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Details

Stereochemistry ABSOLUTE
Molecular Formula C30H48O3
Molecular Weight 456.7003
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OLEANOLIC ACID

SMILES

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

InChI

InChIKey=MIJYXULNPSFWEK-GTOFXWBISA-N
InChI=1S/C30H48O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23-,27-,28+,29+,30-/m0/s1

HIDE SMILES / InChI
Molecular Formula C30H48O3
Molecular Weight 456.7003
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
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/16741586

Oleanolic acid or oleanic acid is a naturally occurring pentacyclic triterpenoid. It is widely distributed in food and plants where it exists as a free acid or as an aglycone of triterpenoid saponins. Oleanolic acid protects the liver from acute chemically induced liver injury, fibrosis and cirrhosis caused by chronic liver diseases. Its possess cytotoxic activity against tumor cell lines

Approval Year

2003
176
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Modulator
828
Activator
1430
Activator
1430
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Inactive ingredient
Not Provided
504
PREVENTAGE FIRMING DEFENSE NORMAL/OILY BROAD SPECTRUM SPF 15 MERLE NORMAN

Approved Use

Unknown
Inactive ingredient
Approved
8429
24 HOUR PIMPLE PUNISHER

Approved Use

For treatment of Acne. Helps keep skin clear of new acne blemishes.
Preventing
Preclinical
Unknown

Approved Use

Unknown
Secondary
Preclinical
Unknown

Approved Use

Unknown
Secondary
Preclinical
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Two new triterpenoid saponins from Aralia subcapitata.
2001
A new biologically active triterpenoid saponin from the leaves of Lepidagathis hyalina Nees.
2001
Topical anti-inflammatory activity of Thymus willdenowii.
2001 Dec
Screening of triterpenoids isolated from Phyllanthus flexuosus for DNA topoisomerase inhibitory activity.
2001 Dec
Junceosides A-C, new triterpene saponins from Arenaria juncea.
2001 Dec
Phytochemical and antimicrobial studies on Drynaria quercifolia.
2001 Dec
The first naturally occurring Tie2 kinase inhibitor.
2001 Dec 13
Synthesis and anti-HIV activity of oleanolic acid derivatives.
2001 Dec 17
Inhibitory role of GDP on saikosaponin (I) stimulated enzymes secretion and rising of [Ca2+]i in rat pancreatic acini.
2001 Jul
Efficient production of saikosaponins in Bupleurum falcatum root fragments combined with signal transducers.
2001 Nov
Hepatoprotective action of an oleanolic acid-enriched extract of Ligustrum lucidum fruits is mediated through an enhancement on hepatic glutathione regeneration capacity in mice.
2001 Nov
Antimycobacterial plant terpenoids.
2001 Nov
Two triterpene saponins from Achyranthes bidentata.
2001 Nov
Superoxide- and 1,1-diphenyl-2-picrylhydrazyl radical-scavenging activities of soyasaponin beta g related to gallic acid.
2001 Oct
Oleanonic acid, a 3-oxotriterpene from Pistacia, inhibits leukotriene synthesis and has anti-inflammatory activity.
2001 Sep 28
Gastroprotective activity of oleanolic acid derivatives on experimentally induced gastric lesions in rats and mice.
2002 Apr
In vitro antiinflammatory activity of kalopanaxsaponin A isolated from Kalopanax pictus in murine macrophage RAW 264.7 cells.
2002 Apr
A new naphthoquinone from Polygonum aviculare.
2002 Apr
High performance liquid chromatography analysis of canthinone alkaloids from Eurycoma longifolia.
2002 Apr
HPLC analysis of plasma 9-methoxycanthin-6-one from Eurycoma longifolia and its application in a bioavailability/pharmacokinetic study.
2002 Apr
Three new triterpene saponins from two species of Carpolobia.
2002 Apr
Quantification of the group B soyasaponins by high-performance liquid chromatography.
2002 Apr 24
A novel dicyanotriterpenoid, 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-onitrile, active at picomolar concentrations for inhibition of nitric oxide production.
2002 Apr 8
In vitro anti-HIV activity of oleanolic acid on infected human mononuclear cells.
2002 Feb
Antiviral activity of seven iridoids, three saikosaponins and one phenylpropanoid glycoside extracted from Bupleurum rigidum and Scrophularia scorodonia.
2002 Feb
Bioactive saponins from Acacia tenuifolia from the suriname rainforest.
2002 Feb
Two major saponins from seeds of Barringtonia asiatica: putative antifeedants toward Epilachna sp. larvae.
2002 Feb
Production of bioactive triterpenes by Eriobotrya japonica calli.
2002 Feb
Diuretic activity of Fabiana patagonica in rats.
2002 Feb
Antinociceptive and anti-rheumatoidal effects of Kalopanax pictus extract and its saponin components in experimental animals.
2002 Feb
Phytosterol content in American ginseng seed oil.
2002 Feb 13
Toxin clues to beetle relationships.
2002 Feb 19
Saponins-mediated potentiation of cisplatin accumulation and cytotoxicity in human colon cancer cells.
2002 Jan
Spasmolytic effects of baccharis conferta and some of its constituents.
2002 Jan
Modulation of radioligand binding to the GABA(A)-benzodiazepine receptor complex by a new component from Cyperus rotundus.
2002 Jan
A new triterpene saponin from Pittosporum viridiflorum from the Madagascar rainforest.
2002 Jan
Kalopanaxsaponin A from Kalopanax pictus, a potent antioxidant in the rheumatoidal rat treated with Freund's complete adjuvant reagent.
2002 Jan
Novel triterpenoid CDDO-Me is a potent inducer of apoptosis and differentiation in acute myelogenous leukemia.
2002 Jan 1
Selective cytotoxicity of betulinic acid on tumor cell lines, but not on normal cells.
2002 Jan 10
Inhibition of alpha-glucosidase by oleanolic acid and its synthetic derivatives.
2002 Jun
A multidisciplinary approach to the study of the fluminense vegetation.
2002 Mar
Induction of differentiation in rat C6 glioma cells with Saikosaponins.
2002 Mar
Microbial transformations of two lupane-type triterpenes and anti-tumor-promoting effects of the transformation products.
2002 Mar
The anti-inflammatory triterpenoid methyl 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oate methanol solvate hydrate.
2002 Mar
Quantitative determination for cytotoxic Friedo-nor-oleanane derivatives from five morphological types of Maytenus ilicifolia (Celastraceae) by reverse-phase high-performance liquid chromatography.
2002 Mar-Apr
[Comparative study of cytotoxic and hemolytic effects of triterpenoids isolated from Ginseng and Sea cucumber].
2002 Mar-Apr
The novel triterpenoid 2-cyano-3,12-dioxooleana-1,9-dien-28-oic acid (CDDO) potently enhances apoptosis induced by tumor necrosis factor in human leukemia cells.
2002 May 10
RP-LC determination of oleane derivatives in Terminalia arjuna.
2002 May 15
Spray freeze drying with polyvinylpyrrolidone and sodium caprate for improved dissolution and oral bioavailability of oleanolic acid, a BCS Class IV compound.
2011 Feb 14
Advancing the delivery of anticancer drugs: Conjugated polymer/triterpenoid composite.
2015 Jun
Patents

Patents

JP1039973A
4
JP4791359B2
5
JPH08133958A
2
JPS62126149A
2
JPS62126150A
2
US2076794 A
2
US4752606 A
2

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Topical
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 20:18:30 GMT 2023
Edited
by admin
on Sat Dec 16 20:18:30 GMT 2023
Record UNII
6SMK8R7TGJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OLEANOLIC ACID
INCI   MI   WHO-DD  
INCI  
Official Name English
OLEANIC ACID
Common Name English
(3.BETA.)-3-HYDROXYOLEAN-12-EN-28-OIC ACID
Common Name English
OLEANOLIC ACID (CONSTITUENT OF HOLY BASIL LEAF) [DSC]
Common Name English
OLEANOLIC ACID (CONSTITUENT OF BANABA LEAF) [DSC]
Common Name English
ASTRANTIAGENIN C
Common Name English
GIGANTEUMGENIN C
Common Name English
VIRGAUREAGENIN B
Common Name English
Oleanolic acid [WHO-DD]
Common Name English
OLEANOLIC ACID [INCI]
Common Name English
OLEANOLIC ACID [MI]
Common Name English
OLEANOLIC ACID [USP-RS]
Common Name English
OLEONOLIC ACID
Common Name English
OLEANOLATE
Common Name English
3.BETA.-HYDROXYOLEAN-12-EN-28-OIC ACID
Common Name English
NSC-114945
Code English
OLEANOL
Common Name English
GLEDIGENIN 1
Common Name English
CARYOPHYLLIN
Common Name English
Classification Tree Code System Code
DSLD 1800 (Number of products:12)
Created by admin on Sat Dec 16 20:18:31 GMT 2023 , Edited by admin on Sat Dec 16 20:18:31 GMT 2023
Code System Code Type Description
CHEBI
82828
Created by admin on Sat Dec 16 20:18:31 GMT 2023 , Edited by admin on Sat Dec 16 20:18:31 GMT 2023
PRIMARY
CAS
508-02-1
Created by admin on Sat Dec 16 20:18:31 GMT 2023 , Edited by admin on Sat Dec 16 20:18:31 GMT 2023
PRIMARY
EVMPD
SUB33853
Created by admin on Sat Dec 16 20:18:31 GMT 2023 , Edited by admin on Sat Dec 16 20:18:31 GMT 2023
PRIMARY
WIKIPEDIA
OLEANOLIC ACID
Created by admin on Sat Dec 16 20:18:31 GMT 2023 , Edited by admin on Sat Dec 16 20:18:31 GMT 2023
PRIMARY
ECHA (EC/EINECS)
208-081-6
Created by admin on Sat Dec 16 20:18:31 GMT 2023 , Edited by admin on Sat Dec 16 20:18:31 GMT 2023
PRIMARY
RXCUI
1370638
Created by admin on Sat Dec 16 20:18:31 GMT 2023 , Edited by admin on Sat Dec 16 20:18:31 GMT 2023
ALTERNATIVE
FDA UNII
6SMK8R7TGJ
Created by admin on Sat Dec 16 20:18:31 GMT 2023 , Edited by admin on Sat Dec 16 20:18:31 GMT 2023
PRIMARY
MESH
D009828
Created by admin on Sat Dec 16 20:18:31 GMT 2023 , Edited by admin on Sat Dec 16 20:18:31 GMT 2023
PRIMARY
NSC
114945
Created by admin on Sat Dec 16 20:18:31 GMT 2023 , Edited by admin on Sat Dec 16 20:18:31 GMT 2023
PRIMARY
RXCUI
1426254
Created by admin on Sat Dec 16 20:18:31 GMT 2023 , Edited by admin on Sat Dec 16 20:18:31 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID50858790
Created by admin on Sat Dec 16 20:18:31 GMT 2023 , Edited by admin on Sat Dec 16 20:18:31 GMT 2023
PRIMARY
SMS_ID
100000127756
Created by admin on Sat Dec 16 20:18:31 GMT 2023 , Edited by admin on Sat Dec 16 20:18:31 GMT 2023
PRIMARY
RS_ITEM_NUM
1478141
Created by admin on Sat Dec 16 20:18:31 GMT 2023 , Edited by admin on Sat Dec 16 20:18:31 GMT 2023
PRIMARY
MERCK INDEX
m8190
Created by admin on Sat Dec 16 20:18:31 GMT 2023 , Edited by admin on Sat Dec 16 20:18:31 GMT 2023
PRIMARY Merck Index
CHEBI
37659
Created by admin on Sat Dec 16 20:18:31 GMT 2023 , Edited by admin on Sat Dec 16 20:18:31 GMT 2023
PRIMARY
DAILYMED
6SMK8R7TGJ
Created by admin on Sat Dec 16 20:18:31 GMT 2023 , Edited by admin on Sat Dec 16 20:18:31 GMT 2023
PRIMARY
PUBCHEM
10494
Created by admin on Sat Dec 16 20:18:31 GMT 2023 , Edited by admin on Sat Dec 16 20:18:31 GMT 2023
PRIMARY
Related Record Type Details
HOLY BASIL LEAF
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
CALENDULA OFFICINALIS FLOWER
PARENT -> CONSTITUENT ALWAYS PRESENT
CALENDULA OFFICINALIS FLOWER terpenoid
PAEONIA LACTIFLORA ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
JUJUBE FRUIT
PARENT -> CONSTITUENT ALWAYS PRESENT
CLEMATIS ARMANDII STEM
PARENT -> CONSTITUENT ALWAYS PRESENT
ASSAY (HPLC)
LAGERSTROEMIA SPECIOSA LEAF
PARENT -> CONSTITUENT ALWAYS PRESENT
CENTAURIUM ERYTHRAEA WHOLE
PARENT -> CONSTITUENT ALWAYS PRESENT
Structure of SODIUM OLEANOLATE
SALT/SOLVATE -> PARENT
PAEONIA X SUFFRUTICOSA ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
Structure of OLEANOLIC ACID
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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