Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C30H47O3.Na |
Molecular Weight | 478.6821 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 10 / 10 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[H][C@@]12CC[C@]3(C)[C@]([H])(CC=C4[C@]5([H])[C@@H](C)[C@H](C)CC[C@@]5(CC[C@@]34C)C([O-])=O)[C@@]1(C)CC[C@H](O)C2(C)C
InChI
InChIKey=DUAZSEDLBBRXQJ-ANQQBNRBSA-M
InChI=1S/C30H48O3.Na/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7;/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33);/q;+1/p-1/t18-,19+,21+,22-,23+,24+,27+,28-,29-,30+;/m1./s1
Molecular Formula | C30H47O3 |
Molecular Weight | 455.6924 |
Charge | -1 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 10 / 10 |
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 |
DescriptionSources: http://korea.in-cosmetics.com/en/Exhibitors/2695677/GfN-GmbH-Selco-GmbH/Products/1138708/Ursolic-acid-Na-salt-natural | https://www.ulprospector.com/en/na/PersonalCare/Detail/6837/373852/Ursolic-Acid-Sodium-Salt-Salvia-Officinalis-Extracthttps://examine.com/supplements/ursolic-acid/Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/24374755 | https://www.ncbi.nlm.nih.gov/pubmed/23499879 | https://www.ncbi.nlm.nih.gov/pubmed/26610440 | https://www.ncbi.nlm.nih.gov/pubmed/26775565
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/na/PersonalCare/Detail/6837/373852/Ursolic-Acid-Sodium-Salt-Salvia-Officinalis-Extracthttps://examine.com/supplements/ursolic-acid/
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/24374755 | https://www.ncbi.nlm.nih.gov/pubmed/23499879 | https://www.ncbi.nlm.nih.gov/pubmed/26610440 | https://www.ncbi.nlm.nih.gov/pubmed/26775565
Ursolic acid is a natural terpene compond found in a wide variety of plants but most well known for being in apple peels. Ursolic acid has a series of biological effects such as sedative, anti-inflammatory, anti-bacterial, anti-diabetic, antiulcer, antitumor etc. Ursolic acid has been shown to target multiple proinflammatory transcription factors, cell cycle proteins, growth factors, kinases, cytokines, chemokines, adhesion molecules, and inflammatory enzymes.
Evidences suggest that ursolic acid could be used as a potential candidate to develop a comprehensive competent strategy towards the treatment and prevention of health disorders.
Although the science is preliminary, it seems to be able to reduce fat accumulation and increase muscle mass gain when in a fed state, and to induce fat burning and preserve muscle mass when in a fasted state.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GO:0006457 |
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Target ID: GO:0032964 |
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Target ID: Elastase |
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Target ID: GO:0006979 |
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Target ID: CHEMBL1744526 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17404266/ |
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Target ID: CHEMBL1978 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18192087 |
32.0 µM [IC50] | ||
Target ID: CHEMBL1900 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22332359 |
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Target ID: CHEMBL335 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16534732 |
3.8 µM [IC50] | ||
Target ID: CHEMBL4235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20100662 |
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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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Sources: https://www.ncbi.nlm.nih.gov/pubmed/15854639 DOI: 10.1002/(SICI)1099-1573(19980201)12:1<32::AID-PTR185>3.0.CO;2-4 https://examine.com/supplements/ursolic-acid/#ref63 |
Preventing | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1835 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23319864 |
37 mg/m² single, intravenous dose: 37 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
URSOLIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
2865 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23319864 |
74 mg/m² single, intravenous dose: 74 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
URSOLIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
3457 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23319864 |
98 mg/m² single, intravenous dose: 98 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
URSOLIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1211 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23319864 |
74 mg/m² 1 times / day multiple, intravenous dose: 74 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
URSOLIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4203 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23319864 |
37 mg/m² single, intravenous dose: 37 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
URSOLIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
7175 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23319864 |
74 mg/m² single, intravenous dose: 74 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
URSOLIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
9696 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23319864 |
98 mg/m² single, intravenous dose: 98 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
URSOLIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
4834 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23319864 |
74 mg/m² 1 times / day multiple, intravenous dose: 74 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
URSOLIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.59 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23319864 |
37 mg/m² single, intravenous dose: 37 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
URSOLIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
4.46 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23319864 |
74 mg/m² single, intravenous dose: 74 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
URSOLIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
3.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23319864 |
98 mg/m² single, intravenous dose: 98 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
URSOLIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23319864 |
74 mg/m² 1 times / day multiple, intravenous dose: 74 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
URSOLIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
130 mg/m2 single, intravenous (total daily dose) Highest studied dose Dose: 130 mg/m2 Route: intravenous Route: single Dose: 130 mg/m2 Sources: |
unhealthy n = 3 Health Status: unhealthy Condition: solid tumors Sex: M Food Status: UNKNOWN Population Size: 3 Sources: |
DLT: ALT increased, AST increased... Other AEs: GGT increased... Dose limiting toxicities: ALT increased (grade 3, 2 patients) Other AEs:AST increased (grade 3, 2 patients) Direct bilirubin increased (grade 3, 2 patients) GGT increased (grade 2, 2 patients) Sources: |
94 mg/m2 single, intravenous (unknown) MTD Dose: 94 mg/m2 Route: intravenous Route: single Dose: 94 mg/m2 Sources: |
unhealthy n = 11 Health Status: unhealthy Condition: solid tumors Sex: M+F Food Status: UNKNOWN Population Size: 11 Sources: |
DLT: ALT increased, GGT increased... Other AEs: AST increased... Dose limiting toxicities: ALT increased (grade 3, 1 pt) Other AEs:GGT increased (grade 3, 1 pt) AST increased (grade 2, 2 patients) Sources: |
74 mg/m2 single, intravenous (unknown) Studied dose Dose: 74 mg/m2 Route: intravenous Route: single Dose: 74 mg/m2 Sources: |
unhealthy n = 6 Health Status: unhealthy Condition: solid tumor Sex: M+F Food Status: UNKNOWN Population Size: 6 Sources: |
DLT: AST increased, ALT increased... Dose limiting toxicities: AST increased (grade 3, 1 pt) Sources: ALT increased (grade 3, 1 pt) diarrhea (grade 3, 1 pt) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
GGT increased | grade 2, 2 patients | 130 mg/m2 single, intravenous (total daily dose) Highest studied dose Dose: 130 mg/m2 Route: intravenous Route: single Dose: 130 mg/m2 Sources: |
unhealthy n = 3 Health Status: unhealthy Condition: solid tumors Sex: M Food Status: UNKNOWN Population Size: 3 Sources: |
ALT increased | grade 3, 2 patients DLT |
130 mg/m2 single, intravenous (total daily dose) Highest studied dose Dose: 130 mg/m2 Route: intravenous Route: single Dose: 130 mg/m2 Sources: |
unhealthy n = 3 Health Status: unhealthy Condition: solid tumors Sex: M Food Status: UNKNOWN Population Size: 3 Sources: |
AST increased | grade 3, 2 patients DLT |
130 mg/m2 single, intravenous (total daily dose) Highest studied dose Dose: 130 mg/m2 Route: intravenous Route: single Dose: 130 mg/m2 Sources: |
unhealthy n = 3 Health Status: unhealthy Condition: solid tumors Sex: M Food Status: UNKNOWN Population Size: 3 Sources: |
Direct bilirubin increased | grade 3, 2 patients DLT |
130 mg/m2 single, intravenous (total daily dose) Highest studied dose Dose: 130 mg/m2 Route: intravenous Route: single Dose: 130 mg/m2 Sources: |
unhealthy n = 3 Health Status: unhealthy Condition: solid tumors Sex: M Food Status: UNKNOWN Population Size: 3 Sources: |
AST increased | grade 2, 2 patients | 94 mg/m2 single, intravenous (unknown) MTD Dose: 94 mg/m2 Route: intravenous Route: single Dose: 94 mg/m2 Sources: |
unhealthy n = 11 Health Status: unhealthy Condition: solid tumors Sex: M+F Food Status: UNKNOWN Population Size: 11 Sources: |
ALT increased | grade 3, 1 pt DLT |
94 mg/m2 single, intravenous (unknown) MTD Dose: 94 mg/m2 Route: intravenous Route: single Dose: 94 mg/m2 Sources: |
unhealthy n = 11 Health Status: unhealthy Condition: solid tumors Sex: M+F Food Status: UNKNOWN Population Size: 11 Sources: |
GGT increased | grade 3, 1 pt DLT |
94 mg/m2 single, intravenous (unknown) MTD Dose: 94 mg/m2 Route: intravenous Route: single Dose: 94 mg/m2 Sources: |
unhealthy n = 11 Health Status: unhealthy Condition: solid tumors Sex: M+F Food Status: UNKNOWN Population Size: 11 Sources: |
ALT increased | grade 3, 1 pt DLT |
74 mg/m2 single, intravenous (unknown) Studied dose Dose: 74 mg/m2 Route: intravenous Route: single Dose: 74 mg/m2 Sources: |
unhealthy n = 6 Health Status: unhealthy Condition: solid tumor Sex: M+F Food Status: UNKNOWN Population Size: 6 Sources: |
AST increased | grade 3, 1 pt DLT |
74 mg/m2 single, intravenous (unknown) Studied dose Dose: 74 mg/m2 Route: intravenous Route: single Dose: 74 mg/m2 Sources: |
unhealthy n = 6 Health Status: unhealthy Condition: solid tumor Sex: M+F Food Status: UNKNOWN Population Size: 6 Sources: |
diarrhea | grade 3, 1 pt DLT |
74 mg/m2 single, intravenous (unknown) Studied dose Dose: 74 mg/m2 Route: intravenous Route: single Dose: 74 mg/m2 Sources: |
unhealthy n = 6 Health Status: unhealthy Condition: solid tumor Sex: M+F Food Status: UNKNOWN Population Size: 6 Sources: |
PubMed
Title | Date | PubMed |
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Oleanolic acid from cranberries. | 1953 Oct |
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Topical anti-inflammatory activity of Thymus willdenowii. | 2001 Dec |
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Proposed active constituents of Dipladenia martiana. | 2001 Dec |
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Ursolic acid enhances nitric oxide and tumor necrosis factor-alpha production via nuclear factor-kappaB activation in the resting macrophages. | 2001 Dec 7 |
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[Studies on the triterpenoidal saponins from flowers of Eriobotrya japonica]. | 2001 Jun |
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[The research on the chemical components of Schizonepeta tenuifolia Briq]. | 2001 Mar |
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Triterpenes and sterols in the flowers and leaves of Prunus spinosa L. (Rosaceae). | 2001 Nov-Dec |
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Influence of the parasite Viscum cruciatum Sieber on the chemical constituents of Crataegus monogyna Jacq. | 2001 Nov-Dec |
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[HPLC determination of oleanolic acid and llrolic acid in Chinese medicinal herbs]. | 2001 Sep |
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Activation of caspase-3 protease during the process of ursolic acid and its derivative-induced apoptosis. | 2001 Sep-Oct |
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[Chemical composition of fructus Liquidambaris--lulutong]. | 2002 Apr |
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[Studies on chemical constituents in fruit of Eucalyptus globulus]. | 2002 Aug |
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Partial synthesis of 23-hydroxyursolic acid isolated from medicinal plants of the Rubiaceae family. | 2002 Aug |
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[Determination of ursolic acid in herba of Verbena officinalis by HPLC]. | 2002 Dec |
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Antithrombin activity of some constituents from Origanum vulgare. | 2002 Dec |
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Alysinol--a new triterpene from Alysicarpus monolifer. | 2002 Dec |
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Triterpenes and saponins from Ilex psammophila. | 2002 Dec |
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Quinovic acid glycosides from Mitragyna stipulosa--first examples of natural inhibitors of snake venom phosphodiesterase I. | 2002 Dec |
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Abietane diterpenoids and triterpenoic acids from Salvia cilicica and their antileishmanial activities. | 2002 Dec |
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Constituents of Gnetum montanum. | 2002 Feb |
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Production of bioactive triterpenes by Eriobotrya japonica calli. | 2002 Feb |
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Ursolic acid of Origanum majorana L. reduces Abeta-induced oxidative injury. | 2002 Feb 28 |
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Liposome-encapsulated ursolic acid increases ceramides and collagen in human skin cells. | 2002 Jan |
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New prenylated benzoic acid and other constituents from almond hulls (Prunus amygdalus Batsch). | 2002 Jan 30 |
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Effects of ursolic acid and oleanolic acid on human colon carcinoma cell line HCT15. | 2002 Jun |
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Microbial transformation of cadina-4,10(15)-dien-3-one, aromadendr-1(10)-en-9-one and methyl ursolate by Mucor plumbeus ATCC 4740. | 2002 Mar |
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Phosphoinositide 3-OH kinase/protein kinase B inhibits apoptotic cell death induced by reactive oxygen species in Saccharomyces cerevisiae. | 2002 May |
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Synthesis of combinatorial libraries based on terpenoid scaffolds. | 2002 May |
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Screening of ubiquitous plant constituents for COX-2 inhibition with a scintillation proximity based assay. | 2002 Nov |
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Ursolic acid as a trypanocidal constituent in rosemary. | 2002 Nov |
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Brine shrimp lethality of the compounds from Phryma leptostachya L. | 2002 Oct |
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Sessiline, a new nitrogenous compound from the fruits of Acanthopanax sessiliflorus. | 2002 Oct |
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Cytotoxic ent-kaurane diterpenoids from Isodon sculponeata. | 2002 Oct |
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Antimicrobial and anti-inflammatory activity of folklore: Mallotus peltatus leaf extract. | 2002 Oct |
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Extract and identify ingredient from Ligustrum Lucidum Ait and study its effect to periodontal pathogen. | 2002 Sep |
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Effect of naturally occurring triterpenoids glycyrrhizic acid, ursolic acid, oleanolic acid and nomilin on the immune system. | 2003 |
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A new in vitro tissue factor inhibitory triterpene from the fruits of Chaenomeles sinensis. | 2003 Apr |
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Development of LC-MS method for determination of ursolic acid: application to the analysis of ursolic acid in Staphylea holocarpa Hemsl. | 2003 Apr 1 |
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[Effects of ursolic acid on liver-protection and bile secretion]. | 2003 Aug |
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Inhibition of ultraviolet-A-modulated signaling pathways by asiatic acid and ursolic acid in HaCaT human keratinocytes. | 2003 Aug 29 |
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Antihypertensive, antiatherosclerotic and antioxidant activity of triterpenoids isolated from Olea europaea, subspecies africana leaves. | 2003 Feb |
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Biomass segregation in sage cell suspension culture. | 2003 Jan |
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The role of hydrogen peroxide produced by polychlorinated biphenyls in PMR1-deficient yeast cells. | 2003 Jul |
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Ursolic acid induces apoptosis through caspase-3 activation and cell cycle arrest in HaCat cells. | 2003 Jul |
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Ursolic acid inhibits proliferation and stimulates apoptosis in HT29 cells following activation of alkaline sphingomyelinase. | 2003 Jul-Aug |
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CNS activity of the methanol extract of Mallotus peltatus (Geist) Muell Arg. leaf: an ethnomedicine of Onge. | 2003 Mar |
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Antifeedant activity of some pentacyclic triterpene acids and their fatty acid ester analogues. | 2003 Mar 26 |
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Sterol and triterpenoid constituents of Verbena littoralis with NGF-potentiating activity. | 2003 May |
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Sterols and triterpenes in cell culture of Hyssopus officinalis L. | 2003 May-Jun |
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A new pentacyclic triterpenoid glucoside from Prunus serrulata var. spontanea. | 2004 Jan |
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 17 12:54:03 UTC 2022
by
admin
on
Sat Dec 17 12:54:03 UTC 2022
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Record UNII |
NV5D25VL1O
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Record Status |
Validated (UNII)
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Record Version |
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-
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Name | Type | Language | ||
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Official Name | English | ||
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Common Name | English | ||
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Common Name | English | ||
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Brand Name | English |
Code System | Code | Type | Description | ||
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71587647
Created by
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1366935
Created by
admin on Sat Dec 17 12:54:03 UTC 2022 , Edited by admin on Sat Dec 17 12:54:03 UTC 2022
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PRIMARY | RxNorm | ||
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NV5D25VL1O
Created by
admin on Sat Dec 17 12:54:03 UTC 2022 , Edited by admin on Sat Dec 17 12:54:03 UTC 2022
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DTXSID90176521
Created by
admin on Sat Dec 17 12:54:03 UTC 2022 , Edited by admin on Sat Dec 17 12:54:03 UTC 2022
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NV5D25VL1O
Created by
admin on Sat Dec 17 12:54:03 UTC 2022 , Edited by admin on Sat Dec 17 12:54:03 UTC 2022
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220435-39-2
Created by
admin on Sat Dec 17 12:54:03 UTC 2022 , Edited by admin on Sat Dec 17 12:54:03 UTC 2022
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |