665    0.7228 S   0  0  0  0  0  6  0  0  0  0  0  0
   -8.2736   -1.6964    2.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8357   -2.5141   -0.1086 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3598   -0.8922    0.8866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7388    0.9351    0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3814    0.8822   -0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8669   -2.6160   -0.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3688   -1.4898   -2.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7929   -2.6519   -1.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1152    0.6857   -1.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0060    0.8736    0.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2533   -0.4981   -1.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1067   -0.2076    0.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1480   -0.5161    0.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5531   -0.3484    0.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4594    2.5750   -0.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8696   -0.7305    0.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0240   -0.7634    1.6512 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2289   -0.8024    1.9341 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2756    3.7940   -0.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8769    3.6270   -0.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8834   -0.4760    1.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0680   -2.0047    0.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3208   -0.8842   -2.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0449    0.7272   -1.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3481   -2.1372   -1.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7661   -1.9937   -1.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5278    0.9222   -0.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9995   -0.7523    2.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3394   -2.2984    2.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0364   -2.1855    2.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0847    1.8320    0.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7218    1.7013    0.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 11 14  2  0
  9 15  1  0
 15 16  2  0
  2 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 24 27  2  0
 22 28  1  0
 28 29  2  0
 16  6  1  0
 29 19  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  7 37  1  0
  8 38  1  0
 10 39  1  0
 12 40  1  0
 12 41  1  0
 12 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 20 49  1  0
 21 50  1  0
 23 51  1  0
 25 52  1  0
 25 53  1  0
 25 54  1  0
 28 55  1  0
 29 56  1  0
M  END

204
  Mrv0541 02231214312D          

 29 30  0  0  1  0            999 V2000
    5.9370    5.1564    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -5.1564    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3495    4.4419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5245    5.8708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -4.4419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -5.8708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    4.7439    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -4.7439    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    5.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -5.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  2  0  0  0  0
  1  5  2  0  0  0  0
  1  9  1  0  0  0  0
  1 28  1  0  0  0  0
  2  6  2  0  0  0  0
  2  7  2  0  0  0  0
  2 10  1  0  0  0  0
  2 29  1  0  0  0  0
  3 15  1  0  0  0  0
  3 22  1  0  0  0  0
  8 11  1  0  0  0  0
  8 13  1  0  0  0  0
  8 16  1  0  0  0  0
  9 19  1  0  0  0  0
 10 23  1  0  0  0  0
 11 12  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 17  2  0  0  0  0
 14 18  1  0  0  0  0
 17 20  1  0  0  0  0
 18 21  2  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 22 24  2  0  0  0  0
 22 25  1  0  0  0  0
 23 26  2  0  0  0  0
 23 27  1  0  0  0  0
 24 26  1  0  0  0  0
 25 27  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014349

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(CCOC1=CC=C(NS(C)(=O)=O)C=C1)CCC1=CC=C(NS(C)(=O)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H27N3O5S2/c1-22(13-12-16-4-6-17(7-5-16)20-28(2,23)24)14-15-27-19-10-8-18(9-11-19)21-29(3,25)26/h4-11,20-21H,12-15H2,1-3H3

> <INCHI_KEY>
IXTMWRCNAAVVAI-UHFFFAOYSA-N

> <FORMULA>
C19H27N3O5S2

> <MOLECULAR_WEIGHT>
441.565

> <EXACT_MASS>
441.139212369

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
46.0314497578555

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[4-(2-{[2-(4-methanesulfonamidophenyl)ethyl](methyl)amino}ethoxy)phenyl]methanesulfonamide

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
0.2379157528062352

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.777111708152624

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.145184001473005

> <JCHEM_PKA_STRONGEST_BASIC>
8.989392984355275

> <JCHEM_POLAR_SURFACE_AREA>
104.81

> <JCHEM_REFRACTIVITY>
113.27430000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.98e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dofetilide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014349
     RDKit          3D
Dofetilide
 56 57  0  0  0  0  0  0  0  0999 V2000
    0.0472   -1.9704   -1.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2733   -1.0467   -0.2180 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3628    0.2311   -0.3713 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8641    0.1477   -0.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4603    1.4169   -0.3521 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8345    1.5395   -0.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6138    0.4383    0.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0019    0.5369    0.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6319    1.7340    0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0042    1.9682    0.1078 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0184    1.3564    1.3270 S   0  0  0  0  0  6  0  0  0  0  0  0
    9.0270   -0.4160    1.2756 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4170    1.8991    1.1969 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5222    1.7360    2.7003 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8202    2.8343   -0.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4604    2.7562   -0.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6760   -0.9632    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4358   -0.3176   -1.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8882   -0.2381   -0.8018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7502   -1.2598   -1.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1072   -1.1882   -0.8830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6288   -0.0589   -0.2428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0264    0.0342    0.0427 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9171   -1.2665    0.7228 S   0  0  0  0  0  6  0  0  0  0  0  0
   -8.2736   -1.6964    2.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8357   -2.5141   -0.1086 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3598   -0.8922    0.8866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7388    0.9351    0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3814    0.8822   -0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8669   -2.6160   -0.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3688   -1.4898   -2.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7929   -2.6519   -1.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1152    0.6857   -1.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0060    0.8736    0.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2533   -0.4981   -1.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1067   -0.2076    0.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1480   -0.5161    0.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5531   -0.3484    0.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4594    2.5750   -0.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8696   -0.7305    0.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0240   -0.7634    1.6512 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2289   -0.8024    1.9341 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2756    3.7940   -0.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8769    3.6270   -0.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8834   -0.4760    1.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0680   -2.0047    0.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3208   -0.8842   -2.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0449    0.7272   -1.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3481   -2.1372   -1.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7661   -1.9937   -1.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5278    0.9222   -0.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9995   -0.7523    2.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3394   -2.2984    2.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0364   -2.1855    2.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0847    1.8320    0.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7218    1.7013    0.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 11 14  2  0
  9 15  1  0
 15 16  2  0
  2 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 24 27  2  0
 22 28  1  0
 28 29  2  0
 16  6  1  0
 29 19  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  7 37  1  0
  8 38  1  0
 10 39  1  0
 12 40  1  0
 12 41  1  0
 12 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 20 49  1  0
 21 50  1  0
 23 51  1  0
 25 52  1  0
 25 53  1  0
 25 54  1  0
 28 55  1  0
 29 56  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 204                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      11.082   9.625   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0       4.414  -9.625   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0       5.748  -2.695   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      11.852   8.292   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      10.312  10.959   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.644  -8.292   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       5.184 -10.959   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       8.415   0.385   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       9.748   8.855   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       5.748  -8.855   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       8.415   1.925   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.748   2.695   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081  -0.385   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.748   4.235   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081  -1.925   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.748  -0.385   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.415   5.005   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.082   5.005   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.748   7.315   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.415   6.545   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.082   6.545   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.748  -4.235   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.748  -7.315   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.414  -5.005   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.081  -5.005   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.414  -6.545   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.081  -6.545   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.416  10.395   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.080 -10.395   0.000  0.00  0.00           C+0
CONECT    1    4    5    9   28                                             
CONECT    2    6    7   10   29                                             
CONECT    3   15   22                                                       
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    2                                                            
CONECT    7    2                                                            
CONECT    8   11   13   16                                                  
CONECT    9    1   19                                                       
CONECT   10    2   23                                                       
CONECT   11    8   12                                                       
CONECT   12   11   14                                                       
CONECT   13    8   15                                                       
CONECT   14   12   17   18                                                  
CONECT   15    3   13                                                       
CONECT   16    8                                                            
CONECT   17   14   20                                                       
CONECT   18   14   21                                                       
CONECT   19    9   20   21                                                  
CONECT   20   17   19                                                       
CONECT   21   18   19                                                       
CONECT   22    3   24   25                                                  
CONECT   23   10   26   27                                                  
CONECT   24   22   26                                                       
CONECT   25   22   27                                                       
CONECT   26   23   24                                                       
CONECT   27   23   25                                                       
CONECT   28    1                                                            
CONECT   29    2                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

COMPND    HMDB0014349
HETATM    1  C1  UNL     1       0.047  -1.970  -1.281  1.00  0.00           C  
HETATM    2  N1  UNL     1      -0.273  -1.047  -0.218  1.00  0.00           N  
HETATM    3  C2  UNL     1       0.363   0.231  -0.371  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.864   0.148  -0.199  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.460   1.417  -0.352  1.00  0.00           O  
HETATM    6  C4  UNL     1       3.834   1.540  -0.234  1.00  0.00           C  
HETATM    7  C5  UNL     1       4.614   0.438   0.027  1.00  0.00           C  
HETATM    8  C6  UNL     1       6.002   0.537   0.150  1.00  0.00           C  
HETATM    9  C7  UNL     1       6.632   1.734   0.015  1.00  0.00           C  
HETATM   10  N2  UNL     1       8.004   1.968   0.108  1.00  0.00           N  
HETATM   11  S1  UNL     1       9.018   1.356   1.327  1.00  0.00           S  
HETATM   12  C8  UNL     1       9.027  -0.416   1.276  1.00  0.00           C  
HETATM   13  O2  UNL     1      10.417   1.899   1.197  1.00  0.00           O  
HETATM   14  O3  UNL     1       8.522   1.736   2.700  1.00  0.00           O  
HETATM   15  C9  UNL     1       5.820   2.834  -0.248  1.00  0.00           C  
HETATM   16  C10 UNL     1       4.460   2.756  -0.372  1.00  0.00           C  
HETATM   17  C11 UNL     1      -1.676  -0.963   0.048  1.00  0.00           C  
HETATM   18  C12 UNL     1      -2.436  -0.318  -1.091  1.00  0.00           C  
HETATM   19  C13 UNL     1      -3.888  -0.238  -0.802  1.00  0.00           C  
HETATM   20  C14 UNL     1      -4.750  -1.260  -1.151  1.00  0.00           C  
HETATM   21  C15 UNL     1      -6.107  -1.188  -0.883  1.00  0.00           C  
HETATM   22  C16 UNL     1      -6.629  -0.059  -0.243  1.00  0.00           C  
HETATM   23  N3  UNL     1      -8.026   0.034   0.043  1.00  0.00           N  
HETATM   24  S2  UNL     1      -8.917  -1.267   0.723  1.00  0.00           S  
HETATM   25  C17 UNL     1      -8.274  -1.696   2.340  1.00  0.00           C  
HETATM   26  O4  UNL     1      -8.836  -2.514  -0.109  1.00  0.00           O  
HETATM   27  O5  UNL     1     -10.360  -0.892   0.887  1.00  0.00           O  
HETATM   28  C18 UNL     1      -5.739   0.935   0.089  1.00  0.00           C  
HETATM   29  C19 UNL     1      -4.381   0.882  -0.171  1.00  0.00           C  
HETATM   30  H1  UNL     1       0.867  -2.616  -0.894  1.00  0.00           H  
HETATM   31  H2  UNL     1       0.369  -1.490  -2.210  1.00  0.00           H  
HETATM   32  H3  UNL     1      -0.793  -2.652  -1.524  1.00  0.00           H  
HETATM   33  H4  UNL     1       0.115   0.686  -1.346  1.00  0.00           H  
HETATM   34  H5  UNL     1      -0.006   0.874   0.473  1.00  0.00           H  
HETATM   35  H6  UNL     1       2.253  -0.498  -1.008  1.00  0.00           H  
HETATM   36  H7  UNL     1       2.107  -0.208   0.817  1.00  0.00           H  
HETATM   37  H8  UNL     1       4.148  -0.516   0.138  1.00  0.00           H  
HETATM   38  H9  UNL     1       6.553  -0.348   0.347  1.00  0.00           H  
HETATM   39  H10 UNL     1       8.459   2.575  -0.639  1.00  0.00           H  
HETATM   40  H11 UNL     1       8.870  -0.731   0.223  1.00  0.00           H  
HETATM   41  H12 UNL     1      10.024  -0.763   1.651  1.00  0.00           H  
HETATM   42  H13 UNL     1       8.229  -0.802   1.934  1.00  0.00           H  
HETATM   43  H14 UNL     1       6.276   3.794  -0.360  1.00  0.00           H  
HETATM   44  H15 UNL     1       3.877   3.627  -0.574  1.00  0.00           H  
HETATM   45  H16 UNL     1      -1.883  -0.476   1.002  1.00  0.00           H  
HETATM   46  H17 UNL     1      -2.068  -2.005   0.123  1.00  0.00           H  
HETATM   47  H18 UNL     1      -2.321  -0.884  -2.033  1.00  0.00           H  
HETATM   48  H19 UNL     1      -2.045   0.727  -1.180  1.00  0.00           H  
HETATM   49  H20 UNL     1      -4.348  -2.137  -1.648  1.00  0.00           H  
HETATM   50  H21 UNL     1      -6.766  -1.994  -1.162  1.00  0.00           H  
HETATM   51  H22 UNL     1      -8.528   0.922  -0.168  1.00  0.00           H  
HETATM   52  H23 UNL     1      -8.000  -0.752   2.888  1.00  0.00           H  
HETATM   53  H24 UNL     1      -7.339  -2.298   2.257  1.00  0.00           H  
HETATM   54  H25 UNL     1      -9.036  -2.186   2.970  1.00  0.00           H  
HETATM   55  H26 UNL     1      -6.085   1.832   0.586  1.00  0.00           H  
HETATM   56  H27 UNL     1      -3.722   1.701   0.115  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3   17
CONECT    3    4   33   34
CONECT    4    5   35   36
CONECT    5    6
CONECT    6    7    7   16
CONECT    7    8   37
CONECT    8    9    9   38
CONECT    9   10   15
CONECT   10   11   39
CONECT   11   12   13   13   14
CONECT   11   14
CONECT   12   40   41   42
CONECT   15   16   16   43
CONECT   16   44
CONECT   17   18   45   46
CONECT   18   19   47   48
CONECT   19   20   20   29
CONECT   20   21   49
CONECT   21   22   22   50
CONECT   22   23   28
CONECT   23   24   51
CONECT   24   25   26   26   27
CONECT   24   27
CONECT   25   52   53   54
CONECT   28   29   29   55
CONECT   29   56
END

HMDB0014349
     RDKit          3D
Dofetilide
 56 57  0  0  0  0  0  0  0  0999 V2000
    0.0472   -1.9704   -1.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2733   -1.0467   -0.2180 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3628    0.2311   -0.3713 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8641    0.1477   -0.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4603    1.4169   -0.3521 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8345    1.5395   -0.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6138    0.4383    0.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0019    0.5369    0.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6319    1.7340    0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0042    1.9682    0.1078 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0184    1.3564    1.3270 S   0  0  0  0  0  6  0  0  0  0  0  0
    9.0270   -0.4160    1.2756 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4170    1.8991    1.1969 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5222    1.7360    2.7003 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8202    2.8343   -0.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4604    2.7562   -0.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6760   -0.9632    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4358   -0.3176   -1.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8882   -0.2381   -0.8018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7502   -1.2598   -1.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1072   -1.1882   -0.8830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6288   -0.0589   -0.2428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0264    0.0342    0.0427 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9171   -1.2665    0.7228 S   0  0  0  0  0  6  0  0  0  0  0  0
   -8.2736   -1.6964    2.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8357   -2.5141   -0.1086 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3598   -0.8922    0.8866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7388    0.9351    0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3814    0.8822   -0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8669   -2.6160   -0.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3688   -1.4898   -2.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7929   -2.6519   -1.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1152    0.6857   -1.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0060    0.8736    0.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2533   -0.4981   -1.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1067   -0.2076    0.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1480   -0.5161    0.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5531   -0.3484    0.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4594    2.5750   -0.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8696   -0.7305    0.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0240   -0.7634    1.6512 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2289   -0.8024    1.9341 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2756    3.7940   -0.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8769    3.6270   -0.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8834   -0.4760    1.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0680   -2.0047    0.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3208   -0.8842   -2.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0449    0.7272   -1.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3481   -2.1372   -1.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7661   -1.9937   -1.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5278    0.9222   -0.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9995   -0.7523    2.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3394   -2.2984    2.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0364   -2.1855    2.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0847    1.8320    0.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7218    1.7013    0.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 11 14  2  0
  9 15  1  0
 15 16  2  0
  2 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 24 27  2  0
 22 28  1  0
 28 29  2  0
 16  6  1  0
 29 19  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  7 37  1  0
  8 38  1  0
 10 39  1  0
 12 40  1  0
 12 41  1  0
 12 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 20 49  1  0
 21 50  1  0
 23 51  1  0
 25 52  1  0
 25 53  1  0
 25 54  1  0
 28 55  1  0
 29 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
beta-((p-Methanesulfonamidophenethyl)methylamino)methanesulfono-p-phenetidide	ChEBI
Dofetilida	ChEBI
Dofetilidum	ChEBI
Tikosyn	ChEBI
b-((p-Methanesulfonamidophenethyl)methylamino)methanesulfono-p-phenetidide	Generator
b-((p-Methanesulphonamidophenethyl)methylamino)methanesulphono-p-phenetidide	Generator
beta-((p-Methanesulphonamidophenethyl)methylamino)methanesulphono-p-phenetidide	Generator
Β-((p-methanesulfonamidophenethyl)methylamino)methanesulfono-p-phenetidide	Generator
Β-((p-methanesulphonamidophenethyl)methylamino)methanesulphono-p-phenetidide	Generator
1-MSPMPE	HMDB
1-(4-Methanesulfonamidophenoxy)-2-(N-(4-methanesulfonamidophenethyl)-N-methylamine)ethane	HMDB

Chemical Formula

C₁₉H₂₇N₃O₅S₂

Average Molecular Weight

441.565

Monoisotopic Molecular Weight

441.139212369

IUPAC Name

N-[4-(2-{[2-(4-methanesulfonamidophenyl)ethyl](methyl)amino}ethoxy)phenyl]methanesulfonamide

Traditional Name

dofetilide

CAS Registry Number

115256-11-6

SMILES

CN(CCOC1=CC=C(NS(C)(=O)=O)C=C1)CCC1=CC=C(NS(C)(=O)=O)C=C1

InChI Identifier

InChI=1S/C19H27N3O5S2/c1-22(13-12-16-4-6-17(7-5-16)20-28(2,23)24)14-15-27-19-10-8-18(9-11-19)21-29(3,25)26/h4-11,20-21H,12-15H2,1-3H3

InChI Key

IXTMWRCNAAVVAI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sulfanilides. These are organic aromatic compounds containing a sulfanilide moiety, with the general structure RS(=O)(=O)NC1=CC=CC=C1.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Sulfanilides

Direct Parent

Sulfanilides

Alternative Parents

Substituents

Sulfanilide
Phenethylamine
Phenoxy compound
Phenol ether
Alkyl aryl ether
Aralkylamine
Organic sulfonic acid amide
Organosulfonic acid amide
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Aminosulfonyl compound
Sulfonyl
Tertiary amine
Tertiary aliphatic amine
Ether
Amine
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tertiary amino compound (CHEBI:4681 )
aromatic ether (CHEBI:4681 )
sulfonamide (CHEBI:4681 )

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: HMDB0014349)

Source

Exogenous

Exogenous (HMDB: HMDB0014349)

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	0.02 g/L	Not Available
LogP	2.1	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.02 g/L	ALOGPS
logP	2.17	ALOGPS
logP	0.24	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	10.15	ChemAxon
pKa (Strongest Basic)	8.99	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	104.81 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	113.27 m³·mol⁻¹	ChemAxon
Polarizability	46.03 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	203.193	31661259
DarkChem	[M-H]-	200.503	31661259
DeepCCS	[M+H]+	199.927	30932474
DeepCCS	[M-H]-	197.569	30932474
DeepCCS	[M-2H]-	231.216	30932474
DeepCCS	[M+Na]+	206.445	30932474
AllCCS	[M+H]+	205.0	32859911
AllCCS	[M+H-H2O]+	202.8	32859911
AllCCS	[M+NH4]+	207.1	32859911
AllCCS	[M+Na]+	207.7	32859911
AllCCS	[M-H]-	195.8	32859911
AllCCS	[M+Na-2H]-	196.8	32859911
AllCCS	[M+HCOO]-	198.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.32 minutes	32390414
Predicted by Siyang on May 30, 2022	10.3474 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.31 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	115.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	932.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	208.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	155.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	189.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	66.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	256.0 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	335.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	815.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	737.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	142.5 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	1011.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	233.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	250.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	404.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	431.3 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	117.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dofetilide	CN(CCOC1=CC=C(NS(C)(=O)=O)C=C1)CCC1=CC=C(NS(C)(=O)=O)C=C1	5886.7	Standard polar	33892256
Dofetilide	CN(CCOC1=CC=C(NS(C)(=O)=O)C=C1)CCC1=CC=C(NS(C)(=O)=O)C=C1	3880.0	Standard non polar	33892256
Dofetilide	CN(CCOC1=CC=C(NS(C)(=O)=O)C=C1)CCC1=CC=C(NS(C)(=O)=O)C=C1	3853.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dofetilide,1TMS,isomer #1	CN(CCOC1=CC=C(N([Si](C)(C)C)S(C)(=O)=O)C=C1)CCC1=CC=C(NS(C)(=O)=O)C=C1	3779.4	Semi standard non polar	33892256
Dofetilide,1TMS,isomer #1	CN(CCOC1=CC=C(N([Si](C)(C)C)S(C)(=O)=O)C=C1)CCC1=CC=C(NS(C)(=O)=O)C=C1	3599.6	Standard non polar	33892256
Dofetilide,1TMS,isomer #1	CN(CCOC1=CC=C(N([Si](C)(C)C)S(C)(=O)=O)C=C1)CCC1=CC=C(NS(C)(=O)=O)C=C1	4934.5	Standard polar	33892256
Dofetilide,1TMS,isomer #2	CN(CCOC1=CC=C(NS(C)(=O)=O)C=C1)CCC1=CC=C(N([Si](C)(C)C)S(C)(=O)=O)C=C1	3727.8	Semi standard non polar	33892256
Dofetilide,1TMS,isomer #2	CN(CCOC1=CC=C(NS(C)(=O)=O)C=C1)CCC1=CC=C(N([Si](C)(C)C)S(C)(=O)=O)C=C1	3608.2	Standard non polar	33892256
Dofetilide,1TMS,isomer #2	CN(CCOC1=CC=C(NS(C)(=O)=O)C=C1)CCC1=CC=C(N([Si](C)(C)C)S(C)(=O)=O)C=C1	4928.9	Standard polar	33892256
Dofetilide,2TMS,isomer #1	CN(CCOC1=CC=C(N([Si](C)(C)C)S(C)(=O)=O)C=C1)CCC1=CC=C(N([Si](C)(C)C)S(C)(=O)=O)C=C1	3578.3	Semi standard non polar	33892256
Dofetilide,2TMS,isomer #1	CN(CCOC1=CC=C(N([Si](C)(C)C)S(C)(=O)=O)C=C1)CCC1=CC=C(N([Si](C)(C)C)S(C)(=O)=O)C=C1	3717.5	Standard non polar	33892256
Dofetilide,2TMS,isomer #1	CN(CCOC1=CC=C(N([Si](C)(C)C)S(C)(=O)=O)C=C1)CCC1=CC=C(N([Si](C)(C)C)S(C)(=O)=O)C=C1	4615.1	Standard polar	33892256
Dofetilide,1TBDMS,isomer #1	CN(CCOC1=CC=C(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)C=C1)CCC1=CC=C(NS(C)(=O)=O)C=C1	4015.5	Semi standard non polar	33892256
Dofetilide,1TBDMS,isomer #1	CN(CCOC1=CC=C(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)C=C1)CCC1=CC=C(NS(C)(=O)=O)C=C1	3833.5	Standard non polar	33892256
Dofetilide,1TBDMS,isomer #1	CN(CCOC1=CC=C(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)C=C1)CCC1=CC=C(NS(C)(=O)=O)C=C1	4907.2	Standard polar	33892256
Dofetilide,1TBDMS,isomer #2	CN(CCOC1=CC=C(NS(C)(=O)=O)C=C1)CCC1=CC=C(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)C=C1	3965.8	Semi standard non polar	33892256
Dofetilide,1TBDMS,isomer #2	CN(CCOC1=CC=C(NS(C)(=O)=O)C=C1)CCC1=CC=C(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)C=C1	3840.7	Standard non polar	33892256
Dofetilide,1TBDMS,isomer #2	CN(CCOC1=CC=C(NS(C)(=O)=O)C=C1)CCC1=CC=C(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)C=C1	4903.0	Standard polar	33892256
Dofetilide,2TBDMS,isomer #1	CN(CCOC1=CC=C(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)C=C1)CCC1=CC=C(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)C=C1	4028.7	Semi standard non polar	33892256
Dofetilide,2TBDMS,isomer #1	CN(CCOC1=CC=C(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)C=C1)CCC1=CC=C(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)C=C1	4182.4	Standard non polar	33892256
Dofetilide,2TBDMS,isomer #1	CN(CCOC1=CC=C(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)C=C1)CCC1=CC=C(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)C=C1	4595.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dofetilide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bvl-4932000000-66e362c3fe81fb58fcc7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dofetilide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dofetilide 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dofetilide , positive-QTOF	splash10-0006-1610900000-368db21beef81a5319f4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dofetilide , positive-QTOF	splash10-0006-0300900000-47394a7ed027cb5ab3cf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dofetilide 35V, Negative-QTOF	splash10-0006-0200900000-5e88add5ce502b3def00	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dofetilide 35V, Positive-QTOF	splash10-0007-0930700000-c49a09c3642ebe80a508	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dofetilide 10V, Positive-QTOF	splash10-0005-0029400000-8d71d52f4a3c4cc520cb	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dofetilide 20V, Positive-QTOF	splash10-014j-0494000000-29318a7a4e340a84b89c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dofetilide 40V, Positive-QTOF	splash10-0gc1-0970000000-ff7ab38dee25c13c628e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dofetilide 10V, Negative-QTOF	splash10-002f-7210900000-61f7904544738c663c26	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dofetilide 20V, Negative-QTOF	splash10-004i-9211100000-40309ebd6f3c937574a4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dofetilide 40V, Negative-QTOF	splash10-004i-9000000000-efa6a192289b1224a063	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dofetilide 10V, Negative-QTOF	splash10-0006-0000900000-562b19ba98459c2cd026	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dofetilide 20V, Negative-QTOF	splash10-004l-9100700000-141e753d4ef538c9f060	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dofetilide 40V, Negative-QTOF	splash10-004i-9400000000-def4b905438245c50110	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dofetilide 10V, Positive-QTOF	splash10-0006-0000900000-14da12b317cbb5fefb49	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dofetilide 20V, Positive-QTOF	splash10-052g-0481900000-6143e73095a8c3c8a7c2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dofetilide 40V, Positive-QTOF	splash10-0002-0910000000-66e5293cc76f8e2d917a	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 DB00204	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00204	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00204

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

64435

KEGG Compound ID

C07751

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dofetilide

METLIN ID

Not Available

PubChem Compound

71329

PDB ID

Not Available

ChEBI ID

4681

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

Torp-Pedersen C, Moller M, Bloch-Thomsen PE, Kober L, Sandoe E, Egstrup K, Agner E, Carlsen J, Videbaek J, Marchant B, Camm AJ: Dofetilide in patients with congestive heart failure and left ventricular dysfunction. Danish Investigations of Arrhythmia and Mortality on Dofetilide Study Group. N Engl J Med. 1999 Sep 16;341(12):857-65. [PubMed:10486417 ]
Lenz TL, Hilleman DE: Dofetilide, a new class III antiarrhythmic agent. Pharmacotherapy. 2000 Jul;20(7):776-86. [PubMed:10907968 ]
Lenz TL, Hilleman DE: Dofetilide: A new antiarrhythmic agent approved for conversion and/or maintenance of atrial fibrillation/atrial flutter. Drugs Today (Barc). 2000 Nov;36(11):759-71. [PubMed:12845335 ]

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

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Potassium voltage-gated channel subfamily H member 2

General function:: Involved in ion channel activity
Specific function:: Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the delayed rectifying potassium current in heart (IKr). Isoform 3 has no channel activity by itself, but modulates channel characteristics when associated with isoform 1
Gene Name:: KCNH2
Uniprot ID:: Q12809
Molecular weight:: 126653.5

References

Lees-Miller JP, Duan Y, Teng GQ, Duff HJ: Molecular determinant of high-affinity dofetilide binding to HERG1 expressed in Xenopus oocytes: involvement of S6 sites. Mol Pharmacol. 2000 Feb;57(2):367-74. [PubMed:10648647 ]
Overholt JL, Ficker E, Yang T, Shams H, Bright GR, Prabhakar NR: HERG-Like potassium current regulates the resting membrane potential in glomus cells of the rabbit carotid body. J Neurophysiol. 2000 Mar;83(3):1150-7. [PubMed:10712445 ]
Finlayson K, Pennington AJ, Kelly JS: [3H]dofetilide binding in SHSY5Y and HEK293 cells expressing a HERG-like K+ channel? Eur J Pharmacol. 2001 Feb 2;412(3):203-12. [PubMed:11166283 ]
Finlayson K, Turnbull L, January CT, Sharkey J, Kelly JS: [3H]dofetilide binding to HERG transfected membranes: a potential high throughput preclinical screen. Eur J Pharmacol. 2001 Oct 26;430(1):147-8. [PubMed:11698075 ]
Ficker E, Jarolimek W, Brown AM: Molecular determinants of inactivation and dofetilide block in ether a-go-go (EAG) channels and EAG-related K(+) channels. Mol Pharmacol. 2001 Dec;60(6):1343-8. [PubMed:11723241 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Ficker E, Jarolimek W, Kiehn J, Baumann A, Brown AM: Molecular determinants of dofetilide block of HERG K+ channels. Circ Res. 1998 Feb 23;82(3):386-95. [PubMed:9486667 ]
Kang J, Chen XL, Wang H, Ji J, Cheng H, Incardona J, Reynolds W, Viviani F, Tabart M, Rampe D: Discovery of a small molecule activator of the human ether-a-go-go-related gene (HERG) cardiac K+ channel. Mol Pharmacol. 2005 Mar;67(3):827-36. Epub 2004 Nov 17. [PubMed:15548764 ]

Enzyme Details

3. ATP-sensitive inward rectifier potassium channel 12

General function:: Involved in inward rectifier potassium channel activity
Specific function:: Probably participates in establishing action potential waveform and excitability of neuronal and muscle tissues. Inward rectifier potassium channels are characterized by a greater tendency to allow potassium to flow into the cell rather than out of it. Their voltage dependence is regulated by the concentration of extracellular potassium; as external potassium is raised, the voltage range of the channel opening shifts to more positive voltages. The inward rectification is mainly due to the blockage of outward current by internal magnesium. Can be blocked by extracellular barium and cesium
Gene Name:: KCNJ12
Uniprot ID:: Q14500
Molecular weight:: 49000.6

References

Kiehn J, Wible B, Lacerda AE, Brown AM: Mapping the block of a cloned human inward rectifier potassium channel by dofetilide. Mol Pharmacol. 1996 Aug;50(2):380-7. [PubMed:8700146 ]

Showing metabocard for Dofetilide (HMDB0014349)

MOL for HMDB0014349 (Dofetilide)

3D MOL for HMDB0014349 (Dofetilide)

3D SDF for HMDB0014349 (Dofetilide)

3D-SDF for HMDB0014349 (Dofetilide)

PDB for HMDB0014349 (Dofetilide)

3D PDB for HMDB0014349 (Dofetilide)

SMILES for HMDB0014349 (Dofetilide)

INCHI for HMDB0014349 (Dofetilide)

Structure for HMDB0014349 (Dofetilide)

3D Structure for HMDB0014349 (Dofetilide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References