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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:57:10 UTC
Update Date2022-03-07 02:57:15 UTC
HMDB IDHMDB0042058
Secondary Accession Numbers
  • HMDB42058
Metabolite Identification
Common NameVelnacrine
DescriptionVelnacrine, also known as 1-hydroxytacrine or 9-ATHCO, belongs to the class of organic compounds known as acridines. These are organic compounds containing the acridine moiety, a linear tricyclic heterocycle which consists of two benzene rings joined by a pyridine ring. Based on a literature review very few articles have been published on Velnacrine.
Structure
Data?1563863726
Synonyms
ValueSource
Velnacrine maleateHMDB
1,2,3,4-Tetrahydro-9-aminoacridine-1-olHMDB
1-HydroxytacrineHMDB
1,2,3,4-Tetrahydro-9-aminoacridin-1-ol maleateHMDB
9-ATHCOHMDB
9-Amino-1,2,3,4-tetrahydroacridin-1-olHMDB
VelnacrineMeSH
Chemical FormulaC13H14N2O
Average Molecular Weight214.2631
Monoisotopic Molecular Weight214.11061308
IUPAC Name9-imino-1,2,3,4,9,10-hexahydroacridin-1-ol
Traditional Name9-imino-2,3,4,10-tetrahydro-1H-acridin-1-ol
CAS Registry Number124027-47-0
SMILES
OC1CCCC2=C1C(=N)C1=CC=CC=C1N2
InChI Identifier
InChI=1S/C13H14N2O/c14-13-8-4-1-2-5-9(8)15-10-6-3-7-11(16)12(10)13/h1-2,4-5,11,16H,3,6-7H2,(H2,14,15)
InChI KeyHLVVITIHAZBPKB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acridines. These are organic compounds containing the acridine moiety, a linear tricyclic heterocycle which consists of two benzene rings joined by a pyridine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassBenzoquinolines
Direct ParentAcridines
Alternative Parents
Substituents
  • Acridine
  • Aminoquinoline
  • 4-aminoquinoline
  • Aminopyridine
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Secondary alcohol
  • Azacycle
  • Alcohol
  • Organic nitrogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source

Route of exposure

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 Solubility0.27 g/LALOGPS
logP1.46ALOGPS
logP1.18ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)9.13ChemAxon
pKa (Strongest Basic)15.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area56.11 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity76.51 m³·mol⁻¹ChemAxon
Polarizability23.42 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+148.86131661259
DarkChem[M-H]-149.52931661259
DeepCCS[M+H]+150.64530932474
DeepCCS[M-H]-148.28730932474
DeepCCS[M-2H]-182.57830932474
DeepCCS[M+Na]+158.45830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
VelnacrineOC1CCCC2=C1C(=N)C1=CC=CC=C1N23372.1Standard polar33892256
VelnacrineOC1CCCC2=C1C(=N)C1=CC=CC=C1N22263.5Standard non polar33892256
VelnacrineOC1CCCC2=C1C(=N)C1=CC=CC=C1N22379.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Velnacrine,1TMS,isomer #1C[Si](C)(C)OC1CCCC2=C1C(=N)C1=CC=CC=C1[NH]22297.3Semi standard non polar33892256
Velnacrine,1TMS,isomer #1C[Si](C)(C)OC1CCCC2=C1C(=N)C1=CC=CC=C1[NH]22297.3Semi standard non polar33892256
Velnacrine,1TMS,isomer #2C[Si](C)(C)N=C1C2=C(CCCC2O)[NH]C2=CC=CC=C122374.2Semi standard non polar33892256
Velnacrine,1TMS,isomer #2C[Si](C)(C)N=C1C2=C(CCCC2O)[NH]C2=CC=CC=C122374.2Semi standard non polar33892256
Velnacrine,1TMS,isomer #3C[Si](C)(C)N1C2=C(C(=N)C3=CC=CC=C31)C(O)CCC22412.7Semi standard non polar33892256
Velnacrine,1TMS,isomer #3C[Si](C)(C)N1C2=C(C(=N)C3=CC=CC=C31)C(O)CCC22412.7Semi standard non polar33892256
Velnacrine,2TMS,isomer #1C[Si](C)(C)OC1CCCC2=C1C(=N)C1=CC=CC=C1N2[Si](C)(C)C2362.8Semi standard non polar33892256
Velnacrine,2TMS,isomer #1C[Si](C)(C)OC1CCCC2=C1C(=N)C1=CC=CC=C1N2[Si](C)(C)C2390.4Standard non polar33892256
Velnacrine,2TMS,isomer #2C[Si](C)(C)N=C1C2=C(CCCC2O[Si](C)(C)C)[NH]C2=CC=CC=C122302.5Semi standard non polar33892256
Velnacrine,2TMS,isomer #2C[Si](C)(C)N=C1C2=C(CCCC2O[Si](C)(C)C)[NH]C2=CC=CC=C122217.3Standard non polar33892256
Velnacrine,2TMS,isomer #3C[Si](C)(C)N=C1C2=C(CCCC2O)N([Si](C)(C)C)C2=CC=CC=C122426.4Semi standard non polar33892256
Velnacrine,2TMS,isomer #3C[Si](C)(C)N=C1C2=C(CCCC2O)N([Si](C)(C)C)C2=CC=CC=C122242.8Standard non polar33892256
Velnacrine,3TMS,isomer #1C[Si](C)(C)N=C1C2=C(CCCC2O[Si](C)(C)C)N([Si](C)(C)C)C2=CC=CC=C122355.6Semi standard non polar33892256
Velnacrine,3TMS,isomer #1C[Si](C)(C)N=C1C2=C(CCCC2O[Si](C)(C)C)N([Si](C)(C)C)C2=CC=CC=C122323.4Standard non polar33892256
Velnacrine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1CCCC2=C1C(=N)C1=CC=CC=C1[NH]22569.2Semi standard non polar33892256
Velnacrine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1CCCC2=C1C(=N)C1=CC=CC=C1[NH]22569.2Semi standard non polar33892256
Velnacrine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N=C1C2=C(CCCC2O)[NH]C2=CC=CC=C122599.6Semi standard non polar33892256
Velnacrine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N=C1C2=C(CCCC2O)[NH]C2=CC=CC=C122599.6Semi standard non polar33892256
Velnacrine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C2=C(C(=N)C3=CC=CC=C31)C(O)CCC22612.5Semi standard non polar33892256
Velnacrine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C2=C(C(=N)C3=CC=CC=C31)C(O)CCC22612.5Semi standard non polar33892256
Velnacrine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1CCCC2=C1C(=N)C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C2721.9Semi standard non polar33892256
Velnacrine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1CCCC2=C1C(=N)C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C2859.9Standard non polar33892256
Velnacrine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N=C1C2=C(CCCC2O[Si](C)(C)C(C)(C)C)[NH]C2=CC=CC=C122717.8Semi standard non polar33892256
Velnacrine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N=C1C2=C(CCCC2O[Si](C)(C)C(C)(C)C)[NH]C2=CC=CC=C122650.2Standard non polar33892256
Velnacrine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N=C1C2=C(CCCC2O)N([Si](C)(C)C(C)(C)C)C2=CC=CC=C122785.3Semi standard non polar33892256
Velnacrine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N=C1C2=C(CCCC2O)N([Si](C)(C)C(C)(C)C)C2=CC=CC=C122644.5Standard non polar33892256
Velnacrine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N=C1C2=C(CCCC2O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C2=CC=CC=C122888.6Semi standard non polar33892256
Velnacrine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N=C1C2=C(CCCC2O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C2=CC=CC=C122887.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Velnacrine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-0900000000-007e82dad188a69323bc2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Velnacrine GC-MS (1 TMS) - 70eV, Positivesplash10-00di-8490000000-eccc38bc318727532d442017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Velnacrine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Velnacrine 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 - Velnacrine 10V, Positive-QTOFsplash10-0002-0930000000-4a8149800ce026c3b6232017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Velnacrine 20V, Positive-QTOFsplash10-0002-0910000000-e8efd7a0d02825ff95802017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Velnacrine 40V, Positive-QTOFsplash10-0537-5900000000-7e2ef4ccefc1decea0642017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Velnacrine 10V, Negative-QTOFsplash10-03dj-0590000000-e0f105b4dee876c860fa2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Velnacrine 20V, Negative-QTOFsplash10-03dj-0690000000-b10c21efc96f9440b36f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Velnacrine 40V, Negative-QTOFsplash10-00lf-0900000000-9399e192046a227531ad2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Velnacrine 10V, Positive-QTOFsplash10-014i-0090000000-011b2ae80d93d1a6c9382021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Velnacrine 20V, Positive-QTOFsplash10-014j-0690000000-c23284675f6f2cfb54402021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Velnacrine 40V, Positive-QTOFsplash10-052b-0900000000-cfb4d0b4069dd7a865fb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Velnacrine 10V, Negative-QTOFsplash10-03di-0090000000-f58ebef816fc4a8a6e352021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Velnacrine 20V, Negative-QTOFsplash10-01ot-0950000000-c53679f8123f884bfb472021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Velnacrine 40V, Negative-QTOFsplash10-00l6-0900000000-29e14f7a70fa42796a6a2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
KNApSAcK IDNot Available
Chemspider ID3528
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3655
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