Page last updated: 2024-12-07

1,2,3,4-tetrahydroxy-nor-tropane

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Description

calystegine B(2): RN given for (2-endo,3-exo,4-endo)-isomer; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID124434
CHEMBL ID526330
SCHEMBL ID2435745
MeSH IDM0251762

Synonyms (28)

Synonym
(1s,2r,3s,4r,5s)-8-azabicyclo[3.2.1]octane-1,2,3,4-tetrol
CGB ,
cid124434
DB04658
2CBV
8-aza-bicyclo[3.2.1]octane-1,2,3,4-tetraol
127E4C51-F774-4783-BF04-584E35802638
CHEMBL526330
bdbm36389
8-aza-bicyclo[3.2.1]octane-1,2,3,4-tetraol, 14
(1r,2s,3r,4s,5r)-8-azabicyclo[3.2.1]octane-1,2,3,4-tetrol
calystegine b(2)
1,2,3,4-tetrahydroxy-nor-tropane
calystegine b(3)
8-azabicyclo(3.2.1)octane-1,2,3,4-tetrol, (2-endo,3-exo,4-endo)-
(2-endo,3-exo,4-endo)-8-azabicyclo(3.2.1)octane-1,2,3,4-tetrol
calystegine b(4)
SCHEMBL2435745
W-200999
Q27095407
8-azabicyclo[3.2.1]octane-1,2,3,4-tetrol, (1r,2s,3r,4s,5r)-
FS-6670
2-epicalystegine b3
7LZN33KW88
(+)-calystegin b2
(+)-calystegine b2
8-azabicyclo[3.2.1]octane-1,2,3,4-tetrol, [1r-(2-endo,3-exo,4-endo)]-
calystegine b2, (+)-
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Lysosomal acid glucosylceramidaseHomo sapiens (human)IC50 (µMol)3.05000.03002.35898.8000AID1125774; AID579723
Lysosomal acid glucosylceramidaseHomo sapiens (human)Ki3.80000.02101.52886.3000AID1125775
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (52)

Processvia Protein(s)Taxonomy
mitochondrion organizationLysosomal acid glucosylceramidaseHomo sapiens (human)
neuron projection developmentLysosomal acid glucosylceramidaseHomo sapiens (human)
glucosylceramide catabolic processLysosomal acid glucosylceramidaseHomo sapiens (human)
autophagyLysosomal acid glucosylceramidaseHomo sapiens (human)
lysosome organizationLysosomal acid glucosylceramidaseHomo sapiens (human)
cholesterol metabolic processLysosomal acid glucosylceramidaseHomo sapiens (human)
determination of adult lifespanLysosomal acid glucosylceramidaseHomo sapiens (human)
cellular response to starvationLysosomal acid glucosylceramidaseHomo sapiens (human)
response to pHLysosomal acid glucosylceramidaseHomo sapiens (human)
microglia differentiationLysosomal acid glucosylceramidaseHomo sapiens (human)
regulation of macroautophagyLysosomal acid glucosylceramidaseHomo sapiens (human)
antigen processing and presentationLysosomal acid glucosylceramidaseHomo sapiens (human)
lipid storageLysosomal acid glucosylceramidaseHomo sapiens (human)
cerebellar Purkinje cell layer formationLysosomal acid glucosylceramidaseHomo sapiens (human)
pyramidal neuron differentiationLysosomal acid glucosylceramidaseHomo sapiens (human)
respiratory electron transport chainLysosomal acid glucosylceramidaseHomo sapiens (human)
termination of signal transductionLysosomal acid glucosylceramidaseHomo sapiens (human)
lipid glycosylationLysosomal acid glucosylceramidaseHomo sapiens (human)
negative regulation of protein-containing complex assemblyLysosomal acid glucosylceramidaseHomo sapiens (human)
regulation of TOR signalingLysosomal acid glucosylceramidaseHomo sapiens (human)
positive regulation of proteasomal ubiquitin-dependent protein catabolic processLysosomal acid glucosylceramidaseHomo sapiens (human)
negative regulation of interleukin-6 productionLysosomal acid glucosylceramidaseHomo sapiens (human)
T cell differentiation in thymusLysosomal acid glucosylceramidaseHomo sapiens (human)
response to testosteroneLysosomal acid glucosylceramidaseHomo sapiens (human)
positive regulation of protein dephosphorylationLysosomal acid glucosylceramidaseHomo sapiens (human)
proteasome-mediated ubiquitin-dependent protein catabolic processLysosomal acid glucosylceramidaseHomo sapiens (human)
positive regulation of protein-containing complex disassemblyLysosomal acid glucosylceramidaseHomo sapiens (human)
negative regulation of MAP kinase activityLysosomal acid glucosylceramidaseHomo sapiens (human)
negative regulation of neuron apoptotic processLysosomal acid glucosylceramidaseHomo sapiens (human)
response to estrogenLysosomal acid glucosylceramidaseHomo sapiens (human)
sphingosine biosynthetic processLysosomal acid glucosylceramidaseHomo sapiens (human)
ceramide biosynthetic processLysosomal acid glucosylceramidaseHomo sapiens (human)
cell maturationLysosomal acid glucosylceramidaseHomo sapiens (human)
brain morphogenesisLysosomal acid glucosylceramidaseHomo sapiens (human)
homeostasis of number of cellsLysosomal acid glucosylceramidaseHomo sapiens (human)
negative regulation of inflammatory responseLysosomal acid glucosylceramidaseHomo sapiens (human)
neuromuscular processLysosomal acid glucosylceramidaseHomo sapiens (human)
neuron apoptotic processLysosomal acid glucosylceramidaseHomo sapiens (human)
establishment of skin barrierLysosomal acid glucosylceramidaseHomo sapiens (human)
microglial cell proliferationLysosomal acid glucosylceramidaseHomo sapiens (human)
motor behaviorLysosomal acid glucosylceramidaseHomo sapiens (human)
cellular response to tumor necrosis factorLysosomal acid glucosylceramidaseHomo sapiens (human)
hematopoietic stem cell proliferationLysosomal acid glucosylceramidaseHomo sapiens (human)
response to dexamethasoneLysosomal acid glucosylceramidaseHomo sapiens (human)
lymphocyte migrationLysosomal acid glucosylceramidaseHomo sapiens (human)
response to thyroid hormoneLysosomal acid glucosylceramidaseHomo sapiens (human)
beta-glucoside catabolic processLysosomal acid glucosylceramidaseHomo sapiens (human)
positive regulation of protein lipidationLysosomal acid glucosylceramidaseHomo sapiens (human)
positive regulation of neuronal action potentialLysosomal acid glucosylceramidaseHomo sapiens (human)
positive regulation of autophagy of mitochondrion in response to mitochondrial depolarizationLysosomal acid glucosylceramidaseHomo sapiens (human)
autophagosome organizationLysosomal acid glucosylceramidaseHomo sapiens (human)
regulation of lysosomal protein catabolic processLysosomal acid glucosylceramidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
galactosylceramidase activityLysosomal acid glucosylceramidaseHomo sapiens (human)
glucosylceramidase activityLysosomal acid glucosylceramidaseHomo sapiens (human)
signaling receptor bindingLysosomal acid glucosylceramidaseHomo sapiens (human)
scavenger receptor bindingLysosomal acid glucosylceramidaseHomo sapiens (human)
protein bindingLysosomal acid glucosylceramidaseHomo sapiens (human)
glucosyltransferase activityLysosomal acid glucosylceramidaseHomo sapiens (human)
steryl-beta-glucosidase activityLysosomal acid glucosylceramidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

Processvia Protein(s)Taxonomy
lysosomeLysosomal acid glucosylceramidaseHomo sapiens (human)
lysosomal membraneLysosomal acid glucosylceramidaseHomo sapiens (human)
endoplasmic reticulumLysosomal acid glucosylceramidaseHomo sapiens (human)
Golgi apparatusLysosomal acid glucosylceramidaseHomo sapiens (human)
trans-Golgi networkLysosomal acid glucosylceramidaseHomo sapiens (human)
lysosomal lumenLysosomal acid glucosylceramidaseHomo sapiens (human)
extracellular exosomeLysosomal acid glucosylceramidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (20)

Assay IDTitleYearJournalArticle
AID355080Antibacterial activity against Cac gene-deficient Rhizobium meliloti RCR20111996Journal of natural products, Dec, Volume: 59, Issue:12
Biological activities of the nortropane alkaloid, calystegine B2, and analogs: structure-function relationships.
AID355085Allellopathic effect in Medicago sativa assessed as reduction in root elongation at 5 mM after 19 hrs1996Journal of natural products, Dec, Volume: 59, Issue:12
Biological activities of the nortropane alkaloid, calystegine B2, and analogs: structure-function relationships.
AID1125777Increase of intracellular activity of beta-glucocerebrosidase in human N370S cells using 4-methylumbelliferyl-beta-D-glucopyranoside as substrate at 250 uM after 4 days relative to control2014Bioorganic & medicinal chemistry, Apr-15, Volume: 22, Issue:8
Docking and SAR studies of calystegines: binding orientation and influence on pharmacological chaperone effects for Gaucher's disease.
AID355082Antibacterial activity against Cac gene-deficient Agrobacterium rhizogenes HRI1996Journal of natural products, Dec, Volume: 59, Issue:12
Biological activities of the nortropane alkaloid, calystegine B2, and analogs: structure-function relationships.
AID1125773Stabilization of human lysosomal beta-glucocerebrosidase using 4-methylumbelliferyl-beta-D-glucopyranoside as substrate assessed as remaining enzyme activity at 50 uM at 53 degC after 60 mins relative to control2014Bioorganic & medicinal chemistry, Apr-15, Volume: 22, Issue:8
Docking and SAR studies of calystegines: binding orientation and influence on pharmacological chaperone effects for Gaucher's disease.
AID355087Allellopathic effect in Medicago sativa assessed as reduction in root elongation at 5 mM after 43 hrs1996Journal of natural products, Dec, Volume: 59, Issue:12
Biological activities of the nortropane alkaloid, calystegine B2, and analogs: structure-function relationships.
AID1125775Competitive inhibition of human lysosomal beta-glucocerebrosidase using 4-methylumbelliferyl-beta-D-glucopyranoside as substrate preincubated for 45 mins before substrate addition measured after 30 mins by double-reciprocal plot analysis2014Bioorganic & medicinal chemistry, Apr-15, Volume: 22, Issue:8
Docking and SAR studies of calystegines: binding orientation and influence on pharmacological chaperone effects for Gaucher's disease.
AID355086Allellopathic effect in Medicago sativa assessed as reduction in root elongation at 10 mM after 19 hrs1996Journal of natural products, Dec, Volume: 59, Issue:12
Biological activities of the nortropane alkaloid, calystegine B2, and analogs: structure-function relationships.
AID1125774Inhibition of human lysosomal beta-glucocerebrosidase using 4-methylumbelliferyl-beta-D-glucopyranoside as substrate preincubated for 45 mins before substrate addition measured after 30 mins by fluorescence spectrophotometer analysis2014Bioorganic & medicinal chemistry, Apr-15, Volume: 22, Issue:8
Docking and SAR studies of calystegines: binding orientation and influence on pharmacological chaperone effects for Gaucher's disease.
AID355083Allellopathic effect in Medicago sativa assessed as inhibition of seed germination at 5 mM1996Journal of natural products, Dec, Volume: 59, Issue:12
Biological activities of the nortropane alkaloid, calystegine B2, and analogs: structure-function relationships.
AID355074Inhibition of almond beta-glucosidase1996Journal of natural products, Dec, Volume: 59, Issue:12
Biological activities of the nortropane alkaloid, calystegine B2, and analogs: structure-function relationships.
AID355078Induction of Cac gene-expressing Rhizobium meliloti 41 growth1996Journal of natural products, Dec, Volume: 59, Issue:12
Biological activities of the nortropane alkaloid, calystegine B2, and analogs: structure-function relationships.
AID398420Inhibition of Aspergillus niger alpha-galactosidase at 1.2 ug/mL by colorimetric assay1995Journal of natural products, Jun, Volume: 58, Issue:6
Identification of the glycosidase inhibitors swainsonine and calystegine B2 in Weir vine (Ipomoea sp. Q6 [aff. calobra]) and correlation with toxicity.
AID355079Antibacterial activity against Cac gene-deficient Rhizobium meliloti GMI131996Journal of natural products, Dec, Volume: 59, Issue:12
Biological activities of the nortropane alkaloid, calystegine B2, and analogs: structure-function relationships.
AID579723Inhibition of partially purified human placental beta-glucocerebrosidase after 15 to 60 mins2011Bioorganic & medicinal chemistry letters, Mar-01, Volume: 21, Issue:5
Synthesis of N-alkylated noeurostegines and evaluation of their potential as treatment for Gaucher's disease.
AID355081Antibacterial activity against Cac gene-deficient Agrobacterium tumefaciens C58C11996Journal of natural products, Dec, Volume: 59, Issue:12
Biological activities of the nortropane alkaloid, calystegine B2, and analogs: structure-function relationships.
AID355075Inhibition of Aspergillus niger alpha-galactosidase1996Journal of natural products, Dec, Volume: 59, Issue:12
Biological activities of the nortropane alkaloid, calystegine B2, and analogs: structure-function relationships.
AID355088Allellopathic effect in Medicago sativa assessed as reduction in root elongation at 10 mM after 43 hrs1996Journal of natural products, Dec, Volume: 59, Issue:12
Biological activities of the nortropane alkaloid, calystegine B2, and analogs: structure-function relationships.
AID398419Inhibition of almond beta-glucosidase at 0.6 ug/mL by colorimetric assay1995Journal of natural products, Jun, Volume: 58, Issue:6
Identification of the glycosidase inhibitors swainsonine and calystegine B2 in Weir vine (Ipomoea sp. Q6 [aff. calobra]) and correlation with toxicity.
AID1799390Btman2A from Article 10.1038/nchembio.81: \\Structural and biochemical evidence for a boat-like transition state in beta-mannosidases.\\2008Nature chemical biology, May, Volume: 4, Issue:5
Structural and biochemical evidence for a boat-like transition state in beta-mannosidases.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (27)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's7 (25.93)18.2507
2000's10 (37.04)29.6817
2010's10 (37.04)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.19

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.19 (24.57)
Research Supply Index3.33 (2.92)
Research Growth Index4.52 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.19)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other27 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]