Chemical substance record

Castanospermine

79831-76-8C₈H₁₅NO₄189.211 g/mol

Organic/Inorganic Small MoleculeChEBI source record

A tetrahydroxyindolizidine alkaloid that consists of octahydroindolizine having four hydroxy substituents located at positions 1, 6, 7 and 8 (the 1S,6S,7R,8R,8aR-diastereomer). — ChEBI

Safety references

Safety documents & references

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Identity & molecular properties

Source-linked values

CAS number	79831-76-8	ChEBI ↗
Molecular formula	C₈H₁₅NO₄	ChEBI ↗
Molar mass	189.211 g/mol	ChEBI ↗
Monoisotopic mass	189.10011 Da	ChEBI ↗
Formal charge	0	ChEBI ↗
ChEBI identifier	CHEBI:27860	ChEBI ↗

Cross-source molecular data

PubChem

Molar mass	189.21 g/mol	PubChem ↗
Exact mass	189.10010796 Da	PubChem ↗
Computed XLogP	-2.2	PubChem ↗
Topological polar surface area (Å²)	84.2	PubChem ↗
H-bond donors	4	PubChem ↗
H-bond acceptors	5	PubChem ↗
Rotatable bonds	0	PubChem ↗

PubChem computed values are shown separately from the ChEBI record. An exact InChIKey match was used to connect the records. Molecular descriptors do not describe a supplied product’s purity, particle size or performance.

Names & structural identifiers

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Source preferred name

castanospermine

IUPAC name

(1S,6S,7R,8R,8aR)-octahydroindolizine-1,6,7,8-tetrol

InChIKey

JDVVGAQPNNXQDW-TVNFTVLESA-N

SMILES

[H][C@]12[C@@H](O)CCN1C[C@H](O)[C@@H](O)[C@@H]2O

InChI

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

Names & synonyms

(1S,6S,7R,8R,8aR)-octahydroindolizine-1,6,7,8-tetrol

Names are supplied by ChEBI. Trade names and related synonyms may describe a broader product context.

Classification & relationships

ChEBI ontology

indolizidine alkaloidChEBI parent class · 38511 ↗

organic heterocyclic compound organic molecular entity

Roles recorded in ChEBI

metaboliteEC 3.2.1.* (glycosidase) inhibitoranti-HIV-1 agentanti-inflammatory agent

Database role annotations describe reported biological or chemical roles; they are not product approvals or recommendations for use.

Mass ↔ amount of substance

Calculated from sourced mass

Amount

Input unit

Equivalent amount

0.0052851 mol

Uses 189.211 g/mol from ChEBI. Assumes the substance described by this record; no purity or concentration correction is applied.

Elemental composition

Theoretical mass fractions

C

Carbon · 8 atoms

50.78%

O

Oxygen · 4 atoms

33.82%

H

Hydrogen · 15 atoms

7.99%

N

Nitrogen · 1 atom

7.40%

Calculated theoretical mass fractions from the reported formula and PubChem periodic-table atomic masses. These are not assay or purity results.

Research & patent references

Selected source associations

Synthesis of N-, S-, and C-glycoside castanospermine analogues with selective neutral alpha-glucosidase inhibitory activity as antitumour agents. ↗Chemical communications (Cambridge, England) · 2010 Aug 7 · PMID 20552113

The effects of Castanospermine, an oligosaccharide processing inhibitor, on mononuclear/endothelial cell binding and the expression of cell adhesion molecules. ↗Transplant immunology · 2012 Aug · PMID 22647882

KR20070061879 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

MX2009004170 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

US5837709 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

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Sources & record history

Checked 27 Sep 2026

Identity, formula, mass, synonyms & ontologyEMBL-EBI ChEBI · CHEBI:27860

Release 255, 9 September 2026. ChEBI three-star (manually annotated) source entry. View original record ↗ · CC BY 4.0

Additional molecular descriptorsNCBI PubChem · CID 54445 · retrieved 2026-09-27

PubCAS formats source data, connects references and computes explicitly labelled conversions. CAS cross-references are supplied by ChEBI; they do not constitute CAS verification or endorsement.

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