AVICIN D

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C98H155NO46
Molecular Weight	2083.2584
Optical Activity	UNSPECIFIED
Defined Stereocenters	50 / 50
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]%13(O[C@H]1[C@H](C)O[C@@]([H])(O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC(=O)[C@]34C[C@H](OC(=O)C(\CO)=C\CC[C@@](C)(O[C@@H]5O[C@H](C)[C@@H](OC(=O)C(\CO)=C\CC[C@@](C)(O)C=C)[C@H](O)[C@H]5O)C=C)C(C)(C)C[C@@]3([H])C6=CC[C@]7([H])[C@@]8(C)CC[C@H](O[C@]9([H])O[C@H](CO[C@@H]%10O[C@H](C)[C@H](O)[C@H](O)[C@H]%10O[C@]%11([H])OC[C@@H](O)[C@H](O)[C@H]%11O)[C@@H](O)[C@H](O)[C@H]9NC(C)=O)C(C)(C)[C@]8([H])CC[C@@]7(C)[C@]6(C)C[C@H]4O)[C@H](O)[C@@H]1O[C@]%12([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]%12O)O[C@@H](CO)[C@H](O)[C@H]%13O

InChI

InChIKey=HKEDBKXRDHFCFB-LUAQNYIXSA-N

InChI=1S/C98H155NO46/c1-16-93(11,127)26-18-20-45(34-101)81(125)139-75-41(4)132-87(73(122)69(75)118)145-94(12,17-2)27-19-21-44(33-100)80(124)137-57-32-98(90(126)144-89-79(68(117)62(111)50(36-103)135-89)143-86-74(123)77(141-85-72(121)66(115)61(110)49(35-102)133-85)76(42(5)131-86)140-84-71(120)63(112)51(37-104)134-84)47(30-91(57,7)8)46-22-23-54-95(13)28-25-56(92(9,10)53(95)24-29-96(54,14)97(46,15)31-55(98)107)138-82-58(99-43(6)105)65(114)64(113)52(136-82)39-129-88-78(67(116)59(108)40(3)130-88)142-83-70(119)60(109)48(106)38-128-83/h16-17,20-22,40-42,47-79,82-89,100-104,106-123,127H,1-2,18-19,23-39H2,3-15H3,(H,99,105)/b44-21+,45-20+/t40-,41-,42+,47+,48-,49-,50-,51+,52-,53+,54-,55-,56+,57+,58-,59+,60+,61-,62-,63+,64-,65-,66+,67+,68+,69-,70-,71-,72-,73-,74-,75-,76+,77+,78-,79-,82+,83+,84+,85+,86+,87+,88-,89+,93+,94+,95+,96-,97-,98-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18496567 | https://www.ncbi.nlm.nih.gov/pubmed/22132201

Avicin D, a natural triterpenoid saponin, is a selective glucocorticoid receptor (GR) modulator. It has been approved by the United States Food and Drug Administration for phase I studies in human cancer patients. In addition, avicin D has the therapeutic potential for patients with Sézary syndrome.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glucocorticoid receptor 172 Target ID: P04150 Gene ID: 2908.0 Gene Symbol: NR3C1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/22132201	Modulator 828

Conditions

Condition	Modality	Targets	Highest Phase	Product
Sézary syndrome 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18496567	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed

Sample Use Guides

In Vitro Use Guide

Avicin D at 0.5-5 mug ml(-1) induced apoptosis in a time- and dose-dependent manner in three cell lines: MJ (-0.2 to 13% and 0.6-37%), Hut78 (2-39% and 3-53%), and HH (13-83% and 44-89%) at 24 and 48 hours, respectively. Avicin D at 0.5-5 microg ml(-1) for 48 hours caused more apoptosis in patients' Sézary cells than in healthy donors' CD4+ T cells and activated CD4+ T cells.

Name

Type

Language

AVICIN D

Common Name

English

ELLIPTOSIDE E

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

467714