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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:55 UTC

HMDB ID

HMDB0015250

Secondary Accession Numbers

HMDB15250

Metabolite Identification

Common Name

Amiodarone

Description

Amiodarone is only found in individuals that have used or taken this drug. It is an antianginal and antiarrhythmic drug. It increases the duration of ventricular and atrial muscle action by inhibiting Na,K-activated myocardial adenosine triphosphatase. There is a resulting decrease in heart rate and in vascular resistance. [PubChem]The antiarrhythmic effect of amiodarone may be due to at least two major actions. It prolongs the myocardial cell-action potential (phase 3) duration and refractory period and acts as a noncompetitive a- and b-adrenergic inhibitor.

Structure

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

1118
  Mrv0541 02231215152D          

 31 33  0  0  0  0            999 V2000
    6.2432    1.7958    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    6.8325   -1.0007    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -2.2249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3451    0.5677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5650    0.5012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6650    2.3062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1662   -1.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412   -1.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -0.8970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5787   -2.2755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4087    1.5220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1662   -2.9899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159   -0.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4723    2.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1140    2.9202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6014    1.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9232    0.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.3860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5787   -3.7044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7286    3.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3703    3.7044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5379    0.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1795    0.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4742   -0.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9868    1.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2815   -0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 30  1  0  0  0  0
  2 31  1  0  0  0  0
  3  8  1  0  0  0  0
  3 12  1  0  0  0  0
  4 18  1  0  0  0  0
  4 25  1  0  0  0  0
  5 15  2  0  0  0  0
  6 13  1  0  0  0  0
  6 16  1  0  0  0  0
  6 17  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  2  0  0  0  0
  9 11  1  0  0  0  0
  9 15  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 11 19  2  0  0  0  0
 12 21  2  0  0  0  0
 13 18  1  0  0  0  0
 14 22  1  0  0  0  0
 15 20  1  0  0  0  0
 16 23  1  0  0  0  0
 17 24  1  0  0  0  0
 19 26  1  0  0  0  0
 20 28  2  0  0  0  0
 20 29  1  0  0  0  0
 21 27  1  0  0  0  0
 25 30  2  0  0  0  0
 25 31  1  0  0  0  0
 26 27  2  0  0  0  0
 28 30  1  0  0  0  0
 29 31  2  0  0  0  0
M  END

HMDB0015250
     RDKit          3D
Amiodarone
 60 62  0  0  0  0  0  0  0  0999 V2000
   -7.0741    0.0210    1.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9324    1.1364    2.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5181    1.5248    2.4701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7389    2.0312    1.3236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5608    1.1424    0.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2613    1.2368   -0.9649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8999    0.3225   -1.8268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3176    0.0191   -3.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7309   -1.0307   -3.7761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7324   -1.7978   -3.2172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3080   -1.4973   -1.9324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9052   -0.4486   -1.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6979    0.0895    0.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7180   -0.4301    0.9237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9962   -0.8161    2.1060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3248   -0.5497    0.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8583    0.1911   -0.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4755    0.0514   -0.8656 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2842    1.1794   -2.4798 I   0  0  0  0  0  0  0  0  0  0  0  0
    1.3406   -0.7956   -0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6652   -0.9122   -0.5783 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7278   -0.1059   -0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0345   -0.5117   -0.6309 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1771    0.2798   -0.1232 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3664   -0.0844    1.2532 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4510    0.6278    1.9883 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2920   -0.1814   -0.9542 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5704    0.5403   -0.7494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8450   -1.5470    0.8738 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1715   -2.8198    1.8844 I   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4711   -1.4063    1.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8828   -0.7140    1.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1969   -0.6035    1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4917    0.3759    0.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3265    0.7491    3.2331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5817    2.0169    2.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0236    0.6659    3.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5442    2.3366    3.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2194    2.9928    0.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7042    2.2788    1.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0973    0.6365   -3.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0912   -1.2509   -4.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3257   -2.5988   -3.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5298   -2.0720   -1.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4666    0.8706   -1.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5124    0.9359   -0.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6616   -0.0623    1.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0534   -0.3502   -1.7230 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2893   -1.5832   -0.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5747   -1.2012    1.2749 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4280    0.0309    1.8348 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2856   -0.0864    2.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8269    1.5419    1.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0652    0.9202    3.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9964   -0.1867   -2.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4714   -1.2441   -0.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1585    0.1582    0.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4619    1.6548   -0.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2044    0.3086   -1.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637   -1.9790    2.0510 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  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  1  0
 20 29  1  0
 29 30  1  0
 29 31  2  0
 13  5  2  0
 31 16  1  0
 12  7  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 17 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  0
 26 53  1  0
 26 54  1  0
 27 55  1  0
 27 56  1  0
 28 57  1  0
 28 58  1  0
 28 59  1  0
 31 60  1  0
M  END

1118
  Mrv0541 02231215152D          

 31 33  0  0  0  0            999 V2000
    6.2432    1.7958    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    6.8325   -1.0007    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -2.2249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3451    0.5677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5650    0.5012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6650    2.3062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1662   -1.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412   -1.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -0.8970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5787   -2.2755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4087    1.5220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1662   -2.9899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159   -0.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4723    2.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1140    2.9202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6014    1.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9232    0.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.3860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5787   -3.7044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7286    3.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3703    3.7044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5379    0.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1795    0.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4742   -0.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9868    1.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2815   -0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 30  1  0  0  0  0
  2 31  1  0  0  0  0
  3  8  1  0  0  0  0
  3 12  1  0  0  0  0
  4 18  1  0  0  0  0
  4 25  1  0  0  0  0
  5 15  2  0  0  0  0
  6 13  1  0  0  0  0
  6 16  1  0  0  0  0
  6 17  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  2  0  0  0  0
  9 11  1  0  0  0  0
  9 15  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 11 19  2  0  0  0  0
 12 21  2  0  0  0  0
 13 18  1  0  0  0  0
 14 22  1  0  0  0  0
 15 20  1  0  0  0  0
 16 23  1  0  0  0  0
 17 24  1  0  0  0  0
 19 26  1  0  0  0  0
 20 28  2  0  0  0  0
 20 29  1  0  0  0  0
 21 27  1  0  0  0  0
 25 30  2  0  0  0  0
 25 31  1  0  0  0  0
 26 27  2  0  0  0  0
 28 30  1  0  0  0  0
 29 31  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015250

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC1=C(C(=O)C2=CC(I)=C(OCCN(CC)CC)C(I)=C2)C2=CC=CC=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C25H29I2NO3/c1-4-7-11-22-23(18-10-8-9-12-21(18)31-22)24(29)17-15-19(26)25(20(27)16-17)30-14-13-28(5-2)6-3/h8-10,12,15-16H,4-7,11,13-14H2,1-3H3

> <INCHI_KEY>
IYIKLHRQXLHMJQ-UHFFFAOYSA-N

> <FORMULA>
C25H29I2NO3

> <MOLECULAR_WEIGHT>
645.3116

> <EXACT_MASS>
645.023680639

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
56.78106575686748

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{2-[4-(2-butyl-1-benzofuran-3-carbonyl)-2,6-diiodophenoxy]ethyl}diethylamine

> <ALOGPS_LOGP>
7.24

> <JCHEM_LOGP>
7.635421424666667

> <ALOGPS_LOGS>
-5.13

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.466812373080668

> <JCHEM_POLAR_SURFACE_AREA>
42.68

> <JCHEM_REFRACTIVITY>
145.05479999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.76e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
amiodarone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015250
     RDKit          3D
Amiodarone
 60 62  0  0  0  0  0  0  0  0999 V2000
   -7.0741    0.0210    1.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9324    1.1364    2.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5181    1.5248    2.4701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7389    2.0312    1.3236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5608    1.1424    0.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2613    1.2368   -0.9649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8999    0.3225   -1.8268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3176    0.0191   -3.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7309   -1.0307   -3.7761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7324   -1.7978   -3.2172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3080   -1.4973   -1.9324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9052   -0.4486   -1.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6979    0.0895    0.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7180   -0.4301    0.9237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9962   -0.8161    2.1060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3248   -0.5497    0.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8583    0.1911   -0.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4755    0.0514   -0.8656 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2842    1.1794   -2.4798 I   0  0  0  0  0  0  0  0  0  0  0  0
    1.3406   -0.7956   -0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6652   -0.9122   -0.5783 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7278   -0.1059   -0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0345   -0.5117   -0.6309 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1771    0.2798   -0.1232 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3664   -0.0844    1.2532 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4510    0.6278    1.9883 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2920   -0.1814   -0.9542 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5704    0.5403   -0.7494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8450   -1.5470    0.8738 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1715   -2.8198    1.8844 I   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4711   -1.4063    1.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8828   -0.7140    1.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1969   -0.6035    1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4917    0.3759    0.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3265    0.7491    3.2331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5817    2.0169    2.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0236    0.6659    3.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5442    2.3366    3.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2194    2.9928    0.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7042    2.2788    1.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0973    0.6365   -3.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0912   -1.2509   -4.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3257   -2.5988   -3.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5298   -2.0720   -1.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4666    0.8706   -1.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5124    0.9359   -0.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6616   -0.0623    1.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0534   -0.3502   -1.7230 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2893   -1.5832   -0.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5747   -1.2012    1.2749 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4280    0.0309    1.8348 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2856   -0.0864    2.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8269    1.5419    1.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0652    0.9202    3.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9964   -0.1867   -2.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4714   -1.2441   -0.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1585    0.1582    0.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4619    1.6548   -0.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2044    0.3086   -1.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637   -1.9790    2.0510 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  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  1  0
 20 29  1  0
 29 30  1  0
 29 31  2  0
 13  5  2  0
 31 16  1  0
 12  7  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 17 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  0
 26 53  1  0
 26 54  1  0
 27 55  1  0
 27 56  1  0
 28 57  1  0
 28 58  1  0
 28 59  1  0
 31 60  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1118                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  I   UNK     0      11.654   3.352   0.000  0.00  0.00           I+0
HETATM    2  I   UNK     0      12.754  -1.868   0.000  0.00  0.00           I+0
HETATM    3  O   UNK     0       7.205  -4.153   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      13.711   1.060   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       6.655   0.936   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      16.175   4.305   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       9.644  -2.914   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.104  -2.914   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.205  -1.674   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.414  -4.248   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.748  -2.144   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748  -3.684   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.696   2.841   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.644  -5.581   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.683  -0.211   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.682   4.622   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.146   5.451   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.189   2.524   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414  -1.374   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.190   0.107   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.414  -4.454   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.414  -6.915   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.160   6.086   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.625   6.915   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.204   0.742   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.080  -2.144   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.080  -3.684   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.668   1.571   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.219  -1.039   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.175   1.888   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.725  -0.722   0.000  0.00  0.00           C+0
CONECT    1   30                                                            
CONECT    2   31                                                            
CONECT    3    8   12                                                       
CONECT    4   18   25                                                       
CONECT    5   15                                                            
CONECT    6   13   16   17                                                  
CONECT    7    8   10                                                       
CONECT    8    3    7    9                                                  
CONECT    9    8   11   15                                                  
CONECT   10    7   14                                                       
CONECT   11    9   12   19                                                  
CONECT   12    3   11   21                                                  
CONECT   13    6   18                                                       
CONECT   14   10   22                                                       
CONECT   15    5    9   20                                                  
CONECT   16    6   23                                                       
CONECT   17    6   24                                                       
CONECT   18    4   13                                                       
CONECT   19   11   26                                                       
CONECT   20   15   28   29                                                  
CONECT   21   12   27                                                       
CONECT   22   14                                                            
CONECT   23   16                                                            
CONECT   24   17                                                            
CONECT   25    4   30   31                                                  
CONECT   26   19   27                                                       
CONECT   27   21   26                                                       
CONECT   28   20   30                                                       
CONECT   29   20   31                                                       
CONECT   30    1   25   28                                                  
CONECT   31    2   25   29                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

COMPND    HMDB0015250
HETATM    1  C1  UNL     1      -7.074   0.021   1.269  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.932   1.136   2.242  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.518   1.525   2.470  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.739   2.031   1.324  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.561   1.142   0.170  1.00  0.00           C  
HETATM    6  O1  UNL     1      -5.261   1.237  -0.965  1.00  0.00           O  
HETATM    7  C6  UNL     1      -4.900   0.322  -1.827  1.00  0.00           C  
HETATM    8  C7  UNL     1      -5.318   0.019  -3.105  1.00  0.00           C  
HETATM    9  C8  UNL     1      -4.731  -1.031  -3.776  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.732  -1.798  -3.217  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.308  -1.497  -1.932  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.905  -0.449  -1.278  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.698   0.090   0.004  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.718  -0.430   0.924  1.00  0.00           C  
HETATM   15  O2  UNL     1      -2.996  -0.816   2.106  1.00  0.00           O  
HETATM   16  C14 UNL     1      -1.325  -0.550   0.545  1.00  0.00           C  
HETATM   17  C15 UNL     1      -0.858   0.191  -0.510  1.00  0.00           C  
HETATM   18  C16 UNL     1       0.476   0.051  -0.866  1.00  0.00           C  
HETATM   19  I1  UNL     1       1.284   1.179  -2.480  1.00  0.00           I  
HETATM   20  C17 UNL     1       1.341  -0.796  -0.205  1.00  0.00           C  
HETATM   21  O3  UNL     1       2.665  -0.912  -0.578  1.00  0.00           O  
HETATM   22  C18 UNL     1       3.728  -0.106  -0.042  1.00  0.00           C  
HETATM   23  C19 UNL     1       5.035  -0.512  -0.631  1.00  0.00           C  
HETATM   24  N1  UNL     1       6.177   0.280  -0.123  1.00  0.00           N  
HETATM   25  C20 UNL     1       6.366  -0.084   1.253  1.00  0.00           C  
HETATM   26  C21 UNL     1       7.451   0.628   1.988  1.00  0.00           C  
HETATM   27  C22 UNL     1       7.292  -0.181  -0.954  1.00  0.00           C  
HETATM   28  C23 UNL     1       8.570   0.540  -0.749  1.00  0.00           C  
HETATM   29  C24 UNL     1       0.845  -1.547   0.874  1.00  0.00           C  
HETATM   30  I2  UNL     1       2.171  -2.820   1.884  1.00  0.00           I  
HETATM   31  C25 UNL     1      -0.471  -1.406   1.222  1.00  0.00           C  
HETATM   32  H1  UNL     1      -7.883  -0.714   1.610  1.00  0.00           H  
HETATM   33  H2  UNL     1      -6.197  -0.604   1.114  1.00  0.00           H  
HETATM   34  H3  UNL     1      -7.492   0.376   0.287  1.00  0.00           H  
HETATM   35  H4  UNL     1      -7.327   0.749   3.233  1.00  0.00           H  
HETATM   36  H5  UNL     1      -7.582   2.017   2.009  1.00  0.00           H  
HETATM   37  H6  UNL     1      -5.024   0.666   3.036  1.00  0.00           H  
HETATM   38  H7  UNL     1      -5.544   2.337   3.288  1.00  0.00           H  
HETATM   39  H8  UNL     1      -5.219   2.993   0.979  1.00  0.00           H  
HETATM   40  H9  UNL     1      -3.704   2.279   1.732  1.00  0.00           H  
HETATM   41  H10 UNL     1      -6.097   0.636  -3.520  1.00  0.00           H  
HETATM   42  H11 UNL     1      -5.091  -1.251  -4.789  1.00  0.00           H  
HETATM   43  H12 UNL     1      -3.326  -2.599  -3.816  1.00  0.00           H  
HETATM   44  H13 UNL     1      -2.530  -2.072  -1.458  1.00  0.00           H  
HETATM   45  H14 UNL     1      -1.467   0.871  -1.078  1.00  0.00           H  
HETATM   46  H15 UNL     1       3.512   0.936  -0.395  1.00  0.00           H  
HETATM   47  H16 UNL     1       3.662  -0.062   1.041  1.00  0.00           H  
HETATM   48  H17 UNL     1       5.053  -0.350  -1.723  1.00  0.00           H  
HETATM   49  H18 UNL     1       5.289  -1.583  -0.426  1.00  0.00           H  
HETATM   50  H19 UNL     1       6.575  -1.201   1.275  1.00  0.00           H  
HETATM   51  H20 UNL     1       5.428   0.031   1.835  1.00  0.00           H  
HETATM   52  H21 UNL     1       8.286  -0.086   2.257  1.00  0.00           H  
HETATM   53  H22 UNL     1       7.827   1.542   1.527  1.00  0.00           H  
HETATM   54  H23 UNL     1       7.065   0.920   3.025  1.00  0.00           H  
HETATM   55  H24 UNL     1       6.996  -0.187  -2.032  1.00  0.00           H  
HETATM   56  H25 UNL     1       7.471  -1.244  -0.610  1.00  0.00           H  
HETATM   57  H26 UNL     1       9.158   0.158   0.092  1.00  0.00           H  
HETATM   58  H27 UNL     1       8.462   1.655  -0.744  1.00  0.00           H  
HETATM   59  H28 UNL     1       9.204   0.309  -1.663  1.00  0.00           H  
HETATM   60  H29 UNL     1      -0.864  -1.979   2.051  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3   35   36
CONECT    3    4   37   38
CONECT    4    5   39   40
CONECT    5    6   13   13
CONECT    6    7
CONECT    7    8    8   12
CONECT    8    9   41
CONECT    9   10   10   42
CONECT   10   11   43
CONECT   11   12   12   44
CONECT   12   13
CONECT   13   14
CONECT   14   15   15   16
CONECT   16   17   17   31
CONECT   17   18   45
CONECT   18   19   20   20
CONECT   20   21   29
CONECT   21   22
CONECT   22   23   46   47
CONECT   23   24   48   49
CONECT   24   25   27
CONECT   25   26   50   51
CONECT   26   52   53   54
CONECT   27   28   55   56
CONECT   28   57   58   59
CONECT   29   30   31   31
CONECT   31   60
END

HMDB0015250
     RDKit          3D
Amiodarone
 60 62  0  0  0  0  0  0  0  0999 V2000
   -7.0741    0.0210    1.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9324    1.1364    2.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5181    1.5248    2.4701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7389    2.0312    1.3236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5608    1.1424    0.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2613    1.2368   -0.9649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8999    0.3225   -1.8268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3176    0.0191   -3.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7309   -1.0307   -3.7761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7324   -1.7978   -3.2172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3080   -1.4973   -1.9324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9052   -0.4486   -1.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6979    0.0895    0.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7180   -0.4301    0.9237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9962   -0.8161    2.1060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3248   -0.5497    0.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8583    0.1911   -0.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4755    0.0514   -0.8656 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2842    1.1794   -2.4798 I   0  0  0  0  0  0  0  0  0  0  0  0
    1.3406   -0.7956   -0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6652   -0.9122   -0.5783 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7278   -0.1059   -0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0345   -0.5117   -0.6309 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1771    0.2798   -0.1232 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3664   -0.0844    1.2532 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4510    0.6278    1.9883 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2920   -0.1814   -0.9542 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5704    0.5403   -0.7494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8450   -1.5470    0.8738 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1715   -2.8198    1.8844 I   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4711   -1.4063    1.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8828   -0.7140    1.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1969   -0.6035    1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4917    0.3759    0.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3265    0.7491    3.2331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5817    2.0169    2.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0236    0.6659    3.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5442    2.3366    3.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2194    2.9928    0.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7042    2.2788    1.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0973    0.6365   -3.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0912   -1.2509   -4.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3257   -2.5988   -3.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5298   -2.0720   -1.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4666    0.8706   -1.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5124    0.9359   -0.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6616   -0.0623    1.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0534   -0.3502   -1.7230 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2893   -1.5832   -0.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5747   -1.2012    1.2749 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4280    0.0309    1.8348 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2856   -0.0864    2.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8269    1.5419    1.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0652    0.9202    3.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9964   -0.1867   -2.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4714   -1.2441   -0.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1585    0.1582    0.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4619    1.6548   -0.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2044    0.3086   -1.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637   -1.9790    2.0510 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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 12 13  1  0
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 22 23  1  0
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 13  5  2  0
 31 16  1  0
 12  7  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  8 41  1  0
  9 42  1  0
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 28 57  1  0
 28 58  1  0
 28 59  1  0
 31 60  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Butyl-3-(3,5-diiodo-4-(2-diethylaminoethoxy)benzoyl)benzofuran	ChEBI
2-Butyl-3-benzofuranyl 4-(2-(diethylamino)ethoxy)-3,5-diiodophenyl ketone	ChEBI
2-N-Butyl-3',5'-diiodo-4'-N-diethylaminoethoxy-3-benzoylbenzofuran	ChEBI
Amiodarona	ChEBI
Amiodaronum	ChEBI
Amiodarone base	HMDB
Alphapharm brand OF amiodarone hydrochloride	HMDB
Corbionax	HMDB
Hexal brand OF amiodarone hydrochloride	HMDB
Leurquin brand OF amiodarone hydrochloride	HMDB
ASTA medica brand OF amiodarone hydrochloride	HMDB
Amiodarex	HMDB
Amiodarone hydrochloride	HMDB
Amiohexal	HMDB
Berenguer infale brand OF amiodarone hydrochloride	HMDB
Betapharm brand OF amiodarone hydrochloride	HMDB
Braxan	HMDB
Cordarex	HMDB
Ortacrone	HMDB
Pharma investi brand OF amiodarone hydrochloride	HMDB
Rytmarone	HMDB
Sanofi winthrop brand OF amiodarone hydrochloride	HMDB
Tachydaron	HMDB
Trangorex	HMDB
Amiobeta	HMDB
Cordarone	HMDB
Hydrochloride, amiodarone	HMDB
Kordaron	HMDB
SKF 33134 a	HMDB
SKF 33134-a	HMDB
Aratac	HMDB
Armstrong brand OF amiodarone hydrochloride	HMDB
g Gam brand OF amiodarone hydrochloride	HMDB
Wyeth brand OF amiodarone hydrochloride	HMDB

Chemical Formula

C₂₅H₂₉I₂NO₃

Average Molecular Weight

645.3116

Monoisotopic Molecular Weight

645.023680639

IUPAC Name

{2-[4-(2-butyl-1-benzofuran-3-carbonyl)-2,6-diiodophenoxy]ethyl}diethylamine

Traditional Name

amiodarone

CAS Registry Number

1951-25-3

SMILES

CCCCC1=C(C(=O)C2=CC(I)=C(OCCN(CC)CC)C(I)=C2)C2=CC=CC=C2O1

InChI Identifier

InChI=1S/C25H29I2NO3/c1-4-7-11-22-23(18-10-8-9-12-21(18)31-22)24(29)17-15-19(26)25(20(27)16-17)30-14-13-28(5-2)6-3/h8-10,12,15-16H,4-7,11,13-14H2,1-3H3

InChI Key

IYIKLHRQXLHMJQ-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
Benzofuran
Phenol ether
3-aroylfuran
Benzoyl
Phenoxy compound
Alkyl aryl ether
Halobenzene
Iodobenzene
Benzenoid
Monocyclic benzene moiety
Aryl iodide
Aryl halide
Heteroaromatic compound
Furan
Tertiary aliphatic amine
Tertiary amine
Oxacycle
Organoheterocyclic compound
Ether
Amine
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organonitrogen compound
Organoiodide
Organohalogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:2663 )
organoiodine compound (CHEBI:2663 )
1-benzofurans (CHEBI:2663 )
aromatic ketone (CHEBI:2663 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015250)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Amiodarone Action Pathway (PathBank: SMP0000665)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0048 g/L	Not Available
LogP	7.9	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	226.4	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0048 g/L	ALOGPS
logP	7.24	ALOGPS
logP	7.64	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Basic)	8.47	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	42.68 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	145.05 m³·mol⁻¹	ChemAxon
Polarizability	56.78 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]+	225.591	30932474
DeepCCS	[M-H]-	223.233	30932474
DeepCCS	[M-2H]-	257.411	30932474
DeepCCS	[M+Na]+	233.272	30932474
AllCCS	[M+H]+	225.6	32859911
AllCCS	[M+H-H2O]+	224.3	32859911
AllCCS	[M+NH4]+	226.8	32859911
AllCCS	[M+Na]+	227.1	32859911
AllCCS	[M-H]-	224.5	32859911
AllCCS	[M+Na-2H]-	226.7	32859911
AllCCS	[M+HCOO]-	229.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Amiodarone	CCCCC1=C(C(=O)C2=CC(I)=C(OCCN(CC)CC)C(I)=C2)C2=CC=CC=C2O1	4395.6	Standard polar	33892256
Amiodarone	CCCCC1=C(C(=O)C2=CC(I)=C(OCCN(CC)CC)C(I)=C2)C2=CC=CC=C2O1	3519.4	Standard non polar	33892256
Amiodarone	CCCCC1=C(C(=O)C2=CC(I)=C(OCCN(CC)CC)C(I)=C2)C2=CC=CC=C2O1	3714.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Amiodarone GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-9000024000-088b6534d1659c5c174d	2017-09-01	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amiodarone LC-ESI-qTof , Positive-QTOF	splash10-004r-0690000000-25202a61d19d3dfaed8b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amiodarone LC-ESI-QFT , positive-QTOF	splash10-0002-0000009000-8cbab89986761a7a1bc9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amiodarone LC-ESI-QFT , positive-QTOF	splash10-0pbj-9300003000-503a542bf1a7678f385e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amiodarone LC-ESI-QFT , positive-QTOF	splash10-0a4i-9110000000-543b8de3c9ba390fa765	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amiodarone LC-ESI-QFT , positive-QTOF	splash10-0udi-0791000000-77d5d18989052c45b006	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amiodarone LC-ESI-QFT , positive-QTOF	splash10-0a59-0980000000-a77e32d189cf8e2acdf1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amiodarone LC-ESI-QFT , positive-QTOF	splash10-0apl-0940000000-30e016c113387b37ca7c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amiodarone , positive-QTOF	splash10-0002-0000009000-e87a9a6e983c00161beb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amiodarone 50V, Positive-QTOF	splash10-0fb9-0192101000-d4f2f8589987e9dee2fc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amiodarone 40V, Positive-QTOF	splash10-0002-0020009000-bc59c51779e07ba2a4a0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amiodarone 40V, Positive-QTOF	splash10-0a4i-9100000000-cf7a06e18403e76cf41c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amiodarone 15V, Positive-QTOF	splash10-0002-0000009000-ec39c036c89b5923fc2c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amiodarone 30V, Positive-QTOF	splash10-0pb9-9200000000-5cde40904f838865e7ba	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amiodarone 20V, Positive-QTOF	splash10-0002-1000009000-3e4fea6e220ba0a42af4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amiodarone 40V, Positive-QTOF	splash10-0a4i-9100000000-cf88edc5ce5babf0e567	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amiodarone 30V, Positive-QTOF	splash10-0002-0000009000-9f22341a9246a58e0df5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amiodarone 20V, Positive-QTOF	splash10-0002-0000009000-7304d2b67fba343a8883	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amiodarone 10V, Positive-QTOF	splash10-0002-0000009000-fad8f001fba3ffb05e41	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amiodarone 35V, Positive-QTOF	splash10-0f6t-6400009000-32088cd4966452222ef5	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amiodarone 10V, Positive-QTOF	splash10-0002-1200419000-3080963b2267302d337a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amiodarone 20V, Positive-QTOF	splash10-0udi-6920532000-f1048ae0af01f6658877	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amiodarone 40V, Positive-QTOF	splash10-006x-7309200000-46ba6e78349f4d182fe7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amiodarone 10V, Negative-QTOF	splash10-0006-1100029000-9b580022f60608cc2810	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amiodarone 20V, Negative-QTOF	splash10-006x-3202296000-a7445663ea627302ddce	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amiodarone 40V, Negative-QTOF	splash10-00di-7902160000-4817e1c5fca0d177a829	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Amiodarone 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 DB01118	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01118	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01118

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2072

KEGG Compound ID

C06823

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Amiodarone

METLIN ID

Not Available

PubChem Compound

2157

PDB ID

Not Available

ChEBI ID

2663

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

Rosenbaum MB, Chiale PA, Halpern MS, Nau GJ, Przybylski J, Levi RJ, Lazzari JO, Elizari MV: Clinical efficacy of amiodarone as an antiarrhythmic agent. Am J Cardiol. 1976 Dec;38(7):934-44. [PubMed:793369 ]
Singh BN, Vaughan Williams EM: The effect of amiodarone, a new anti-anginal drug, on cardiac muscle. Br J Pharmacol. 1970 Aug;39(4):657-67. [PubMed:5485142 ]
Rosenbaum MB, Chiale PA, Haedo A, Lazzari JO, Elizari MV: Ten years of experience with amiodarone. Am Heart J. 1983 Oct;106(4 Pt 2):957-64. [PubMed:6613843 ]
CHARLIER R, DELTOUR G, TONDEUR R, BINON F: [Studies in the benzofuran series. VII. Preliminary pharmacological study of 2-butyl-3-(3,5-diiodo-4-beta-N-diethylaminoethoxybenzoyl)-benzofuran]. Arch Int Pharmacodyn Ther. 1962 Sep 1;139:255-64. [PubMed:14020244 ]
DELTOUR G, BINON F, TONDEUR R, GOLDENBERG C, HENAUX F, SION R, DERAY E, CHARLIER R: [Studies in the benzofuran series. VI. Coronary-dilating activity of alkylated and aminoalkylated derivatives of 3-benzoylbenzofuran]. Arch Int Pharmacodyn Ther. 1962 Sep 1;139:247-54. [PubMed:14026835 ]

Showing metabocard for Amiodarone (HMDB0015250)

MOL for HMDB0015250 (Amiodarone)

3D MOL for HMDB0015250 (Amiodarone)

3D SDF for HMDB0015250 (Amiodarone)

3D-SDF for HMDB0015250 (Amiodarone)

PDB for HMDB0015250 (Amiodarone)

3D PDB for HMDB0015250 (Amiodarone)

SMILES for HMDB0015250 (Amiodarone)

INCHI for HMDB0015250 (Amiodarone)

Structure for HMDB0015250 (Amiodarone)

3D Structure for HMDB0015250 (Amiodarone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra