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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:01 UTC
HMDB IDHMDB0015562
Secondary Accession Numbers
  • HMDB15562
Metabolite Identification
Common NameIsopropamide
DescriptionIsopropamide is only found in individuals that have used or taken this drug. It is a long-acting quaternary anticholinergic drug. It is used in the treatment of peptic ulcer and other gastrointestinal disorders marked by hyperacidity and hypermotility.Anticholinergics are a class of medications that inhibit parasympathetic nerve impulses by selectively blocking the binding of the neurotransmitter acetylcholine to its receptor in nerve cells. The nerve fibers of the parasympathetic system are responsible for the involuntary movements of smooth muscles present in the gastrointestinal tract. Inhibition here decreases acidity and motility, aiding in the treatment of gastrointestinal disorders.
Structure
Data?1582753310
Synonyms
ValueSource
2,2-Diphenyl-4-diisopropylaminobutyramide methiodideHMDB
4-(Diisopropylamino)-2,2-diphenylbutyramide methiodideHMDB
ChloroisopropamideHMDB
Isopropamide iodideHMDB
Isoproponum iodideHMDB
Chemical FormulaC23H33N2O
Average Molecular Weight353.5209
Monoisotopic Molecular Weight353.259288688
IUPAC Name(3-carbamoyl-3,3-diphenylpropyl)(methyl)bis(propan-2-yl)azanium
Traditional Nameisopropamide
CAS Registry Number7492-32-2
SMILES
CC(C)[N+](C)(CCC(C(N)=O)(C1=CC=CC=C1)C1=CC=CC=C1)C(C)C
InChI Identifier
InChI=1S/C23H32N2O/c1-18(2)25(5,19(3)4)17-16-23(22(24)26,20-12-8-6-9-13-20)21-14-10-7-11-15-21/h6-15,18-19H,16-17H2,1-5H3,(H-,24,26)/p+1
InChI KeyJTPUMZTWMWIVPA-UHFFFAOYSA-O
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Aralkylamine
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic salt
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic cation
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.2e-05 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available186.874http://allccs.zhulab.cn/database/detail?ID=AllCCS00000809
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.2e-05 g/LALOGPS
logP2.27ALOGPS
logP0.14ChemAxon
logS-7ALOGPS
pKa (Strongest Acidic)16.31ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity120.74 m³·mol⁻¹ChemAxon
Polarizability41.28 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]+183.47331661259
DarkChem[M-H]-178.60131661259
DeepCCS[M+H]+188.85230932474
DeepCCS[M-H]-186.49430932474
DeepCCS[M-2H]-220.37530932474
DeepCCS[M+Na]+195.60330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IsopropamideCC(C)[N+](C)(CCC(C(N)=O)(C1=CC=CC=C1)C1=CC=CC=C1)C(C)C3397.6Standard polar33892256
IsopropamideCC(C)[N+](C)(CCC(C(N)=O)(C1=CC=CC=C1)C1=CC=CC=C1)C(C)C2529.4Standard non polar33892256
IsopropamideCC(C)[N+](C)(CCC(C(N)=O)(C1=CC=CC=C1)C1=CC=CC=C1)C(C)C2720.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isopropamide,1TMS,isomer #1CC(C)[N+](C)(CCC(C(=O)N[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=C1)C(C)C2614.8Semi standard non polar33892256
Isopropamide,1TMS,isomer #1CC(C)[N+](C)(CCC(C(=O)N[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=C1)C(C)C2600.3Standard non polar33892256
Isopropamide,1TMS,isomer #1CC(C)[N+](C)(CCC(C(=O)N[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=C1)C(C)C3237.1Standard polar33892256
Isopropamide,2TMS,isomer #1CC(C)[N+](C)(CCC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=C1)C(C)C2686.6Semi standard non polar33892256
Isopropamide,2TMS,isomer #1CC(C)[N+](C)(CCC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=C1)C(C)C2740.7Standard non polar33892256
Isopropamide,2TMS,isomer #1CC(C)[N+](C)(CCC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=C1)C(C)C3089.2Standard polar33892256
Isopropamide,1TBDMS,isomer #1CC(C)[N+](C)(CCC(C(=O)N[Si](C)(C)C(C)(C)C)(C1=CC=CC=C1)C1=CC=CC=C1)C(C)C2876.1Semi standard non polar33892256
Isopropamide,1TBDMS,isomer #1CC(C)[N+](C)(CCC(C(=O)N[Si](C)(C)C(C)(C)C)(C1=CC=CC=C1)C1=CC=CC=C1)C(C)C2839.8Standard non polar33892256
Isopropamide,1TBDMS,isomer #1CC(C)[N+](C)(CCC(C(=O)N[Si](C)(C)C(C)(C)C)(C1=CC=CC=C1)C1=CC=CC=C1)C(C)C3273.9Standard polar33892256
Isopropamide,2TBDMS,isomer #1CC(C)[N+](C)(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=C1)C(C)C3178.2Semi standard non polar33892256
Isopropamide,2TBDMS,isomer #1CC(C)[N+](C)(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=C1)C(C)C3132.9Standard non polar33892256
Isopropamide,2TBDMS,isomer #1CC(C)[N+](C)(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=C1)C(C)C3152.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isopropamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-052o-7449000000-f279105f11d6b98a55c82017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isopropamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isopropamide 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 - Isopropamide 10V, Positive-QTOFsplash10-0udi-0009000000-53e6e25ea65e997651ee2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopropamide 20V, Positive-QTOFsplash10-029i-0669000000-e183c9c931ea4fceb0a82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopropamide 40V, Positive-QTOFsplash10-010c-3930000000-778efc637cd308af4c852017-09-01Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01625 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01625 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01625
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3643
KEGG Compound IDC07055
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIsopropamide
METLIN IDNot Available
PubChem Compound3775
PDB IDNot Available
ChEBI ID775183
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

Enzymes

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
  1. Eglen RM, Whiting RL: Competitive and non-competitive antagonism exhibited by 'selective' antagonists at atrial and ileal muscarinic receptor subtypes. Br J Pharmacol. 1987 Apr;90(4):701-7. [PubMed:3580704 ]
  2. Lane MA: Muscarinic cholinergic activation of mouse spleen cells cytotoxic to tumor cells in vitro. J Natl Cancer Inst. 1978 Sep;61(3):923-6. [PubMed:29133 ]
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 inhibition of adenylate cyclase
Gene Name:
CHRM4
Uniprot ID:
P08173
Molecular weight:
53048.7
References
  1. Lane MA: Muscarinic cholinergic activation of mouse spleen cells cytotoxic to tumor cells in vitro. J Natl Cancer Inst. 1978 Sep;61(3):923-6. [PubMed:29133 ]
  2. Eglen RM, Whiting RL: Competitive and non-competitive antagonism exhibited by 'selective' antagonists at atrial and ileal muscarinic receptor subtypes. Br J Pharmacol. 1987 Apr;90(4):701-7. [PubMed:3580704 ]