Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (9) Show 9 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:38 UTC

HMDB ID

HMDB0014453

Secondary Accession Numbers

HMDB14453

Metabolite Identification

Common Name

Ibutilide

Description

Ibutilide is only found in individuals that have used or taken this drug. It is a Class III antiarrhythmic agent that is indicated for acute cardioconversion of atrial fibrillation and atrial flutter of a recent onset to sinus rhythm. [Wikipedia ]Ibutilide is a 'pure' class III antiarrhythmic drug, used intravenously against atrial flutter and fibrillation. At a cellular level it exerts two main actions: induction of a persistent Na+ current sensitive to dihydropyridine Ca²⁺ channel blockers and potent inhibition of the cardiac rapid delayed rectifier K⁺ current, by binding within potassium channel pores. In other words, Ibutilide binds to and alters the activity of hERG potassium channels, delayed inward rectifier potassium (IKr) channels and L-type (dihydropyridine sensitive) calcium channels

Structure

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

 
  Mrv0541 02231214352D          
 
 26 26  0  0  0  0            999 V2000
   18.2793  -11.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2793  -12.0050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9904  -10.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5264  -10.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9904  -12.4651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7434  -11.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8153  -11.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5264   -9.9135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7434  -12.0050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0624  -10.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4545  -12.4233    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3513  -11.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2074  -12.0050    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.6402  -10.7501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9185  -12.4233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4545  -11.5867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8348  -11.5867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6402   -9.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3513   -9.4952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8873  -11.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1762  -10.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4651  -11.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7540  -10.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0011  -11.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2900  -10.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5789  -11.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  7 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  2  0  0  0  0
 13 17  2  0  0  0  0
 14 18  1  0  0  0  0
  6  9  2  0  0  0  0
 18 19  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END

HMDB0259364
     RDKit          3D
N-(4-((1R)-4-(Ethylheptylamino)-1-hydroxybutyl)phenyl)methanesulfonamide
 62 62  0  0  0  0  0  0  0  0999 V2000
   -7.5622    1.9649    0.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8962    0.7594   -0.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1870   -0.0339    0.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5675   -1.2300   -0.1107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8133   -2.1401    0.7725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6465   -1.7043    1.5275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3374   -1.3795    0.9984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0960   -0.4510   -0.0337 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3583   -0.9930   -1.3845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3841    0.0777   -2.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6594   -0.1126   -0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1385    0.6764    1.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3135    1.0162    0.8483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2038   -0.1784    0.7778 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9637   -1.0279   -0.2802 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6331    0.2482    0.6795 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2020    0.6254   -0.5220 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5319    1.0054   -0.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3167    1.0183    0.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6804    1.3981    0.5463 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7759    0.7744   -0.6197 S   0  0  0  0  0  6  0  0  0  0  0  0
    8.3888    1.2007   -2.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1609    1.2602   -0.2613 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7854   -0.7467   -0.5094 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7220    0.6355    1.7236 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4161    0.2588    1.8085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6937    1.8121    1.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6051    2.0801   -0.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0284    2.8912   -0.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6405    0.1652   -1.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1316    1.0594   -1.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8922   -0.3404    1.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3698    0.5933    1.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4563   -1.8005   -0.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0448   -0.8200   -0.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4978   -3.0201    0.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5718   -2.6876    1.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9885   -0.8598    2.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5237   -2.5450    2.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7459   -0.9637    1.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7130   -2.3303    0.7883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4040   -1.6119   -1.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1211   -1.7456   -1.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5021    0.0505   -3.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5569    1.0890   -1.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2574   -0.1728   -3.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1838   -1.1234   -0.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5248    0.4414   -1.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1657    0.1284    2.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6778    1.6533    1.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4270    1.5614   -0.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6565    1.6683    1.6987 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1383   -0.7881    1.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6760   -1.6893   -0.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5936    0.6183   -1.4145 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9311    1.2929   -1.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9912    2.0671    1.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9626    2.2386   -2.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7855    0.4643   -2.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3499    1.2662   -2.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3562    0.6493    2.6059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9807   -0.0363    2.7623 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 21 24  2  0
 19 25  1  0
 25 26  2  0
 26 16  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  9 42  1  0
  9 43  1  0
 10 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 12 49  1  0
 12 50  1  0
 13 51  1  0
 13 52  1  0
 14 53  1  0
 15 54  1  0
 17 55  1  0
 18 56  1  0
 20 57  1  0
 22 58  1  0
 22 59  1  0
 22 60  1  0
 25 61  1  0
 26 62  1  0
M  END

 
  Mrv0541 02231214352D          
 
 26 26  0  0  0  0            999 V2000
   18.2793  -11.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2793  -12.0050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9904  -10.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5264  -10.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9904  -12.4651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7434  -11.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8153  -11.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5264   -9.9135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7434  -12.0050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0624  -10.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4545  -12.4233    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3513  -11.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2074  -12.0050    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.6402  -10.7501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9185  -12.4233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4545  -11.5867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8348  -11.5867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6402   -9.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3513   -9.4952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8873  -11.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1762  -10.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4651  -11.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7540  -10.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0011  -11.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2900  -10.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5789  -11.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  7 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  2  0  0  0  0
 13 17  2  0  0  0  0
 14 18  1  0  0  0  0
  6  9  2  0  0  0  0
 18 19  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014453

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCN(CC)CCCC(O)C1=CC=C(NS(C)(=O)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H36N2O3S/c1-4-6-7-8-9-16-22(5-2)17-10-11-20(23)18-12-14-19(15-13-18)21-26(3,24)25/h12-15,20-21,23H,4-11,16-17H2,1-3H3

> <INCHI_KEY>
ALOBUEHUHMBRLE-UHFFFAOYSA-N

> <FORMULA>
C20H36N2O3S

> <MOLECULAR_WEIGHT>
384.576

> <EXACT_MASS>
384.244663718

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
46.45346141936455

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(4-{4-[ethyl(heptyl)amino]-1-hydroxybutyl}phenyl)methanesulfonamide

> <ALOGPS_LOGP>
4.72

> <JCHEM_LOGP>
2.5426521951915055

> <ALOGPS_LOGS>
-4.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.462657225568144

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.720054597587202

> <JCHEM_PKA_STRONGEST_BASIC>
10.396987315808701

> <JCHEM_POLAR_SURFACE_AREA>
69.64

> <JCHEM_REFRACTIVITY>
109.18159999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.73e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ibutilide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259364
     RDKit          3D
N-(4-((1R)-4-(Ethylheptylamino)-1-hydroxybutyl)phenyl)methanesulfonamide
 62 62  0  0  0  0  0  0  0  0999 V2000
   -7.5622    1.9649    0.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8962    0.7594   -0.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1870   -0.0339    0.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5675   -1.2300   -0.1107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8133   -2.1401    0.7725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6465   -1.7043    1.5275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3374   -1.3795    0.9984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0960   -0.4510   -0.0337 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3583   -0.9930   -1.3845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3841    0.0777   -2.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6594   -0.1126   -0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1385    0.6764    1.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3135    1.0162    0.8483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2038   -0.1784    0.7778 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9637   -1.0279   -0.2802 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6331    0.2482    0.6795 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2020    0.6254   -0.5220 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5319    1.0054   -0.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3167    1.0183    0.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6804    1.3981    0.5463 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7759    0.7744   -0.6197 S   0  0  0  0  0  6  0  0  0  0  0  0
    8.3888    1.2007   -2.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1609    1.2602   -0.2613 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7854   -0.7467   -0.5094 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7220    0.6355    1.7236 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4161    0.2588    1.8085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6937    1.8121    1.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6051    2.0801   -0.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0284    2.8912   -0.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6405    0.1652   -1.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1316    1.0594   -1.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8922   -0.3404    1.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3698    0.5933    1.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4563   -1.8005   -0.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0448   -0.8200   -0.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4978   -3.0201    0.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5718   -2.6876    1.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9885   -0.8598    2.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5237   -2.5450    2.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7459   -0.9637    1.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7130   -2.3303    0.7883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4040   -1.6119   -1.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1211   -1.7456   -1.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5021    0.0505   -3.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5569    1.0890   -1.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2574   -0.1728   -3.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1838   -1.1234   -0.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5248    0.4414   -1.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1657    0.1284    2.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6778    1.6533    1.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4270    1.5614   -0.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6565    1.6683    1.6987 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1383   -0.7881    1.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6760   -1.6893   -0.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5936    0.6183   -1.4145 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9311    1.2929   -1.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9912    2.0671    1.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9626    2.2386   -2.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7855    0.4643   -2.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3499    1.2662   -2.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3562    0.6493    2.6059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9807   -0.0363    2.7623 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 21 24  2  0
 19 25  1  0
 25 26  2  0
 26 16  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  9 42  1  0
  9 43  1  0
 10 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 12 49  1  0
 12 50  1  0
 13 51  1  0
 13 52  1  0
 14 53  1  0
 15 54  1  0
 17 55  1  0
 18 56  1  0
 20 57  1  0
 22 58  1  0
 22 59  1  0
 22 60  1  0
 25 61  1  0
 26 62  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      34.121 -20.848   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      34.121 -22.409   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      35.449 -20.067   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      32.716 -20.067   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      35.449 -23.268   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      36.854 -20.848   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.389 -20.848   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      32.716 -18.505   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      36.854 -22.409   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      29.983 -20.067   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      38.182 -23.190   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      28.656 -20.848   0.000  0.00  0.00           C+0
HETATM   13  S   UNK     0      39.587 -22.409   0.000  0.00  0.00           S+0
HETATM   14  N   UNK     0      27.328 -20.067   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      40.915 -23.190   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      38.182 -21.629   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      40.758 -21.629   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      27.328 -18.505   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      28.656 -17.724   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      25.923 -20.848   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      24.596 -20.067   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      23.268 -20.848   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      21.941 -20.067   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      20.535 -20.848   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      19.208 -20.067   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.881 -20.848   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1    7    8                                                  
CONECT    5    2    9                                                       
CONECT    6    3    9                                                       
CONECT    7    4   10                                                       
CONECT    8    4                                                            
CONECT    9    5   11    6                                                  
CONECT   10    7   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   15   16   17                                             
CONECT   14   12   18   20                                                  
CONECT   15   13                                                            
CONECT   16   13                                                            
CONECT   17   13                                                            
CONECT   18   14   19                                                       
CONECT   19   18                                                            
CONECT   20   14   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   52    0
END

COMPND    HMDB0014453
HETATM    1  C1  UNL     1      -3.816   0.817  -2.083  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.003   1.459  -1.388  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.986   0.523  -0.837  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.630  -0.468   0.202  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.156  -0.014   1.512  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.905   0.694   1.744  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.575   0.106   1.671  1.00  0.00           C  
HETATM    8  N1  UNL     1      -1.993  -0.592   0.653  1.00  0.00           N  
HETATM    9  C8  UNL     1      -2.277  -1.930   0.369  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.726  -2.500  -0.898  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.963   0.027  -0.113  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.294   0.287   0.677  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.865  -0.970   1.257  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.138  -0.604   2.020  1.00  0.00           C  
HETATM   15  O1  UNL     1       2.704  -1.746   2.594  1.00  0.00           O  
HETATM   16  C14 UNL     1       3.068  -0.011   1.026  1.00  0.00           C  
HETATM   17  C15 UNL     1       3.339   1.324   0.979  1.00  0.00           C  
HETATM   18  C16 UNL     1       4.223   1.855   0.033  1.00  0.00           C  
HETATM   19  C17 UNL     1       4.846   1.030  -0.882  1.00  0.00           C  
HETATM   20  N2  UNL     1       5.754   1.528  -1.859  1.00  0.00           N  
HETATM   21  S1  UNL     1       7.239   0.741  -2.186  1.00  0.00           S  
HETATM   22  C18 UNL     1       8.227   0.739  -0.720  1.00  0.00           C  
HETATM   23  O2  UNL     1       7.027  -0.678  -2.695  1.00  0.00           O  
HETATM   24  O3  UNL     1       7.961   1.452  -3.315  1.00  0.00           O  
HETATM   25  C19 UNL     1       4.562  -0.314  -0.822  1.00  0.00           C  
HETATM   26  C20 UNL     1       3.689  -0.840   0.112  1.00  0.00           C  
HETATM   27  H1  UNL     1      -4.033   0.648  -3.176  1.00  0.00           H  
HETATM   28  H2  UNL     1      -3.461  -0.102  -1.603  1.00  0.00           H  
HETATM   29  H3  UNL     1      -2.995   1.572  -2.022  1.00  0.00           H  
HETATM   30  H4  UNL     1      -5.552   1.979  -2.270  1.00  0.00           H  
HETATM   31  H5  UNL     1      -4.712   2.329  -0.779  1.00  0.00           H  
HETATM   32  H6  UNL     1      -6.926   1.051  -0.504  1.00  0.00           H  
HETATM   33  H7  UNL     1      -6.371  -0.094  -1.721  1.00  0.00           H  
HETATM   34  H8  UNL     1      -6.604  -1.063   0.399  1.00  0.00           H  
HETATM   35  H9  UNL     1      -4.995  -1.246  -0.254  1.00  0.00           H  
HETATM   36  H10 UNL     1      -5.076  -0.979   2.158  1.00  0.00           H  
HETATM   37  H11 UNL     1      -6.030   0.484   2.070  1.00  0.00           H  
HETATM   38  H12 UNL     1      -4.021   1.107   2.848  1.00  0.00           H  
HETATM   39  H13 UNL     1      -3.851   1.697   1.207  1.00  0.00           H  
HETATM   40  H14 UNL     1      -1.845   0.985   1.923  1.00  0.00           H  
HETATM   41  H15 UNL     1      -2.366  -0.527   2.643  1.00  0.00           H  
HETATM   42  H16 UNL     1      -1.723  -2.529   1.206  1.00  0.00           H  
HETATM   43  H17 UNL     1      -3.303  -2.227   0.534  1.00  0.00           H  
HETATM   44  H18 UNL     1      -0.654  -2.759  -0.803  1.00  0.00           H  
HETATM   45  H19 UNL     1      -1.895  -1.897  -1.802  1.00  0.00           H  
HETATM   46  H20 UNL     1      -2.243  -3.483  -1.121  1.00  0.00           H  
HETATM   47  H21 UNL     1      -1.353   1.046  -0.401  1.00  0.00           H  
HETATM   48  H22 UNL     1      -0.685  -0.463  -1.040  1.00  0.00           H  
HETATM   49  H23 UNL     1       0.117   1.057   1.453  1.00  0.00           H  
HETATM   50  H24 UNL     1       1.048   0.764  -0.020  1.00  0.00           H  
HETATM   51  H25 UNL     1       1.057  -1.688   0.464  1.00  0.00           H  
HETATM   52  H26 UNL     1       0.204  -1.433   2.006  1.00  0.00           H  
HETATM   53  H27 UNL     1       1.959   0.129   2.816  1.00  0.00           H  
HETATM   54  H28 UNL     1       2.763  -2.503   1.985  1.00  0.00           H  
HETATM   55  H29 UNL     1       2.859   1.978   1.688  1.00  0.00           H  
HETATM   56  H30 UNL     1       4.451   2.909  -0.021  1.00  0.00           H  
HETATM   57  H31 UNL     1       5.515   2.391  -2.392  1.00  0.00           H  
HETATM   58  H32 UNL     1       7.641   1.025   0.179  1.00  0.00           H  
HETATM   59  H33 UNL     1       9.054   1.470  -0.811  1.00  0.00           H  
HETATM   60  H34 UNL     1       8.617  -0.294  -0.513  1.00  0.00           H  
HETATM   61  H35 UNL     1       5.038  -0.984  -1.532  1.00  0.00           H  
HETATM   62  H36 UNL     1       3.469  -1.901   0.154  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3   30   31
CONECT    3    4   32   33
CONECT    4    5   34   35
CONECT    5    6   36   37
CONECT    6    7   38   39
CONECT    7    8   40   41
CONECT    8    9   11
CONECT    9   10   42   43
CONECT   10   44   45   46
CONECT   11   12   47   48
CONECT   12   13   49   50
CONECT   13   14   51   52
CONECT   14   15   16   53
CONECT   15   54
CONECT   16   17   17   26
CONECT   17   18   55
CONECT   18   19   19   56
CONECT   19   20   25
CONECT   20   21   57
CONECT   21   22   23   23   24
CONECT   21   24
CONECT   22   58   59   60
CONECT   25   26   26   61
CONECT   26   62
END

HMDB0259364
     RDKit          3D
N-(4-((1R)-4-(Ethylheptylamino)-1-hydroxybutyl)phenyl)methanesulfonamide
 62 62  0  0  0  0  0  0  0  0999 V2000
   -7.5622    1.9649    0.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8962    0.7594   -0.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1870   -0.0339    0.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5675   -1.2300   -0.1107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8133   -2.1401    0.7725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6465   -1.7043    1.5275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3374   -1.3795    0.9984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0960   -0.4510   -0.0337 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3583   -0.9930   -1.3845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3841    0.0777   -2.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6594   -0.1126   -0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1385    0.6764    1.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3135    1.0162    0.8483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2038   -0.1784    0.7778 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9637   -1.0279   -0.2802 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6331    0.2482    0.6795 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2020    0.6254   -0.5220 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5319    1.0054   -0.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3167    1.0183    0.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6804    1.3981    0.5463 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7759    0.7744   -0.6197 S   0  0  0  0  0  6  0  0  0  0  0  0
    8.3888    1.2007   -2.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1609    1.2602   -0.2613 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7854   -0.7467   -0.5094 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7220    0.6355    1.7236 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4161    0.2588    1.8085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6937    1.8121    1.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6051    2.0801   -0.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0284    2.8912   -0.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6405    0.1652   -1.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1316    1.0594   -1.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8922   -0.3404    1.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3698    0.5933    1.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4563   -1.8005   -0.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0448   -0.8200   -0.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4978   -3.0201    0.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5718   -2.6876    1.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9885   -0.8598    2.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5237   -2.5450    2.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7459   -0.9637    1.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7130   -2.3303    0.7883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4040   -1.6119   -1.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1211   -1.7456   -1.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5021    0.0505   -3.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5569    1.0890   -1.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2574   -0.1728   -3.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1838   -1.1234   -0.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5248    0.4414   -1.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1657    0.1284    2.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6778    1.6533    1.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4270    1.5614   -0.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6565    1.6683    1.6987 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1383   -0.7881    1.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6760   -1.6893   -0.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5936    0.6183   -1.4145 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9311    1.2929   -1.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9912    2.0671    1.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9626    2.2386   -2.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7855    0.4643   -2.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3499    1.2662   -2.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3562    0.6493    2.6059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9807   -0.0363    2.7623 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 21 24  2  0
 19 25  1  0
 25 26  2  0
 26 16  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  9 42  1  0
  9 43  1  0
 10 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 12 49  1  0
 12 50  1  0
 13 51  1  0
 13 52  1  0
 14 53  1  0
 15 54  1  0
 17 55  1  0
 18 56  1  0
 20 57  1  0
 22 58  1  0
 22 59  1  0
 22 60  1  0
 25 61  1  0
 26 62  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ibutilide fumarate	HMDB
Ibutilide, (+)-isomer	MeSH, HMDB
N-(4-(4-(ethylheptylamino)-1-Hydroxybutyl)phenyl)methanesulfonamide	MeSH, HMDB
Ibutilide, (+-)-isomer	MeSH, HMDB
Ibutilide, fumarate salt (2:1), (+-)-isomer	MeSH, HMDB
Corvert	MeSH, HMDB
Ibutilide, (-)-isomer	MeSH, HMDB
Ibutilide, fumarate salt (2:1), (+)-isomer	MeSH, HMDB

Chemical Formula

C₂₀H₃₆N₂O₃S

Average Molecular Weight

384.576

Monoisotopic Molecular Weight

384.244663718

IUPAC Name

N-(4-{4-[ethyl(heptyl)amino]-1-hydroxybutyl}phenyl)methanesulfonamide

Traditional Name

ibutilide

CAS Registry Number

122647-32-9

SMILES

CCCCCCCN(CC)CCCC(O)C1=CC=C(NS(C)(=O)=O)C=C1

InChI Identifier

InChI=1S/C20H36N2O3S/c1-4-6-7-8-9-16-22(5-2)17-10-11-20(23)18-12-14-19(15-13-18)21-26(3,24)25/h12-15,20-21,23H,4-11,16-17H2,1-3H3

InChI Key

ALOBUEHUHMBRLE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylbutylamines

Direct Parent

Phenylbutylamines

Alternative Parents

Substituents

Phenylbutylamine
Sulfanilide
Aralkylamine
Organic sulfonic acid amide
Organosulfonic acid amide
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Aminosulfonyl compound
Sulfonyl
Secondary alcohol
Tertiary aliphatic amine
Tertiary amine
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organopnictogen compound
Organic nitrogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Aromatic alcohol
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organic amino compound (CHEBI:5856 )
benzenes (CHEBI:5856 )

Ontology

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	0.0047 g/L	Not Available
LogP	4.6	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0047 g/L	ALOGPS
logP	4.72	ALOGPS
logP	2.54	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	9.72	ChemAxon
pKa (Strongest Basic)	10.4	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.64 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	109.18 m³·mol⁻¹	ChemAxon
Polarizability	46.45 Å³	ChemAxon
Number of Rings	1	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]+	194.717	31661259
DarkChem	[M-H]-	193.925	31661259
DeepCCS	[M+H]+	205.275	30932474
DeepCCS	[M-H]-	201.943	30932474
DeepCCS	[M-2H]-	236.902	30932474
DeepCCS	[M+Na]+	213.191	30932474
AllCCS	[M+H]+	198.7	32859911
AllCCS	[M+H-H2O]+	196.5	32859911
AllCCS	[M+NH4]+	200.7	32859911
AllCCS	[M+Na]+	201.3	32859911
AllCCS	[M-H]-	189.8	32859911
AllCCS	[M+Na-2H]-	191.4	32859911
AllCCS	[M+HCOO]-	193.2	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.	8.13 minutes	32390414
Predicted by Siyang on May 30, 2022	10.9165 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.64 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	56.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ibutilide	CCCCCCCN(CC)CCCC(O)C1=CC=C(NS(C)(=O)=O)C=C1	4756.0	Standard polar	33892256
Ibutilide	CCCCCCCN(CC)CCCC(O)C1=CC=C(NS(C)(=O)=O)C=C1	3036.5	Standard non polar	33892256
Ibutilide	CCCCCCCN(CC)CCCC(O)C1=CC=C(NS(C)(=O)=O)C=C1	2990.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ibutilide,1TMS,isomer #1	CCCCCCCN(CC)CCCC(O[Si](C)(C)C)C1=CC=C(NS(C)(=O)=O)C=C1	2973.3	Semi standard non polar	33892256
Ibutilide,1TMS,isomer #2	CCCCCCCN(CC)CCCC(O)C1=CC=C(N([Si](C)(C)C)S(C)(=O)=O)C=C1	3013.4	Semi standard non polar	33892256
Ibutilide,2TMS,isomer #1	CCCCCCCN(CC)CCCC(O[Si](C)(C)C)C1=CC=C(N([Si](C)(C)C)S(C)(=O)=O)C=C1	2926.7	Semi standard non polar	33892256
Ibutilide,2TMS,isomer #1	CCCCCCCN(CC)CCCC(O[Si](C)(C)C)C1=CC=C(N([Si](C)(C)C)S(C)(=O)=O)C=C1	3131.1	Standard non polar	33892256
Ibutilide,2TMS,isomer #1	CCCCCCCN(CC)CCCC(O[Si](C)(C)C)C1=CC=C(N([Si](C)(C)C)S(C)(=O)=O)C=C1	3527.9	Standard polar	33892256
Ibutilide,1TBDMS,isomer #1	CCCCCCCN(CC)CCCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(NS(C)(=O)=O)C=C1	3231.2	Semi standard non polar	33892256
Ibutilide,1TBDMS,isomer #2	CCCCCCCN(CC)CCCC(O)C1=CC=C(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)C=C1	3256.9	Semi standard non polar	33892256
Ibutilide,2TBDMS,isomer #1	CCCCCCCN(CC)CCCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)C=C1	3406.8	Semi standard non polar	33892256
Ibutilide,2TBDMS,isomer #1	CCCCCCCN(CC)CCCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)C=C1	3629.5	Standard non polar	33892256
Ibutilide,2TBDMS,isomer #1	CCCCCCCN(CC)CCCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)C=C1	3623.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ibutilide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-3494000000-4216adb870d24524f3f8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ibutilide GC-MS (1 TMS) - 70eV, Positive	splash10-00di-7594700000-e10d1f60942f779d0b69	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ibutilide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ibutilide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ibutilide 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 - Ibutilide 10V, Positive-QTOF	splash10-00kr-1049000000-878a4988359cc2b11375	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ibutilide 20V, Positive-QTOF	splash10-00du-1291000000-8799afa11da8453ab702	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ibutilide 40V, Positive-QTOF	splash10-0595-9440000000-b36c8a40d5b1b8695387	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ibutilide 10V, Negative-QTOF	splash10-003r-6009000000-c0b15b1b2eb0e206020f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ibutilide 20V, Negative-QTOF	splash10-004i-9002000000-a45fd07019d442a5c6b5	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ibutilide 40V, Negative-QTOF	splash10-004i-9000000000-5d0b14017a866bd34ada	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ibutilide 10V, Positive-QTOF	splash10-00rl-0079000000-032e11908e2e6e83894f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ibutilide 20V, Positive-QTOF	splash10-00dl-0093000000-7e58bd1519eeaa416c8c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ibutilide 40V, Positive-QTOF	splash10-00b9-3490000000-96978d620f1889ac59e5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ibutilide 10V, Negative-QTOF	splash10-001i-0009000000-f62c9ba5a2e4fcd8c148	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ibutilide 20V, Negative-QTOF	splash10-001i-1009000000-84070d0a4a2c0d89576c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ibutilide 40V, Negative-QTOF	splash10-00b9-6693000000-c855bbc813471812d69f	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Ibutilide Action Pathway		Not Available

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 DB00308	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00308	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00308

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

54755

KEGG Compound ID

C07753

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ibutilide

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. 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

Perry M, de Groot MJ, Helliwell R, Leishman D, Tristani-Firouzi M, Sanguinetti MC, Mitcheson J: Structural determinants of HERG channel block by clofilium and ibutilide. Mol Pharmacol. 2004 Aug;66(2):240-9. [PubMed:15266014 ]
Perry M, Stansfeld PJ, Leaney J, Wood C, de Groot MJ, Leishman D, Sutcliffe MJ, Mitcheson JS: Drug binding interactions in the inner cavity of HERG channels: molecular insights from structure-activity relationships of clofilium and ibutilide analogs. Mol Pharmacol. 2006 Feb;69(2):509-19. Epub 2005 Nov 16. [PubMed:16291873 ]
Wolpert C, Schimpf R, Veltmann C, Borggrefe M: [Short QT syndrome]. Herz. 2007 May;32(3):206-10. [PubMed:17497253 ]
Wolpert C, Schimpf R, Veltmann C, Giustetto C, Gaita F, Borggrefe M: Clinical characteristics and treatment of short QT syndrome. Expert Rev Cardiovasc Ther. 2005 Jul;3(4):611-7. [PubMed:16076272 ]
Yang T, Snyders D, Roden DM: Drug block of I(kr): model systems and relevance to human arrhythmias. J Cardiovasc Pharmacol. 2001 Nov;38(5):737-44. [PubMed:11602820 ]
Doggrell SA, Hancox JC: Ibutilide--recent molecular insights and accumulating evidence for use in atrial flutter and fibrillation. Expert Opin Investig Drugs. 2005 May;14(5):655-69. [PubMed:15926871 ]

Enzyme Details

2. Voltage-dependent L-type calcium channel subunit alpha-1C

General function:: Involved in ion channel activity
Specific function:: Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. The isoform alpha-1C gives rise to L-type calcium currents. Long-lasting (L-type) calcium channels belong to the 'high-voltage activated' (HVA) group. They are blocked by dihydropyridines (DHP), phenylalkylamines, benzothiazepines, and by omega-agatoxin-IIIA (omega-Aga-IIIA). They are however insensitive to omega-conotoxin- GVIA (omega-CTx-GVIA) and omega-agatoxin-IVA (omega-Aga-IVA). Calcium channels containing the alpha-1C subunit play an important role in excitation-contraction coupling in the heart. The various isoforms display marked differences in the sensitivity to DHP compounds. Binding of calmodulin or CABP1 at the same regulatory sites results in an opposit effects on the channel function
Gene Name:: CACNA1C
Uniprot ID:: Q13936
Molecular weight:: 248974.1

References

Doggrell SA, Hancox JC: Ibutilide--recent molecular insights and accumulating evidence for use in atrial flutter and fibrillation. Expert Opin Investig Drugs. 2005 May;14(5):655-69. [PubMed:15926871 ]
Foster RH, Wilde MI, Markham A: Ibutilide. A review of its pharmacological properties and clinical potential in the acute management of atrial flutter and fibrillation. Drugs. 1997 Aug;54(2):312-30. [PubMed:9257085 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

3. Potassium voltage-gated channel subfamily H member 6

General function:: Involved in ion channel activity
Specific function:: Pore-forming (alpha) subunit of voltage-gated potassium channel. Elicits a slowly activating, rectifying current. Channel properties may be modulated by cAMP and subunit assembly
Gene Name:: KCNH6
Uniprot ID:: Q9H252
Molecular weight:: 109923.7

References

Doggrell SA, Hancox JC: Ibutilide--recent molecular insights and accumulating evidence for use in atrial flutter and fibrillation. Expert Opin Investig Drugs. 2005 May;14(5):655-69. [PubMed:15926871 ]
Foster RH, Wilde MI, Markham A: Ibutilide. A review of its pharmacological properties and clinical potential in the acute management of atrial flutter and fibrillation. Drugs. 1997 Aug;54(2):312-30. [PubMed:9257085 ]

Enzyme Details

4. ATP-sensitive inward rectifier potassium channel 11

General function:: Involved in inward rectifier potassium channel activity
Specific function:: This receptor is controlled by G proteins. 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
Gene Name:: KCNJ11
Uniprot ID:: Q14654
Molecular weight:: 43540.4

References

Doggrell SA, Hancox JC: Ibutilide--recent molecular insights and accumulating evidence for use in atrial flutter and fibrillation. Expert Opin Investig Drugs. 2005 May;14(5):655-69. [PubMed:15926871 ]
Foster RH, Wilde MI, Markham A: Ibutilide. A review of its pharmacological properties and clinical potential in the acute management of atrial flutter and fibrillation. Drugs. 1997 Aug;54(2):312-30. [PubMed:9257085 ]

Enzyme Details

5. Voltage-dependent calcium channel subunit alpha-2/delta-1

General function:: Involved in metal ion binding
Specific function:: The alpha-2/delta subunit of voltage-dependent calcium channels regulates calcium current density and activation/inactivation kinetics of the calcium channel. Plays an important role in excitation-contraction coupling
Gene Name:: CACNA2D1
Uniprot ID:: P54289
Molecular weight:: 124566.9

References

Doggrell SA, Hancox JC: Ibutilide--recent molecular insights and accumulating evidence for use in atrial flutter and fibrillation. Expert Opin Investig Drugs. 2005 May;14(5):655-69. [PubMed:15926871 ]
Foster RH, Wilde MI, Markham A: Ibutilide. A review of its pharmacological properties and clinical potential in the acute management of atrial flutter and fibrillation. Drugs. 1997 Aug;54(2):312-30. [PubMed:9257085 ]

Enzyme Details

6. Voltage-dependent L-type calcium channel subunit beta-1

General function:: Involved in voltage-gated calcium channel activity
Specific function:: The beta subunit of voltage-dependent calcium channels contributes to the function of the calcium channel by increasing peak calcium current, shifting the voltage dependencies of activation and inactivation, modulating G protein inhibition and controlling the alpha-1 subunit membrane targeting
Gene Name:: CACNB1
Uniprot ID:: Q02641
Molecular weight:: 65713.0

References

Doggrell SA, Hancox JC: Ibutilide--recent molecular insights and accumulating evidence for use in atrial flutter and fibrillation. Expert Opin Investig Drugs. 2005 May;14(5):655-69. [PubMed:15926871 ]
Foster RH, Wilde MI, Markham A: Ibutilide. A review of its pharmacological properties and clinical potential in the acute management of atrial flutter and fibrillation. Drugs. 1997 Aug;54(2):312-30. [PubMed:9257085 ]

Enzyme Details

7. Voltage-dependent calcium channel gamma-1 subunit

General function:: Involved in voltage-gated calcium channel activity
Specific function:: This protein is a subunit of the dihydropyridine (DHP) sensitive calcium channel. Plays a role in excitation-contraction coupling. The skeletal muscle DHP-sensitive Ca(2+) channel may function only as a multiple subunit complex
Gene Name:: CACNG1
Uniprot ID:: Q06432
Molecular weight:: 25028.1

References

Doggrell SA, Hancox JC: Ibutilide--recent molecular insights and accumulating evidence for use in atrial flutter and fibrillation. Expert Opin Investig Drugs. 2005 May;14(5):655-69. [PubMed:15926871 ]
Foster RH, Wilde MI, Markham A: Ibutilide. A review of its pharmacological properties and clinical potential in the acute management of atrial flutter and fibrillation. Drugs. 1997 Aug;54(2):312-30. [PubMed:9257085 ]

Enzyme Details

8. Potassium voltage-gated channel subfamily H member 7

General function:: Involved in ion channel activity
Specific function:: Pore-forming (alpha) subunit of voltage-gated potassium channel. Channel properties may be modulated by cAMP and subunit assembly
Gene Name:: KCNH7
Uniprot ID:: Q9NS40
Molecular weight:: 134998.5

References

Doggrell SA, Hancox JC: Ibutilide--recent molecular insights and accumulating evidence for use in atrial flutter and fibrillation. Expert Opin Investig Drugs. 2005 May;14(5):655-69. [PubMed:15926871 ]
Foster RH, Wilde MI, Markham A: Ibutilide. A review of its pharmacological properties and clinical potential in the acute management of atrial flutter and fibrillation. Drugs. 1997 Aug;54(2):312-30. [PubMed:9257085 ]

Enzyme Details

9. Potassium channel subfamily K member 1

General function:: Involved in potassium channel activity
Specific function:: Weakly inward rectifying potassium channel
Gene Name:: KCNK1
Uniprot ID:: O00180
Molecular weight:: 38142.8

References

Doggrell SA, Hancox JC: Ibutilide--recent molecular insights and accumulating evidence for use in atrial flutter and fibrillation. Expert Opin Investig Drugs. 2005 May;14(5):655-69. [PubMed:15926871 ]
Foster RH, Wilde MI, Markham A: Ibutilide. A review of its pharmacological properties and clinical potential in the acute management of atrial flutter and fibrillation. Drugs. 1997 Aug;54(2):312-30. [PubMed:9257085 ]

Showing metabocard for Ibutilide (HMDB0014453)

MOL for HMDB0014453 (Ibutilide)

3D MOL for HMDB0014453 (Ibutilide)

3D SDF for HMDB0014453 (Ibutilide)

3D-SDF for HMDB0014453 (Ibutilide)

PDB for HMDB0014453 (Ibutilide)

3D PDB for HMDB0014453 (Ibutilide)

SMILES for HMDB0014453 (Ibutilide)

INCHI for HMDB0014453 (Ibutilide)

Structure for HMDB0014453 (Ibutilide)

3D Structure for HMDB0014453 (Ibutilide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

References

References