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Details

Stereochemistry ABSOLUTE
Molecular Formula C42H66O14
Molecular Weight 794.9667
Optical Activity UNSPECIFIED
Defined Stereocenters 20 / 20
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUINOVIC ACID GLYCOSIDE 2

SMILES

C[C@]1([H])CC[C@@]2(CC[C@@]3(C(=CC[C@]4([H])[C@@]5(C)CC[C@@]([H])(C(C)(C)[C@]5([H])CC[C@]43C)O[C@@]6([H])[C@@]([H])([C@]([H])([C@]([H])([C@@]([H])(C)O6)O)O[C@@]7([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(CO)O7)O)O)O)O)[C@]2([H])[C@@]1([H])C)C(=O)O)C(=O)O

InChI

InChIKey=BZXXSUZFEIFGEX-LCSOEGAZSA-N
InChI=1S/C42H66O14/c1-19-10-15-41(36(49)50)16-17-42(37(51)52)22(27(41)20(19)2)8-9-25-39(6)13-12-26(38(4,5)24(39)11-14-40(25,42)7)55-35-32(48)33(28(44)21(3)53-35)56-34-31(47)30(46)29(45)23(18-43)54-34/h8,19-21,23-35,43-48H,9-18H2,1-7H3,(H,49,50)(H,51,52)/t19-,20+,21-,23-,24+,25-,26+,27+,28+,29-,30+,31-,32-,33+,34+,35+,39+,40-,41+,42-/m1/s1

HIDE SMILES / InChI

Molecular Formula C42H66O14
Molecular Weight 794.9667
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 20 / 20
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/2553871

Quinovic acid glycoside 2 was isolated from the bark of Uncaria tomentosa, the Peruvian flora, widely used in local medicine for the treatment of cancer, arthritis, gastritis and certain epidermic diseases. Quinovic acid glycoside 2 demonstrated efficacy against vesicular stomatitis virus infection in vitro.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PubMed

PubMed

TitleDatePubMed
Plant metabolites. Structure and in vitro antiviral activity of quinovic acid glycosides from Uncaria tomentosa and Guettarda platypoda.
1989 Jul-Aug
Plant metabolites. New compounds and anti-inflammatory activity of Uncaria tomentosa.
1991 Mar-Apr

Sample Use Guides

In Vitro Use Guide
Confluent monolayers of CER cells in 6-well plates were infected with 200 uL of a virus dilution containing approx. 100 plaque forming units (pfu). Following a 1h adsorption period at 37C, the cells were added with an overlay medium containing doubling concentrations of compounds and incubated until plaques developed (36-48 h at 37C). The antiviral activity of the compounds was expressed as the minimal inhibitory concentration (MIC50) required to reduce the plaque number by 50% with respect to control infected cells. The MIC50 for Quinovic acid glycoside 2 (compound 3) was 25 uM.
Substance Class Chemical
Created
by admin
on Sat Jun 26 15:13:56 UTC 2021
Edited
by admin
on Sat Jun 26 15:13:56 UTC 2021
Record UNII
P84Z2WDZ9J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
QUINOVIC ACID GLYCOSIDE 2
Common Name English
URS-12-ENE-27,28-DIOIC ACID, 3-((6-DEOXY-3-O-.BETA.-D-GLUCOPYRANOSYL-.BETA.-D-GALACTOPYRANOSYL)OXY)-, (3.BETA.)-
Systematic Name English
Code System Code Type Description
CAS
115569-78-3
Created by admin on Sat Jun 26 15:13:56 UTC 2021 , Edited by admin on Sat Jun 26 15:13:56 UTC 2021
PRIMARY
FDA UNII
P84Z2WDZ9J
Created by admin on Sat Jun 26 15:13:56 UTC 2021 , Edited by admin on Sat Jun 26 15:13:56 UTC 2021
PRIMARY
PUBCHEM
44593500
Created by admin on Sat Jun 26 15:13:56 UTC 2021 , Edited by admin on Sat Jun 26 15:13:56 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT