Compounds > quillaic acid
Page last updated: 2024-11-07

quillaic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Quillaic acid is a triterpenoid saponin, a naturally occurring compound found in the bark of the Quillaja saponaria tree, also known as the soapbark tree. This compound has a complex structure, with a triterpene aglycone (the non-sugar portion) attached to multiple sugar molecules (glycones). It is known for its potent foaming properties, hence the common name soapbark. Due to its diverse biological activities, quillaic acid has been extensively researched for various applications. It exhibits immunostimulatory properties, stimulating the immune system by activating macrophages and lymphocytes. This has led to its investigation as an adjuvant in vaccines, enhancing their efficacy. It also has antiviral activity against several viruses, including HIV and influenza. Additionally, quillaic acid has shown promise as an anti-cancer agent, demonstrating cytotoxic effects against various cancer cell lines. Its ability to disrupt cell membranes and induce apoptosis (programmed cell death) is attributed to its saponin structure. Furthermore, quillaic acid has been explored for its potential in drug delivery, acting as a carrier molecule to enhance the absorption and bioavailability of other drugs. The unique properties of quillaic acid, including its foaming capabilities, immunostimulatory effects, antiviral activity, and anticancer potential, have made it an intriguing subject of scientific study. '

quillaic acid : A pentacyclic triterpenoid that is olean-12-ene substituted by hydroxy groups at positions 3 and 16, an oxo group at position 23 and a carboxy group at position 28 (the 3beta,16alpha stereoisomer). [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID101810
CHEMBL ID260060
CHEBI ID8710
SCHEMBL ID867115
MeSH IDM0047199

Synonyms (29)

Synonym
quillaic acid
631-01-6
C08972
CHEMBL260060
chebi:8710 ,
(4ar,5r,6ar,6as,6br,8ar,9s,10s,12ar,14bs)-9-formyl-5,10-dihydroxy-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
(3beta,16alpha)-3,16-dihydroxy-23-oxoolean-12-en-28-oic acid
einecs 211-149-8
69o8e4g02b ,
unii-69o8e4g02b
(3beta,4alpha,16alpha)-3,16-dihydroxy-23-oxoolean-12-en-28-oic acid
quillaic acid [mi]
olean-12-en-28-oic acid, 3.beta.,16.alpha.-dihydroxy-23-oxo-
(+)-quillaic acid
olean-12-en-28-oic acid, 3,16-dihydroxy-23-oxo-, (3.beta.,4.alpha.,16.alpha.)-
S9019
SCHEMBL867115
HY-N0839
3beta,16alpha-dihydroxy-23-oxoolean-12-en-28-oic acid
LMPR0106150037
(4ar,5r,6as,6br,8ar,9s,10s,12ar,12br,14bs)-9-formyl-5,10-dihydroxy-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2h)-carboxylic acid
quillaic acid(quillaja sapogenin)
mfcd22479218
AKOS032949114
AS-35340
Q27108137
CCG-269595
A868243
DTXSID001026576
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
anti-inflammatory agentAny compound that has anti-inflammatory effects.
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
pentacyclic triterpenoid
hydroxy monocarboxylic acidAny monocarboxylic acid which also contains a separate (alcoholic or phenolic) hydroxy substituent.
aldehydeA compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID750465Antiviral activity against pseudo VSV infected in human 293T cells assessed as inhibition of vesicular stromatis G protein pseudo particles entry at 1 uM after 72 hrs by luciferase reporter gene assay2013Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11
Development of oleanane-type triterpenes as a new class of HCV entry inhibitors.
AID750467Antiviral activity against pseudo HCV infected in human 293T cells assessed as inhibition of HCV pseudo particles entry at 1 uM after 72 hrs by luciferase reporter gene assay2013Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11
Development of oleanane-type triterpenes as a new class of HCV entry inhibitors.
AID750464Antiviral activity against pseudo VSV infected in human 293T cells assessed as inhibition of vesicular stromatis G protein pseudo particles entry at 5 uM after 72 hrs by luciferase reporter gene assay2013Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11
Development of oleanane-type triterpenes as a new class of HCV entry inhibitors.
AID323184Inhibition of Gypsophila oldhamiana alpha-glucosidase2008Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6
New triterpenoid saponins with strong alpha-glucosidase inhibitory activity from the roots of Gypsophila oldhamiana.
AID750462Antiviral activity against pseudo HCV infected in human 293T cells assessed as inhibition of HCV pseudo particles entry at 10 uM after 72 hrs by luciferase reporter gene assay2013Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11
Development of oleanane-type triterpenes as a new class of HCV entry inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (22)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's5 (22.73)18.2507
2000's9 (40.91)29.6817
2010's7 (31.82)24.3611
2020's1 (4.55)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 28.55

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index28.55 (24.57)
Research Supply Index3.18 (2.92)
Research Growth Index4.54 (4.65)
Search Engine Demand Index34.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (28.55)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (13.04%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other20 (86.96%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
methanol
Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.		2.110alkyl alcohol;
one-carbon compound;
primary alcohol;
volatile organic compound		amphiprotic solvent;
Escherichia coli metabolite;
fuel;
human metabolite;
mouse metabolite;
Mycoplasma genitalium metabolite
taurine
[no description available]		210amino sulfonic acid;
zwitterion		antioxidant;
Escherichia coli metabolite;
glycine receptor agonist;
human metabolite;
mouse metabolite;
nutrient;
radical scavenger;
Saccharomyces cerevisiae metabolite
sodium fluoride
[no description available]		210fluoride saltmutagen
glycyrrhetinic acid
[no description available]		2.0810cyclic terpene ketone;
hydroxy monocarboxylic acid;
pentacyclic triterpenoid		immunomodulator;
plant metabolite
thiazolidines
Thiazolidines: Reduced (protonated) form of THIAZOLES. They can be oxidized to THIAZOLIDINEDIONES.		2.0510thiazolidine
oleanolic acid
[no description available]		6.37210hydroxy monocarboxylic acid;
pentacyclic triterpenoid		plant metabolite
ursolic acid
[no description available]		2.0810hydroxy monocarboxylic acid;
pentacyclic triterpenoid		geroprotector;
plant metabolite
betulinic acid
[no description available]		2.0810hydroxy monocarboxylic acid;
pentacyclic triterpenoid		anti-HIV agent;
anti-inflammatory agent;
antimalarial;
antineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
plant metabolite
hederagenin
[no description available]		2.0810dihydroxy monocarboxylic acid;
pentacyclic triterpenoid;
sapogenin		plant metabolite
arjunolic acid
arjunolic acid: oleanane type; isol from Cochlospermum tinctorium (Bixaceae); structure given in first source; RN given refers to (2alpha,3beta,4alpha)-isomer; RN for cpd without isomeric designation not avail 12/89. arjunolic acid : A pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by hydroxy groups at positions 2, 3 and 23 (the 2alpha,3beta stereoisomer). Isolated from Symplocos lancifolia and Juglans sinensis, it exhibits antioxidant and antimicrobial activities.		2.0810hydroxy monocarboxylic acid;
pentacyclic triterpenoid		antibacterial agent;
antifungal agent;
antioxidant;
metabolite
maslinic acid
(2Alpha,3beta)-2,3-dihydroxyolean-12-en-28-oic acid: from Luehea divaricata and Agrimonia eupatoria		2.0810dihydroxy monocarboxylic acid;
pentacyclic triterpenoid		anti-inflammatory agent;
antineoplastic agent;
antioxidant;
plant metabolite
fosthiazate
fosthiazate: structure in first source		2.0510organic phosphonate;
organothiophosphate insecticide;
phosphonic ester		agrochemical;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
nematicide
gypsogenin
gypsogenin: originally from Gypsophila species; structure in first source. gypsogenin : A sapogenin that is olean-12-en-28-oic acid substituted by a beta-hydroxy group at position 3 and an oxo group at position 23.		7.520aldehyde;
monocarboxylic acid;
pentacyclic triterpenoid;
sapogenin
oleanolic acid 3-acetate
oleanolic acid 3-acetate: from Gardenia jasminoides; RN given for (3beta)-isomer		2.0810
acarbose
[no description available]		2.0410amino cyclitol;
glycoside
arachidonic acid
icosa-5,8,11,14-tetraenoic acid : Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.. arachidonate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of arachidonic acid.		2.0610icosa-5,8,11,14-tetraenoic acid;
long-chain fatty acid;
omega-6 fatty acid		Daphnia galeata metabolite;
EC 3.1.1.1 (carboxylesterase) inhibitor;
human metabolite;
mouse metabolite
glycosides
[no description available]		2.0810
lithium
Lithium: An element in the alkali metals family. It has the atomic symbol Li, atomic number 3, and atomic weight [6.938; 6.997]. Salts of lithium are used in treating BIPOLAR DISORDER.		210alkali metal atom
ovalbumin
Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.		210
azadirachtin
azadirachtin A : A member of the family of azadirachtins that is isolated from the neem tree (Azadirachta indica).. azadirachtin : A family of terpenoids isolated from the neem tree (Azadirachta indica).		2.0510acetate ester;
azadirachtin;
cyclic hemiketal;
enoate ester;
epoxide;
methyl ester;
organic heterotetracyclic compound;
secondary alcohol;
tertiary alcohol		hepatoprotective agent
sulfur
Sulfur: An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine.		2.0510chalcogen;
nonmetal atom		macronutrient
beta-escin
[no description available]		5.35100
oleanonic acid
oleanonic acid: structure in first source		2.0810
bisdesmoside
bisdesmoside: cytotoxic saponin from tubers of Bolbostemma paniculatum; structure in first source		2.1110
sapogenins
Sapogenins: The aglucon moiety of a saponin molecule. It may be triterpenoid or steroid, usually spirostan, in nature.		5.82120
quil a
Quil A: produces antibodies to bovine ephemeral fever virus		3.0810
qs 21
[no description available]		2.4920
quillaja saponins
Quillaja Saponins: Natural detergents made up of a heterogeneous mixture of molecules having a triterpenoid core structure. They vary in aglycone (sapogenin) and sugar moieties, including glucose.		3.0810
ConditionIndicatedRelationship StrengthStudiesTrials
Cancer of Stomach
[description not available]		02.2510
Stomach Neoplasms
Tumors or cancer of the STOMACH.		02.2510
Ache
[description not available]		02.5220
Pain
An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.		02.5220
Innate Inflammatory Response
[description not available]		02.0610
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.0610
Swine Diseases
Diseases of domestic swine and of the wild boar of the genus Sus.		02.0110
Salmonella Infections, Animal
Infections in animals with bacteria of the genus SALMONELLA.		02.0110
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		0210
Weight Gain
Increase in BODY WEIGHT over existing weight.		0210