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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:13:14 UTC
Update Date2021-09-14 15:47:16 UTC
HMDB IDHMDB0061024
Secondary Accession Numbers
  • HMDB61024
Metabolite Identification
Common Namemono-isopropyl-disopyramide
Descriptionmono-isopropyl-disopyramide is a metabolite of disopyramide. Disopyramide (trade names Norpace and Rythmodan) is an antiarrhythmic medication used in the treatment of Ventricular Tachycardia. It is a sodium channel blocker and therefor classified as a Class 1a anti-arrhythmic agent. ’ Disopyramide has a negative inotropic effect on the ventricular myocardium, significantly decreasing the contractility. ' Disopyramide also has an anticholinergic effect on the heart which accounts for many adverse side effects. (Wikipedia)
Structure
Data?1563866136
Synonyms
ValueSource
DeisopropyldisopyramideHMDB
DesisopropyldisopyramideHMDB
mono-N-Dealkylated disopyramideHMDB
mono-DealkyldisopyramideHMDB
4-(Isopropylamino)-2-(2-pyridyl)-2-phenylbutyramideHMDB
4-(Isopropylamino)-2-(2-pyridyl)-2-phenylbutyramide phosphateHMDB
Chemical FormulaC18H23N3O
Average Molecular Weight297.3947
Monoisotopic Molecular Weight297.184112373
IUPAC Name2-phenyl-4-[(propan-2-yl)amino]-2-(pyridin-2-yl)butanimidic acid
Traditional Name4-(isopropylamino)-2-phenyl-2-(pyridin-2-yl)butanimidic acid
CAS Registry NumberNot Available
SMILES
CC(C)NCCC(C(O)=N)(C1=CC=CC=C1)C1=CC=CC=N1
InChI Identifier
InChI=1S/C18H23N3O/c1-14(2)20-13-11-18(17(19)22,15-8-4-3-5-9-15)16-10-6-7-12-21-16/h3-10,12,14,20H,11,13H2,1-2H3,(H2,19,22)
InChI KeyUWNSWIXIVDMCHZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGamma amino acids and derivatives
Alternative Parents
Substituents
  • Gamma amino acid or derivatives
  • Phenylacetamide
  • Aralkylamine
  • Monocyclic benzene moiety
  • Fatty amide
  • Pyridine
  • Fatty acyl
  • Benzenoid
  • Heteroaromatic compound
  • Carboxamide group
  • Primary carboxylic acid amide
  • Secondary aliphatic amine
  • Azacycle
  • Secondary amine
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.038 g/LALOGPS
logP2.16ALOGPS
logP0.44ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)-1.3ChemAxon
pKa (Strongest Basic)12.92ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity109.39 m³·mol⁻¹ChemAxon
Polarizability33.55 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+172.93131661259
DarkChem[M-H]-169.99631661259
DeepCCS[M+H]+174.72430932474
DeepCCS[M-H]-172.36630932474
DeepCCS[M-2H]-205.25230932474
DeepCCS[M+Na]+180.81730932474
AllCCS[M+H]+172.432859911
AllCCS[M+H-H2O]+169.032859911
AllCCS[M+NH4]+175.632859911
AllCCS[M+Na]+176.632859911
AllCCS[M-H]-177.232859911
AllCCS[M+Na-2H]-177.332859911
AllCCS[M+HCOO]-177.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
mono-isopropyl-disopyramideCC(C)NCCC(C(O)=N)(C1=CC=CC=C1)C1=CC=CC=N13198.3Standard polar33892256
mono-isopropyl-disopyramideCC(C)NCCC(C(O)=N)(C1=CC=CC=C1)C1=CC=CC=N12407.1Standard non polar33892256
mono-isopropyl-disopyramideCC(C)NCCC(C(O)=N)(C1=CC=CC=C1)C1=CC=CC=N12320.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
mono-isopropyl-disopyramide,1TMS,isomer #1CC(C)NCCC(C(=N)O[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N12337.4Semi standard non polar33892256
mono-isopropyl-disopyramide,1TMS,isomer #2CC(C)N(CCC(C(=N)O)(C1=CC=CC=C1)C1=CC=CC=N1)[Si](C)(C)C2506.2Semi standard non polar33892256
mono-isopropyl-disopyramide,1TMS,isomer #3CC(C)NCCC(C(O)=N[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N12376.8Semi standard non polar33892256
mono-isopropyl-disopyramide,2TMS,isomer #1CC(C)N(CCC(C(=N)O[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N1)[Si](C)(C)C2487.3Semi standard non polar33892256
mono-isopropyl-disopyramide,2TMS,isomer #1CC(C)N(CCC(C(=N)O[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N1)[Si](C)(C)C2492.5Standard non polar33892256
mono-isopropyl-disopyramide,2TMS,isomer #1CC(C)N(CCC(C(=N)O[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N1)[Si](C)(C)C3132.4Standard polar33892256
mono-isopropyl-disopyramide,2TMS,isomer #2CC(C)NCCC(C(=N[Si](C)(C)C)O[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N12352.5Semi standard non polar33892256
mono-isopropyl-disopyramide,2TMS,isomer #2CC(C)NCCC(C(=N[Si](C)(C)C)O[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N12297.3Standard non polar33892256
mono-isopropyl-disopyramide,2TMS,isomer #2CC(C)NCCC(C(=N[Si](C)(C)C)O[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N12928.5Standard polar33892256
mono-isopropyl-disopyramide,2TMS,isomer #3CC(C)N(CCC(C(O)=N[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N1)[Si](C)(C)C2487.2Semi standard non polar33892256
mono-isopropyl-disopyramide,2TMS,isomer #3CC(C)N(CCC(C(O)=N[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N1)[Si](C)(C)C2405.5Standard non polar33892256
mono-isopropyl-disopyramide,2TMS,isomer #3CC(C)N(CCC(C(O)=N[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N1)[Si](C)(C)C3198.1Standard polar33892256
mono-isopropyl-disopyramide,3TMS,isomer #1CC(C)N(CCC(C(=N[Si](C)(C)C)O[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N1)[Si](C)(C)C2533.1Semi standard non polar33892256
mono-isopropyl-disopyramide,3TMS,isomer #1CC(C)N(CCC(C(=N[Si](C)(C)C)O[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N1)[Si](C)(C)C2394.5Standard non polar33892256
mono-isopropyl-disopyramide,3TMS,isomer #1CC(C)N(CCC(C(=N[Si](C)(C)C)O[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N1)[Si](C)(C)C2862.7Standard polar33892256
mono-isopropyl-disopyramide,1TBDMS,isomer #1CC(C)NCCC(C(=N)O[Si](C)(C)C(C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N12556.1Semi standard non polar33892256
mono-isopropyl-disopyramide,1TBDMS,isomer #2CC(C)N(CCC(C(=N)O)(C1=CC=CC=C1)C1=CC=CC=N1)[Si](C)(C)C(C)(C)C2771.1Semi standard non polar33892256
mono-isopropyl-disopyramide,1TBDMS,isomer #3CC(C)NCCC(C(O)=N[Si](C)(C)C(C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N12614.9Semi standard non polar33892256
mono-isopropyl-disopyramide,2TBDMS,isomer #1CC(C)N(CCC(C(=N)O[Si](C)(C)C(C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N1)[Si](C)(C)C(C)(C)C2950.8Semi standard non polar33892256
mono-isopropyl-disopyramide,2TBDMS,isomer #1CC(C)N(CCC(C(=N)O[Si](C)(C)C(C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N1)[Si](C)(C)C(C)(C)C2907.7Standard non polar33892256
mono-isopropyl-disopyramide,2TBDMS,isomer #1CC(C)N(CCC(C(=N)O[Si](C)(C)C(C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N1)[Si](C)(C)C(C)(C)C3243.3Standard polar33892256
mono-isopropyl-disopyramide,2TBDMS,isomer #2CC(C)NCCC(C(=N[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N12750.3Semi standard non polar33892256
mono-isopropyl-disopyramide,2TBDMS,isomer #2CC(C)NCCC(C(=N[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N12685.9Standard non polar33892256
mono-isopropyl-disopyramide,2TBDMS,isomer #2CC(C)NCCC(C(=N[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N13093.0Standard polar33892256
mono-isopropyl-disopyramide,2TBDMS,isomer #3CC(C)N(CCC(C(O)=N[Si](C)(C)C(C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N1)[Si](C)(C)C(C)(C)C2962.6Semi standard non polar33892256
mono-isopropyl-disopyramide,2TBDMS,isomer #3CC(C)N(CCC(C(O)=N[Si](C)(C)C(C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N1)[Si](C)(C)C(C)(C)C2783.8Standard non polar33892256
mono-isopropyl-disopyramide,2TBDMS,isomer #3CC(C)N(CCC(C(O)=N[Si](C)(C)C(C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N1)[Si](C)(C)C(C)(C)C3327.7Standard polar33892256
mono-isopropyl-disopyramide,3TBDMS,isomer #1CC(C)N(CCC(C(=N[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N1)[Si](C)(C)C(C)(C)C3152.8Semi standard non polar33892256
mono-isopropyl-disopyramide,3TBDMS,isomer #1CC(C)N(CCC(C(=N[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N1)[Si](C)(C)C(C)(C)C2933.2Standard non polar33892256
mono-isopropyl-disopyramide,3TBDMS,isomer #1CC(C)N(CCC(C(=N[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)(C1=CC=CC=C1)C1=CC=CC=N1)[Si](C)(C)C(C)(C)C3093.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - mono-isopropyl-disopyramide GC-MS (Non-derivatized) - 70eV, Positivesplash10-00rx-8290000000-0dffd4842c9146481c972017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - mono-isopropyl-disopyramide GC-MS (1 TMS) - 70eV, Positivesplash10-0fl0-9153000000-843ba800f53011da18a52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - mono-isopropyl-disopyramide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - mono-isopropyl-disopyramide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - mono-isopropyl-disopyramide 10V, Positive-QTOFsplash10-0002-0090000000-fbe702cf7b37d99cca542017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - mono-isopropyl-disopyramide 20V, Positive-QTOFsplash10-0buc-0190000000-fc5c15603a5e7649ae602017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - mono-isopropyl-disopyramide 40V, Positive-QTOFsplash10-000f-4290000000-71ab35fab1b6baf611d32017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - mono-isopropyl-disopyramide 10V, Negative-QTOFsplash10-0f6t-0090000000-0685aacbd126567472a52017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - mono-isopropyl-disopyramide 20V, Negative-QTOFsplash10-0udi-1190000000-1cd4d951d25e9b6327152017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - mono-isopropyl-disopyramide 40V, Negative-QTOFsplash10-07do-9740000000-c7faa024dc75af4199602017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - mono-isopropyl-disopyramide 10V, Positive-QTOFsplash10-0002-0090000000-98b3505f56e2200c19012021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - mono-isopropyl-disopyramide 20V, Positive-QTOFsplash10-000i-0490000000-df48823172124d509ab12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - mono-isopropyl-disopyramide 40V, Positive-QTOFsplash10-00kg-0900000000-3b5349c966a6cf3b64f62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - mono-isopropyl-disopyramide 10V, Negative-QTOFsplash10-0002-0090000000-fa0cc794940c8ad4b4ba2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - mono-isopropyl-disopyramide 20V, Negative-QTOFsplash10-0k96-3790000000-47e9e3b7c38a80ca054d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - mono-isopropyl-disopyramide 40V, Negative-QTOFsplash10-052f-6940000000-2e2522bf82fef6ae5fdc2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound107858
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available