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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

CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2C1)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
181
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Modulator
846
Activator
1447
Activator
1447
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Inactive ingredient
Not Provided
511
PREVENTAGE FIRMING DEFENSE NORMAL/OILY BROAD SPECTRUM SPF 15 MERLE NORMAN

Approved Use

Unknown
Inactive ingredient
Approved
8583
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
Advancing the delivery of anticancer drugs: Conjugated polymer/triterpenoid composite.
2015-06
Spray freeze drying with polyvinylpyrrolidone and sodium caprate for improved dissolution and oral bioavailability of oleanolic acid, a BCS Class IV compound.
2011-02-14
Inhibition of alpha-glucosidase by oleanolic acid and its synthetic derivatives.
2002-06
Quantitative determination for cytotoxic Friedo-nor-oleanane derivatives from five morphological types of Maytenus ilicifolia (Celastraceae) by reverse-phase high-performance liquid chromatography.
2002-05-23
RP-LC determination of oleane derivatives in Terminalia arjuna.
2002-05-15
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.
2002-05-10
Quantification of the group B soyasaponins by high-performance liquid chromatography.
2002-04-24
[Comparative study of cytotoxic and hemolytic effects of triterpenoids isolated from Ginseng and Sea cucumber].
2002-04-20
A novel dicyanotriterpenoid, 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-onitrile, active at picomolar concentrations for inhibition of nitric oxide production.
2002-04-08
Gastroprotective activity of oleanolic acid derivatives on experimentally induced gastric lesions in rats and mice.
2002-04
In vitro antiinflammatory activity of kalopanaxsaponin A isolated from Kalopanax pictus in murine macrophage RAW 264.7 cells.
2002-04
A new naphthoquinone from Polygonum aviculare.
2002-04
High performance liquid chromatography analysis of canthinone alkaloids from Eurycoma longifolia.
2002-04
HPLC analysis of plasma 9-methoxycanthin-6-one from Eurycoma longifolia and its application in a bioavailability/pharmacokinetic study.
2002-04
Three new triterpene saponins from two species of Carpolobia.
2002-04
A multidisciplinary approach to the study of the fluminense vegetation.
2002-03
Induction of differentiation in rat C6 glioma cells with Saikosaponins.
2002-03
Microbial transformations of two lupane-type triterpenes and anti-tumor-promoting effects of the transformation products.
2002-03
The anti-inflammatory triterpenoid methyl 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oate methanol solvate hydrate.
2002-03
Toxin clues to beetle relationships.
2002-02-19
Phytosterol content in American ginseng seed oil.
2002-02-13
In vitro anti-HIV activity of oleanolic acid on infected human mononuclear cells.
2002-02
Antiviral activity of seven iridoids, three saikosaponins and one phenylpropanoid glycoside extracted from Bupleurum rigidum and Scrophularia scorodonia.
2002-02
Bioactive saponins from Acacia tenuifolia from the suriname rainforest.
2002-02
Two major saponins from seeds of Barringtonia asiatica: putative antifeedants toward Epilachna sp. larvae.
2002-02
Production of bioactive triterpenes by Eriobotrya japonica calli.
2002-02
Diuretic activity of Fabiana patagonica in rats.
2002-02
Antinociceptive and anti-rheumatoidal effects of Kalopanax pictus extract and its saponin components in experimental animals.
2002-02
Selective cytotoxicity of betulinic acid on tumor cell lines, but not on normal cells.
2002-01-10
Novel triterpenoid CDDO-Me is a potent inducer of apoptosis and differentiation in acute myelogenous leukemia.
2002-01-01
Saponins-mediated potentiation of cisplatin accumulation and cytotoxicity in human colon cancer cells.
2002-01
Spasmolytic effects of baccharis conferta and some of its constituents.
2002-01
Modulation of radioligand binding to the GABA(A)-benzodiazepine receptor complex by a new component from Cyperus rotundus.
2002-01
A new triterpene saponin from Pittosporum viridiflorum from the Madagascar rainforest.
2002-01
Kalopanaxsaponin A from Kalopanax pictus, a potent antioxidant in the rheumatoidal rat treated with Freund's complete adjuvant reagent.
2002-01
Synthesis and anti-HIV activity of oleanolic acid derivatives.
2001-12-17
The first naturally occurring Tie2 kinase inhibitor.
2001-12-13
Topical anti-inflammatory activity of Thymus willdenowii.
2001-12
Screening of triterpenoids isolated from Phyllanthus flexuosus for DNA topoisomerase inhibitory activity.
2001-12
Junceosides A-C, new triterpene saponins from Arenaria juncea.
2001-12
Phytochemical and antimicrobial studies on Drynaria quercifolia.
2001-12
Efficient production of saikosaponins in Bupleurum falcatum root fragments combined with signal transducers.
2001-11
Hepatoprotective action of an oleanolic acid-enriched extract of Ligustrum lucidum fruits is mediated through an enhancement on hepatic glutathione regeneration capacity in mice.
2001-11
Antimycobacterial plant terpenoids.
2001-11
Two triterpene saponins from Achyranthes bidentata.
2001-11
Superoxide- and 1,1-diphenyl-2-picrylhydrazyl radical-scavenging activities of soyasaponin beta g related to gallic acid.
2001-10
Oleanonic acid, a 3-oxotriterpene from Pistacia, inhibits leukotriene synthesis and has anti-inflammatory activity.
2001-09-28
Inhibitory role of GDP on saikosaponin (I) stimulated enzymes secretion and rising of [Ca2+]i in rat pancreatic acini.
2001-07
Two new triterpenoid saponins from Aralia subcapitata.
2001
A new biologically active triterpenoid saponin from the leaves of Lepidagathis hyalina Nees.
2001
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 Wed Apr 02 18:52:36 GMT 2025
Edited
by admin
on Wed Apr 02 18:52:36 GMT 2025
Record UNII
6SMK8R7TGJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NSC-114945
Preferred Name English
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 [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
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 Wed Apr 02 18:52:36 GMT 2025 , Edited by admin on Wed Apr 02 18:52:36 GMT 2025
Code System Code Type Description
CHEBI
82828
Created by admin on Wed Apr 02 18:52:36 GMT 2025 , Edited by admin on Wed Apr 02 18:52:36 GMT 2025
PRIMARY
CAS
508-02-1
Created by admin on Wed Apr 02 18:52:36 GMT 2025 , Edited by admin on Wed Apr 02 18:52:36 GMT 2025
PRIMARY
EVMPD
SUB33853
Created by admin on Wed Apr 02 18:52:36 GMT 2025 , Edited by admin on Wed Apr 02 18:52:36 GMT 2025
PRIMARY
WIKIPEDIA
OLEANOLIC ACID
Created by admin on Wed Apr 02 18:52:36 GMT 2025 , Edited by admin on Wed Apr 02 18:52:36 GMT 2025
PRIMARY
ECHA (EC/EINECS)
208-081-6
Created by admin on Wed Apr 02 18:52:36 GMT 2025 , Edited by admin on Wed Apr 02 18:52:36 GMT 2025
PRIMARY
RXCUI
1370638
Created by admin on Wed Apr 02 18:52:36 GMT 2025 , Edited by admin on Wed Apr 02 18:52:36 GMT 2025
ALTERNATIVE
FDA UNII
6SMK8R7TGJ
Created by admin on Wed Apr 02 18:52:36 GMT 2025 , Edited by admin on Wed Apr 02 18:52:36 GMT 2025
PRIMARY
MESH
D009828
Created by admin on Wed Apr 02 18:52:36 GMT 2025 , Edited by admin on Wed Apr 02 18:52:36 GMT 2025
PRIMARY
NSC
114945
Created by admin on Wed Apr 02 18:52:36 GMT 2025 , Edited by admin on Wed Apr 02 18:52:36 GMT 2025
PRIMARY
RXCUI
1426254
Created by admin on Wed Apr 02 18:52:36 GMT 2025 , Edited by admin on Wed Apr 02 18:52:36 GMT 2025
PRIMARY RxNorm
EPA CompTox
DTXSID50858790
Created by admin on Wed Apr 02 18:52:36 GMT 2025 , Edited by admin on Wed Apr 02 18:52:36 GMT 2025
PRIMARY
SMS_ID
100000127756
Created by admin on Wed Apr 02 18:52:36 GMT 2025 , Edited by admin on Wed Apr 02 18:52:36 GMT 2025
PRIMARY
RS_ITEM_NUM
1478141
Created by admin on Wed Apr 02 18:52:36 GMT 2025 , Edited by admin on Wed Apr 02 18:52:36 GMT 2025
PRIMARY
MERCK INDEX
m8190
Created by admin on Wed Apr 02 18:52:36 GMT 2025 , Edited by admin on Wed Apr 02 18:52:36 GMT 2025
PRIMARY Merck Index
CHEBI
37659
Created by admin on Wed Apr 02 18:52:36 GMT 2025 , Edited by admin on Wed Apr 02 18:52:36 GMT 2025
PRIMARY
DAILYMED
6SMK8R7TGJ
Created by admin on Wed Apr 02 18:52:36 GMT 2025 , Edited by admin on Wed Apr 02 18:52:36 GMT 2025
PRIMARY
PUBCHEM
10494
Created by admin on Wed Apr 02 18:52:36 GMT 2025 , Edited by admin on Wed Apr 02 18:52:36 GMT 2025
PRIMARY
Related Record Type Details
CALENDULA OFFICINALIS FLOWER
PARENT -> CONSTITUENT ALWAYS PRESENT
CALENDULA OFFICINALIS FLOWER terpenoid
PAEONIA LACTIFLORA ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
JUJUBE FRUIT
PARENT -> CONSTITUENT ALWAYS PRESENT
LAGERSTROEMIA SPECIOSA LEAF
PARENT -> CONSTITUENT ALWAYS PRESENT
HOLY BASIL LEAF
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
CLEMATIS ARMANDII STEM
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 NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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