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Details

Stereochemistry ABSOLUTE
Molecular Formula C30H46O5
Molecular Weight 486.6832
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUILLAIC ACID

SMILES

[H][C@@]12CC(C)(C)CC[C@@]1([C@H](O)C[C@]3(C)C2=CC[C@]4([H])[C@@]5(C)CC[C@H](O)[C@@](C)(C=O)[C@]5([H])CC[C@@]34C)C(O)=O

InChI

InChIKey=MQUFAARYGOUYEV-UAWZMHPWSA-N
InChI=1S/C30H46O5/c1-25(2)13-14-30(24(34)35)19(15-25)18-7-8-21-26(3)11-10-22(32)27(4,17-31)20(26)9-12-28(21,5)29(18,6)16-23(30)33/h7,17,19-23,32-33H,8-16H2,1-6H3,(H,34,35)/t19-,20+,21+,22-,23+,26-,27-,28+,29+,30+/m0/s1

HIDE SMILES / InChI

Molecular Formula C30H46O5
Molecular Weight 486.6832
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/17323426 | https://www.ncbi.nlm.nih.gov/pubmed/20951193

Quillaic acid (Quillaja sapogenin) is the major aglycone of the widely studied saponins of the Chilean indigenous tree Quillaja saponaria Mol. Quillaja saponaria bark contains a high percentage of triterpene saponins and has been used for centuries as a cleansing and analgesic agent in Chilean folk medicine. Quillaic acid shows potent antiproliferative activity against different cancer cell lines. Quillaic acid elicit dose-dependent antinociceptive effects in two murine thermal models. Quillaic acid exhibited strong topical anti-inflammatory activity in different animal models.

Originator

Sources: Pharmaceutical Journal (1916), 96, 220-1.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Antiproliferative quillaic acid and gypsogenin saponins from Saponaria officinalis L. roots.
2015 May
Patents

Patents

Sample Use Guides

In Hot - plate test rats were treated with QA (Quillaic acid) at doses 0.5, 1.0, 1.5, 2.0 mg/kg (i.p.) In Tail flick test rats were treated with QA (Quillaic acid) at doses 2.5, 7.5 and 22.5 mg/kg (Topical)
Route of Administration: Other
MDA-MB-231 human breast cancer and PC-3 human prostate cancer cell lines were used for activity evaluation. The antiproliferative activity of extracts was evaluated using the AbD serotec alamarBlue assay. Cells were seeded at 2500 cells per well in 96-well tissue culture plates. After 18–24 h, cells were exposed to various concentrations of saponins with the final concentration of DMSO not exceeding 0.1%. Cells were incubated for 48 h, with alamar-Blue dye solution added to each well to make up 10% of the final volume for the final six to eight hours. Fluorescence was measured at an excitation of 560 nm and emission of 590 nm on a Perkin Elmer 1420 VICTOR3V Multilabel Counter.
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:42:18 GMT 2023
Edited
by admin
on Fri Dec 15 19:42:18 GMT 2023
Record UNII
69O8E4G02B
Record Status Validated (UNII)
Record Version
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Name Type Language
QUILLAIC ACID
MI  
Common Name English
QUILLAJA SAPOGENIN
Common Name English
OLEAN-12-EN-28-OIC ACID, 3,16-DIHYDROXY-23-OXO-, (3.BETA.,4.ALPHA.,16.ALPHA.)-
Common Name English
QUILLAIC ACID [MI]
Common Name English
OLEAN-12-EN-28-OIC ACID, 3.BETA.,16.ALPHA.-DIHYDROXY-23-OXO-
Common Name English
(+)-QUILLAIC ACID
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID001026576
Created by admin on Fri Dec 15 19:42:19 GMT 2023 , Edited by admin on Fri Dec 15 19:42:19 GMT 2023
PRIMARY
FDA UNII
69O8E4G02B
Created by admin on Fri Dec 15 19:42:19 GMT 2023 , Edited by admin on Fri Dec 15 19:42:19 GMT 2023
PRIMARY
ECHA (EC/EINECS)
211-149-8
Created by admin on Fri Dec 15 19:42:19 GMT 2023 , Edited by admin on Fri Dec 15 19:42:19 GMT 2023
PRIMARY
PUBCHEM
101810
Created by admin on Fri Dec 15 19:42:19 GMT 2023 , Edited by admin on Fri Dec 15 19:42:19 GMT 2023
PRIMARY
CHEBI
8710
Created by admin on Fri Dec 15 19:42:19 GMT 2023 , Edited by admin on Fri Dec 15 19:42:19 GMT 2023
PRIMARY
CAS
631-01-6
Created by admin on Fri Dec 15 19:42:19 GMT 2023 , Edited by admin on Fri Dec 15 19:42:19 GMT 2023
PRIMARY
MESH
C005564
Created by admin on Fri Dec 15 19:42:19 GMT 2023 , Edited by admin on Fri Dec 15 19:42:19 GMT 2023
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MERCK INDEX
m447
Created by admin on Fri Dec 15 19:42:19 GMT 2023 , Edited by admin on Fri Dec 15 19:42:19 GMT 2023
PRIMARY Merck Index