Page last updated: 2024-12-11

huperzine b

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Description

huperzine B: Chinese drug isolated from Huperzia serrata; structure given in first source; also isolated from Phlegmariurus fordii [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
HuperziagenusA plant genus of the family LYCOPODIACEAE. Members contain huperzine, one of the CHOLINESTERASE INHIBITORS.[MeSH]LycopodiaceaeThe club-moss plant family of the order Lycopodiales, class Lycopodiopsida, division Lycopodiophyta, subkingdom TRACHEOPHYTA. The common name of clubmoss applies to several genera of this family. Despite the name this is not one of the true mosses (BRYOPSIDA ).[MeSH]

Cross-References

ID SourceID
PubMed CID5462442
CHEMBL ID245079
CHEBI ID5770
SCHEMBL ID17272304
MeSH IDM0150307

Synonyms (34)

Synonym
lycodin-1(18h)-one, 8,15-didehydro-
hub ,
huperzine b
103548-82-9
C09866
1GPN ,
(-)-huperzine b
fordimine
bdbm50199518
CHEMBL245079 ,
S9219
DB03348
hupb
CHEBI:5770
Q-100033
SCHEMBL17272304
AKOS025312527
(4ar,5r,10br)-12-methyl-2,3,4,4a,5,6-hexahydro-1h-5,10b-prop[1]eno-1,7-phenanthrolin-8(7h)-one
(1r,9r,10r)-16-methyl-6,14-diazatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,16-trien-5-one
ammoniumhexachlororuthenate(iv)
HMS3886F20
HY-N2043
CS-0018533
CCG-267025
MS-23612
DTXSID30908464
12-methyl-2,3,4,4a,5,6-hexahydro-1h-5,10b-prop[1]eno-1,7-phenanthrolin-8-ol
195964-68-2
(4ar,5r,10br)-12-methyl-2,3,4,4a,5,6-hexahydro-1h-5,10b-prop[1]eno-1,7-phenanthrolin-8-ol
(4ar,5r,10br)-2,3,4,4a,5,6-hexahydro-12-methyl-1h-5,10b-propeno-1,7-phenanthrolin-8(7h)-one
DC3Z5425Y5
1h-5,10b-propeno-1,7-phenanthrolin-8(7h)-one, 2,3,4,4a,5,6-hexahydro-12-methyl-, (4ar,5r,10br)-
1h-5,10b-propeno-1,7-phenanthrolin-8(7h)-one, 2,3,4,4a,5,6-hexahydro-12-methyl-, [4ar-(4aalpha,5alpha,10balpha)]-
huperzine b, (-)-
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
phenanthrol
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (7)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, ACETYLCHOLINESTERASETetronarce californica (Pacific electric ray)Ki0.33400.33400.33400.3340AID977610
Chain A, ACETYLCHOLINESTERASETetronarce californica (Pacific electric ray)Ki0.33400.33400.33400.3340AID977610
AcetylcholinesteraseTetronarce californica (Pacific electric ray)Ki0.33400.00000.76714.3000AID404434
AcetylcholinesteraseHomo sapiens (human)IC50 (µMol)0.03000.00000.933210.0000AID31037
Acetylcholinesterase Bos taurus (cattle)Ki0.79400.00130.08930.7940AID30696
AcetylcholinesteraseRattus norvegicus (Norway rat)IC50 (µMol)19.30000.00020.52597.2000AID293034
Carboxylic ester hydrolase Rattus norvegicus (Norway rat)IC50 (µMol)227.00000.00041.48119.8700AID241762
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AcetylcholinesteraseHomo sapiens (human)EC50 (µMol)0.01900.01900.57551.1400AID73711
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (14)

Processvia Protein(s)Taxonomy
acetylcholine catabolic process in synaptic cleftAcetylcholinesteraseHomo sapiens (human)
regulation of receptor recyclingAcetylcholinesteraseHomo sapiens (human)
osteoblast developmentAcetylcholinesteraseHomo sapiens (human)
acetylcholine catabolic processAcetylcholinesteraseHomo sapiens (human)
cell adhesionAcetylcholinesteraseHomo sapiens (human)
nervous system developmentAcetylcholinesteraseHomo sapiens (human)
synapse assemblyAcetylcholinesteraseHomo sapiens (human)
receptor internalizationAcetylcholinesteraseHomo sapiens (human)
negative regulation of synaptic transmission, cholinergicAcetylcholinesteraseHomo sapiens (human)
amyloid precursor protein metabolic processAcetylcholinesteraseHomo sapiens (human)
positive regulation of protein secretionAcetylcholinesteraseHomo sapiens (human)
retina development in camera-type eyeAcetylcholinesteraseHomo sapiens (human)
acetylcholine receptor signaling pathwayAcetylcholinesteraseHomo sapiens (human)
positive regulation of cold-induced thermogenesisAcetylcholinesteraseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
amyloid-beta bindingAcetylcholinesteraseHomo sapiens (human)
acetylcholinesterase activityAcetylcholinesteraseHomo sapiens (human)
cholinesterase activityAcetylcholinesteraseHomo sapiens (human)
protein bindingAcetylcholinesteraseHomo sapiens (human)
collagen bindingAcetylcholinesteraseHomo sapiens (human)
hydrolase activityAcetylcholinesteraseHomo sapiens (human)
serine hydrolase activityAcetylcholinesteraseHomo sapiens (human)
acetylcholine bindingAcetylcholinesteraseHomo sapiens (human)
protein homodimerization activityAcetylcholinesteraseHomo sapiens (human)
laminin bindingAcetylcholinesteraseHomo sapiens (human)
amyloid-beta bindingAcetylcholinesterase Bos taurus (cattle)
protein bindingAcetylcholinesterase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (13)

Processvia Protein(s)Taxonomy
extracellular regionAcetylcholinesteraseHomo sapiens (human)
basement membraneAcetylcholinesteraseHomo sapiens (human)
extracellular spaceAcetylcholinesteraseHomo sapiens (human)
nucleusAcetylcholinesteraseHomo sapiens (human)
Golgi apparatusAcetylcholinesteraseHomo sapiens (human)
plasma membraneAcetylcholinesteraseHomo sapiens (human)
cell surfaceAcetylcholinesteraseHomo sapiens (human)
membraneAcetylcholinesteraseHomo sapiens (human)
neuromuscular junctionAcetylcholinesteraseHomo sapiens (human)
synaptic cleftAcetylcholinesteraseHomo sapiens (human)
synapseAcetylcholinesteraseHomo sapiens (human)
perinuclear region of cytoplasmAcetylcholinesteraseHomo sapiens (human)
side of membraneAcetylcholinesteraseHomo sapiens (human)
synapseAcetylcholinesterase Bos taurus (cattle)
side of membraneAcetylcholinesterase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (18)

Assay IDTitleYearJournalArticle
AID1300690Inhibition of ACAT in human monocyte derived macrophages assessed as reduction in foam cell formation by measuring acetyl LDL-induced cholesterol ester accumulation at 30 uM after 24 hrs in presence of cholesteryl-[3H]oleate2016Bioorganic & medicinal chemistry letters, 06-01, Volume: 26, Issue:11
Serralongamines B-D, three new Lycopodium alkaloids from Lycopodium serratum var. longipetiolatum, and their inhibitory effects on foam cell formation in macrophages.
AID47966Effective dose required for the reversal of vecuronium-induced neuromuscular block in-vivo in Chloaralose anaesthetised cats2002Bioorganic & medicinal chemistry letters, Sep-16, Volume: 12, Issue:18
Quaternary salts of E2020 analogues as acetylcholinesterase inhibitors for the reversal of neuromuscular block.
AID293035Inhibition of BuChE in rat serum2007Bioorganic & medicinal chemistry, Feb-01, Volume: 15, Issue:3
Study on dual-site inhibitors of acetylcholinesterase: Highly potent derivatives of bis- and bifunctional huperzine B.
AID49085Change in response to vagal stimulation was detected in anaesthetised cats on administration of the compound2002Bioorganic & medicinal chemistry letters, Sep-16, Volume: 12, Issue:18
Quaternary salts of E2020 analogues as acetylcholinesterase inhibitors for the reversal of neuromuscular block.
AID73711In vitro reversal of vecuronium-induced neuromuscular block in guinea pig hemi-diaphragm.2002Bioorganic & medicinal chemistry letters, Sep-16, Volume: 12, Issue:18
Quaternary salts of E2020 analogues as acetylcholinesterase inhibitors for the reversal of neuromuscular block.
AID244395Selectivity index for acetylcholinesterase and butyrylcholinesterase as ratio of IC502005Journal of medicinal chemistry, Feb-10, Volume: 48, Issue:3
Bis-huperzine B: highly potent and selective acetylcholinesterase inhibitors.
AID31037In vitro inhibition of human recombinant AChE.2002Bioorganic & medicinal chemistry letters, Sep-16, Volume: 12, Issue:18
Quaternary salts of E2020 analogues as acetylcholinesterase inhibitors for the reversal of neuromuscular block.
AID404434Inhibition of Torpedo californica AChE2008Journal of medicinal chemistry, Jun-12, Volume: 51, Issue:11
Exploiting protein fluctuations at the active-site gorge of human cholinesterases: further optimization of the design strategy to develop extremely potent inhibitors.
AID293036Selectivity ratio of IC50 for rat BuChE to rat IC50 for AchE2007Bioorganic & medicinal chemistry, Feb-01, Volume: 15, Issue:3
Study on dual-site inhibitors of acetylcholinesterase: Highly potent derivatives of bis- and bifunctional huperzine B.
AID293034Inhibition of AChE in rat cortex at pH 52007Bioorganic & medicinal chemistry, Feb-01, Volume: 15, Issue:3
Study on dual-site inhibitors of acetylcholinesterase: Highly potent derivatives of bis- and bifunctional huperzine B.
AID30696Inhibitory constant against fetal bovine serum (FBS) acetylcholinesterase2002Bioorganic & medicinal chemistry letters, Jun-03, Volume: 12, Issue:11
Synthesis of more potent analogues of the acetylcholinesterase inhibitor, huperzine B.
AID241762Inhibitory concentration against butyrylcholinesterase of rat serum2005Journal of medicinal chemistry, Feb-10, Volume: 48, Issue:3
Bis-huperzine B: highly potent and selective acetylcholinesterase inhibitors.
AID48700Mean arterial pressure change was detected in anaesthetised cats on administration of the compound2002Bioorganic & medicinal chemistry letters, Sep-16, Volume: 12, Issue:18
Quaternary salts of E2020 analogues as acetylcholinesterase inhibitors for the reversal of neuromuscular block.
AID48158Change in heart rate was detected in anaesthetised cats on administration of the compound2002Bioorganic & medicinal chemistry letters, Sep-16, Volume: 12, Issue:18
Quaternary salts of E2020 analogues as acetylcholinesterase inhibitors for the reversal of neuromuscular block.
AID48731Maximum reversal of vecuronium-induced neuromuscular block in-vivo in anaesthetised cats2002Bioorganic & medicinal chemistry letters, Sep-16, Volume: 12, Issue:18
Quaternary salts of E2020 analogues as acetylcholinesterase inhibitors for the reversal of neuromuscular block.
AID242054Inhibitory concentration against acetylcholinesterase of rat cortex homogenate2005Journal of medicinal chemistry, Feb-10, Volume: 48, Issue:3
Bis-huperzine B: highly potent and selective acetylcholinesterase inhibitors.
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB2002Biochemistry, Sep-03, Volume: 41, Issue:35
X-ray structures of Torpedo californica acetylcholinesterase complexed with (+)-huperzine A and (-)-huperzine B: structural evidence for an active site rearrangement.
AID1811Experimentally measured binding affinity data derived from PDB2002Biochemistry, Sep-03, Volume: 41, Issue:35
X-ray structures of Torpedo californica acetylcholinesterase complexed with (+)-huperzine A and (-)-huperzine B: structural evidence for an active site rearrangement.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (31)

TimeframeStudies, This Drug (%)All Drugs %
pre-19906 (19.35)18.7374
1990's2 (6.45)18.2507
2000's13 (41.94)29.6817
2010's9 (29.03)24.3611
2020's1 (3.23)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 19.13

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index19.13 (24.57)
Research Supply Index3.50 (2.92)
Research Growth Index4.86 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index3.00 (0.95)

This Compound (19.13)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (3.13%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other31 (96.88%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]