Saikosaponin C

HCID 167927CAS 20736-08-7

基本情報

標準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
分子式: C48H78O17
平均分子量: 927.1 g/mol
単同位体質量: 926.52390104

概要

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.

名称と識別子

優先名称: 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

名称と別名

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)]-

名称をさらに表示

(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

データベース識別子

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

物性

構造計算による物性

XLogP: 1.6
極性表面積: 267 Å²
水素結合供与体数: 10
水素結合受容体数: 17
回転可能結合数: 8
重原子数: 65
形式電荷: 0
複雑度: 1,780

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

化学と産業

薬理情報

MeSH Pharmacological Classification · 4 件

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.