SODIUM OLEANOLATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C30H47O3.Na
Molecular Weight	478.6821
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].[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=QNELTPKHJFMSNK-RLFONNADSA-M

InChI=1S/C30H48O3.Na/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);/q;+1/p-1/t20-,21-,22+,23-,27-,28+,29+,30-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	C30H47O3
Molecular Weight	455.6924
Charge	-1
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	Na
Molecular Weight	22.9898
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://korea.in-cosmetics.com/en/Exhibitors/2695677/GfN-GmbH-Selco-GmbH/Products/1138708/Ursolic-acid-Na-salt-natural | https://www.ulprospector.com/en/eu/PersonalCare/Detail/3345/93891/Ursolic-Acid-Sodium-Salthttps://www.ncbi.nlm.nih.gov/pubmed/22377690
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

Targets

Primary Target	Pharmacology	Condition	Potency
Elastase 4 Target ID: Elastase Sources: http://korea.in-cosmetics.com/en/Exhibitors/2695677/GfN-GmbH-Selco-GmbH/Products/1138708/Ursolic-acid-Na-salt-natural	Inhibitor 8297
Bile acid receptor FXR 31 Target ID: CHEMBL2047 Sources: http://www.ncbi.nlm.nih.gov/pubmed/19653193	Modulator 828
MAPK signaling pathway 26 Target ID: map04010 Sources: http://www.ncbi.nlm.nih.gov/pubmed/21328610	Activator 1430
PI3K-Akt signaling pathway 24 Target ID: map04151 Sources: http://www.ncbi.nlm.nih.gov/pubmed/21328610	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Photoaging of skin 4 Sources: https://www.ulprospector.com/en/eu/PersonalCare/Detail/3345/93891/Ursolic-Acid-Sodium-Salt https://dailymed.nlm.nih.gov/dailymed/getFile.cfm?setid=27ced99b-59a5-473f-90c5-f72b7e48ebdc&type=pdf&name=27ced99b-59a5-473f-90c5-f72b7e48ebdc	Inactive ingredient	Not Provided 504	PREVENTAGE FIRMING DEFENSE NORMAL/OILY BROAD SPECTRUM SPF 15 MERLE NORMAN Approved Use Unknown
Acne 98 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=636ceab4-b6f2-4198-9574-94f123a5299b	Inactive ingredient	Approved 8429	24 HOUR PIMPLE PUNISHER Approved Use For treatment of Acne. Helps keep skin clear of new acne blemishes.
Renal fibrosis 7 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24393202	Preventing	Preclinical	Unknown Approved Use Unknown
Drug-induced liver injury 10 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17392098	Secondary	Preclinical	Unknown Approved Use Unknown
Tuberculosis 83 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27393091	Secondary	Preclinical	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16741586	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Two new triterpenoid saponins from Aralia subcapitata.	2001	11858547
A new biologically active triterpenoid saponin from the leaves of Lepidagathis hyalina Nees.	2001	11841115
Topical anti-inflammatory activity of Thymus willdenowii.	2001 Dec	11804395
Screening of triterpenoids isolated from Phyllanthus flexuosus for DNA topoisomerase inhibitory activity.	2001 Dec	11754608
Junceosides A-C, new triterpene saponins from Arenaria juncea.	2001 Dec	11754605
Phytochemical and antimicrobial studies on Drynaria quercifolia.	2001 Dec	11731121
The first naturally occurring Tie2 kinase inhibitor.	2001 Dec 13	11735581
Synthesis and anti-HIV activity of oleanolic acid derivatives.	2001 Dec 17	11720855
Inhibitory role of GDP on saikosaponin (I) stimulated enzymes secretion and rising of [Ca2+]i in rat pancreatic acini.	2001 Jul	11749835
Efficient production of saikosaponins in Bupleurum falcatum root fragments combined with signal transducers.	2001 Nov	11762592
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	11746839
Antimycobacterial plant terpenoids.	2001 Nov	11731906
Two triterpene saponins from Achyranthes bidentata.	2001 Nov	11724247
Superoxide- and 1,1-diphenyl-2-picrylhydrazyl radical-scavenging activities of soyasaponin beta g related to gallic acid.	2001 Oct	11758904
Oleanonic acid, a 3-oxotriterpene from Pistacia, inhibits leukotriene synthesis and has anti-inflammatory activity.	2001 Sep 28	11779030
Gastroprotective activity of oleanolic acid derivatives on experimentally induced gastric lesions in rats and mice.	2002 Apr	11999138
In vitro antiinflammatory activity of kalopanaxsaponin A isolated from Kalopanax pictus in murine macrophage RAW 264.7 cells.	2002 Apr	11995927
A new naphthoquinone from Polygonum aviculare.	2002 Apr	11990427
High performance liquid chromatography analysis of canthinone alkaloids from Eurycoma longifolia.	2002 Apr	11988873
HPLC analysis of plasma 9-methoxycanthin-6-one from Eurycoma longifolia and its application in a bioavailability/pharmacokinetic study.	2002 Apr	11988862
Three new triterpene saponins from two species of Carpolobia.	2002 Apr	11975499
Quantification of the group B soyasaponins by high-performance liquid chromatography.	2002 Apr 24	11958627
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	11909709
In vitro anti-HIV activity of oleanolic acid on infected human mononuclear cells.	2002 Feb	11859458
Antiviral activity of seven iridoids, three saikosaponins and one phenylpropanoid glycoside extracted from Bupleurum rigidum and Scrophularia scorodonia.	2002 Feb	11859457
Bioactive saponins from Acacia tenuifolia from the suriname rainforest.	2002 Feb	11858750
Two major saponins from seeds of Barringtonia asiatica: putative antifeedants toward Epilachna sp. larvae.	2002 Feb	11858740
Production of bioactive triterpenes by Eriobotrya japonica calli.	2002 Feb	11830140
Diuretic activity of Fabiana patagonica in rats.	2002 Feb	11807970
Antinociceptive and anti-rheumatoidal effects of Kalopanax pictus extract and its saponin components in experimental animals.	2002 Feb	11801382
Phytosterol content in American ginseng seed oil.	2002 Feb 13	11829639
Toxin clues to beetle relationships.	2002 Feb 19	11864581
Saponins-mediated potentiation of cisplatin accumulation and cytotoxicity in human colon cancer cells.	2002 Jan	11842333
Spasmolytic effects of baccharis conferta and some of its constituents.	2002 Jan	11829135
Modulation of radioligand binding to the GABA(A)-benzodiazepine receptor complex by a new component from Cyperus rotundus.	2002 Jan	11824542
A new triterpene saponin from Pittosporum viridiflorum from the Madagascar rainforest.	2002 Jan	11809069
Kalopanaxsaponin A from Kalopanax pictus, a potent antioxidant in the rheumatoidal rat treated with Freund's complete adjuvant reagent.	2002 Jan	11744304
Novel triterpenoid CDDO-Me is a potent inducer of apoptosis and differentiation in acute myelogenous leukemia.	2002 Jan 1	11756188
Selective cytotoxicity of betulinic acid on tumor cell lines, but not on normal cells.	2002 Jan 10	11734332
Inhibition of alpha-glucosidase by oleanolic acid and its synthetic derivatives.	2002 Jun	12031449
A multidisciplinary approach to the study of the fluminense vegetation.	2002 Mar	11960185
Induction of differentiation in rat C6 glioma cells with Saikosaponins.	2002 Mar	11933111
Microbial transformations of two lupane-type triterpenes and anti-tumor-promoting effects of the transformation products.	2002 Mar	11908965
The anti-inflammatory triterpenoid methyl 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oate methanol solvate hydrate.	2002 Mar	11870328
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	12018026
[Comparative study of cytotoxic and hemolytic effects of triterpenoids isolated from Ginseng and Sea cucumber].	2002 Mar-Apr	11963541
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	11880365
RP-LC determination of oleane derivatives in Terminalia arjuna.	2002 May 15	12008123
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	21094233
Advancing the delivery of anticancer drugs: Conjugated polymer/triterpenoid composite.	2015 Jun	25770926

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Topical

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 21:17:08 GMT 2023` Edited by `admin` on `Fri Dec 15 21:17:08 GMT 2023`
Record UNII	LVB19G8AUT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SODIUM OLEANOLATE

Official Name

English

OLEAN-12-EN-28-OIC ACID, 3-HYDROXY-, MONOSODIUM SALT, (3.BETA.)-

Common Name

English

OLEAN-12-EN-28-OIC ACID, 3-HYDROXY-, SODIUM SALT (1:1), (3.BETA.)-

Common Name

English

URSOLIC ACID SODIUM SALT

Brand Name

English

SODIUM OLEANOLATE [INCI]

Common Name

English

Code System Code Type Description

PUBCHEM

49857633