Saikosaponin C

HCID 167927CAS 20736-08-7
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Grundinformationen

Standard-SMILES
C[C@@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O[C@H]3CC[C@]4(C)[C@H]5C=C[C@]67OC[C@@]8(CCC(C)(C)C[C@H]86)[C@@H](O)C[C@@]7(C)[C@]5(C)CC[C@H]4C3(C)C)O[C@@H]2CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H](O)[C@H]1O
InChIKey
VJEMOEYSQDKAQF-JDRYWMLESA-N
Summenformel
C48H78O17
Durchschnittliche Molmasse
927,1 g/mol
Monoisotopische Masse
926,52390104

Überblick

Saikosaponin C is a member of the class of saikosaponins that is saikogenin E substituted by a 6-deoxy-alpha-L-mannopyranosyl-(14)-[beta-D-glucopyranosyl-(16)]-beta-D-glucopyranosyl group at position 3beta. It is a natural product isolated from the traditional Chinese herb, Radix Bupleuri and exhibits anti-HBV replication activity. It has a role as an anti-HBV agent and a plant metabolite. It is a saikosaponin, a bridged compound, a cyclic ether, a trisaccharide derivative and a hexacyclic triterpenoid. It is functionally related to a saikogenin E.

Namen und Bezeichner

Bevorzugter Name
Saikosaponin C
IUPAC
(2S,3R,4R,5R,6S)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-[[(1S,2S,4S,5R,8R,10S,13S,14R,17S,18R)-2-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracos-15-en-10-yl]oxy]-2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-3-yl]oxy-6-methyloxane-3,4,5-triol

Namen und Synonyme

Saikosaponin-CCHEBI:189704DTXSID801317381(2S,3R,4R,5R,6S)-2-((2R,3S,4R,5R,6R)-4,5-dihydroxy-6-(((1S,2S,4S,5R,8R,10S,13S,14R,17S,18R)-2-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo(15.5.2.01,18.04,17.05,14.08,13)tetracos-15-en-10-yl)oxy)-2-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxymethyl)oxan-3-yl)oxy-6-methyloxane-3,4,5-triol(2S,3R,4R,5R,6S)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-[[(1S,2S,4S,5R,8R,10S,13S,14R,17S,18R)-2-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracos-15-en-10-yl]oxy]-2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-3-yl]oxy-6-methyloxane-3,4,5-triolRefChem:884374DTXCID301747197633-797-420736-08-7Saikosaponin CSaikosaponin C (Standard)beta-D-Glucopyranoside, (3beta,16beta)-13,28-epoxy-16-hydroxyolean-11-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-->4)-O-[beta-D-glucopyranosyl-(1-->6)]-
Weitere Namen anzeigen
(3beta,16beta)-13,28-epoxy-16-hydroxyolean-11-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1->4)-O-[beta-D-glucopyranosyl-(1->6)]-beta-D-glucopyranosideC48H78O17ss-D-Glucopyranoside, (3ss,16ss)-13,28-epoxy-16-hydroxyolean-11-en-3-yl O-6-deoxy-a-L-mannopyranosyl-(1?4)-O-[ss-D-glucopyranosyl-(1?6)]-; Saikosaponin C (8CI); Oleanane, ss-D-glucopyranoside deriv.; (3ss,16ss)-13,28-Epoxy-16-hydroxyolean-11-en-3-yl O-6-deoxy-a-L-mannopyranosyl-(1?4)-O-[ss-D-glucopyranosyl-(1?6)]-ss-D-glucopyranosideSCHEMBL928987orb1222525CHEMBL3613725HY-N0249RHY-N0249

Datenbank-Bezeichner

CAS
20736-08-7
PubChem CID
167927
DTXSID
DTXSID801317381
ChEMBL
CHEMBL1159427、CHEMBL3613725
ChEBI
CHEBI:189704
EC Number
633-797-4
Nikkaji
J16.220E

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,6
Polarare Oberfläche (TPSA)
267 Ų
H-Brücken-Donoren
10
H-Brücken-Akzeptoren
17
Frei drehbare Bindungen
8
Schwere Atome
65

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological Classification · 4 Einträge

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.

Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity.

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly.

Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging.

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