CASTANOSPERMINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C8H15NO4
Molecular Weight	189.209
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@H]1CCN2C[C@H](O)[C@@H](O)[C@H](O)[C@@H]12

InChI

InChIKey=JDVVGAQPNNXQDW-TVNFTVLESA-N

InChI=1S/C8H15NO4/c10-4-1-2-9-3-5(11)7(12)8(13)6(4)9/h4-8,10-13H,1-3H2/t4-,5-,6+,7+,8+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C8H15NO4
Molecular Weight	189.209
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3881759https://www.ncbi.nlm.nih.gov/pubmed/27509020 | https://www.ncbi.nlm.nih.gov/pubmed/19649930 | https://www.ncbi.nlm.nih.gov/pubmed/26794905
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27986123 | https://www.ncbi.nlm.nih.gov/pubmed/15994763 | https://www.ncbi.nlm.nih.gov/pubmed/3300654

Celgosivir is a butanoyl ester derivative of castanospermine, a compound derived from the Australian chestnut with activity against hepatitis C virus. Celgosivir rapidly converts to castanospermine in the body, where it is a potent inhibitor of alpha-glucosidase I, a host enzyme required for viral assembly, release, and infectivity.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-glucosidase 3 Target ID: CHEMBL3761 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23363020	Inhibitor 8504		19.0 µM [IC50]
Alpha-glucosidase I 3 Target ID: Alpha-glucosidase I Sources: https://www.ncbi.nlm.nih.gov/pubmed/7986008	Inhibitor 8504		127.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Dengue virus infection 12 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15994763	Curative		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
A new synthetic access to bicyclic polyhydroxylated alkaloid analogues from pyranosides.	2010-06-07	20376396
A flexible approach to azasugars: asymmetric total syntheses of (+)-castanospermine, (+)-7-deoxy-6-epi-castanospermine, and (+)-1-epi-castanospermine.	2010-05-17	20379975
N-Glycosylation plays a role in protein folding of human UGT1A9.	2010-04-15	19951703
N-glycan-dependent quality control of the Na,K-ATPase beta(2) subunit.	2010-04-13	20199105
QSAR Studies on andrographolide derivatives as α-glucosidase inhibitors.	2010-03-02	20479989
Glycosidase inhibition: assessing mimicry of the transition state.	2010-01-21	20066263
Disruption of N-linked glycosylation enhances ubiquitin-mediated proteasomal degradation of the human ATP-binding cassette transporter ABCG2.	2009-12	19909340
A concise synthesis of castanospermine by the use of a transannular cyclization.	2009-11-20	19856948
Alternative splicing and transcriptome profiling of experimental autoimmune encephalomyelitis using genome-wide exon arrays.	2009-11-10	19915720
Tetrapisispora phaffii killer toxin is a highly specific beta-glucanase that disrupts the integrity of the yeast cell wall.	2009-10-27	19860881
Inhibition of the exo-beta-D-glucosaminidase CsxA by a glucosamine-configured castanospermine and an amino-australine analogue.	2009-10-21	19795054
Single chain variable fragment against nicastrin inhibits the gamma-secretase activity.	2009-10-09	19684016
Six host range variants of the xenotropic/polytropic gammaretroviruses define determinants for entry in the XPR1 cell surface receptor.	2009-10-07	19811656
Alpha-glucosidase promotes hemozoin formation in a blood-sucking bug: an evolutionary history.	2009-09-09	19742319
Celgosivir, an alpha-glucosidase I inhibitor for the potential treatment of HCV infection.	2009-08	19649930
Glycosidase inhibition by ring-modified castanospermine analogues: tackling enzyme selectivity by inhibitor tailoring.	2009-07-07	19532990
Loss of specific chaperones involved in membrane glycoprotein biosynthesis during the maturation of human erythroid progenitor cells.	2009-05-22	19258325
Asymmetric synthesis of (+)-castanospermine through enol ether metathesis-hydroboration/oxidation.	2009-05-21	19421437
Synthesis of thiohydantoin-castanospermine glycomimetics as glycosidase inhibitors.	2009-05-01	19334717
Promotion of IL-4- and IL-5-dependent differentiation of anti-mu-primed B cells by ascorbic acid 2-glucoside.	2009-02-21	19201381
Substrate specificity of the oxidoreductase ERp57 is determined primarily by its interaction with calnexin and calreticulin.	2009-01-23	19054761
Divergence of catalytic mechanism within a glycosidase family provides insight into evolution of carbohydrate metabolism by human gut flora.	2008-10-20	18848471
Broad-spectrum drugs against viral agents.	2008-09	19325820
The comparative pathology of the glycosidase inhibitors swainsonine, castanospermine, and calystegines A3, B2, and C1 in mice.	2008-07	18497426
Inhibition of the glucosyltransferase activity of clostridial Rho/Ras-glucosylating toxins by castanospermine.	2008-06-25	18505687
Synthesis and evaluation of sulfamide-type indolizidines as glycosidase inhibitors.	2008-05-01	18420407
Efficient synthesis of (+)-1,8,8a-tri-epi-swainsonine, (+)-1,2-di-epi-lentiginosine, (+)-9a-epi-homocastanospermine and (-)-9-deoxy-9a-epi-homocastanospermine from a D-glucose-derived aziridine carboxylate, and study of their glycosidase inhibitory activities.	2008-02-21	18264570
Indolizidine and quinolizidine alkaloids.	2008-02	18250900
Role of receptor polymorphism and glycosylation in syncytium induction and host range variation of ecotropic mouse gammaretroviruses.	2008-01-10	18186934
Carboazidation of chiral allylsilanes: experimental and theoretical investigations.	2008	18213673
A divergent asymmetric approach to aza-spiropyran derivative and (1S,8aR)-1-hydroxyindolizidine.	2007-11-08	17996045
Vinylogous Mukaiyama aldol reactions with 4-oxy-2-trimethylsilyloxypyrroles: relevance to castanospermine synthesis.	2007-11-03	17980041
Synthesis of 1-deoxy-1-hydroxymethyl- and 1-deoxy-1-epi-hydroxymethyl castanospermine as new potential immunomodulating agents.	2007-11-01	17918922
Posttranslational N-glycosylation of the hepatitis B virus large envelope protein.	2007-05-30	17537250
Indolizidine and quinolizidine alkaloids.	2007-02	17268613
Asymmetric [2 + 2] cycloaddition: total synthesis of (-)-swainsonine and (+)-6-epicastanospermine.	2006-10-12	17020291
Antiviral effects of glycosylation and glucose trimming inhibitors on human parainfluenza virus type 3.	2006-10	16730076
Interference with O-glycosylation in RMA lymphoma cells leads to a reduced in vivo growth of the tumor.	2006-09-15	16615117
Intramolecular 5-endo-trig aminomercuration of beta-hydroxy-gamma-alkenylamines: efficient route to a pyrrolidine ring and its application for the synthesis of (+)-castanospermine and analogues.	2006-06-09	16749803
Characterization of endoplasmic reticulum-associated degradation of a protein S mutant identified in a family of quantitative protein S deficiency.	2006	15893367
A novel approach for N-glycosylation studies using detergent extracted microsomes.	2005-10	16180101
Glucose trimming of N-glycan in endoplasmic reticulum is indispensable for the growth of Raphanus sativus seedling (kaiware radish).	2005-07	16041142
Novel synthesis of castanospermine and 1-epicastanospermine.	2005-06-23	15957923
Combined donor leucocyte administration and immunosuppressive drug treatment for survival of rat heart allografts.	2004-11	15381200
Conversion of the carbohydrate structures of glycoproteins in roots of Raphanus sativus using several glycosidase inhibitors.	2004-10	15625323
Indolizidine and quinolizidine alkaloids.	2004-10	15459758
Inhibition of N-linked glycosylation.	2001-05	18432854
Inhibition of AIDS virus replication by acemannan in vitro.	1991-09	1768365
6-0-butanoylcastanospermine (MDL 28,574) inhibits glycoprotein processing and the growth of HIVs.	1991-06	1652979
Castanospermine vs. its 6-O-butanoyl analog: a comparison of toxicity and antiviral activity in vitro and in vivo.	1991	1984055

Patents

Sample Use Guides

In Vivo Use Guide

Rats were treated with Castanospermine at a doses of 10, 50, 100, 200 and 500 mg/kg.

Route of Administration: Intraperitoneal

In Vitro Use Guide

LoVo/Dx, W1PR, W1TR and A2780T1 cell lines were used for activity evaluation. The cells were seeded at 4x10^3 cells/well (200 μl) in 96-well culture plates and pre-incubated for 48 h. To examine the effect of BFA, CAS or chemotherapeutic drugs on cell survival, the cells were treated with increasing concentrations of BFA, CAS (Castanospermine, 10 μg/ml for LoVo/Dx, 50 μg/ml for W1PR and W1TR and 60 μg/ml for A2780T1 cells.) for 72 h. Subsequently, 10 μl of MTT labeling reagent was added to the medium (the final concentration of MTT was 0.5 mg/ml) for 4 h and 100 μl of the solubilized solution was then added to each well. After an overnight incubation, the absorbance was measured in a microplate reader at 570 nm with a reference wavelength of 720 nm.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:12:09 GMT 2025` Edited by `admin` on `Mon Mar 31 18:12:09 GMT 2025`
Record UNII	Q0I3184XM7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CASTANOSPERMINE

Common Name

English

NSC-625381

Preferred Name

English

(1S,6S,7R,8R,8AR)-OCTAHYDRO-1,6,7,8-INDOLIZINETETROL

Common Name

English

CASTANOSPERMINE [MI]

Common Name

English

Code System Code Type Description

NSC

625381