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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-04 18:56:10 UTC
Update Date2023-02-21 17:30:13 UTC
HMDB IDHMDB0060738
Secondary Accession Numbers
  • HMDB60738
Metabolite Identification
Common Name3-Amino-1-hydroxy-5,7-dimethyl-adamantane
Description3-Amino-1-hydroxy-5,7-dimethyl-adamantane is a metabolite of memantine. Memantine is the first in a novel class of Alzheimer's disease medications acting on the glutamatergic system by blocking NMDA glutamate receptors. It was first synthesized by Eli Lilly and Company in 1968. Memantine is marketed under the brands Axura and Akatinol by Merz, Namenda by Forest, Ebixa and Abixa by Lundbeck and Memox by Unipharm. Despite years of research, there is little evidence of effect in mild to moderate Alzheimer's disease. (Wikipedia)
Structure
Data?1677000613
SynonymsNot Available
Chemical FormulaC12H21NO
Average Molecular Weight195.3012
Monoisotopic Molecular Weight195.162314299
IUPAC Name3-amino-5,7-dimethyladamantan-1-ol
Traditional Name3-amino-5,7-dimethyladamantan-1-ol
CAS Registry NumberNot Available
SMILES
CC12CC3(C)CC(N)(C1)CC(O)(C2)C3
InChI Identifier
InChI=1S/C12H21NO/c1-9-3-10(2)5-11(13,4-9)8-12(14,6-9)7-10/h14H,3-8,13H2,1-2H3
InChI KeyHSRBAOBUCHCHTQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentTertiary alcohols
Alternative Parents
Substituents
  • Tertiary alcohol
  • Cyclic alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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 Solubility0.99 g/LALOGPS
logP1.5ALOGPS
logP0.68ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)14.69ChemAxon
pKa (Strongest Basic)10.32ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area46.25 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity56.12 m³·mol⁻¹ChemAxon
Polarizability22.68 ųChemAxon
Number of Rings3ChemAxon
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]+147.46231661259
DarkChem[M-H]-142.29431661259
DeepCCS[M-2H]-184.79930932474
DeepCCS[M+Na]+159.58130932474
AllCCS[M+H]+145.232859911
AllCCS[M+H-H2O]+141.332859911
AllCCS[M+NH4]+148.832859911
AllCCS[M+Na]+149.832859911
AllCCS[M-H]-149.032859911
AllCCS[M+Na-2H]-149.432859911
AllCCS[M+HCOO]-150.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Amino-1-hydroxy-5,7-dimethyl-adamantaneCC12CC3(C)CC(N)(C1)CC(O)(C2)C32126.2Standard polar33892256
3-Amino-1-hydroxy-5,7-dimethyl-adamantaneCC12CC3(C)CC(N)(C1)CC(O)(C2)C31545.1Standard non polar33892256
3-Amino-1-hydroxy-5,7-dimethyl-adamantaneCC12CC3(C)CC(N)(C1)CC(O)(C2)C31499.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Amino-1-hydroxy-5,7-dimethyl-adamantane,1TMS,isomer #1CC12CC3(C)CC(N)(C1)CC(O[Si](C)(C)C)(C2)C31524.0Semi standard non polar33892256
3-Amino-1-hydroxy-5,7-dimethyl-adamantane,1TMS,isomer #2CC12CC3(C)CC(O)(C1)CC(N[Si](C)(C)C)(C2)C31749.5Semi standard non polar33892256
3-Amino-1-hydroxy-5,7-dimethyl-adamantane,2TMS,isomer #1CC12CC3(C)CC(N[Si](C)(C)C)(C1)CC(O[Si](C)(C)C)(C2)C31695.3Semi standard non polar33892256
3-Amino-1-hydroxy-5,7-dimethyl-adamantane,2TMS,isomer #1CC12CC3(C)CC(N[Si](C)(C)C)(C1)CC(O[Si](C)(C)C)(C2)C31820.4Standard non polar33892256
3-Amino-1-hydroxy-5,7-dimethyl-adamantane,2TMS,isomer #1CC12CC3(C)CC(N[Si](C)(C)C)(C1)CC(O[Si](C)(C)C)(C2)C32204.5Standard polar33892256
3-Amino-1-hydroxy-5,7-dimethyl-adamantane,2TMS,isomer #2CC12CC3(C)CC(O)(C1)CC(N([Si](C)(C)C)[Si](C)(C)C)(C2)C31843.2Semi standard non polar33892256
3-Amino-1-hydroxy-5,7-dimethyl-adamantane,2TMS,isomer #2CC12CC3(C)CC(O)(C1)CC(N([Si](C)(C)C)[Si](C)(C)C)(C2)C31952.0Standard non polar33892256
3-Amino-1-hydroxy-5,7-dimethyl-adamantane,2TMS,isomer #2CC12CC3(C)CC(O)(C1)CC(N([Si](C)(C)C)[Si](C)(C)C)(C2)C32095.1Standard polar33892256
3-Amino-1-hydroxy-5,7-dimethyl-adamantane,3TMS,isomer #1CC12CC3(C)CC(O[Si](C)(C)C)(C1)CC(N([Si](C)(C)C)[Si](C)(C)C)(C2)C31876.3Semi standard non polar33892256
3-Amino-1-hydroxy-5,7-dimethyl-adamantane,3TMS,isomer #1CC12CC3(C)CC(O[Si](C)(C)C)(C1)CC(N([Si](C)(C)C)[Si](C)(C)C)(C2)C32003.3Standard non polar33892256
3-Amino-1-hydroxy-5,7-dimethyl-adamantane,3TMS,isomer #1CC12CC3(C)CC(O[Si](C)(C)C)(C1)CC(N([Si](C)(C)C)[Si](C)(C)C)(C2)C32087.0Standard polar33892256
3-Amino-1-hydroxy-5,7-dimethyl-adamantane,1TBDMS,isomer #1CC12CC3(C)CC(N)(C1)CC(O[Si](C)(C)C(C)(C)C)(C2)C31847.9Semi standard non polar33892256
3-Amino-1-hydroxy-5,7-dimethyl-adamantane,1TBDMS,isomer #2CC12CC3(C)CC(O)(C1)CC(N[Si](C)(C)C(C)(C)C)(C2)C32029.1Semi standard non polar33892256
3-Amino-1-hydroxy-5,7-dimethyl-adamantane,2TBDMS,isomer #1CC12CC3(C)CC(N[Si](C)(C)C(C)(C)C)(C1)CC(O[Si](C)(C)C(C)(C)C)(C2)C32191.3Semi standard non polar33892256
3-Amino-1-hydroxy-5,7-dimethyl-adamantane,2TBDMS,isomer #1CC12CC3(C)CC(N[Si](C)(C)C(C)(C)C)(C1)CC(O[Si](C)(C)C(C)(C)C)(C2)C32207.5Standard non polar33892256
3-Amino-1-hydroxy-5,7-dimethyl-adamantane,2TBDMS,isomer #1CC12CC3(C)CC(N[Si](C)(C)C(C)(C)C)(C1)CC(O[Si](C)(C)C(C)(C)C)(C2)C32439.6Standard polar33892256
3-Amino-1-hydroxy-5,7-dimethyl-adamantane,2TBDMS,isomer #2CC12CC3(C)CC(O)(C1)CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C2)C32312.4Semi standard non polar33892256
3-Amino-1-hydroxy-5,7-dimethyl-adamantane,2TBDMS,isomer #2CC12CC3(C)CC(O)(C1)CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C2)C32346.8Standard non polar33892256
3-Amino-1-hydroxy-5,7-dimethyl-adamantane,2TBDMS,isomer #2CC12CC3(C)CC(O)(C1)CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C2)C32328.0Standard polar33892256
3-Amino-1-hydroxy-5,7-dimethyl-adamantane,3TBDMS,isomer #1CC12CC3(C)CC(O[Si](C)(C)C(C)(C)C)(C1)CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C2)C32521.5Semi standard non polar33892256
3-Amino-1-hydroxy-5,7-dimethyl-adamantane,3TBDMS,isomer #1CC12CC3(C)CC(O[Si](C)(C)C(C)(C)C)(C1)CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C2)C32575.2Standard non polar33892256
3-Amino-1-hydroxy-5,7-dimethyl-adamantane,3TBDMS,isomer #1CC12CC3(C)CC(O[Si](C)(C)C(C)(C)C)(C1)CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C2)C32365.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Amino-1-hydroxy-5,7-dimethyl-adamantane GC-MS (Non-derivatized) - 70eV, Positivesplash10-004j-0900000000-0de57ed45fedb5df1bbb2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Amino-1-hydroxy-5,7-dimethyl-adamantane GC-MS (1 TMS) - 70eV, Positivesplash10-0fmi-9250000000-d240c86a88cba3dfd75a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Amino-1-hydroxy-5,7-dimethyl-adamantane 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 - 3-Amino-1-hydroxy-5,7-dimethyl-adamantane 10V, Positive-QTOFsplash10-004j-0900000000-f14a75d3c6375f6877552016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Amino-1-hydroxy-5,7-dimethyl-adamantane 20V, Positive-QTOFsplash10-004j-0900000000-c6a74a67de98daf1499d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Amino-1-hydroxy-5,7-dimethyl-adamantane 40V, Positive-QTOFsplash10-03di-0900000000-81538db36c1c7485b0452016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Amino-1-hydroxy-5,7-dimethyl-adamantane 10V, Negative-QTOFsplash10-0006-0900000000-f389e57b70398bd3a32c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Amino-1-hydroxy-5,7-dimethyl-adamantane 20V, Negative-QTOFsplash10-002f-0900000000-0c50e5b1ea10b8fb4c2d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Amino-1-hydroxy-5,7-dimethyl-adamantane 40V, Negative-QTOFsplash10-002f-0900000000-51b17f9d72633f50a66e2016-08-03Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3382167
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