Castanospermine
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Grundinformationen
- CAS
79831-76-8- Standard-SMILES
O[C@H]1[C@H](O)[C@@H](O)CN2CC[C@H](O)[C@H]12- InChIKey
JDVVGAQPNNXQDW-TVNFTVLESA-N- Summenformel
- C8H15NO4
- Durchschnittliche Molmasse
- 189,211 g/mol
- Monoisotopische Masse
- 189,10010796
Namen und Bezeichner
- Bevorzugter Name
- Castanospermine
- Englischer Name
- CASTANOSPERMINE
- Summenformel
- C8H15NO4
- Molmasse
- 189.21
Namen und Synonyme
CastanosperMinCASTANOSPERMINE(+)-CastanospermineCastanospermine ,98%Castanospermine, 10 mM in DMSO1,6,7,8-TETRAHYDROXYOCTAHYDROINDOLIZINECASTANOSPERMINE, CASTANOSPERMUM AUSTRALE(1S,6S,7R,8R,8AR)-1,6,7,8-TETRAHYDROXY-&Castanospermine from Castanospermum austral(8aα)-Octahydroindolizine-1β,6α,7β,8α-tetrol
Datenbank-Bezeichner
- CAS
79831-76-8- PubChem CID
- 54445
- DTXSID
DTXSID601026043- ChEMBL
CHEMBL311226- ChEBI
CHEBI:27860- UNII
- Q0I3184XM7
- EC Number
- 616-743-4
- Nikkaji
- J52.984B
Eigenschaften
Physikochemische Eigenschaften
- Schmelzpunkt
- 213 · 213-217 °C (lit.)
- Siedepunkt
- 421.9 · 421.9±45.0 °C(Predicted)
- Dichte
- 1.53 · 1.53±0.1 g/cm3(Predicted)
- storage temp.
- 2 · Sealed in dry,2-8°C
- Löslichkeit
- 1 M · 1 M HCl: 20 mg/mL, clear, very faintly yellow
- Aggregatzustand
- White solid
- pka
- 6.09 · 6.09(at 25℃)
- Farbe
- White or off-white
- Wasserlöslichkeit
- Soluble in water
- Merck
- 13 · 13,1906
- BRN
- 3588654 · 3588654
- Stabilität
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in distilled water may be stored at -20°C for up to 3 months.
- 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
- InChIKey
- JDVVGAQPNNXQDW-TVNFTVLESA-N
- SMILES
- [H][C@]12[C@@H](O)CCN1C[C@H](O)[C@@H](O)[C@@H]2O
- CAS Datenbank
- 79831 · 79831-76-8(CAS DataBase Reference)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- F
- 10-21
- wgk
- 3
- hs_code
- 2921290090
- risk_code
- 20/21/22-36/37/38
- hazard_code
- Xn,Xi
- safety_code
- 26-36
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Anwendungen
BeschreibungGlucosidases catalyze the cleavage of individual glucosyl residues from various glycoconjugates, including complex carbohydrates and glycoproteins. Castanospermine is an inhibitor of both α- and β-glucosidases, inhibiting lysosomal and neutral α-glucosidases with Ki values of 0.1 and 10 μM, respectively, and lysosomal and cytosolic β-glucosidases with Ki values of 7 and 40 μM, respectively. It is effective both in vitro and in vivo. Through its effects on glucosidases, castanospermine blocks N-linked glycosylation during post-translational modification of proteins, affecting protein trafficking and cell functions that are dependent on glycosylation, including angiogenesis. Castanospermine also interferes with viral replication and infection that is dependent on glucosidase activity.
OccurrenceThe seeds of Castanospermum australe yield this simple alkaloid. It forms colourless crystals from EtOH and is dextrorotatory with a specific rotation of [α]D25 +79.7° (c 0.93, H20). Castano spermine has been characterized as the crystalline methiodide, m.p. 11O-112°C.
VerwendenCastanospermine is a plant alkaloid shown to be a potent inhibitor of lysosomal a-or beta- glucosidase. It also inhibits mammalian glucosidase 1 and beta-mannosidase from sweet almonds and fungal beta-xylosidase.
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