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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7)transporters (1) Show 8 proteins XML

enzymes (7)transporters (1) Show 8 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:56 UTC

HMDB ID

HMDB0015313

Secondary Accession Numbers

HMDB15313

Metabolite Identification

Common Name

Propafenone

Description

Propafenone is only found in individuals that have used or taken this drug. It is an antiarrhythmia agent that is particularly effective in ventricular arrhythmias. It also has weak beta-blocking activity. The drug is generally well tolerated. [PubChem]The electrophysiological effect of propafenone manifests itself in a reduction of upstroke velocity (Phase 0) of the monophasic action potential. In Purkinje fibers, and to a lesser extent myocardial fibers, propafenone reduces the fast inward current carried by sodium ions, which is responsible for the drugs antiarrhythmic actions. Diastolic excitability threshold is increased and effective refractory period prolonged. Propafenone reduces spontaneous automaticity and depresses triggered activity. At very high concentrations in vitro, propafenone can inhibit the slow inward current carried by calcium but this calcium antagonist effect probably does not contribute to antiarrhythmic efficacy.

Structure

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

HMDB0243696
     RDKit          3D
(R)-Propafenone
 52 53  0  0  0  0  0  0  0  0999 V2000
    6.0554    2.4045   -1.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8375    2.4804    0.4723 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3416    1.1842    0.9779 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1366    0.6482    0.5624 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8899    0.2302   -0.7477 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5688   -0.5227   -0.7780 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2459   -0.9412   -2.0839 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4286    0.2289   -0.1669 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2501   -0.4436   -0.0026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1364   -1.5184    0.7295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6940   -2.2169    1.5839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1965   -3.2880    2.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1213   -3.7416    2.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9325   -3.0192    1.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4706   -1.9459    0.6109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4034   -1.2008   -0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9987   -0.2044   -0.8627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7666   -1.7042   -0.3761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7499   -0.8803   -1.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0047    0.4563   -0.5547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4056    1.5886   -1.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6433    2.8018   -0.4482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4702    2.9254    0.6207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0982    1.8123    1.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8559    0.5978    0.5468 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3164    2.9353   -1.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0573    2.8908   -1.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2173    1.3573   -1.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8377    2.6574    0.9274 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2364    3.3649    0.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3245    1.2305    2.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1594    0.4202    0.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6756    0.0734    1.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6595   -0.4944   -1.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8850    1.0250   -1.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6887   -1.4986   -0.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7526   -1.7657   -2.2843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2027    1.1336   -0.8201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7545    0.6315    0.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7489   -1.9025    1.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8722   -3.8185    2.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4575   -4.5920    2.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9732   -3.3703    1.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7996   -2.7665   -0.7630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1567   -1.8481    0.6961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3120   -0.7164   -2.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6980   -1.4314   -1.3472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7431    1.5208   -1.9140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1300    3.6677   -0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6207    3.9083    1.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7438    1.9555    1.9937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3414   -0.2989    0.9399 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 15 10  1  0
 25 20  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
 11 40  1  0
 12 41  1  0
 13 42  1  0
 14 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 24 51  1  0
 25 52  1  0
M  END

1182
  Mrv0541 02231215182D          

 25 26  0  0  1  0            999 V2000
    6.6515   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.0313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5094    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5094    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2239    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2239    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9383    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9383    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1 13  1  0  0  0  0
  2  5  1  0  0  0  0
  3 14  2  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  1  0  0  0  0
 10 15  1  0  0  0  0
 11 18  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 16  2  0  0  0  0
 13 17  2  0  0  0  0
 15 20  2  0  0  0  0
 15 21  1  0  0  0  0
 16 19  1  0  0  0  0
 17 22  1  0  0  0  0
 19 22  2  0  0  0  0
 20 23  1  0  0  0  0
 21 24  2  0  0  0  0
 23 25  2  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015313

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCNCC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H27NO3/c1-2-14-22-15-18(23)16-25-21-11-7-6-10-19(21)20(24)13-12-17-8-4-3-5-9-17/h3-11,18,22-23H,2,12-16H2,1H3

> <INCHI_KEY>
JWHAUXFOSRPERK-UHFFFAOYSA-N

> <FORMULA>
C21H27NO3

> <MOLECULAR_WEIGHT>
341.444

> <EXACT_MASS>
341.199093735

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
39.74880850778689

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-{2-[2-hydroxy-3-(propylamino)propoxy]phenyl}-3-phenylpropan-1-one

> <ALOGPS_LOGP>
3.10

> <JCHEM_LOGP>
3.5367225463333334

> <ALOGPS_LOGS>
-4.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.339790850366647

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.085882553836743

> <JCHEM_PKA_STRONGEST_BASIC>
9.63308700825053

> <JCHEM_POLAR_SURFACE_AREA>
58.56

> <JCHEM_REFRACTIVITY>
100.20640000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.58e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
propafenone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0243696
     RDKit          3D
(R)-Propafenone
 52 53  0  0  0  0  0  0  0  0999 V2000
    6.0554    2.4045   -1.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8375    2.4804    0.4723 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3416    1.1842    0.9779 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1366    0.6482    0.5624 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8899    0.2302   -0.7477 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5688   -0.5227   -0.7780 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2459   -0.9412   -2.0839 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4286    0.2289   -0.1669 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2501   -0.4436   -0.0026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1364   -1.5184    0.7295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6940   -2.2169    1.5839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1965   -3.2880    2.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1213   -3.7416    2.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9325   -3.0192    1.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4706   -1.9459    0.6109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4034   -1.2008   -0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9987   -0.2044   -0.8627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7666   -1.7042   -0.3761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7499   -0.8803   -1.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0047    0.4563   -0.5547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4056    1.5886   -1.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6433    2.8018   -0.4482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4702    2.9254    0.6207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0982    1.8123    1.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8559    0.5978    0.5468 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3164    2.9353   -1.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0573    2.8908   -1.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2173    1.3573   -1.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8377    2.6574    0.9274 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2364    3.3649    0.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3245    1.2305    2.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1594    0.4202    0.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6756    0.0734    1.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6595   -0.4944   -1.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8850    1.0250   -1.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6887   -1.4986   -0.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7526   -1.7657   -2.2843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2027    1.1336   -0.8201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7545    0.6315    0.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7489   -1.9025    1.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8722   -3.8185    2.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4575   -4.5920    2.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9732   -3.3703    1.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7996   -2.7665   -0.7630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1567   -1.8481    0.6961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3120   -0.7164   -2.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6980   -1.4314   -1.3472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7431    1.5208   -1.9140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1300    3.6677   -0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6207    3.9083    1.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7438    1.9555    1.9937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3414   -0.2989    0.9399 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 15 10  1  0
 25 20  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
 11 40  1  0
 12 41  1  0
 13 42  1  0
 14 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 24 51  1  0
 25 52  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1182                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      12.416  -1.925   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       9.748  -0.385   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      13.750   0.385   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       7.081  -1.925   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       9.748  -1.925   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.415  -2.695   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.082  -2.695   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.748  -2.695   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.417   0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.417   1.925   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -1.925   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.083  -1.925   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.750  -2.695   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.083  -0.385   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.751   2.695   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.417  -2.695   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.750  -4.235   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.080  -2.695   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.417  -4.235   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.751   4.235   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      19.085   1.925   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.083  -5.005   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      19.085   5.005   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      20.418   2.695   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      20.418   4.235   0.000  0.00  0.00           C+0
CONECT    1    7   13                                                       
CONECT    2    5                                                            
CONECT    3   14                                                            
CONECT    4    6    8                                                       
CONECT    5    2    6    7                                                  
CONECT    6    4    5                                                       
CONECT    7    1    5                                                       
CONECT    8    4   11                                                       
CONECT    9   10   14                                                       
CONECT   10    9   15                                                       
CONECT   11    8   18                                                       
CONECT   12   13   14   16                                                  
CONECT   13    1   12   17                                                  
CONECT   14    3    9   12                                                  
CONECT   15   10   20   21                                                  
CONECT   16   12   19                                                       
CONECT   17   13   22                                                       
CONECT   18   11                                                            
CONECT   19   16   22                                                       
CONECT   20   15   23                                                       
CONECT   21   15   24                                                       
CONECT   22   17   19                                                       
CONECT   23   20   25                                                       
CONECT   24   21   25                                                       
CONECT   25   23   24                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0243696
HETATM    1  C1  UNL     1       6.055   2.404  -1.025  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.838   2.480   0.472  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.342   1.184   0.978  1.00  0.00           C  
HETATM    4  N1  UNL     1       4.137   0.648   0.562  1.00  0.00           N  
HETATM    5  C4  UNL     1       3.890   0.230  -0.748  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.569  -0.523  -0.778  1.00  0.00           C  
HETATM    7  O1  UNL     1       2.246  -0.941  -2.084  1.00  0.00           O  
HETATM    8  C6  UNL     1       1.429   0.229  -0.167  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.250  -0.444  -0.003  1.00  0.00           O  
HETATM   10  C7  UNL     1      -0.136  -1.518   0.729  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.694  -2.217   1.584  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.196  -3.288   2.275  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.121  -3.742   2.182  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.933  -3.019   1.315  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.471  -1.946   0.611  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.403  -1.201  -0.269  1.00  0.00           C  
HETATM   17  O3  UNL     1      -1.999  -0.204  -0.863  1.00  0.00           O  
HETATM   18  C14 UNL     1      -3.767  -1.704  -0.376  1.00  0.00           C  
HETATM   19  C15 UNL     1      -4.750  -0.880  -1.135  1.00  0.00           C  
HETATM   20  C16 UNL     1      -5.005   0.456  -0.555  1.00  0.00           C  
HETATM   21  C17 UNL     1      -4.406   1.589  -1.037  1.00  0.00           C  
HETATM   22  C18 UNL     1      -4.643   2.802  -0.448  1.00  0.00           C  
HETATM   23  C19 UNL     1      -5.470   2.925   0.621  1.00  0.00           C  
HETATM   24  C20 UNL     1      -6.098   1.812   1.142  1.00  0.00           C  
HETATM   25  C21 UNL     1      -5.856   0.598   0.547  1.00  0.00           C  
HETATM   26  H1  UNL     1       5.316   2.935  -1.616  1.00  0.00           H  
HETATM   27  H2  UNL     1       7.057   2.891  -1.231  1.00  0.00           H  
HETATM   28  H3  UNL     1       6.217   1.357  -1.367  1.00  0.00           H  
HETATM   29  H4  UNL     1       6.838   2.657   0.927  1.00  0.00           H  
HETATM   30  H5  UNL     1       5.236   3.365   0.764  1.00  0.00           H  
HETATM   31  H6  UNL     1       5.325   1.230   2.115  1.00  0.00           H  
HETATM   32  H7  UNL     1       6.159   0.420   0.795  1.00  0.00           H  
HETATM   33  H8  UNL     1       3.676   0.073   1.296  1.00  0.00           H  
HETATM   34  H9  UNL     1       4.659  -0.494  -1.084  1.00  0.00           H  
HETATM   35  H10 UNL     1       3.885   1.025  -1.523  1.00  0.00           H  
HETATM   36  H11 UNL     1       2.689  -1.499  -0.213  1.00  0.00           H  
HETATM   37  H12 UNL     1       2.753  -1.766  -2.284  1.00  0.00           H  
HETATM   38  H13 UNL     1       1.203   1.134  -0.820  1.00  0.00           H  
HETATM   39  H14 UNL     1       1.755   0.632   0.836  1.00  0.00           H  
HETATM   40  H15 UNL     1       1.749  -1.903   1.733  1.00  0.00           H  
HETATM   41  H16 UNL     1       0.872  -3.819   2.941  1.00  0.00           H  
HETATM   42  H17 UNL     1      -1.457  -4.592   2.751  1.00  0.00           H  
HETATM   43  H18 UNL     1      -2.973  -3.370   1.231  1.00  0.00           H  
HETATM   44  H19 UNL     1      -3.800  -2.766  -0.763  1.00  0.00           H  
HETATM   45  H20 UNL     1      -4.157  -1.848   0.696  1.00  0.00           H  
HETATM   46  H21 UNL     1      -4.312  -0.716  -2.166  1.00  0.00           H  
HETATM   47  H22 UNL     1      -5.698  -1.431  -1.347  1.00  0.00           H  
HETATM   48  H23 UNL     1      -3.743   1.521  -1.914  1.00  0.00           H  
HETATM   49  H24 UNL     1      -4.130   3.668  -0.886  1.00  0.00           H  
HETATM   50  H25 UNL     1      -5.621   3.908   1.049  1.00  0.00           H  
HETATM   51  H26 UNL     1      -6.744   1.956   1.994  1.00  0.00           H  
HETATM   52  H27 UNL     1      -6.341  -0.299   0.940  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4   31   32
CONECT    4    5   33
CONECT    5    6   34   35
CONECT    6    7    8   36
CONECT    7   37
CONECT    8    9   38   39
CONECT    9   10
CONECT   10   11   11   15
CONECT   11   12   40
CONECT   12   13   13   41
CONECT   13   14   42
CONECT   14   15   15   43
CONECT   15   16
CONECT   16   17   17   18
CONECT   18   19   44   45
CONECT   19   20   46   47
CONECT   20   21   21   25
CONECT   21   22   48
CONECT   22   23   23   49
CONECT   23   24   50
CONECT   24   25   25   51
CONECT   25   52
END

HMDB0243696
     RDKit          3D
(R)-Propafenone
 52 53  0  0  0  0  0  0  0  0999 V2000
    6.0554    2.4045   -1.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8375    2.4804    0.4723 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3416    1.1842    0.9779 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1366    0.6482    0.5624 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8899    0.2302   -0.7477 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5688   -0.5227   -0.7780 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2459   -0.9412   -2.0839 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4286    0.2289   -0.1669 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2501   -0.4436   -0.0026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1364   -1.5184    0.7295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6940   -2.2169    1.5839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1965   -3.2880    2.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1213   -3.7416    2.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9325   -3.0192    1.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4706   -1.9459    0.6109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4034   -1.2008   -0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9987   -0.2044   -0.8627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7666   -1.7042   -0.3761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7499   -0.8803   -1.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0047    0.4563   -0.5547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4056    1.5886   -1.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6433    2.8018   -0.4482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4702    2.9254    0.6207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0982    1.8123    1.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8559    0.5978    0.5468 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3164    2.9353   -1.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0573    2.8908   -1.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2173    1.3573   -1.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8377    2.6574    0.9274 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2364    3.3649    0.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3245    1.2305    2.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1594    0.4202    0.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6756    0.0734    1.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6595   -0.4944   -1.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8850    1.0250   -1.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6887   -1.4986   -0.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7526   -1.7657   -2.2843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2027    1.1336   -0.8201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7545    0.6315    0.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7489   -1.9025    1.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8722   -3.8185    2.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4575   -4.5920    2.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9732   -3.3703    1.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7996   -2.7665   -0.7630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1567   -1.8481    0.6961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3120   -0.7164   -2.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6980   -1.4314   -1.3472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7431    1.5208   -1.9140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1300    3.6677   -0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6207    3.9083    1.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7438    1.9555    1.9937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3414   -0.2989    0.9399 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 15 10  1  0
 25 20  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
 11 40  1  0
 12 41  1  0
 13 42  1  0
 14 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 24 51  1  0
 25 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(2-(2-Hydroxy-3-(propylamino)propoxy)phenyl)-3-phenyl-1-propanone	ChEBI
2-(2'-Hydroxy-3'-propylaminopropoxy)-omega-phenylpropiophenone	ChEBI
Propafenona	ChEBI
Propafenonum	ChEBI
Propafenon hexal	Kegg
Abbott brand OF propafenone hydrochloride	HMDB
Aliud brand OF propafenone hydrochloride	HMDB
Arythmol	HMDB
Knoll brand OF propafenone hydrochloride	HMDB
Merck dura brand OF propafenone hydrochloride	HMDB
Propafenone hydrochloride, (R)-isomer	HMDB
Propafenone, (+-)-isomer	HMDB
Propafenone, (R)-isomer	HMDB
Q-Pharm brand OF propafenone hydrochloride	HMDB
SA-79	HMDB
Apotex brand OF propafenone hydrochloride	HMDB
Azupharma brand OF propafenone hydrochloride	HMDB
Fenoprain	HMDB
Hydrochloride, propafenone	HMDB
Kendrick brand OF propafenone hydrochloride	HMDB
Nistaken	HMDB
Pintoform	HMDB
Propafenon al	HMDB
Rytmogenat	HMDB
SA 79	HMDB
TAD brand OF propafenone hydrochloride	HMDB
Alpharma brand OF propafenone hydrochloride	HMDB
Apo-propafenone	HMDB
Baxarytmon	HMDB
Cuxafenon	HMDB
Juta brand OF propafenone hydrochloride	HMDB
Jutanorm	HMDB
Norfenon	HMDB
Propafenon minden	HMDB
Propafenone hydrochloride	HMDB
Propafenone hydrochloride, (S)-isomer	HMDB
Propafenone, (S)-isomer	HMDB
Rythmol	HMDB
Rytmonorm	HMDB
Hexal brand OF propafenone	HMDB
Prolecofen	HMDB
Propamerck	HMDB
Rytmo-puren	HMDB

Chemical Formula

C₂₁H₂₇NO₃

Average Molecular Weight

341.444

Monoisotopic Molecular Weight

341.199093735

IUPAC Name

1-{2-[2-hydroxy-3-(propylamino)propoxy]phenyl}-3-phenylpropan-1-one

Traditional Name

propafenone

CAS Registry Number

54063-53-5

SMILES

CCCNCC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1

InChI Identifier

InChI=1S/C21H27NO3/c1-2-14-22-15-18(23)16-25-21-11-7-6-10-19(21)20(24)13-12-17-8-4-3-5-9-17/h3-11,18,22-23H,2,12-16H2,1H3

InChI Key

JWHAUXFOSRPERK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as linear 1,3-diarylpropanoids. These are organic compounds with a structure based on a C6-C3-C6 skeleton, where the two benzene rings are not linked together.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Not Available

Direct Parent

Linear 1,3-diarylpropanoids

Alternative Parents

Substituents

Linear 1,3-diarylpropanoid
Alkyl-phenylketone
Butyrophenone
Phenylketone
Benzoyl
Phenol ether
Phenoxy compound
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
1,2-aminoalcohol
Secondary alcohol
Ketone
Secondary amine
Secondary aliphatic amine
Ether
Organic oxide
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Organopnictogen compound
Alcohol
Hydrocarbon derivative
Amine
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

secondary alcohol (CHEBI:63619 )
secondary amino compound (CHEBI:63619 )
aromatic ketone (CHEBI:63619 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015313)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0076 g/L	Not Available
LogP	3.2	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	178.5	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0076 g/L	ALOGPS
logP	3.1	ALOGPS
logP	3.54	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	14.09	ChemAxon
pKa (Strongest Basic)	9.63	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.56 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	100.21 m³·mol⁻¹	ChemAxon
Polarizability	39.75 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	180.836	31661259
DarkChem	[M-H]-	179.986	31661259
DeepCCS	[M+H]+	181.585	30932474
DeepCCS	[M-H]-	179.227	30932474
DeepCCS	[M-2H]-	212.112	30932474
DeepCCS	[M+Na]+	187.678	30932474
AllCCS	[M+H]+	185.7	32859911
AllCCS	[M+H-H2O]+	182.7	32859911
AllCCS	[M+NH4]+	188.5	32859911
AllCCS	[M+Na]+	189.3	32859911
AllCCS	[M-H]-	187.1	32859911
AllCCS	[M+Na-2H]-	187.6	32859911
AllCCS	[M+HCOO]-	188.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Propafenone	CCCNCC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1	3460.2	Standard polar	33892256
Propafenone	CCCNCC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1	2761.1	Standard non polar	33892256
Propafenone	CCCNCC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1	2784.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Propafenone,1TMS,isomer #1	CCCNCC(COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1)O[Si](C)(C)C	2746.3	Semi standard non polar	33892256
Propafenone,1TMS,isomer #2	CCCN(CC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1)[Si](C)(C)C	2848.2	Semi standard non polar	33892256
Propafenone,2TMS,isomer #1	CCCN(CC(COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1)O[Si](C)(C)C)[Si](C)(C)C	2866.1	Semi standard non polar	33892256
Propafenone,2TMS,isomer #1	CCCN(CC(COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1)O[Si](C)(C)C)[Si](C)(C)C	2807.7	Standard non polar	33892256
Propafenone,2TMS,isomer #1	CCCN(CC(COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1)O[Si](C)(C)C)[Si](C)(C)C	3386.1	Standard polar	33892256
Propafenone,1TBDMS,isomer #1	CCCNCC(COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C	2963.3	Semi standard non polar	33892256
Propafenone,1TBDMS,isomer #2	CCCN(CC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	3095.7	Semi standard non polar	33892256
Propafenone,2TBDMS,isomer #1	CCCN(CC(COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3333.4	Semi standard non polar	33892256
Propafenone,2TBDMS,isomer #1	CCCN(CC(COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3182.7	Standard non polar	33892256
Propafenone,2TBDMS,isomer #1	CCCN(CC(COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3504.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Propafenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00fu-9661000000-5a3b283abe6f4fa18370	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Propafenone GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-5941000000-1bd9e888e17c18e5eda6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Propafenone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Propafenone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Propafenone GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Propafenone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Propafenone GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Propafenone 30V, Positive-QTOF	splash10-014l-0938000000-4fc047fb73a9c112ee9e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Propafenone 20V, Positive-QTOF	splash10-0006-0009000000-8e7611116e2e4a94aec8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Propafenone 50V, Positive-QTOF	splash10-014i-0900000000-6ff611d8723c8022f29a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Propafenone 50V, Positive-QTOF	splash10-014i-0900000000-cf7e72fbf28789c8e096	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Propafenone 10V, Positive-QTOF	splash10-0006-0009000000-e42eaceeda61852a1d45	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Propafenone 40V, Positive-QTOF	splash10-014i-0900000000-4e2f8790ce24653b645d	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propafenone 10V, Positive-QTOF	splash10-0006-4259000000-db02fbdb690f6a7abda6	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propafenone 20V, Positive-QTOF	splash10-0006-9331000000-1670ffe4cfbdee77edf4	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propafenone 40V, Positive-QTOF	splash10-0006-9300000000-98775b8539725e2733e6	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propafenone 10V, Negative-QTOF	splash10-002f-1279000000-b0a57792d0fdae6c0f21	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propafenone 20V, Negative-QTOF	splash10-004i-2490000000-353b7cfa03ccff93c167	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propafenone 40V, Negative-QTOF	splash10-000x-6920000000-1a80cf689c71ff876908	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propafenone 10V, Positive-QTOF	splash10-0006-0119000000-0f23d8f92480b0f437ab	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propafenone 20V, Positive-QTOF	splash10-006y-9532000000-8fbea5d6d30d45f689d8	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propafenone 40V, Positive-QTOF	splash10-0a4l-9400000000-f3c5e2f9dc21ab65ee70	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propafenone 10V, Negative-QTOF	splash10-004i-0193000000-b84f5acad0c86a19dd12	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propafenone 20V, Negative-QTOF	splash10-054o-6690000000-300ca25f1c8bcdc4878d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propafenone 40V, Negative-QTOF	splash10-052b-6930000000-6b52076ab2a13bc3af5d	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01182	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01182	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01182

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4763

KEGG Compound ID

C07381

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Propafenone

METLIN ID

Not Available

PubChem Compound

4932

PDB ID

Not Available

ChEBI ID

63619

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

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

Enzyme Details

2. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

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

Enzyme Details

3. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Botsch S, Gautier JC, Beaune P, Eichelbaum M, Kroemer HK: Identification and characterization of the cytochrome P450 enzymes involved in N-dealkylation of propafenone: molecular base for interaction potential and variable disposition of active metabolites. Mol Pharmacol. 1993 Jan;43(1):120-6. [PubMed:8423765 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Botsch S, Gautier JC, Beaune P, Eichelbaum M, Kroemer HK: Identification and characterization of the cytochrome P450 enzymes involved in N-dealkylation of propafenone: molecular base for interaction potential and variable disposition of active metabolites. Mol Pharmacol. 1993 Jan;43(1):120-6. [PubMed:8423765 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. Cytochrome P450 2C8

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

References

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

Enzyme Details

6. Potassium voltage-gated channel subfamily H member 2

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

References

Mergenthaler J, Haverkamp W, Huttenhofer A, Skryabin BV, Musshoff U, Borggrefe M, Speckmann EJ, Breithardt G, Madeja M: Blocking effects of the antiarrhythmic drug propafenone on the HERG potassium channel. Naunyn Schmiedebergs Arch Pharmacol. 2001 Apr;363(4):472-80. [PubMed:11330342 ]
Arias C, Gonzalez T, Moreno I, Caballero R, Delpon E, Tamargo J, Valenzuela C: Effects of propafenone and its main metabolite, 5-hydroxypropafenone, on HERG channels. Cardiovasc Res. 2003 Mar;57(3):660-9. [PubMed:12618228 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

7. Sodium channel protein type 5 subunit alpha

General function:: Involved in ion channel activity
Specific function:: This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is responsible for the initial upstroke of the action potential in the electrocardiogram
Gene Name:: SCN5A
Uniprot ID:: Q14524
Molecular weight:: 226937.5

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Schmid D, Ecker G, Kopp S, Hitzler M, Chiba P: Structure-activity relationship studies of propafenone analogs based on P-glycoprotein ATPase activity measurements. Biochem Pharmacol. 1999 Nov 1;58(9):1447-56. [PubMed:10513988 ]
Bachmakov I, Rekersbrink S, Hofmann U, Eichelbaum M, Fromm MF: Characterisation of (R/S)-propafenone and its metabolites as substrates and inhibitors of P-glycoprotein. Naunyn Schmiedebergs Arch Pharmacol. 2005 Mar;371(3):195-201. Epub 2005 Apr 15. [PubMed:15900513 ]
Singh P, Paul K: Studies of interactions between uracil-based hybrid molecules and P-glycoprotein--search for multidrug resistance modulators. Bioorg Med Chem. 2006 Nov 1;14(21):7183-6. Epub 2006 Jul 14. [PubMed:16843673 ]
Woodland C, Verjee Z, Giesbrecht E, Koren G, Ito S: The digoxin-propafenone interaction: characterization of a mechanism using renal tubular cell monolayers. J Pharmacol Exp Ther. 1997 Oct;283(1):39-45. [PubMed:9336306 ]
Tmej C, Chiba P, Huber M, Richter E, Hitzler M, Schaper KJ, Ecker G: A combined Hansch/Free-Wilson approach as predictive tool in QSAR studies on propafenone-type modulators of multidrug resistance. Arch Pharm (Weinheim). 1998 Jul-Aug;331(7-8):233-40. [PubMed:9747179 ]

Showing metabocard for Propafenone (HMDB0015313)

MOL for HMDB0015313 (Propafenone)

3D MOL for HMDB0015313 (Propafenone)

3D SDF for HMDB0015313 (Propafenone)

3D-SDF for HMDB0015313 (Propafenone)

PDB for HMDB0015313 (Propafenone)

3D PDB for HMDB0015313 (Propafenone)

SMILES for HMDB0015313 (Propafenone)

INCHI for HMDB0015313 (Propafenone)

Structure for HMDB0015313 (Propafenone)

3D Structure for HMDB0015313 (Propafenone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

Transporters

References