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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:00 UTC
HMDB IDHMDB0015499
Secondary Accession Numbers
  • HMDB15499
Metabolite Identification
Common NameAlmitrine
DescriptionA respiratory stimulant that enhances respiration by acting as an agonist of peripheral chemoreceptors located on the carotid bodies. The drug increases arterial oxygen tension while decreasing arterial carbon dioxide tension in patients with chronic obstructive pulmonary disease. It may also prove useful in the treatment of nocturnal oxygen desaturation without impairing the quality of sleep. [PubChem]
Structure
Data?1582753304
Synonyms
ValueSource
2,4-Bis(allylamino)-6-(4-(bis(p-fluorophenyl)methyl)-1-piperazinyl)-S-triazineChEBI
AlmitrinaChEBI
AlmitrinumChEBI
Almitrine bismesylateHMDB
Almitrine dimesylateHMDB
Servier brand OF almitrine dimesilateHMDB
Almitrine bis(methanesulfonate)HMDB
VectarionHMDB
Euthérapie brand OF almitrine dimesilateHMDB
Monomesylate, almitrineHMDB
Almitrine monomesylateHMDB
Chemical FormulaC26H29F2N7
Average Molecular Weight477.5522
Monoisotopic Molecular Weight477.245250373
IUPAC Name6-{4-[bis(4-fluorophenyl)methyl]piperazin-1-yl}-N2,N4-bis(prop-2-en-1-yl)-1,3,5-triazine-2,4-diamine
Traditional Namealmitrine
CAS Registry Number27469-53-0
SMILES
FC1=CC=C(C=C1)C(N1CCN(CC1)C1=NC(NCC=C)=NC(NCC=C)=N1)C1=CC=C(F)C=C1
InChI Identifier
InChI=1S/C26H29F2N7/c1-3-13-29-24-31-25(30-14-4-2)33-26(32-24)35-17-15-34(16-18-35)23(19-5-9-21(27)10-6-19)20-7-11-22(28)12-8-20/h3-12,23H,1-2,13-18H2,(H2,29,30,31,32,33)
InChI KeyOBDOVFRMEYHSQB-UHFFFAOYSA-N
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
  • N-arylpiperazine
  • Dialkylarylamine
  • Amino-1,3,5-triazine
  • Aminotriazine
  • Halobenzene
  • Fluorobenzene
  • Secondary aliphatic/aromatic amine
  • Aralkylamine
  • N-aliphatic s-triazine
  • N-alkylpiperazine
  • Aryl fluoride
  • Piperazine
  • Aryl halide
  • 1,4-diazinane
  • Triazine
  • 1,3,5-triazine
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Organopnictogen compound
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.014 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP4.9ALOGPS
logP6.05ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)14.27ChemAxon
pKa (Strongest Basic)7.49ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area69.21 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity140.88 m³·mol⁻¹ChemAxon
Polarizability51.12 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+213.39930932474
DeepCCS[M-H]-211.00330932474
DeepCCS[M-2H]-243.88830932474
DeepCCS[M+Na]+219.64730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AlmitrineFC1=CC=C(C=C1)C(N1CCN(CC1)C1=NC(NCC=C)=NC(NCC=C)=N1)C1=CC=C(F)C=C14410.9Standard polar33892256
AlmitrineFC1=CC=C(C=C1)C(N1CCN(CC1)C1=NC(NCC=C)=NC(NCC=C)=N1)C1=CC=C(F)C=C13617.9Standard non polar33892256
AlmitrineFC1=CC=C(C=C1)C(N1CCN(CC1)C1=NC(NCC=C)=NC(NCC=C)=N1)C1=CC=C(F)C=C13715.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Almitrine,1TMS,isomer #1C=CCNC1=NC(N2CCN(C(C3=CC=C(F)C=C3)C3=CC=C(F)C=C3)CC2)=NC(N(CC=C)[Si](C)(C)C)=N13743.0Semi standard non polar33892256
Almitrine,1TMS,isomer #1C=CCNC1=NC(N2CCN(C(C3=CC=C(F)C=C3)C3=CC=C(F)C=C3)CC2)=NC(N(CC=C)[Si](C)(C)C)=N12132.6Standard non polar33892256
Almitrine,1TMS,isomer #1C=CCNC1=NC(N2CCN(C(C3=CC=C(F)C=C3)C3=CC=C(F)C=C3)CC2)=NC(N(CC=C)[Si](C)(C)C)=N14944.9Standard polar33892256
Almitrine,2TMS,isomer #1C=CCN(C1=NC(N2CCN(C(C3=CC=C(F)C=C3)C3=CC=C(F)C=C3)CC2)=NC(N(CC=C)[Si](C)(C)C)=N1)[Si](C)(C)C3679.0Semi standard non polar33892256
Almitrine,2TMS,isomer #1C=CCN(C1=NC(N2CCN(C(C3=CC=C(F)C=C3)C3=CC=C(F)C=C3)CC2)=NC(N(CC=C)[Si](C)(C)C)=N1)[Si](C)(C)C2224.3Standard non polar33892256
Almitrine,2TMS,isomer #1C=CCN(C1=NC(N2CCN(C(C3=CC=C(F)C=C3)C3=CC=C(F)C=C3)CC2)=NC(N(CC=C)[Si](C)(C)C)=N1)[Si](C)(C)C4609.5Standard polar33892256
Almitrine,1TBDMS,isomer #1C=CCNC1=NC(N2CCN(C(C3=CC=C(F)C=C3)C3=CC=C(F)C=C3)CC2)=NC(N(CC=C)[Si](C)(C)C(C)(C)C)=N13863.7Semi standard non polar33892256
Almitrine,1TBDMS,isomer #1C=CCNC1=NC(N2CCN(C(C3=CC=C(F)C=C3)C3=CC=C(F)C=C3)CC2)=NC(N(CC=C)[Si](C)(C)C(C)(C)C)=N12269.0Standard non polar33892256
Almitrine,1TBDMS,isomer #1C=CCNC1=NC(N2CCN(C(C3=CC=C(F)C=C3)C3=CC=C(F)C=C3)CC2)=NC(N(CC=C)[Si](C)(C)C(C)(C)C)=N14975.1Standard polar33892256
Almitrine,2TBDMS,isomer #1C=CCN(C1=NC(N2CCN(C(C3=CC=C(F)C=C3)C3=CC=C(F)C=C3)CC2)=NC(N(CC=C)[Si](C)(C)C(C)(C)C)=N1)[Si](C)(C)C(C)(C)C3940.1Semi standard non polar33892256
Almitrine,2TBDMS,isomer #1C=CCN(C1=NC(N2CCN(C(C3=CC=C(F)C=C3)C3=CC=C(F)C=C3)CC2)=NC(N(CC=C)[Si](C)(C)C(C)(C)C)=N1)[Si](C)(C)C(C)(C)C2631.5Standard non polar33892256
Almitrine,2TBDMS,isomer #1C=CCN(C1=NC(N2CCN(C(C3=CC=C(F)C=C3)C3=CC=C(F)C=C3)CC2)=NC(N(CC=C)[Si](C)(C)C(C)(C)C)=N1)[Si](C)(C)C(C)(C)C4644.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Almitrine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f89-0096200000-41257a678ccba5a72f462017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Almitrine 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 - Almitrine 10V, Positive-QTOFsplash10-004i-1000900000-be1c41fd8c662996a0302016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Almitrine 20V, Positive-QTOFsplash10-0006-8011900000-5e85f712e4187bd2fd832016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Almitrine 40V, Positive-QTOFsplash10-0006-9225000000-d21bf327498d2000746a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Almitrine 10V, Negative-QTOFsplash10-004i-1000900000-e3e136edc21c164d08822016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Almitrine 20V, Negative-QTOFsplash10-0550-5114900000-d3711393e650233f90072016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Almitrine 40V, Negative-QTOFsplash10-0udi-4749100000-4ac637bcab2b8a98bc752016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Almitrine 10V, Positive-QTOFsplash10-004i-0000900000-11d22de4e97087d1fcb42021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Almitrine 20V, Positive-QTOFsplash10-004i-0010900000-6da6380e9d3d9932fdf12021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Almitrine 40V, Positive-QTOFsplash10-0udi-0191000000-517afe0139803fe56ae12021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Almitrine 10V, Negative-QTOFsplash10-004i-0000900000-fd80bb6e613003d0b81e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Almitrine 20V, Negative-QTOFsplash10-00os-1102900000-bb418b0606dbb4011cea2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Almitrine 40V, Negative-QTOFsplash10-0w4m-4469700000-ed9a7153ae99932369a32021-10-11Wishart 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 DB01430 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01430 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01430
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID31235
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAlmitrine
METLIN IDNot Available
PubChem Compound33887
PDB IDNot Available
ChEBI ID53778
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 ATP binding
Specific function:
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients.
Gene Name:
ATP1A1
Uniprot ID:
P05023
Molecular weight:
112895.01
References
  1. Rigoulet M: Control processes in oxidative phosphorylation: kinetic constraints and stoichiometry. Biochim Biophys Acta. 1990 Jul 25;1018(2-3):185-9. [PubMed:2144185 ]
  2. Rigoulet M, Fraisse L, Ouhabi R, Guerin B, Fontaine E, Leverve X: Flux-dependent increase in the stoichiometry of charge translocation by mitochondrial ATPase/ATP synthase induced by almitrine. Biochim Biophys Acta. 1990 Jul 17;1018(1):91-7. [PubMed:2165421 ]
  3. Rigoulet M, Ouhabi R, Leverve X, Putod-Paramelle F, Guerin B: Almitrine, a new kind of energy-transduction inhibitor acting on mitochondrial ATP synthase. Biochim Biophys Acta. 1989 Aug 3;975(3):325-9. [PubMed:2527061 ]
  4. Benzi G, Gorini A, Ghigini B, Arnaboldi R, Villa RF: Synaptosomal non-mitochondrial ATPase activities and drug treatment. Neurochem Res. 1993 Jun;18(6):719-26. [PubMed:8099718 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]