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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:21:18 UTC
Update Date2021-09-14 15:45:11 UTC
HMDB IDHMDB0012224
Secondary Accession Numbers
  • HMDB12224
Metabolite Identification
Common NameEmopamil
DescriptionEmopamil, also known as levemopamil, belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine. In humans, emopamil is involved in the metabolic disorder called the child syndrome pathway. Emopamil has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make emopamil a potential biomarker for the consumption of these foods. Emopamil 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 Emopamil.
Structure
Data?1582753029
Synonyms
ValueSource
2-Isopropyl-5(methylphen-ethylamino)-2-phenylvaleronitrile hydrochlorideMeSH
Emopamil, (+)-isomerMeSH
Emopamil, (+-)-isomerMeSH
Emopamil, (-)-isomerMeSH
LevemopamilMeSH
(+-)EmopamilHMDB
2-Isopropyl-5-(methylphenethylamino)-2-phenylvaleronitrileHMDB
Chemical FormulaC23H30N2
Average Molecular Weight334.4977
Monoisotopic Molecular Weight334.24089897
IUPAC Name5-[methyl(2-phenylethyl)amino]-2-phenyl-2-(propan-2-yl)pentanenitrile
Traditional Nameemopamil
CAS Registry Number78370-13-5
SMILES
CC(C)C(CCCN(C)CCC1=CC=CC=C1)(C#N)C1=CC=CC=C1
InChI Identifier
InChI=1S/C23H30N2/c1-20(2)23(19-24,22-13-8-5-9-14-22)16-10-17-25(3)18-15-21-11-6-4-7-12-21/h4-9,11-14,20H,10,15-18H2,1-3H3
InChI KeyDWAWDSVKAUWFHC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylbutylamines
Direct ParentPhenylbutylamines
Alternative Parents
Substituents
  • Phenylbutylamine
  • Phenylpropane
  • Phenethylamine
  • Aralkylamine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Nitrile
  • Carbonitrile
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
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 Solubility0.0042 g/LALOGPS
logP5.41ALOGPS
logP5.67ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)9.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area27.03 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity106.8 m³·mol⁻¹ChemAxon
Polarizability40.65 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+176.32631661259
DarkChem[M-H]-173.00331661259
DeepCCS[M+H]+181.26430932474
DeepCCS[M-H]-178.71430932474
DeepCCS[M-2H]-212.80430932474
DeepCCS[M+Na]+189.09430932474
AllCCS[M+H]+185.932859911
AllCCS[M+H-H2O]+182.832859911
AllCCS[M+NH4]+188.732859911
AllCCS[M+Na]+189.532859911
AllCCS[M-H]-190.532859911
AllCCS[M+Na-2H]-190.832859911
AllCCS[M+HCOO]-191.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
EmopamilCC(C)C(CCCN(C)CCC1=CC=CC=C1)(C#N)C1=CC=CC=C13134.1Standard polar33892256
EmopamilCC(C)C(CCCN(C)CCC1=CC=CC=C1)(C#N)C1=CC=CC=C12568.0Standard non polar33892256
EmopamilCC(C)C(CCCN(C)CCC1=CC=CC=C1)(C#N)C1=CC=CC=C12514.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Emopamil GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-2920000000-0f8171ce72f986b507862017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Emopamil GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Emopamil GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Emopamil 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 - Emopamil 10V, Positive-QTOFsplash10-000i-0019000000-d9c7d51dae7992aa00a72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Emopamil 20V, Positive-QTOFsplash10-0aor-0965000000-5bfe006a62e00aaa4fc62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Emopamil 40V, Positive-QTOFsplash10-0a4i-4910000000-8940118c0a757a892d402017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Emopamil 10V, Negative-QTOFsplash10-001i-0009000000-5fe73ce9eb9cb8343db22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Emopamil 20V, Negative-QTOFsplash10-001i-0159000000-808f91c86725a4d6aed02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Emopamil 40V, Negative-QTOFsplash10-0h03-6980000000-ccf42091fa8bd0c2bcd52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Emopamil 10V, Negative-QTOFsplash10-001i-0009000000-9e4a9bcc27e0f5a394fa2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Emopamil 20V, Negative-QTOFsplash10-0zfr-1409000000-155b5a96fe7dc41315732021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Emopamil 40V, Negative-QTOFsplash10-0v00-7961000000-96e27f3a3d6a635303cf2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Emopamil 10V, Positive-QTOFsplash10-000i-0009000000-98191f36d1ba8f7048cc2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Emopamil 20V, Positive-QTOFsplash10-0k9f-2943000000-a413b68727271996ef3e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Emopamil 40V, Positive-QTOFsplash10-0a4i-1900000000-5cb962fe8b2f1f9cb59d2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028868
KNApSAcK IDNot Available
Chemspider ID64360
KEGG Compound IDC13766
BioCyc IDCPD-4543
BiGG IDNot Available
Wikipedia LinkEmopamil
METLIN IDNot Available
PubChem Compound71225
PDB IDNot Available
ChEBI ID388533
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