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Details

Stereochemistry ABSOLUTE
Molecular Formula C41H66O13
Molecular Weight 766.9549
Optical Activity UNSPECIFIED
Defined Stereocenters 18 / 18
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CAULOSIDE C

SMILES

[H][C@@]7(O[C@@H]1[C@@H](O)[C@@H](O)CO[C@@]1([H])O[C@H]2CC[C@@]3(C)[C@@]([H])(CC[C@]4(C)[C@]3([H])CC=C5[C@]6([H])CC(C)(C)CC[C@@]6(CC[C@@]45C)C(O)=O)[C@]2(C)CO)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O

InChI

InChIKey=RROGHRHLBLVQSG-UUWFFIQNSA-N
InChI=1S/C41H66O13/c1-36(2)13-15-41(35(49)50)16-14-39(5)21(22(41)17-36)7-8-26-37(3)11-10-27(38(4,20-43)25(37)9-12-40(26,39)6)53-34-32(28(45)23(44)19-51-34)54-33-31(48)30(47)29(46)24(18-42)52-33/h7,22-34,42-48H,8-20H2,1-6H3,(H,49,50)/t22-,23-,24+,25+,26+,27-,28-,29+,30-,31+,32+,33-,34-,37-,38-,39+,40+,41-/m0/s1

HIDE SMILES / InChI

Molecular Formula C41H66O13
Molecular Weight 766.9549
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 18 / 18
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/911157 | https://www.ncbi.nlm.nih.gov/pubmed/10216931

Cauloside C isolated from Caulophyllum robustum Maxim. is a naturally occurring carboxyl-containing triterpene glycoside. Cauloside C is water soluble and thermostable compound. It was also isolated from plants such as Akebia quinata Decne. and Caltha sil6estris Worosch. Cauloside C showed cytotoxic activity against HL-60 cells in micromolar range.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
[Effect of triterpene glycosides on RNA biosynthesis in a yeast cell culture of Saccharomyces carlsbergensis].
1977 Sep
The effect of pH on biological activity of plant cytotoxin cauloside C.
1999 Jan
Triterpene glycosides from the underground parts of Caulophyllum thalictroides.
2009 Jun
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
Cauloside C in concentrations of 7.5 gamma/ml inhibited multiplication of the yeast cells by 65 per cent. Cauloside C showed cytotoxic activity against HL-60 cells with IC50 values of 15.9+/- 0.24 ug/mL
Substance Class Chemical
Created
by admin
on Fri Dec 15 21:50:02 UTC 2023
Edited
by admin
on Fri Dec 15 21:50:02 UTC 2023
Record UNII
909OGZ2782
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CAULOSIDE C
Common Name English
AKEBIA SAPONIN C
Common Name English
FATSIASIDE D1
Common Name English
OLEAN-12-EN-28-OIC ACID, 3.BETA.-((2-O-.BETA.-D-GLUCOPYRANOSYL-.ALPHA.-L-ARABINOPYRANOSYL)OXY)-23-HYDROXY-
Common Name English
OLEAN-12-EN-28-OIC ACID, 3-((2-O-.BETA.-D-GLUCOPYRANOSYL-.ALPHA.-L-ARABINOPYRANOSYL)OXY)-23-HYDROXY-, (3.BETA.,4.ALPHA.)-
Common Name English
.ALPHA.-FATSIN
Common Name English
HEDEROSIDE D2
Common Name English
HEDERAGENIN 3-O-.BETA.-D-GLUCOPYRANOSYL(1->2)-O-.ALPHA.-L-ARABINOPYRANOSID
Common Name English
CALTHOSIDE D
Common Name English
AKEBOSIDE STD
Common Name English
3-((2-0-.BETA.-D-GLUCOPYRANOSYL-.ALPHA.-L-ARABINOPYRANOSYL)OXY)-23-HYDROXYOLEAN-12-EN-28-OIC ACID
Common Name English
Code System Code Type Description
PUBCHEM
13878151
Created by admin on Fri Dec 15 21:50:02 UTC 2023 , Edited by admin on Fri Dec 15 21:50:02 UTC 2023
PRIMARY
EPA CompTox
DTXSID50943110
Created by admin on Fri Dec 15 21:50:02 UTC 2023 , Edited by admin on Fri Dec 15 21:50:02 UTC 2023
PRIMARY
FDA UNII
909OGZ2782
Created by admin on Fri Dec 15 21:50:02 UTC 2023 , Edited by admin on Fri Dec 15 21:50:02 UTC 2023
PRIMARY
CAS
20853-58-1
Created by admin on Fri Dec 15 21:50:02 UTC 2023 , Edited by admin on Fri Dec 15 21:50:02 UTC 2023
PRIMARY
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