Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C30H48O3 |
Molecular Weight | 456.7014 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 8 / 8 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@]4([H])[C@@]5(C)CC[C@@]([H])(C(C)(C)[C@]5([H])CC[C@]43C)O)[C@]2([H])C1)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
Molecular Formula | C30H48O3 |
Molecular Weight | 456.7014 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 8 / 8 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/22377690http://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-SaltCurator's Comment:: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/16741586
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22377690http://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-Salt
Curator's Comment:: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/16741586
Sodium Oleanolate is a natural active ingredient derived from many plants. This pentacyclic triterpenoid acid is manufactured by extraction of Salvia officinalis leaves, also known as common sage, Loquat leaves and Olea europea. It can be also found mainly in the balm of rosemary leaves. Ursolic acid and Oleanolic acid have an isomer structure and belong to one of the strongest triterpenoids, which is of most interest to use in Anti-Aging and Anti-Photo-Aging products.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: Elastase |
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Target ID: CHEMBL2047 Sources: http://www.ncbi.nlm.nih.gov/pubmed/19653193 |
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Target ID: map04010 Sources: http://www.ncbi.nlm.nih.gov/pubmed/21328610 |
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Target ID: map04151 Sources: http://www.ncbi.nlm.nih.gov/pubmed/21328610 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Inactive ingredient | PREVENTAGE FIRMING DEFENSE NORMAL/OILY BROAD SPECTRUM SPF 15 MERLE NORMAN Approved UseUnknown |
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Inactive ingredient | 24 HOUR PIMPLE PUNISHER Approved UseFor treatment of Acne. Helps keep skin clear of new acne blemishes. |
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Preventing | Unknown Approved UseUnknown |
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Secondary | Unknown Approved UseUnknown |
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Secondary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Two new triterpenoid saponins from Aralia subcapitata. | 2001 |
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A new biologically active triterpenoid saponin from the leaves of Lepidagathis hyalina Nees. | 2001 |
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Topical anti-inflammatory activity of Thymus willdenowii. | 2001 Dec |
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Screening of triterpenoids isolated from Phyllanthus flexuosus for DNA topoisomerase inhibitory activity. | 2001 Dec |
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Junceosides A-C, new triterpene saponins from Arenaria juncea. | 2001 Dec |
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Phytochemical and antimicrobial studies on Drynaria quercifolia. | 2001 Dec |
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The first naturally occurring Tie2 kinase inhibitor. | 2001 Dec 13 |
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Synthesis and anti-HIV activity of oleanolic acid derivatives. | 2001 Dec 17 |
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NMR and LC-MSn characterisation of two minor saponins from Ilex paraguariensis. | 2001 Jan-Feb |
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Inhibitory role of GDP on saikosaponin (I) stimulated enzymes secretion and rising of [Ca2+]i in rat pancreatic acini. | 2001 Jul |
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Efficient production of saikosaponins in Bupleurum falcatum root fragments combined with signal transducers. | 2001 Nov |
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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 |
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Antimycobacterial plant terpenoids. | 2001 Nov |
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Two triterpene saponins from Achyranthes bidentata. | 2001 Nov |
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Superoxide- and 1,1-diphenyl-2-picrylhydrazyl radical-scavenging activities of soyasaponin beta g related to gallic acid. | 2001 Oct |
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Triterpenoids. | 2001 Oct |
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Oleanonic acid, a 3-oxotriterpene from Pistacia, inhibits leukotriene synthesis and has anti-inflammatory activity. | 2001 Sep 28 |
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Gastroprotective activity of oleanolic acid derivatives on experimentally induced gastric lesions in rats and mice. | 2002 Apr |
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In vitro antiinflammatory activity of kalopanaxsaponin A isolated from Kalopanax pictus in murine macrophage RAW 264.7 cells. | 2002 Apr |
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A new naphthoquinone from Polygonum aviculare. | 2002 Apr |
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High performance liquid chromatography analysis of canthinone alkaloids from Eurycoma longifolia. | 2002 Apr |
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HPLC analysis of plasma 9-methoxycanthin-6-one from Eurycoma longifolia and its application in a bioavailability/pharmacokinetic study. | 2002 Apr |
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Three new triterpene saponins from two species of Carpolobia. | 2002 Apr |
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Quantification of the group B soyasaponins by high-performance liquid chromatography. | 2002 Apr 24 |
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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 |
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In vitro anti-HIV activity of oleanolic acid on infected human mononuclear cells. | 2002 Feb |
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Antiviral activity of seven iridoids, three saikosaponins and one phenylpropanoid glycoside extracted from Bupleurum rigidum and Scrophularia scorodonia. | 2002 Feb |
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Bioactive saponins from Acacia tenuifolia from the suriname rainforest. | 2002 Feb |
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Two major saponins from seeds of Barringtonia asiatica: putative antifeedants toward Epilachna sp. larvae. | 2002 Feb |
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Production of bioactive triterpenes by Eriobotrya japonica calli. | 2002 Feb |
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Diuretic activity of Fabiana patagonica in rats. | 2002 Feb |
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Antinociceptive and anti-rheumatoidal effects of Kalopanax pictus extract and its saponin components in experimental animals. | 2002 Feb |
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Phytosterol content in American ginseng seed oil. | 2002 Feb 13 |
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Toxin clues to beetle relationships. | 2002 Feb 19 |
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Saponins-mediated potentiation of cisplatin accumulation and cytotoxicity in human colon cancer cells. | 2002 Jan |
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Spasmolytic effects of baccharis conferta and some of its constituents. | 2002 Jan |
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Modulation of radioligand binding to the GABA(A)-benzodiazepine receptor complex by a new component from Cyperus rotundus. | 2002 Jan |
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A new triterpene saponin from Pittosporum viridiflorum from the Madagascar rainforest. | 2002 Jan |
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Kalopanaxsaponin A from Kalopanax pictus, a potent antioxidant in the rheumatoidal rat treated with Freund's complete adjuvant reagent. | 2002 Jan |
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Novel triterpenoid CDDO-Me is a potent inducer of apoptosis and differentiation in acute myelogenous leukemia. | 2002 Jan 1 |
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Selective cytotoxicity of betulinic acid on tumor cell lines, but not on normal cells. | 2002 Jan 10 |
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Inhibition of alpha-glucosidase by oleanolic acid and its synthetic derivatives. | 2002 Jun |
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A multidisciplinary approach to the study of the fluminense vegetation. | 2002 Mar |
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Induction of differentiation in rat C6 glioma cells with Saikosaponins. | 2002 Mar |
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Microbial transformations of two lupane-type triterpenes and anti-tumor-promoting effects of the transformation products. | 2002 Mar |
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The anti-inflammatory triterpenoid methyl 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oate methanol solvate hydrate. | 2002 Mar |
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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 |
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[Comparative study of cytotoxic and hemolytic effects of triterpenoids isolated from Ginseng and Sea cucumber]. | 2002 Mar-Apr |
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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 |
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RP-LC determination of oleane derivatives in Terminalia arjuna. | 2002 May 15 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24393202
In model of kidney disease, oleanolic acid was dissolved in 2% w/v dimethyl sulfoxide (DMSO) and then diluted with distilled water for each injection to a final DMSO concentration of 0.2% w/v. Oleanolic acid or vehicle was administered intraperitoneally (60 mg/kg i.p). one day before UUO, and was continued for 3 or 7 days after surgery.
Route of Administration:
Other
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/19653193
For cell viability assay, HepG2 cells were plated at a density of 5000 per well in a 96-well plate. After culturing overnight, the cells were exposed to fresh medium containing different concentrations of OA. 24 hours later, the cell viability was determined by CellTiter-Glo Luminescence Cell Viability Assay (Promega) according to the manufacturer’s instructions.
In order to determine whether OA would affect the activity of FXR-LBD, HepG2 cells were transfected with an expression vector for Gal4-DBD-FXR-LBD, a reporter plasmid pFR-Luc, an internal control Renilla luciferase vector and then treated with FXR agonist CDCA in the presence of increasing amounts of OA.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 08:12:12 UTC 2021
by
admin
on
Sat Jun 26 08:12:12 UTC 2021
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Record UNII |
6SMK8R7TGJ
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Record Status |
Validated (UNII)
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Record Version |
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DSLD |
1800 (Number of products:12)
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1478141
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PRIMARY | USP-RS | ||
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508-02-1
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SUB33853
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OLEANOLIC ACID
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208-081-6
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1370638
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6SMK8R7TGJ
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D009828
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1426254
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508-02-1
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M8190
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PRIMARY | Merck Index | ||
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10494
Created by
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Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
ASSAY (HPLC)
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PARENT -> CONSTITUENT ALWAYS PRESENT |
CALENDULA OFFICINALIS FLOWER terpenoid
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |