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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7)transporters (2) Show 9 proteins XML

enzymes (7)transporters (2) Show 9 proteins

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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:37 UTC

HMDB ID

HMDB0014425

Secondary Accession Numbers

HMDB14425

Metabolite Identification

Common Name

Disopyramide

Description

Disopyramide, also known as rythmodan p, belongs to the class of organic compounds known as pheniramines. Pheniramines are compounds containing a pheniramine moiety, which is structurally characterized by the presence of a 2-benzylpyridine linked to an dimethyl(propyl)amine to form a dimethyl[3-phenyl-3-(pyridin-2-yl)propyl]amine skeleton. Disopyramide is a drug which is used for the treatment of documented ventricular arrhythmias, such as sustained ventricular tachycardia, ventricular pre-excitation and cardiac dysrhythmias. it is a class ia antiarrhythmic drug. In humans, disopyramide is involved in the disopyramide action pathway. Disopyramide is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Disopyramide.

Structure

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

HMDB0259462
     RDKit          3D
Disopiramide
 54 55  0  0  0  0  0  0  0  0999 V2000
    2.6536    1.1727   -1.8869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7632   -0.2454   -1.4648 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2124   -0.6540   -1.5147 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1521   -0.5670   -0.1875 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7737   -0.3389   -0.2373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0487   -0.5220    0.9840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5367   -0.2912    0.7666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2024   -0.5005    2.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6104   -0.4093    2.2495 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4814   -0.7618    3.0776 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8411    1.0959    0.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8235    1.4718   -1.0197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1118    2.7796   -1.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4250    3.7278   -0.4759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4451    3.3551    0.8559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1570    2.0547    1.2399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1540   -1.2881   -0.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204   -2.5352   -0.3140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2267   -3.4544   -1.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3660   -3.0854   -1.8535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8788   -1.8261   -1.6556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2685   -0.9718   -0.8145 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9521   -0.2518    0.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2560    1.2086    1.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7164   -0.9295    2.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2024    1.2629   -2.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0266    1.8303   -1.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6712    1.6461   -2.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2280   -0.8788   -2.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3996   -1.6725   -1.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8746    0.1214   -1.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4990   -0.6884   -2.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4966    0.6550   -0.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3521   -1.0669   -1.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0327   -1.4655    1.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3053    0.2632    1.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1791    0.2552    1.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1489   -0.9865    2.9364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5858    0.7400   -1.7806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0949    3.0614   -2.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6512    4.7400   -0.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6940    4.1174    1.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1855    1.8197    2.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7278   -2.7901    0.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7857   -4.4235   -1.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8274   -3.8114   -2.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7772   -1.5832   -2.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0083   -0.6518    0.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7729    1.7233    0.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9932    1.2073    2.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3628    1.7197    1.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2085   -0.2884    2.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7092   -1.1654    2.7262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2325   -1.9243    2.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  7 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  7 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  4 23  1  0
 23 24  1  0
 23 25  1  0
 16 11  1  0
 22 17  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  9 37  1  0
  9 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 16 43  1  0
 18 44  1  0
 19 45  1  0
 20 46  1  0
 21 47  1  0
 23 48  1  0
 24 49  1  0
 24 50  1  0
 24 51  1  0
 25 52  1  0
 25 53  1  0
 25 54  1  0
M  END

  Mrv0541 09251317272D          

 25 26  0  0  0  0            999 V2000
   -3.4473    0.0884    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1618   -0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1618   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4473   -1.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7329   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7329   -0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0184    0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039   -0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5894    0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1250   -0.3241    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8395    0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5540   -0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8395    0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1250   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5894   -1.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8395   -1.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0184    0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039    1.3259    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9889   -2.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7329    1.3259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7033   -2.5339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7033   -3.3589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9889   -3.7715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2745   -3.3589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2745   -2.5339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  0  0  0  0
  7 19  1  0  0  0  0
 17 20  2  0  0  0  0
 19 21  2  0  0  0  0
 19 25  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014425

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)N(CCC(C(N)=O)(C1=CC=CC=C1)C1=NC=CC=C1)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C21H29N3O/c1-16(2)24(17(3)4)15-13-21(20(22)25,18-10-6-5-7-11-18)19-12-8-9-14-23-19/h5-12,14,16-17H,13,15H2,1-4H3,(H2,22,25)

> <INCHI_KEY>
UVTNFZQICZKOEM-UHFFFAOYSA-N

> <FORMULA>
C21H29N3O

> <MOLECULAR_WEIGHT>
339.4745

> <EXACT_MASS>
339.231062565

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
38.81875419881408

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[bis(propan-2-yl)amino]-2-phenyl-2-(pyridin-2-yl)butanamide

> <ALOGPS_LOGP>
3.21

> <JCHEM_LOGP>
3.4684364846666664

> <ALOGPS_LOGS>
-3.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.190354871132648

> <JCHEM_PKA_STRONGEST_BASIC>
10.419003409368996

> <JCHEM_POLAR_SURFACE_AREA>
59.220000000000006

> <JCHEM_REFRACTIVITY>
102.3002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.93e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
disopyramide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259462
     RDKit          3D
Disopiramide
 54 55  0  0  0  0  0  0  0  0999 V2000
    2.6536    1.1727   -1.8869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7632   -0.2454   -1.4648 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2124   -0.6540   -1.5147 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1521   -0.5670   -0.1875 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7737   -0.3389   -0.2373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0487   -0.5220    0.9840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5367   -0.2912    0.7666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2024   -0.5005    2.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6104   -0.4093    2.2495 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4814   -0.7618    3.0776 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8411    1.0959    0.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8235    1.4718   -1.0197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1118    2.7796   -1.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4250    3.7278   -0.4759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4451    3.3551    0.8559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1570    2.0547    1.2399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1540   -1.2881   -0.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204   -2.5352   -0.3140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2267   -3.4544   -1.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3660   -3.0854   -1.8535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8788   -1.8261   -1.6556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2685   -0.9718   -0.8145 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9521   -0.2518    0.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2560    1.2086    1.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7164   -0.9295    2.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2024    1.2629   -2.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0266    1.8303   -1.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6712    1.6461   -2.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2280   -0.8788   -2.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3996   -1.6725   -1.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8746    0.1214   -1.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4990   -0.6884   -2.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4966    0.6550   -0.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3521   -1.0669   -1.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0327   -1.4655    1.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3053    0.2632    1.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1791    0.2552    1.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1489   -0.9865    2.9364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5858    0.7400   -1.7806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0949    3.0614   -2.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6512    4.7400   -0.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6940    4.1174    1.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1855    1.8197    2.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7278   -2.7901    0.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7857   -4.4235   -1.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8274   -3.8114   -2.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7772   -1.5832   -2.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0083   -0.6518    0.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7729    1.7233    0.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9932    1.2073    2.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3628    1.7197    1.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2085   -0.2884    2.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7092   -1.1654    2.7262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2325   -1.9243    2.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  7 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  7 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  4 23  1  0
 23 24  1  0
 23 25  1  0
 16 11  1  0
 22 17  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  9 37  1  0
  9 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 16 43  1  0
 18 44  1  0
 19 45  1  0
 20 46  1  0
 21 47  1  0
 23 48  1  0
 24 49  1  0
 24 50  1  0
 24 51  1  0
 25 52  1  0
 25 53  1  0
 25 54  1  0
M  END

HEADER    PROTEIN                                 25-SEP-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-SEP-13         0                                  
HETATM    1  N   UNK     0      -6.435   0.165   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -7.769  -0.605   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.769  -2.145   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.435  -2.915   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.101  -2.145   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.101  -0.605   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.768   0.165   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.434  -0.605   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.100   0.165   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       0.233  -0.605   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       1.567   0.165   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.901  -0.605   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.567   1.705   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.233  -2.145   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.100  -2.915   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.567  -2.915   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.768   1.705   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      -2.434   2.475   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      -3.713  -3.960   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.101   2.475   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -5.046  -4.730   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.046  -6.270   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.713  -7.040   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.379  -6.270   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.379  -4.730   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8   17   19                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    7   18   20                                                  
CONECT   18   17                                                            
CONECT   19    7   21   25                                                  
CONECT   20   17                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   19   24                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0259629
HETATM    1  C1  UNL     1       2.681   0.732  -2.072  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.834  -0.209  -0.865  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.302  -0.300  -0.597  1.00  0.00           C  
HETATM    4  N1  UNL     1       1.989   0.123   0.194  1.00  0.00           N  
HETATM    5  C4  UNL     1       0.606   0.015  -0.121  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.356   0.285   0.977  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.799   0.170   0.582  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.684   0.458   1.771  1.00  0.00           C  
HETATM    9  N2  UNL     1      -2.554   1.702   2.439  1.00  0.00           N  
HETATM   10  O1  UNL     1      -3.498  -0.392   2.135  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.124  -1.185   0.127  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.383  -2.253   0.548  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.657  -3.549   0.133  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.701  -3.766  -0.724  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.440  -2.686  -1.143  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.181  -1.425  -0.745  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.122   1.203  -0.433  1.00  0.00           C  
HETATM   18  C15 UNL     1      -1.895   1.007  -1.772  1.00  0.00           C  
HETATM   19  C16 UNL     1      -2.204   2.013  -2.670  1.00  0.00           C  
HETATM   20  C17 UNL     1      -2.734   3.192  -2.193  1.00  0.00           C  
HETATM   21  C18 UNL     1      -2.955   3.372  -0.845  1.00  0.00           C  
HETATM   22  N3  UNL     1      -2.636   2.361  -0.024  1.00  0.00           N  
HETATM   23  C19 UNL     1       2.385   0.018   1.520  1.00  0.00           C  
HETATM   24  C20 UNL     1       3.546   0.927   1.916  1.00  0.00           C  
HETATM   25  C21 UNL     1       2.702  -1.415   1.953  1.00  0.00           C  
HETATM   26  H1  UNL     1       2.996   1.762  -1.823  1.00  0.00           H  
HETATM   27  H2  UNL     1       1.698   0.649  -2.537  1.00  0.00           H  
HETATM   28  H3  UNL     1       3.433   0.355  -2.820  1.00  0.00           H  
HETATM   29  H4  UNL     1       2.551  -1.214  -1.296  1.00  0.00           H  
HETATM   30  H5  UNL     1       4.846  -0.678  -1.522  1.00  0.00           H  
HETATM   31  H6  UNL     1       4.561  -1.085   0.163  1.00  0.00           H  
HETATM   32  H7  UNL     1       4.731   0.689  -0.375  1.00  0.00           H  
HETATM   33  H8  UNL     1       0.420   0.761  -0.954  1.00  0.00           H  
HETATM   34  H9  UNL     1       0.391  -0.979  -0.582  1.00  0.00           H  
HETATM   35  H10 UNL     1      -0.207  -0.396   1.837  1.00  0.00           H  
HETATM   36  H11 UNL     1      -0.198   1.340   1.339  1.00  0.00           H  
HETATM   37  H12 UNL     1      -1.821   2.379   2.204  1.00  0.00           H  
HETATM   38  H13 UNL     1      -3.221   1.933   3.188  1.00  0.00           H  
HETATM   39  H14 UNL     1      -0.533  -2.188   1.236  1.00  0.00           H  
HETATM   40  H15 UNL     1      -1.071  -4.396   0.466  1.00  0.00           H  
HETATM   41  H16 UNL     1      -2.935  -4.779  -1.064  1.00  0.00           H  
HETATM   42  H17 UNL     1      -4.269  -2.879  -1.827  1.00  0.00           H  
HETATM   43  H18 UNL     1      -3.747  -0.558  -1.059  1.00  0.00           H  
HETATM   44  H19 UNL     1      -1.487   0.084  -2.167  1.00  0.00           H  
HETATM   45  H20 UNL     1      -2.037   1.890  -3.736  1.00  0.00           H  
HETATM   46  H21 UNL     1      -2.991   4.009  -2.875  1.00  0.00           H  
HETATM   47  H22 UNL     1      -3.379   4.316  -0.470  1.00  0.00           H  
HETATM   48  H23 UNL     1       1.547   0.352   2.202  1.00  0.00           H  
HETATM   49  H24 UNL     1       3.340   1.261   2.982  1.00  0.00           H  
HETATM   50  H25 UNL     1       3.514   1.839   1.305  1.00  0.00           H  
HETATM   51  H26 UNL     1       4.508   0.420   1.974  1.00  0.00           H  
HETATM   52  H27 UNL     1       3.706  -1.432   2.377  1.00  0.00           H  
HETATM   53  H28 UNL     1       2.586  -2.085   1.066  1.00  0.00           H  
HETATM   54  H29 UNL     1       1.946  -1.767   2.678  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    4   29
CONECT    3   30   31   32
CONECT    4    5   23
CONECT    5    6   33   34
CONECT    6    7   35   36
CONECT    7    8   11   17
CONECT    8    9   10   10
CONECT    9   37   38
CONECT   11   12   12   16
CONECT   12   13   39
CONECT   13   14   14   40
CONECT   14   15   41
CONECT   15   16   16   42
CONECT   16   43
CONECT   17   18   18   22
CONECT   18   19   44
CONECT   19   20   20   45
CONECT   20   21   46
CONECT   21   22   22   47
CONECT   23   24   25   48
CONECT   24   49   50   51
CONECT   25   52   53   54
END

HMDB0259462
     RDKit          3D
Disopiramide
 54 55  0  0  0  0  0  0  0  0999 V2000
    2.6536    1.1727   -1.8869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7632   -0.2454   -1.4648 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2124   -0.6540   -1.5147 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1521   -0.5670   -0.1875 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7737   -0.3389   -0.2373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0487   -0.5220    0.9840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5367   -0.2912    0.7666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2024   -0.5005    2.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6104   -0.4093    2.2495 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4814   -0.7618    3.0776 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8411    1.0959    0.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8235    1.4718   -1.0197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1118    2.7796   -1.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4250    3.7278   -0.4759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4451    3.3551    0.8559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1570    2.0547    1.2399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1540   -1.2881   -0.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204   -2.5352   -0.3140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2267   -3.4544   -1.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3660   -3.0854   -1.8535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8788   -1.8261   -1.6556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2685   -0.9718   -0.8145 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9521   -0.2518    0.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2560    1.2086    1.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7164   -0.9295    2.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2024    1.2629   -2.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0266    1.8303   -1.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6712    1.6461   -2.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2280   -0.8788   -2.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3996   -1.6725   -1.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8746    0.1214   -1.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4990   -0.6884   -2.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4966    0.6550   -0.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3521   -1.0669   -1.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0327   -1.4655    1.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3053    0.2632    1.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1791    0.2552    1.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1489   -0.9865    2.9364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5858    0.7400   -1.7806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0949    3.0614   -2.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6512    4.7400   -0.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6940    4.1174    1.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1855    1.8197    2.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7278   -2.7901    0.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7857   -4.4235   -1.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8274   -3.8114   -2.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7772   -1.5832   -2.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0083   -0.6518    0.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7729    1.7233    0.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9932    1.2073    2.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3628    1.7197    1.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2085   -0.2884    2.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7092   -1.1654    2.7262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2325   -1.9243    2.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  7 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  7 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  4 23  1  0
 23 24  1  0
 23 25  1  0
 16 11  1  0
 22 17  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  9 37  1  0
  9 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 16 43  1  0
 18 44  1  0
 19 45  1  0
 20 46  1  0
 21 47  1  0
 23 48  1  0
 24 49  1  0
 24 50  1  0
 24 51  1  0
 25 52  1  0
 25 53  1  0
 25 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
alpha-(2-(Diisopropylamino)ethyl)-alpha-phenyl-2-pyridineacetamide	ChEBI
Disopiramida	ChEBI
Disopyramidum	ChEBI
gamma-Diisopropylamino-alpha-phenyl-alpha-(2-pyridyl)butyramide	ChEBI
Rythmodan p	Kegg
a-(2-(Diisopropylamino)ethyl)-a-phenyl-2-pyridineacetamide	Generator
Α-(2-(diisopropylamino)ethyl)-α-phenyl-2-pyridineacetamide	Generator
g-Diisopropylamino-a-phenyl-a-(2-pyridyl)butyramide	Generator
Γ-diisopropylamino-α-phenyl-α-(2-pyridyl)butyramide	Generator
Disopyramide free base	HMDB
Disopyramide phosphate	HMDB, MeSH
Diisopyramide	MeSH, HMDB
Disopyramide phosphate (1:1), (S)-isomer	MeSH, HMDB
Disopyramide, (+-)-isomer	MeSH, HMDB
Disopyramide, L-tartrate (1:1), (R)-isomer	MeSH, HMDB
Disopyramide, L-tartrate (1:1), (S)-isomer	MeSH, HMDB
Searle brand OF disopyramide phosphate	MeSH, HMDB
Disopyramide phosphate (1:1), (+-)-isomer	MeSH, HMDB
Disopyramide phosphate (1:1), (R)-isomer	MeSH, HMDB
Disopyramide, L-tartrate (1:2), (+-)-isomer	MeSH, HMDB
Disopyramide, L-tartrate, (S)-isomer	MeSH, HMDB
Norpace	MeSH, HMDB
Palpitin	MeSH, HMDB
Rythmilen	MeSH, HMDB
Disopyramide phosphate (1:1)	MeSH, HMDB
Disopyramide, D-tartrate (1:1), (S)-isomer	MeSH, HMDB
Palpitine	MeSH, HMDB
Disopyramide monohydrochloride	MeSH, HMDB
Disopyramide, (R)-isomer	MeSH, HMDB
Disopyramide, (S)-isomer	MeSH, HMDB
Rhythmodan	MeSH, HMDB
Ritmilen	MeSH, HMDB

Chemical Formula

C₂₁H₂₉N₃O

Average Molecular Weight

339.4745

Monoisotopic Molecular Weight

339.231062565

IUPAC Name

4-[bis(propan-2-yl)amino]-2-phenyl-2-(pyridin-2-yl)butanamide

Traditional Name

disopyramide

CAS Registry Number

3737-09-5

SMILES

CC(C)N(CCC(C(N)=O)(C1=CC=CC=C1)C1=NC=CC=C1)C(C)C

InChI Identifier

InChI=1S/C21H29N3O/c1-16(2)24(17(3)4)15-13-21(20(22)25,18-10-6-5-7-11-18)19-12-8-9-14-23-19/h5-12,14,16-17H,13,15H2,1-4H3,(H2,22,25)

InChI Key

UVTNFZQICZKOEM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pheniramines. Pheniramines are compounds containing a pheniramine moiety, which is structurally characterized by the presence of a 2-benzylpyridine linked to an dimethyl(propyl)amine to form a dimethyl[3-phenyl-3-(pyridin-2-yl)propyl]amine skeleton.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pheniramines

Direct Parent

Pheniramines

Alternative Parents

Substituents

Pheniramine
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Tertiary amine
Tertiary aliphatic amine
Carboximidic acid derivative
Carboximidic acid
Azacycle
Organopnictogen compound
Amine
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

tertiary amino compound (CHEBI:4657 )
monocarboxylic acid amide (CHEBI:4657 )
pyridines (CHEBI:4657 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	94.5 - 95 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.049 g/L	Not Available
LogP	3.5	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	179.946	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001003

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.049 g/L	ALOGPS
logP	3.21	ALOGPS
logP	3.47	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	16.19	ChemAxon
pKa (Strongest Basic)	10.42	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.22 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	102.3 m³·mol⁻¹	ChemAxon
Polarizability	38.82 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]+	179.82	31661259
DarkChem	[M-H]-	180.566	31661259
DeepCCS	[M+H]+	182.784	30932474
DeepCCS	[M-H]-	180.426	30932474
DeepCCS	[M-2H]-	214.429	30932474
DeepCCS	[M+Na]+	189.657	30932474
AllCCS	[M+H]+	184.5	32859911
AllCCS	[M+H-H2O]+	181.5	32859911
AllCCS	[M+NH4]+	187.3	32859911
AllCCS	[M+Na]+	188.1	32859911
AllCCS	[M-H]-	190.5	32859911
AllCCS	[M+Na-2H]-	190.9	32859911
AllCCS	[M+HCOO]-	191.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Disopyramide	CC(C)N(CCC(C(N)=O)(C1=CC=CC=C1)C1=NC=CC=C1)C(C)C	3342.8	Standard polar	33892256
Disopyramide	CC(C)N(CCC(C(N)=O)(C1=CC=CC=C1)C1=NC=CC=C1)C(C)C	2602.0	Standard non polar	33892256
Disopyramide	CC(C)N(CCC(C(N)=O)(C1=CC=CC=C1)C1=NC=CC=C1)C(C)C	2513.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Disopyramide,1TMS,isomer #1	CC(C)N(CCC(C(=O)N[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N1)C(C)C	2543.7	Semi standard non polar	33892256
Disopyramide,1TMS,isomer #1	CC(C)N(CCC(C(=O)N[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N1)C(C)C	2479.0	Standard non polar	33892256
Disopyramide,1TMS,isomer #1	CC(C)N(CCC(C(=O)N[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N1)C(C)C	3135.6	Standard polar	33892256
Disopyramide,2TMS,isomer #1	CC(C)N(CCC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N1)C(C)C	2631.8	Semi standard non polar	33892256
Disopyramide,2TMS,isomer #1	CC(C)N(CCC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N1)C(C)C	2623.6	Standard non polar	33892256
Disopyramide,2TMS,isomer #1	CC(C)N(CCC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N1)C(C)C	2997.6	Standard polar	33892256
Disopyramide,1TBDMS,isomer #1	CC(C)N(CCC(C(=O)N[Si](C)(C)C(C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N1)C(C)C	2759.8	Semi standard non polar	33892256
Disopyramide,1TBDMS,isomer #1	CC(C)N(CCC(C(=O)N[Si](C)(C)C(C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N1)C(C)C	2695.0	Standard non polar	33892256
Disopyramide,1TBDMS,isomer #1	CC(C)N(CCC(C(=O)N[Si](C)(C)C(C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N1)C(C)C	3226.6	Standard polar	33892256
Disopyramide,2TBDMS,isomer #1	CC(C)N(CCC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N1)C(C)C	3093.4	Semi standard non polar	33892256
Disopyramide,2TBDMS,isomer #1	CC(C)N(CCC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N1)C(C)C	2963.8	Standard non polar	33892256
Disopyramide,2TBDMS,isomer #1	CC(C)N(CCC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N1)C(C)C	3133.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Disopyramide GC-MS (Non-derivatized) - 70eV, Positive	splash10-044m-6591000000-ade312d81f3d174aaf2d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Disopyramide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Disopyramide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Disopyramide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Disopyramide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Disopyramide , positive-QTOF	splash10-0005-2920000000-e596d22799910844ad71	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Disopyramide 10V, Positive-QTOF	splash10-0006-0019000000-d1d8426d9efe63a8f3fd	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Disopyramide 20V, Positive-QTOF	splash10-00dj-0295000000-27ad50b3e8f64e45b5f4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Disopyramide 40V, Positive-QTOF	splash10-059l-7590000000-29c623252c76f0cfe4e8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Disopyramide 10V, Negative-QTOF	splash10-000j-0179000000-d43460de1f53211201c4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Disopyramide 20V, Negative-QTOF	splash10-0002-1491000000-c6005857bfdac87779c4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Disopyramide 40V, Negative-QTOF	splash10-0uxr-7920000000-c8e9f71b29cfc8635a28	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Disopyramide 10V, Positive-QTOF	splash10-000f-0049000000-d7931ec90cdb1287fd3e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Disopyramide 20V, Positive-QTOF	splash10-000l-0292000000-4ce9f6848ae81d59c7e9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Disopyramide 40V, Positive-QTOF	splash10-00kf-0900000000-ce002f8854f066661807	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Disopyramide 10V, Negative-QTOF	splash10-000i-0029000000-6569595ba95c091f548b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Disopyramide 20V, Negative-QTOF	splash10-000g-8695000000-4b18e01643972a8c9216	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Disopyramide 40V, Negative-QTOF	splash10-001m-9720000000-fc09dce8697633f796e9	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Disopyramide 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 DB00280	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00280	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00280

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3002

KEGG Compound ID

C06965

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Disopyramide

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

4657

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

Echizen H, Tanizaki M, Tatsuno J, Chiba K, Berwick T, Tani M, Gonzalez FJ, Ishizaki T: Identification of CYP3A4 as the enzyme involved in the mono-N-dealkylation of disopyramide enantiomers in humans. Drug Metab Dispos. 2000 Aug;28(8):937-44. [PubMed:10901704 ]
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 ]
Zhang L, Fitzloff JF, Engel LC, Cook CS: Species difference in stereoselective involvement of CYP3A in the mono-N-dealkylation of disopyramide. Xenobiotica. 2001 Feb;31(2):73-83. [PubMed:11407536 ]

Enzyme Details

2. 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

Sugao M, Fujiki A, Nishida K, Sakabe M, Tsuneda T, Iwamoto J, Mizumaki K, Inoue H: Repolarization dynamics in patients with idiopathic ventricular fibrillation: pharmacological therapy with bepridil and disopyramide. J Cardiovasc Pharmacol. 2005 Jun;45(6):545-9. [PubMed:15897781 ]
Fujiki A, Sugao M, Nishida K, Sakabe M, Tsuneda T, Mizumaki K, Inoue H: Repolarization abnormality in idiopathic ventricular fibrillation: assessment using 24-hour QT-RR and QaT-RR relationships. J Cardiovasc Electrophysiol. 2004 Jan;15(1):59-63. [PubMed:15028073 ]
Shimizu W, Antzelevitch C, Suyama K, Kurita T, Taguchi A, Aihara N, Takaki H, Sunagawa K, Kamakura S: Effect of sodium channel blockers on ST segment, QRS duration, and corrected QT interval in patients with Brugada syndrome. J Cardiovasc Electrophysiol. 2000 Dec;11(12):1320-9. [PubMed:11196553 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

3. Muscarinic acetylcholine receptor M3

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:: CHRM3
Uniprot ID:: P20309
Molecular weight:: 66127.4

References

Yamamoto N, Ozaki T, Keida Y, Ohtsuka M, Goto T: A comparison of the binding characteristics of class I antiarrhythmic agents for human muscarinic m1-m3 receptors. J Cardiovasc Pharmacol. 1999 Jul;34(1):53-9. [PubMed:10413067 ]

Enzyme Details

4. Muscarinic acetylcholine receptor M1

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:: CHRM1
Uniprot ID:: P11229
Molecular weight:: 51420.4

References

Yamamoto N, Ozaki T, Keida Y, Ohtsuka M, Goto T: A comparison of the binding characteristics of class I antiarrhythmic agents for human muscarinic m1-m3 receptors. J Cardiovasc Pharmacol. 1999 Jul;34(1):53-9. [PubMed:10413067 ]
Ishida Y, Mizukami M, Taniguchi T, Satake N, Fujiwara M, Shibata S: Anticholinergic action of disopyramide in intestinal smooth muscle of the guinea pig: inhibition of muscarinic receptors (M1 and M2). Jpn J Pharmacol. 1990 Feb;52(2):363-70. [PubMed:1690310 ]

Enzyme Details

5. Muscarinic acetylcholine receptor M2

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition
Gene Name:: CHRM2
Uniprot ID:: P08172
Molecular weight:: 51714.6

References

Yamamoto N, Ozaki T, Keida Y, Ohtsuka M, Goto T: A comparison of the binding characteristics of class I antiarrhythmic agents for human muscarinic m1-m3 receptors. J Cardiovasc Pharmacol. 1999 Jul;34(1):53-9. [PubMed:10413067 ]
Ishida Y, Mizukami M, Taniguchi T, Satake N, Fujiwara M, Shibata S: Anticholinergic action of disopyramide in intestinal smooth muscle of the guinea pig: inhibition of muscarinic receptors (M1 and M2). Jpn J Pharmacol. 1990 Feb;52(2):363-70. [PubMed:1690310 ]

Enzyme Details

6. Potassium voltage-gated channel subfamily D member 2

General function:: Involved in protein binding
Specific function:: Pore-forming (alpha) subunit of voltage-gated rapidly inactivating A-type potassium channels. May contribute to I(To) current in heart and I(Sa) current in neurons. Channel properties are modulated by interactions with other alpha subunits and with regulatory subunits
Gene Name:: KCND2
Uniprot ID:: Q9NZV8
Molecular weight:: 70535.8

References

Casis O, Sanchez-Chapula JA: Disopyramide, imipramine, and amitriptyline bind to a common site on the transient outward K+ channel. J Cardiovasc Pharmacol. 1998 Oct;32(4):521-6. [PubMed:9781919 ]

Enzyme Details

7. Potassium voltage-gated channel subfamily D member 3

General function:: Involved in protein binding
Specific function:: Pore-forming (alpha) subunit of voltage-gated rapidly inactivating A-type potassium channels. May contribute to I(To) current in heart and I(Sa) current in neurons. Channel properties are modulated by interactions with other alpha subunits and with regulatory subunits
Gene Name:: KCND3
Uniprot ID:: Q9UK17
Molecular weight:: 73450.5

References

Casis O, Sanchez-Chapula JA: Disopyramide, imipramine, and amitriptyline bind to a common site on the transient outward K+ channel. J Cardiovasc Pharmacol. 1998 Oct;32(4):521-6. [PubMed:9781919 ]

Transporters

Enzyme Details

1. Solute carrier family 22 member 1

General function:: Involved in ion transmembrane transporter activity
Specific function:: Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
Gene Name:: SLC22A1
Uniprot ID:: O15245
Molecular weight:: 61187.4

References

Zhang L, Schaner ME, Giacomini KM: Functional characterization of an organic cation transporter (hOCT1) in a transiently transfected human cell line (HeLa). J Pharmacol Exp Ther. 1998 Jul;286(1):354-61. [PubMed:9655880 ]
Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759 ]

Enzyme Details

2. Solute carrier family 22 member 2

General function:: Involved in ion transmembrane transporter activity
Specific function:: Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, cisplatin and oxaliplatin. Cisplatin may develop a nephrotoxic action. Transport of creatinine is inhibited by fluoroquinolones such as DX-619 and LVFX. This transporter is a major determinant of the anticancer activity of oxaliplatin and may contribute to antitumor specificity
Gene Name:: SLC22A2
Uniprot ID:: O15244
Molecular weight:: 62564.0

References

Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759 ]

Showing metabocard for Disopyramide (HMDB0014425)

MOL for HMDB0014425 (Disopyramide)

3D MOL for HMDB0014425 (Disopyramide)

3D SDF for HMDB0014425 (Disopyramide)

3D-SDF for HMDB0014425 (Disopyramide)

PDB for HMDB0014425 (Disopyramide)

3D PDB for HMDB0014425 (Disopyramide)

SMILES for HMDB0014425 (Disopyramide)

INCHI for HMDB0014425 (Disopyramide)

Structure for HMDB0014425 (Disopyramide)

3D Structure for HMDB0014425 (Disopyramide)

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

References