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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-04 18:53:44 UTC
Update Date2023-02-21 17:30:11 UTC
HMDB IDHMDB0060703
Secondary Accession Numbers
  • HMDB60703
Metabolite Identification
Common Name1-Amino-3-hydroxymethyl-5-methyl-adamantane
Description1-Amino-3-hydroxymethyl-5-methyl-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?1677000611
SynonymsNot Available
Chemical FormulaC12H21NO
Average Molecular Weight195.3012
Monoisotopic Molecular Weight195.162314299
IUPAC Name(3-amino-5-methyladamantan-1-yl)methanol
Traditional Name(3-amino-5-methyladamantan-1-yl)methanol
CAS Registry NumberNot Available
SMILES
CC12CC3CC(N)(C1)CC(CO)(C3)C2
InChI Identifier
InChI=1S/C12H21NO/c1-10-2-9-3-11(5-10,8-14)7-12(13,4-9)6-10/h9,14H,2-8,13H2,1H3
InChI KeyYANGLOGEEOBUMT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentPrimary alcohols
Alternative Parents
Substituents
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • 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 Solubility0.92 g/LALOGPS
logP1.46ALOGPS
logP0.79ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)15.11ChemAxon
pKa (Strongest Basic)10.39ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area46.25 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity56.26 m³·mol⁻¹ChemAxon
Polarizability22.76 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]+142.52431661259
DarkChem[M-H]-139.28431661259
DeepCCS[M-2H]-191.25530932474
DeepCCS[M+Na]+166.73330932474
AllCCS[M+H]+145.632859911
AllCCS[M+H-H2O]+141.832859911
AllCCS[M+NH4]+149.132859911
AllCCS[M+Na]+150.232859911
AllCCS[M-H]-149.232859911
AllCCS[M+Na-2H]-149.632859911
AllCCS[M+HCOO]-150.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-Amino-3-hydroxymethyl-5-methyl-adamantaneCC12CC3CC(N)(C1)CC(CO)(C3)C22383.5Standard polar33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantaneCC12CC3CC(N)(C1)CC(CO)(C3)C21630.4Standard non polar33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantaneCC12CC3CC(N)(C1)CC(CO)(C3)C21601.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1-Amino-3-hydroxymethyl-5-methyl-adamantane,1TMS,isomer #1CC12CC3CC(N)(C1)CC(CO[Si](C)(C)C)(C3)C21654.4Semi standard non polar33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,1TMS,isomer #2CC12CC3CC(CO)(C1)CC(N[Si](C)(C)C)(C3)C21872.5Semi standard non polar33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,2TMS,isomer #1CC12CC3CC(CO[Si](C)(C)C)(C1)CC(N[Si](C)(C)C)(C3)C21823.5Semi standard non polar33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,2TMS,isomer #1CC12CC3CC(CO[Si](C)(C)C)(C1)CC(N[Si](C)(C)C)(C3)C21888.7Standard non polar33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,2TMS,isomer #1CC12CC3CC(CO[Si](C)(C)C)(C1)CC(N[Si](C)(C)C)(C3)C22239.1Standard polar33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,2TMS,isomer #2CC12CC3CC(CO)(C1)CC(N([Si](C)(C)C)[Si](C)(C)C)(C3)C21966.6Semi standard non polar33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,2TMS,isomer #2CC12CC3CC(CO)(C1)CC(N([Si](C)(C)C)[Si](C)(C)C)(C3)C22004.5Standard non polar33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,2TMS,isomer #2CC12CC3CC(CO)(C1)CC(N([Si](C)(C)C)[Si](C)(C)C)(C3)C22278.2Standard polar33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,3TMS,isomer #1CC12CC3CC(CO[Si](C)(C)C)(C1)CC(N([Si](C)(C)C)[Si](C)(C)C)(C3)C21975.4Semi standard non polar33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,3TMS,isomer #1CC12CC3CC(CO[Si](C)(C)C)(C1)CC(N([Si](C)(C)C)[Si](C)(C)C)(C3)C22061.8Standard non polar33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,3TMS,isomer #1CC12CC3CC(CO[Si](C)(C)C)(C1)CC(N([Si](C)(C)C)[Si](C)(C)C)(C3)C22146.3Standard polar33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,1TBDMS,isomer #1CC12CC3CC(N)(C1)CC(CO[Si](C)(C)C(C)(C)C)(C3)C21943.1Semi standard non polar33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,1TBDMS,isomer #2CC12CC3CC(CO)(C1)CC(N[Si](C)(C)C(C)(C)C)(C3)C22121.3Semi standard non polar33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,2TBDMS,isomer #1CC12CC3CC(CO[Si](C)(C)C(C)(C)C)(C1)CC(N[Si](C)(C)C(C)(C)C)(C3)C22289.6Semi standard non polar33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,2TBDMS,isomer #1CC12CC3CC(CO[Si](C)(C)C(C)(C)C)(C1)CC(N[Si](C)(C)C(C)(C)C)(C3)C22297.7Standard non polar33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,2TBDMS,isomer #1CC12CC3CC(CO[Si](C)(C)C(C)(C)C)(C1)CC(N[Si](C)(C)C(C)(C)C)(C3)C22500.3Standard polar33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,2TBDMS,isomer #2CC12CC3CC(CO)(C1)CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C3)C22390.6Semi standard non polar33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,2TBDMS,isomer #2CC12CC3CC(CO)(C1)CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C3)C22427.4Standard non polar33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,2TBDMS,isomer #2CC12CC3CC(CO)(C1)CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C3)C22481.8Standard polar33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,3TBDMS,isomer #1CC12CC3CC(CO[Si](C)(C)C(C)(C)C)(C1)CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C3)C22611.0Semi standard non polar33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,3TBDMS,isomer #1CC12CC3CC(CO[Si](C)(C)C(C)(C)C)(C1)CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C3)C22674.4Standard non polar33892256
1-Amino-3-hydroxymethyl-5-methyl-adamantane,3TBDMS,isomer #1CC12CC3CC(CO[Si](C)(C)C(C)(C)C)(C1)CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C3)C22441.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1-Amino-3-hydroxymethyl-5-methyl-adamantane GC-MS (Non-derivatized) - 70eV, Positivesplash10-03gj-0900000000-239a470b7a7f717f372a2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Amino-3-hydroxymethyl-5-methyl-adamantane GC-MS (1 TMS) - 70eV, Positivesplash10-0umi-9640000000-6c1f4b68b351929b109e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Amino-3-hydroxymethyl-5-methyl-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 - 1-Amino-3-hydroxymethyl-5-methyl-adamantane 10V, Positive-QTOFsplash10-004j-0900000000-7c3f69c532e70bc656442016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Amino-3-hydroxymethyl-5-methyl-adamantane 20V, Positive-QTOFsplash10-01t9-0900000000-c02fade9e295b01b60642016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Amino-3-hydroxymethyl-5-methyl-adamantane 40V, Positive-QTOFsplash10-03di-0900000000-565d74909c0bf810f6972016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Amino-3-hydroxymethyl-5-methyl-adamantane 10V, Negative-QTOFsplash10-0006-0900000000-ffc3c256cf08fdf0c59a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Amino-3-hydroxymethyl-5-methyl-adamantane 20V, Negative-QTOFsplash10-01r6-0900000000-fd832ea7f1d7b2f28ace2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Amino-3-hydroxymethyl-5-methyl-adamantane 40V, Negative-QTOFsplash10-03dj-0900000000-adae6857a9872ccb9da22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Amino-3-hydroxymethyl-5-methyl-adamantane 10V, Positive-QTOFsplash10-0002-0900000000-0e0b6e8e50016270ad142021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Amino-3-hydroxymethyl-5-methyl-adamantane 20V, Positive-QTOFsplash10-002b-0900000000-7a75a3560ff1e26fd6252021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Amino-3-hydroxymethyl-5-methyl-adamantane 40V, Positive-QTOFsplash10-004j-0900000000-e5f85a05e8d59e580be72021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Amino-3-hydroxymethyl-5-methyl-adamantane 10V, Negative-QTOFsplash10-0006-0900000000-7656e1a7f93372378cd42021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Amino-3-hydroxymethyl-5-methyl-adamantane 20V, Negative-QTOFsplash10-0006-0900000000-7656e1a7f93372378cd42021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Amino-3-hydroxymethyl-5-methyl-adamantane 40V, Negative-QTOFsplash10-0006-0900000000-7656e1a7f93372378cd42021-10-12Wishart 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 Compound2850520
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