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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:57:13 UTC
Update Date2022-03-07 02:57:15 UTC
HMDB IDHMDB0042059
Secondary Accession Numbers
  • HMDB42059
Metabolite Identification
Common NameVesnarinone
DescriptionVesnarinone (INN) is a cardiotonic agent. A mixed phosphodiesterase 3 inhibitor and ion-channel modifier that has modest, dose-dependent, positive inotropic activity, but minimal negative chronotropic activity. Vesnarinone improves ventricular performance most in patients with the worst degree of heart failure.
Structure
Data?1563863726
Synonyms
ValueSource
Arkin ZKegg
3,4-Dihydro-6-(4-(3,4-dimethoxybenzoyl)-1-piperazinyl)-2-1H-quinolinoneHMDB
Chemical FormulaC22H25N3O4
Average Molecular Weight395.4516
Monoisotopic Molecular Weight395.184506303
IUPAC Name6-[4-(3,4-dimethoxybenzoyl)piperazin-1-yl]-1,2,3,4-tetrahydroquinolin-2-one
Traditional Namevesnarinone
CAS Registry Number81840-15-5
SMILES
COC1=C(OC)C=C(C=C1)C(=O)N1CCN(CC1)C1=CC=C2NC(=O)CCC2=C1
InChI Identifier
InChI=1S/C22H25N3O4/c1-28-19-7-3-16(14-20(19)29-2)22(27)25-11-9-24(10-12-25)17-5-6-18-15(13-17)4-8-21(26)23-18/h3,5-7,13-14H,4,8-12H2,1-2H3,(H,23,26)
InChI KeyZVNYJIZDIRKMBF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-arylpiperazines. These are organic compounds containing a piperazine ring where the nitrogen ring atom carries an aryl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazinanes
Sub ClassPiperazines
Direct ParentN-arylpiperazines
Alternative Parents
Substituents
  • N-arylpiperazine
  • Aminoquinoline
  • Tetrahydroquinolone
  • Quinolone
  • Tetrahydroquinoline
  • Dimethoxybenzene
  • O-dimethoxybenzene
  • Benzamide
  • Benzoic acid or derivatives
  • Anisole
  • Phenoxy compound
  • Benzoyl
  • Phenol ether
  • Tertiary aliphatic/aromatic amine
  • Dialkylarylamine
  • Methoxybenzene
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Tertiary carboxylic acid amide
  • Secondary carboxylic acid amide
  • Tertiary amine
  • Amino acid or derivatives
  • Carboxamide group
  • Lactam
  • Carboxylic acid derivative
  • Azacycle
  • Ether
  • Carbonyl group
  • Amine
  • Organic oxygen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot 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 Solubility0.097 g/LALOGPS
logP2.34ALOGPS
logP2.24ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)15.28ChemAxon
pKa (Strongest Basic)2.94ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area71.11 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity112.53 m³·mol⁻¹ChemAxon
Polarizability42.72 ųChemAxon
Number of Rings4ChemAxon
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]+195.19931661259
DarkChem[M-H]-194.00731661259
DeepCCS[M+H]+190.64430932474
DeepCCS[M-H]-188.28630932474
DeepCCS[M-2H]-222.09230932474
DeepCCS[M+Na]+197.3230932474
AllCCS[M+H]+196.032859911
AllCCS[M+H-H2O]+193.532859911
AllCCS[M+NH4]+198.332859911
AllCCS[M+Na]+199.032859911
AllCCS[M-H]-195.732859911
AllCCS[M+Na-2H]-196.032859911
AllCCS[M+HCOO]-196.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
VesnarinoneCOC1=C(OC)C=C(C=C1)C(=O)N1CCN(CC1)C1=CC=C2NC(=O)CCC2=C14642.2Standard polar33892256
VesnarinoneCOC1=C(OC)C=C(C=C1)C(=O)N1CCN(CC1)C1=CC=C2NC(=O)CCC2=C13414.3Standard non polar33892256
VesnarinoneCOC1=C(OC)C=C(C=C1)C(=O)N1CCN(CC1)C1=CC=C2NC(=O)CCC2=C14155.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Vesnarinone,1TMS,isomer #1COC1=CC=C(C(=O)N2CCN(C3=CC=C4C(=C3)CCC(=O)N4[Si](C)(C)C)CC2)C=C1OC3871.3Semi standard non polar33892256
Vesnarinone,1TMS,isomer #1COC1=CC=C(C(=O)N2CCN(C3=CC=C4C(=C3)CCC(=O)N4[Si](C)(C)C)CC2)C=C1OC3584.2Standard non polar33892256
Vesnarinone,1TBDMS,isomer #1COC1=CC=C(C(=O)N2CCN(C3=CC=C4C(=C3)CCC(=O)N4[Si](C)(C)C(C)(C)C)CC2)C=C1OC4119.4Semi standard non polar33892256
Vesnarinone,1TBDMS,isomer #1COC1=CC=C(C(=O)N2CCN(C3=CC=C4C(=C3)CCC(=O)N4[Si](C)(C)C(C)(C)C)CC2)C=C1OC3802.8Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Vesnarinone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00li-0927000000-754895724af1ecfea8412017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vesnarinone 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 - Vesnarinone 10V, Positive-QTOFsplash10-0002-0009000000-0e5f37473ec2cf3a7d952017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vesnarinone 20V, Positive-QTOFsplash10-0002-0309000000-3ddb6c64a47b77bcb1722017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vesnarinone 40V, Positive-QTOFsplash10-0002-0901000000-dd0deabfe3b7e9140e492017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vesnarinone 10V, Negative-QTOFsplash10-0006-0009000000-9d6936e8b1fa8465b8782017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vesnarinone 20V, Negative-QTOFsplash10-0006-2119000000-524f3b6af424f0c0fc052017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vesnarinone 40V, Negative-QTOFsplash10-0006-9337000000-e2d551f42f82f85ed7522017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vesnarinone 10V, Positive-QTOFsplash10-0002-0009000000-5219ce8a0684a2e068af2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vesnarinone 20V, Positive-QTOFsplash10-0002-0219000000-079327a9e77034c13ff12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vesnarinone 40V, Positive-QTOFsplash10-000l-0935000000-8f54ed9c96060dd61aab2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vesnarinone 10V, Negative-QTOFsplash10-0006-0009000000-3c16d595d445d736ff022021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vesnarinone 20V, Negative-QTOFsplash10-0006-0009000000-a5181fc183843f202a652021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vesnarinone 40V, Negative-QTOFsplash10-05cr-0579000000-c3815409f090deb5e6c12021-09-25Wishart 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 IDDB12082
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5461
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVesnarinone
METLIN IDNot Available
PubChem Compound5663
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