Huperzine A (CHEM018705)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:28:00 UTC
Update Date2016-11-09 01:15:51 UTC
Accession NumberCHEM018705
Identification
Common NameHuperzine A
ClassSmall Molecule
DescriptionHuperzine A, is a naturally occurring sesquiterpene alkaloid found in the extracts of the firmoss Huperzia serrata. The botanical has been used in China for centuries for the treatment of swelling, fever and blood disorders. Recently in clinical trials in China, it has demonstrated neuroprotective effects. It is currently being investigated as a possible treatment for diseases characterized by neurodegeneration – particularly Alzheimer’s disease.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-Huperazine aChEBI
(-)-SelagineChEBI
SelagineChEBI
Huperzine a, (5alpha,9beta,11Z)-(-)-isomerMeSH
Chemical FormulaC15H18N2O
Average Molecular Mass242.316 g/mol
Monoisotopic Mass242.142 g/mol
CAS Registry Number102518-79-6
IUPAC Name(1R,9R,13E)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0²,⁷]trideca-2(7),3,10-trien-5-one
Traditional Namehuperaine A
SMILES[H][C@@]12CC3=C(C=CC(=O)N3)[C@@](N)(CC(C)=C1)\C2=C\C
InChI IdentifierInChI=1S/C15H18N2O/c1-3-11-10-6-9(2)8-15(11,16)12-4-5-14(18)17-13(12)7-10/h3-6,10H,7-8,16H2,1-2H3,(H,17,18)/b11-3+/t10-,15+/m0/s1
InChI KeyZRJBHWIHUMBLCN-YQEJDHNASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as quinolones and derivatives. Quinolones and derivatives are compounds containing a quinoline moiety which bears a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassQuinolones and derivatives
Direct ParentQuinolones and derivatives
Alternative Parents
Substituents
  • Quinolone
  • Pyridinone
  • Aralkylamine
  • Pyridine
  • Heteroaromatic compound
  • Lactam
  • Azacycle
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.17 g/LALOGPS
logP1.78ALOGPS
logP0.62ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)11.11ChemAxon
pKa (Strongest Basic)9.09ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area55.12 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity75.8 m³·mol⁻¹ChemAxon
Polarizability26.87 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0090000000-81b00566e7122478dbcfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-0190000000-50d78cb42c6b30c601e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06si-3950000000-3ce310573fb34eed1106Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-6e36a078ff83d4350ecdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-0090000000-a0decd3bed2e15aa4ca6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9670000000-2ee5721f5772417f14e3Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB04864
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkHuperzine_A
Chemspider IDNot Available
ChEBI ID78330
PubChem Compound ID854026
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12895686
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23306162
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24129696
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24190328
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24299147
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=24332448
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24639880