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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 08:59:29 UTC

Update Date

2021-09-26 23:03:43 UTC

HMDB ID

HMDB0251621

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Dronedarone

Description

Dronedarone, also known as multaq or SR 33589, belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group. Dronedarone (development codename SR33589 and marketed as Multaq) is a drug by Sanofi-Aventis, mainly for the indication of cardiac arrhythmias. " Dronedarone is also associated with rare cases of severe liver damage, including liver failure. Dronedarone has been termed a “multichannel blocker” however it is unclear which channel(s) play a pivotal role in its success. Thus, dronedarone's actions at the cellular level are controversial with most studies suggesting an inhibition in multiple outward potassium currents including rapid delayed rectifier, slow delayed rectifier and ACh-activated inward rectifier. It is also believed to reduce inward rapid Na current and L-type Ca channels. The reduction in K current in some studies was shown to be due to the inhibition of K-ACh channel or associated GTP-binding proteins. Reduction of K+ current by 69% led to increased AP duration and increased effective refractory periods, thus shown to suppress pacemaker potential of the SA node and return patients to a normal heart rhythm. In a European trial, the average time to recurrence of an arrhythmia was 41 days in the placebo group vs. 96 days in the dronedarone group (similar results obtained in the non-European trial, 59 and 158 days respectively).Chemically, dronedarone is a benzofuran derivative related to amiodarone, a popular antiarrhythmic. The use of amiodarone is limited by toxicity due its high iodine content (pulmonary fibrosis, thyroid disease) as well as by liver disease. In dronedarone, the iodine moieties are not present, reducing toxic effects on the thyroid and other organs. A methylsulfonamide group is added to reduce solubility in fats (lipophobicity) and thus reduce neurotoxic effects. Dronedarone displays amiodarone-like class III antiarrhythmic activity in vitro and in clinical trials. The drug also appears to exhibit activity in each of the 4 Vaughan-Williams antiarrhythmic classes. Dronedarone is less lipophilic than amiodarone, has a much smaller volume of distribution, and has an elimination half-life of 13–19 hours—this stands in contrast to amiodarone's half-life of several weeks. As a result of these pharmacokinetic characteristics, dronedarone dosing may be less complicated than amiodarone. Permanent AF (patients in whom normal sinus rhythm will not or cannot be restored)Recently decompensated heart failure requiring hospitalization or Class IV heart failure. Second-or third-degree AV block or sick sinus syndrome (except when used in conjunction with a functioning pacemaker)BradycardiaConcomitant use of a strong CYP3A inhibitorConcomitant use of drugs or herbal products that prolong the QT interval and may induce Torsade de PointesLiver or lung toxicity related to the previous use of amiodaroneSevere hepatic impairmentQTc Bazett interval ≥500 ms, or use with drugs or herbal supplements that prolong QT interval or increase risk of torsades de points (Class I or III antiarrhythmic agents, phenothiazines, tricyclic antidepressants, certain oral macrolides, ephedra).Pregnancy and nursing mothersHypersensitivity to dronedaroneHepatic impairment. In Jan 2011 the FDA advised about cases of rare, but severe, liver injury, including two cases of acute liver failure leading to liver transplant in patients treated with dronedarone (Multaq). It is not known whether routine periodic monitoring of serum liver enzymes (ALT, AST, and alkaline phosphatase) and bilirubin in patients taking dronedarone will prevent the development of severe liver injury. PR interval exceeding 280 msUse of cytochrome P-450 (CYP) 3a isoenzyme inhibitors (includes: clarithromycin, cyclosporine, itraconazole, ketoconazole, nefazodone, ritonavir, telithromycin, voriconazole)Clinical trials have compared dronedarone to placebo and to amiodarone, for its ability to reduce atrial fibrillation, to reduce mortality overall and from cardiac causes, and for its adverse effects, including excess mortality. Dronedarone is a non-iodinated class III anti-arrhythmic drug which helps patients return to normal sinus rhythm. This treatment for AF is also known to reduce associated mortality and hospitalizations compared to other similar antiarrhythmic agents. In the EURIDIS and ADONIS trials in atrial fibrillation (2007), dronedarone was significantly more effective than placebo in maintaining sinus rhythm, with no difference in lung and thyroid function in the short term. However, in the ANDROMEDA study (2007), dronedarone doubled the death rate compared to placebo, and the trial was halted early. ANDROMEDA enrolled patients with moderate to severe congestive heart failure, a relatively sicker patient population. In a more recent atrial fibrillation trial, ATHENA, with 4628 subjects, dronedarone was significantly more effective than placebo in reducing the composite endpoint of first hospitalization due to cardiovascular events or death. There was a significant reduction in the rate of cardiovascular death, but not in the rate of death from any cause. Later post-hoc analysis of the ATHENA-results showed a significant reduction in the rate of stroke. Patients randomized to dronedarone were more likely to develop bradycardia and QT-interval prolongation (but only 1 case of Torsades). Nausea, diarrhea, rash, and creatinine elevation also were more common in the dronedarone arm. The PALLAS trial (2011) was stopped for safety concerns due to the finding that "dronedarone increased rates of heart failure, stroke, and death from cardiovascular causes in patients with permanent atrial fibrillation who were at risk for major vascular events". A Black Box warning was subsequently added by the FDA stating that the risk of death, stroke, and hospitalization for congestive heart failure doubled in patients with permanent atrial fibrillation. Dronedarone has been tested in some trials as a way to improve the success rate of electrical cardioversion. In one such trial by the Veteran's Administration it was used prepare patients for electrical conversion to sinus rhythm. In the ATHENA study, 25% of patients were started on dronedarone before cardioversion. The results of a recently concluded randomized study (ELECTRA) may clarify the safety and ideal modalities of dronedarone use at the time of cardioversion. Originally submitted as a New Drug Application in 2005, dronedarone was reviewed and recommended for approval on March 18, 2009 by an Advisory Committee of the United States Food and Drug Administration (FDA). The FDA is not bound by the Committee's recommendation, but it takes its advice into consideration when reviewing new drug applications. The FDA approved dronedarone on July 2, 2009. Health Canada was the second major regulatory body to approve the drug, giving its approval on August 12, 2009. The approval is for "treatment of patients with a history of, or current atrial fibrillation to reduce their risk of cardiovascular hospitalization due to this condition. Dronedarone is a very strong basic compound (based on its pKa). It was approved by the FDA on July 2, 2009. In the United States, the FDA approved label includes a claim for reducing hospitalization, but not for reducing mortality, as a reduction in mortality was not demonstrated in the clinical development program. It was recommended as an alternative to amiodarone for the treatment of atrial fibrillation and atrial flutter in people whose hearts have either returned to normal rhythm or who undergo drug therapy or electric shock treatment i.e. direct current cardioversion (DCCV) to maintain normal rhythm. It is a class III antiarrhythmic drug. A trial of the drug in heart failure was stopped as an interim analysis showed a possible increase in heart failure deaths, in patients with moderate to severe CHF.The U.S. label for dronedarone includes a boxed warning, stating that dronedarone is contraindicated in patients with NYHA Class IV heart failure, with NYHA Class II–III heart failure with a recent decompensation requiring hospitalization or referral to a specialized heart failure clinic, or with permanent atrial fibrillation. "The European Medicines Agency issued a Summary of Positive Opinion regarding dronedarone on 24 September 2009 recommending to the European Commission to grant a marketing authorization within the European Union. This compound has been identified in human blood as reported by (PMID: 31557052 ). Dronedarone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Dronedarone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

  Mrv0541 02231217572D          

 39 41  0  0  0  0            999 V2000
    2.3645   -1.8460    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.0031   -2.9224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4885   -0.1299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7085   -0.1964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -2.5604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -1.1315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6158    1.7788    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.4335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8720    2.5630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1667    1.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8085    1.6087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6793    2.7331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9740    1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5521    0.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9356    3.5173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5250    0.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7449    0.6543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4846   -2.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0031   -1.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3097   -2.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7222   -2.9730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7429    3.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3323    0.8909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2594   -0.8104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5472   -2.9730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0667   -0.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6813   -0.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -3.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3230    0.1440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6177   -1.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1303    0.3141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4250   -1.0842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9597   -3.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  2  0  0  0  0
  1  6  2  0  0  0  0
  1  8  1  0  0  0  0
  1 39  1  0  0  0  0
  2 18  1  0  0  0  0
  2 25  1  0  0  0  0
  3 17  1  0  0  0  0
  3 31  1  0  0  0  0
  4 26  2  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  7 11  1  0  0  0  0
  8 30  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 14 17  1  0  0  0  0
 15 23  1  0  0  0  0
 16 24  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 26  1  0  0  0  0
 20 22  1  0  0  0  0
 21 25  2  0  0  0  0
 21 28  1  0  0  0  0
 22 27  1  0  0  0  0
 25 32  1  0  0  0  0
 26 29  1  0  0  0  0
 27 38  1  0  0  0  0
 28 30  2  0  0  0  0
 29 34  2  0  0  0  0
 29 35  1  0  0  0  0
 30 33  1  0  0  0  0
 31 36  2  0  0  0  0
 31 37  1  0  0  0  0
 32 33  2  0  0  0  0
 34 36  1  0  0  0  0
 35 37  2  0  0  0  0
M  END

HMDB0251621
     RDKit          3D
Dronedarone
 83 85  0  0  0  0  0  0  0  0999 V2000
   -7.0625    4.6864   -1.3455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9266    3.6841   -1.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0804    4.1163    0.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9817    3.1639    0.3537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4392    1.7964    0.7284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1956    1.5206    1.7967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4591    0.2654    1.8786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1834   -0.5381    2.7596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3106   -1.9009    2.6140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6851   -2.5104    1.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7474   -3.8933    1.3387 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1890   -4.6352   -0.1217 S   0  0  0  0  0  6  0  0  0  0  0  0
   -7.8728   -4.2335   -0.6186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1599   -6.1267    0.0788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2033   -4.2479   -1.1956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9582   -1.7037    0.6501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8481   -0.3441    0.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1850    0.6393    0.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4274    0.2876   -1.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0765   -0.1377   -2.1437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9818    0.3718   -1.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1909    1.2238   -0.4605 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2022    1.2635   -0.5888 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8486    0.4051   -1.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2505    0.4557   -1.5891 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0016    1.3392   -0.7698 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9747    0.8667    0.6492 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7649   -0.4660    0.7853 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0971   -0.2291    0.3210 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284    0.6444    1.1267 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2529    0.8899    0.8467 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5207    1.4993   -0.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8733    2.8580   -0.5718 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6967   -1.4454   -0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9475   -2.3168    1.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5658   -3.6253    0.6625 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8720   -3.3297   -0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0654   -0.4550   -2.2016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3152   -0.4938   -2.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6074    5.6639   -1.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6239    4.7034   -0.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6704    4.2766   -2.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3214    3.6039   -2.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3687    2.6854   -0.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6087    5.1188   -0.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7493    4.2683    0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2338    3.5384    1.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4044    3.0502   -0.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6853   -0.0536    3.5892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8915   -2.5144    3.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4681   -4.4734    2.1969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8708   -3.2128   -0.9813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5074   -4.3499    0.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2345   -4.9494   -1.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4578   -2.1959   -0.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5956    1.9012    0.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7639    1.9827   -0.0382 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5843    2.3518   -0.8637 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0540    1.4084   -1.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9422    0.5647    1.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3215    1.6335    1.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2360   -1.3075    0.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8545   -0.6684    1.8950 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3174    1.6622    1.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6818    0.3525    2.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9305    0.0424    1.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5832    1.6893    1.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0540    0.9171   -1.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6033    1.5264   -0.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5038    3.5234   -1.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8810    2.8508   -1.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7562    3.3531    0.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9947   -2.0213   -0.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6293   -1.3345   -0.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0055   -2.5403    1.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5910   -1.7797    1.8426 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7023   -4.3048    1.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8153   -4.1138   -0.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7273   -2.9180   -1.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4243   -4.3068   -0.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4664   -2.6465    0.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5347   -1.1517   -2.9072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9417   -1.1705   -2.6428 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 12 15  2  0
 10 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
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M  END

  Mrv0541 02231217572D          

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M  END
> <DATABASE_ID>
HMDB0251621

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCN(CCCC)CCCOC1=CC=C(C=C1)C(=O)C1=C(CCCC)OC2=C1C=C(NS(C)(=O)=O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C31H44N2O5S/c1-5-8-12-29-30(27-23-25(32-39(4,35)36)15-18-28(27)38-29)31(34)24-13-16-26(17-14-24)37-22-11-21-33(19-9-6-2)20-10-7-3/h13-18,23,32H,5-12,19-22H2,1-4H3

> <INCHI_KEY>
ZQTNQVWKHCQYLQ-UHFFFAOYSA-N

> <FORMULA>
C31H44N2O5S

> <MOLECULAR_WEIGHT>
556.756

> <EXACT_MASS>
556.297093218

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
66.05334854234121

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-(2-butyl-3-{4-[3-(dibutylamino)propoxy]benzoyl}-1-benzofuran-5-yl)methanesulfonamide

> <ALOGPS_LOGP>
6.46

> <JCHEM_LOGP>
5.277915882139469

> <ALOGPS_LOGS>
-5.44

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.081649410353782

> <JCHEM_PKA_STRONGEST_BASIC>
9.786987822800464

> <JCHEM_POLAR_SURFACE_AREA>
88.85

> <JCHEM_REFRACTIVITY>
158.12839999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.01e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
multaq

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0251621
     RDKit          3D
Dronedarone
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M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       4.414  -3.446   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0      11.206  -5.455   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      17.712  -0.242   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      10.656  -0.367   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.184  -4.779   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.644  -2.112   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      21.683   3.320   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       5.748  -2.676   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      22.161   4.784   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.711   2.174   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.176   3.003   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.668   5.102   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.218   2.492   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.697   1.539   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      24.146   6.566   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.247   1.345   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.190   1.221   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.105  -4.216   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.206  -2.977   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.645  -4.216   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.748  -3.446   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.415  -5.550   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      25.653   6.883   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      26.754   1.663   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.748  -4.986   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.684  -1.513   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.955  -5.550   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.415  -2.676   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.191  -1.195   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.081  -3.446   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.205  -0.560   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.415  -5.756   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.081  -4.986   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      13.670   0.269   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      14.220  -2.341   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      15.177   0.586   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      15.727  -2.024   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      16.725  -6.883   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.080  -4.216   0.000  0.00  0.00           C+0
CONECT    1    5    6    8   39                                             
CONECT    2   18   25                                                       
CONECT    3   17   31                                                       
CONECT    4   26                                                            
CONECT    5    1                                                            
CONECT    6    1                                                            
CONECT    7    9   10   11                                                  
CONECT    8    1   30                                                       
CONECT    9    7   12                                                       
CONECT   10    7   13                                                       
CONECT   11    7   14                                                       
CONECT   12    9   15                                                       
CONECT   13   10   16                                                       
CONECT   14   11   17                                                       
CONECT   15   12   23                                                       
CONECT   16   13   24                                                       
CONECT   17    3   14                                                       
CONECT   18    2   19   20                                                  
CONECT   19   18   21   26                                                  
CONECT   20   18   22                                                       
CONECT   21   19   25   28                                                  
CONECT   22   20   27                                                       
CONECT   23   15                                                            
CONECT   24   16                                                            
CONECT   25    2   21   32                                                  
CONECT   26    4   19   29                                                  
CONECT   27   22   38                                                       
CONECT   28   21   30                                                       
CONECT   29   26   34   35                                                  
CONECT   30    8   28   33                                                  
CONECT   31    3   36   37                                                  
CONECT   32   25   33                                                       
CONECT   33   30   32                                                       
CONECT   34   29   36                                                       
CONECT   35   29   37                                                       
CONECT   36   31   34                                                       
CONECT   37   31   35                                                       
CONECT   38   27                                                            
CONECT   39    1                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

COMPND    HMDB0251621
HETATM    1  C1  UNL     1      -7.063   4.686  -1.345  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.927   3.684  -1.110  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.080   4.116   0.032  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.982   3.164   0.354  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.439   1.796   0.728  1.00  0.00           C  
HETATM    6  O1  UNL     1      -5.196   1.521   1.797  1.00  0.00           O  
HETATM    7  C6  UNL     1      -5.459   0.265   1.879  1.00  0.00           C  
HETATM    8  C7  UNL     1      -6.183  -0.538   2.760  1.00  0.00           C  
HETATM    9  C8  UNL     1      -6.311  -1.901   2.614  1.00  0.00           C  
HETATM   10  C9  UNL     1      -5.685  -2.510   1.539  1.00  0.00           C  
HETATM   11  N1  UNL     1      -5.747  -3.893   1.339  1.00  0.00           N  
HETATM   12  S1  UNL     1      -6.189  -4.635  -0.122  1.00  0.00           S  
HETATM   13  C10 UNL     1      -7.873  -4.233  -0.619  1.00  0.00           C  
HETATM   14  O2  UNL     1      -6.160  -6.127   0.079  1.00  0.00           O  
HETATM   15  O3  UNL     1      -5.203  -4.248  -1.196  1.00  0.00           O  
HETATM   16  C11 UNL     1      -4.958  -1.704   0.650  1.00  0.00           C  
HETATM   17  C12 UNL     1      -4.848  -0.344   0.814  1.00  0.00           C  
HETATM   18  C13 UNL     1      -4.185   0.639   0.059  1.00  0.00           C  
HETATM   19  C14 UNL     1      -3.427   0.288  -1.103  1.00  0.00           C  
HETATM   20  O4  UNL     1      -4.077  -0.138  -2.144  1.00  0.00           O  
HETATM   21  C15 UNL     1      -1.982   0.372  -1.176  1.00  0.00           C  
HETATM   22  C16 UNL     1      -1.191   1.224  -0.461  1.00  0.00           C  
HETATM   23  C17 UNL     1       0.202   1.263  -0.589  1.00  0.00           C  
HETATM   24  C18 UNL     1       0.849   0.405  -1.479  1.00  0.00           C  
HETATM   25  O5  UNL     1       2.251   0.456  -1.589  1.00  0.00           O  
HETATM   26  C19 UNL     1       3.002   1.339  -0.770  1.00  0.00           C  
HETATM   27  C20 UNL     1       2.975   0.867   0.649  1.00  0.00           C  
HETATM   28  C21 UNL     1       3.765  -0.466   0.785  1.00  0.00           C  
HETATM   29  N2  UNL     1       5.097  -0.229   0.321  1.00  0.00           N  
HETATM   30  C22 UNL     1       5.828   0.644   1.127  1.00  0.00           C  
HETATM   31  C23 UNL     1       7.253   0.890   0.847  1.00  0.00           C  
HETATM   32  C24 UNL     1       7.521   1.499  -0.497  1.00  0.00           C  
HETATM   33  C25 UNL     1       6.873   2.858  -0.572  1.00  0.00           C  
HETATM   34  C26 UNL     1       5.697  -1.445  -0.097  1.00  0.00           C  
HETATM   35  C27 UNL     1       5.948  -2.317   1.111  1.00  0.00           C  
HETATM   36  C28 UNL     1       6.566  -3.625   0.662  1.00  0.00           C  
HETATM   37  C29 UNL     1       7.872  -3.330  -0.028  1.00  0.00           C  
HETATM   38  C30 UNL     1       0.065  -0.455  -2.202  1.00  0.00           C  
HETATM   39  C31 UNL     1      -1.315  -0.494  -2.076  1.00  0.00           C  
HETATM   40  H1  UNL     1      -6.607   5.664  -1.549  1.00  0.00           H  
HETATM   41  H2  UNL     1      -7.624   4.703  -0.369  1.00  0.00           H  
HETATM   42  H3  UNL     1      -7.670   4.277  -2.165  1.00  0.00           H  
HETATM   43  H4  UNL     1      -5.321   3.604  -2.036  1.00  0.00           H  
HETATM   44  H5  UNL     1      -6.369   2.685  -0.943  1.00  0.00           H  
HETATM   45  H6  UNL     1      -4.609   5.119  -0.174  1.00  0.00           H  
HETATM   46  H7  UNL     1      -5.749   4.268   0.927  1.00  0.00           H  
HETATM   47  H8  UNL     1      -3.234   3.538   1.091  1.00  0.00           H  
HETATM   48  H9  UNL     1      -3.404   3.050  -0.636  1.00  0.00           H  
HETATM   49  H10 UNL     1      -6.685  -0.054   3.589  1.00  0.00           H  
HETATM   50  H11 UNL     1      -6.892  -2.514   3.302  1.00  0.00           H  
HETATM   51  H12 UNL     1      -5.468  -4.473   2.197  1.00  0.00           H  
HETATM   52  H13 UNL     1      -7.871  -3.213  -0.981  1.00  0.00           H  
HETATM   53  H14 UNL     1      -8.507  -4.350   0.289  1.00  0.00           H  
HETATM   54  H15 UNL     1      -8.234  -4.949  -1.392  1.00  0.00           H  
HETATM   55  H16 UNL     1      -4.458  -2.196  -0.201  1.00  0.00           H  
HETATM   56  H17 UNL     1      -1.596   1.901   0.268  1.00  0.00           H  
HETATM   57  H18 UNL     1       0.764   1.983  -0.038  1.00  0.00           H  
HETATM   58  H19 UNL     1       2.584   2.352  -0.864  1.00  0.00           H  
HETATM   59  H20 UNL     1       4.054   1.408  -1.163  1.00  0.00           H  
HETATM   60  H21 UNL     1       1.942   0.565   1.009  1.00  0.00           H  
HETATM   61  H22 UNL     1       3.321   1.634   1.314  1.00  0.00           H  
HETATM   62  H23 UNL     1       3.236  -1.308   0.338  1.00  0.00           H  
HETATM   63  H24 UNL     1       3.854  -0.668   1.895  1.00  0.00           H  
HETATM   64  H25 UNL     1       5.317   1.662   1.070  1.00  0.00           H  
HETATM   65  H26 UNL     1       5.682   0.352   2.199  1.00  0.00           H  
HETATM   66  H27 UNL     1       7.930   0.042   1.076  1.00  0.00           H  
HETATM   67  H28 UNL     1       7.583   1.689   1.599  1.00  0.00           H  
HETATM   68  H29 UNL     1       7.054   0.917  -1.328  1.00  0.00           H  
HETATM   69  H30 UNL     1       8.603   1.526  -0.742  1.00  0.00           H  
HETATM   70  H31 UNL     1       7.504   3.523  -1.227  1.00  0.00           H  
HETATM   71  H32 UNL     1       5.881   2.851  -1.079  1.00  0.00           H  
HETATM   72  H33 UNL     1       6.756   3.353   0.411  1.00  0.00           H  
HETATM   73  H34 UNL     1       4.995  -2.021  -0.747  1.00  0.00           H  
HETATM   74  H35 UNL     1       6.629  -1.334  -0.665  1.00  0.00           H  
HETATM   75  H36 UNL     1       5.006  -2.540   1.644  1.00  0.00           H  
HETATM   76  H37 UNL     1       6.591  -1.780   1.843  1.00  0.00           H  
HETATM   77  H38 UNL     1       6.702  -4.305   1.530  1.00  0.00           H  
HETATM   78  H39 UNL     1       5.815  -4.114  -0.026  1.00  0.00           H  
HETATM   79  H40 UNL     1       7.727  -2.918  -1.040  1.00  0.00           H  
HETATM   80  H41 UNL     1       8.424  -4.307  -0.101  1.00  0.00           H  
HETATM   81  H42 UNL     1       8.466  -2.647   0.644  1.00  0.00           H  
HETATM   82  H43 UNL     1       0.535  -1.152  -2.907  1.00  0.00           H  
HETATM   83  H44 UNL     1      -1.942  -1.171  -2.643  1.00  0.00           H  
CONECT    1    2   40   41   42
CONECT    2    3   43   44
CONECT    3    4   45   46
CONECT    4    5   47   48
CONECT    5    6   18   18
CONECT    6    7
CONECT    7    8    8   17
CONECT    8    9   49
CONECT    9   10   10   50
CONECT   10   11   16
CONECT   11   12   51
CONECT   12   13   14   14   15
CONECT   12   15
CONECT   13   52   53   54
CONECT   16   17   17   55
CONECT   17   18
CONECT   18   19
CONECT   19   20   20   21
CONECT   21   22   22   39
CONECT   22   23   56
CONECT   23   24   24   57
CONECT   24   25   38
CONECT   25   26
CONECT   26   27   58   59
CONECT   27   28   60   61
CONECT   28   29   62   63
CONECT   29   30   34
CONECT   30   31   64   65
CONECT   31   32   66   67
CONECT   32   33   68   69
CONECT   33   70   71   72
CONECT   34   35   73   74
CONECT   35   36   75   76
CONECT   36   37   77   78
CONECT   37   79   80   81
CONECT   38   39   39   82
CONECT   39   83
END

HMDB0251621
     RDKit          3D
Dronedarone
 83 85  0  0  0  0  0  0  0  0999 V2000
   -7.0625    4.6864   -1.3455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9266    3.6841   -1.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0804    4.1163    0.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9817    3.1639    0.3537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4392    1.7964    0.7284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1956    1.5206    1.7967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4591    0.2654    1.8786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1834   -0.5381    2.7596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3106   -1.9009    2.6140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6851   -2.5104    1.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7474   -3.8933    1.3387 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1890   -4.6352   -0.1217 S   0  0  0  0  0  6  0  0  0  0  0  0
   -7.8728   -4.2335   -0.6186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1599   -6.1267    0.0788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2033   -4.2479   -1.1956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9582   -1.7037    0.6501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8481   -0.3441    0.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1850    0.6393    0.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4274    0.2876   -1.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0765   -0.1377   -2.1437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9818    0.3718   -1.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1909    1.2238   -0.4605 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2022    1.2635   -0.5888 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8486    0.4051   -1.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2505    0.4557   -1.5891 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0016    1.3392   -0.7698 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9747    0.8667    0.6492 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7649   -0.4660    0.7853 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0971   -0.2291    0.3210 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284    0.6444    1.1267 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2529    0.8899    0.8467 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5207    1.4993   -0.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8733    2.8580   -0.5718 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6967   -1.4454   -0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9475   -2.3168    1.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5658   -3.6253    0.6625 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8720   -3.3297   -0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0654   -0.4550   -2.2016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3152   -0.4938   -2.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6074    5.6639   -1.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6239    4.7034   -0.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6704    4.2766   -2.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3214    3.6039   -2.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3687    2.6854   -0.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6087    5.1188   -0.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7493    4.2683    0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2338    3.5384    1.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4044    3.0502   -0.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6853   -0.0536    3.5892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8915   -2.5144    3.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4681   -4.4734    2.1969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8708   -3.2128   -0.9813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5074   -4.3499    0.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2345   -4.9494   -1.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4578   -2.1959   -0.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5956    1.9012    0.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7639    1.9827   -0.0382 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5843    2.3518   -0.8637 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0540    1.4084   -1.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9422    0.5647    1.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3215    1.6335    1.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2360   -1.3075    0.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8545   -0.6684    1.8950 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3174    1.6622    1.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6818    0.3525    2.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9305    0.0424    1.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5832    1.6893    1.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0540    0.9171   -1.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6033    1.5264   -0.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5038    3.5234   -1.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8810    2.8508   -1.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7562    3.3531    0.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9947   -2.0213   -0.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6293   -1.3345   -0.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0055   -2.5403    1.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5910   -1.7797    1.8426 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7023   -4.3048    1.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8153   -4.1138   -0.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7273   -2.9180   -1.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4243   -4.3068   -0.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4664   -2.6465    0.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5347   -1.1517   -2.9072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9417   -1.1705   -2.6428 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  2  0
  8  9  1  0
  9 10  2  0
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 24 38  1  0
 38 39  2  0
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 39 21  1  0
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  1 40  1  0
  1 41  1  0
  1 42  1  0
  2 43  1  0
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  3 45  1  0
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  4 47  1  0
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 37 81  1  0
 38 82  1  0
 39 83  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Multaq	ChEBI
N-(2-Butyl-3-(4-(3-(dibutylamino)propoxy)benzoyl)-5-benzofuranyl)-methanesulfonamide	ChEBI
N-(2-Butyl-3-(p-(3-(dibutylamino)propoxy)benzoyl)-5-benzofuranyl)methanesulfonamide	ChEBI
SR 33589	ChEBI
SR 33589b	ChEBI
N-(2-Butyl-3-(4-(3-(dibutylamino)propoxy)benzoyl)-5-benzofuranyl)-methanesulphonamide	Generator
N-(2-Butyl-3-(p-(3-(dibutylamino)propoxy)benzoyl)-5-benzofuranyl)methanesulphonamide	Generator

Chemical Formula

C₃₁H₄₄N₂O₅S

Average Molecular Weight

556.756

Monoisotopic Molecular Weight

556.297093218

IUPAC Name

N-(2-butyl-3-{4-[3-(dibutylamino)propoxy]benzoyl}-1-benzofuran-5-yl)methanesulfonamide

Traditional Name

multaq

CAS Registry Number

Not Available

SMILES

CCCCN(CCCC)CCCOC1=CC=C(C=C1)C(=O)C1=C(CCCC)OC2=C1C=C(NS(C)(=O)=O)C=C2

InChI Identifier

InChI=1S/C31H44N2O5S/c1-5-8-12-29-30(27-23-25(32-39(4,35)36)15-18-28(27)38-29)31(34)24-13-16-26(17-14-24)37-22-11-21-33(19-9-6-2)20-10-7-3/h13-18,23,32H,5-12,19-22H2,1-4H3

InChI Key

ZQTNQVWKHCQYLQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl-phenylketones

Alternative Parents

Substituents

Aryl-phenylketone
Sulfanilide
Benzofuran
Phenoxy compound
Benzoyl
Phenol ether
3-aroylfuran
Alkyl aryl ether
Monocyclic benzene moiety
Organic sulfonic acid amide
Benzenoid
Organosulfonic acid amide
Furan
Heteroaromatic compound
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Aminosulfonyl compound
Sulfonyl
Tertiary amine
Tertiary aliphatic amine
Oxacycle
Ether
Organoheterocyclic compound
Amine
Organosulfur compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:50659 )
aromatic ether (CHEBI:50659 )
sulfonamide (CHEBI:50659 )
1-benzofurans (CHEBI:50659 )
aromatic ketone (CHEBI:50659 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0251621)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	6.46	ALOGPS
logP	5.28	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	9.08	ChemAxon
pKa (Strongest Basic)	9.79	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	88.85 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	158.13 m³·mol⁻¹	ChemAxon
Polarizability	66.05 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	231.309	30932474
DeepCCS	[M-H]-	228.914	30932474
DeepCCS	[M-2H]-	261.797	30932474
DeepCCS	[M+Na]+	237.222	30932474
AllCCS	[M+H]+	232.0	32859911
AllCCS	[M+H-H2O]+	230.7	32859911
AllCCS	[M+NH4]+	233.1	32859911
AllCCS	[M+Na]+	233.4	32859911
AllCCS	[M-H]-	217.9	32859911
AllCCS	[M+Na-2H]-	220.9	32859911
AllCCS	[M+HCOO]-	224.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dronedarone	CCCCN(CCCC)CCCOC1=CC=C(C=C1)C(=O)C1=C(CCCC)OC2=C1C=C(NS(C)(=O)=O)C=C2	6536.5	Standard polar	33892256
Dronedarone	CCCCN(CCCC)CCCOC1=CC=C(C=C1)C(=O)C1=C(CCCC)OC2=C1C=C(NS(C)(=O)=O)C=C2	4339.8	Standard non polar	33892256
Dronedarone	CCCCN(CCCC)CCCOC1=CC=C(C=C1)C(=O)C1=C(CCCC)OC2=C1C=C(NS(C)(=O)=O)C=C2	4284.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dronedarone,1TMS,isomer #1	CCCCC1=C(C(=O)C2=CC=C(OCCCN(CCCC)CCCC)C=C2)C2=CC(N([Si](C)(C)C)S(C)(=O)=O)=CC=C2O1	4186.5	Semi standard non polar	33892256
Dronedarone,1TMS,isomer #1	CCCCC1=C(C(=O)C2=CC=C(OCCCN(CCCC)CCCC)C=C2)C2=CC(N([Si](C)(C)C)S(C)(=O)=O)=CC=C2O1	4395.5	Standard non polar	33892256
Dronedarone,1TMS,isomer #1	CCCCC1=C(C(=O)C2=CC=C(OCCCN(CCCC)CCCC)C=C2)C2=CC(N([Si](C)(C)C)S(C)(=O)=O)=CC=C2O1	5344.2	Standard polar	33892256
Dronedarone,1TBDMS,isomer #1	CCCCC1=C(C(=O)C2=CC=C(OCCCN(CCCC)CCCC)C=C2)C2=CC(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)=CC=C2O1	4357.4	Semi standard non polar	33892256
Dronedarone,1TBDMS,isomer #1	CCCCC1=C(C(=O)C2=CC=C(OCCCN(CCCC)CCCC)C=C2)C2=CC(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)=CC=C2O1	4610.8	Standard non polar	33892256
Dronedarone,1TBDMS,isomer #1	CCCCC1=C(C(=O)C2=CC=C(OCCCN(CCCC)CCCC)C=C2)C2=CC(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)=CC=C2O1	5311.6	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dronedarone LC-ESI-QTOF , negative-QTOF	splash10-0a4i-0000090000-8897a71d0d4436083f2f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dronedarone LC-ESI-QTOF , negative-QTOF	splash10-0a4i-0000090000-0412b5e5e921a14ade8e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dronedarone LC-ESI-QTOF , negative-QTOF	splash10-0a4i-0000090000-77777b7e67d24302cc61	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dronedarone LC-ESI-QTOF , negative-QTOF	splash10-0a4i-0000090000-98e3b8bdab6f810350d0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dronedarone LC-ESI-QTOF , negative-QTOF	splash10-0a4i-0009020000-46fc09138b4d4c98f7db	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dronedarone LC-ESI-QTOF , positive-QTOF	splash10-0a4i-0000090000-5fc376f78fcd143923df	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dronedarone LC-ESI-QTOF , positive-QTOF	splash10-0a4i-0000090000-a4ea4fac6f54cdcb7cbc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dronedarone LC-ESI-QTOF , positive-QTOF	splash10-0a4i-0000090000-c3aef714c9268fa971ca	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dronedarone LC-ESI-QTOF , positive-QTOF	splash10-0a4i-0100290000-55925fc920832a562317	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dronedarone LC-ESI-QTOF , positive-QTOF	splash10-052o-0922440000-21a75dc14e4f6eec2a80	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dronedarone LC-ESI-ITFT , positive-QTOF	splash10-000i-0011920000-b36c2c2ac812fdf862c0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dronedarone LC-ESI-ITFT , positive-QTOF	splash10-0a4i-0000090000-6af26e1e5383a4521666	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dronedarone LC-ESI-ITFT , positive-QTOF	splash10-0a4i-0000090000-8a1e04d2d220b7c178b7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dronedarone LC-ESI-ITFT , positive-QTOF	splash10-0udl-1900000000-1526ae7b1c72d66d17f7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dronedarone LC-ESI-ITFT , positive-QTOF	splash10-0zfr-3900000000-5720b31639362bc77d45	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dronedarone LC-ESI-ITFT , positive-QTOF	splash10-0pb9-6900000000-5862d8b2fbe4b55544fd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dronedarone LC-ESI-ITFT , positive-QTOF	splash10-0a4i-9800000000-52425d2c67f0ee9e6833	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dronedarone LC-ESI-ITFT , positive-QTOF	splash10-0a4i-0000090000-91af4261328f04d47762	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dronedarone LC-ESI-ITFT , positive-QTOF	splash10-0a4i-0000090000-e6261075748cb68a6673	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dronedarone 10V, Positive-QTOF	splash10-0bt9-1361890000-485adc9ead96e1d0a90f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dronedarone 20V, Positive-QTOF	splash10-0006-3962700000-388ed05e794d0743e410	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dronedarone 40V, Positive-QTOF	splash10-00dl-2950100000-3c38e3c11372073c9f72	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dronedarone 10V, Negative-QTOF	splash10-0a6r-8113090000-ef5ce0f0517c1aa19f51	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dronedarone 20V, Negative-QTOF	splash10-004i-9212010000-6d4d9ab4db7a67494fce	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dronedarone 40V, Negative-QTOF	splash10-004i-9001000000-4888079beaaa7b004e91	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB04855

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dronedarone

METLIN ID

Not Available

PubChem Compound

208898

PDB ID

Not Available

ChEBI ID

50659

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Dronedarone (HMDB0251621)

MOL for HMDB0251621 (Dronedarone)

3D MOL for HMDB0251621 (Dronedarone)

3D SDF for HMDB0251621 (Dronedarone)

3D-SDF for HMDB0251621 (Dronedarone)

PDB for HMDB0251621 (Dronedarone)

3D PDB for HMDB0251621 (Dronedarone)

SMILES for HMDB0251621 (Dronedarone)

INCHI for HMDB0251621 (Dronedarone)

Structure for HMDB0251621 (Dronedarone)

3D Structure for HMDB0251621 (Dronedarone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

MS/MS Spectra