Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C30H48O3 |
Molecular Weight | 456.7003 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 10 / 10 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[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=WCGUUGGRBIKTOS-GPOJBZKASA-N
InChI=1S/C30H48O3/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)/t18-,19+,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1
Molecular Formula | C30H48O3 |
Molecular Weight | 456.7003 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 10 / 10 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://examine.com/supplements/ursolic-acid/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-ExtractCurator'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: https://examine.com/supplements/ursolic-acid/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-Extract
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
Sodium Ursolate (Ursolic acid sodium salt) 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. Sodium Ursolate provides a targeted approach to anti-aging skin repair and sun protection through reactivation, protection and optimization of the skins own cellular mechanisms. Furthermore, it protects and refolds proteins damaged by UV and free radical exposure and stimulates new collagen synthesis to counter the effects of thinning and sagging skin caused by photodamage, inhibits elastase and stabilizes liposomal membranes. It is of most interest to use in Anti-Aging and Anti-Photo-Aging cosmetics products.
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 |
---|---|---|
[Lipid chemical constituents of Salvia sochifolia C. Y. Wu]. | 2001 Apr |
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[Studies on chemical constituents of Gaultheria leucocarpa var. Yunnanensis (Franch.) T. Z. Hsu & R. C. Fang]. | 2001 Dec |
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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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[HPLC determination of oleanolic acid and llrolic acid in Chinese medicinal herbs]. | 2001 Sep |
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[Chemical composition of fructus Liquidambaris--lulutong]. | 2002 Apr |
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In vitro screening for antitumour activity of Clinopodium vulgare L. (Lamiaceae) extracts. | 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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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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Antiviral activity of Plantago major extracts and related compounds in vitro. | 2002 Jul |
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Phytochemical constituents from the fruits of Acanthopanax sessiliflorus. | 2002 Jun |
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Structure-activity relationship of triterpenoids isolated from Mitragyna stipulosa on cytotoxicity. | 2002 Jun |
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Antiviral and antioxidant activity of flavonoids and proanthocyanidins from Crataegus sinaica. | 2002 Jun |
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Effects of ursolic acid and oleanolic acid on human colon carcinoma cell line HCT15. | 2002 Jun |
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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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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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Antimicrobial triterpenes from Debregeasia salicifolia. | 2002 Oct |
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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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Triterpenes and phytosterols as human leucocyte elastase inhibitors. | 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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Antileukemic activity of selected natural products in Taiwan. | 2003 |
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Eremophilenolides and other constituents from the roots of Ligularia sagitta. | 2003 Apr |
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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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Ursolic acid inhibits nuclear factor-kappaB activation induced by carcinogenic agents through suppression of IkappaBalpha kinase and p65 phosphorylation: correlation with down-regulation of cyclooxygenase 2, matrix metalloproteinase 9, and cyclin D1. | 2003 Aug 1 |
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Epicuticular waxes from caatinga and cerrado species and their efficiency against water loss. | 2003 Dec |
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Antihypertensive, antiatherosclerotic and antioxidant activity of triterpenoids isolated from Olea europaea, subspecies africana leaves. | 2003 Feb |
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Isolation, characterization and biological activity of betulinic acid and ursolic acid from Vitex negundo L. | 2003 Feb |
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Biomass segregation in sage cell suspension culture. | 2003 Jan |
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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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Cardiovascular, antihyperlipidemic and antioxidant effects of oleanolic and ursolic acids in experimental hypertension. | 2003 Mar |
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New cytotoxic lupane triterpenoids from the twigs of Coussarea paniculata. | 2003 Mar |
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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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Sterol and triterpenoid constituents of Verbena littoralis with NGF-potentiating activity. | 2003 May |
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Biological activity of some naturally occurring resins, gums and pigments against in vitro LDL oxidation. | 2003 May |
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Sterols and triterpenes in cell culture of Hyssopus officinalis L. | 2003 May-Jun |
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A review of natural and modified betulinic, ursolic and echinocystic acid derivatives as potential antitumor and anti-HIV agents. | 2003 Sep |
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A new pentacyclic triterpenoid glucoside from Prunus serrulata var. spontanea. | 2004 Jan |
Sample Use Guides
The intravenous infusion of ursolic acid nanoliposomes (UANL) was well tolerated by healthy volunteers and patients with advanced tumors: UANL exhibits relatively linear pharmacokinetics behavior with dose levels from 37 mg/m(2) to 98 mg/m(2). Rats were treated with ursolic acid (50 mg/kg), per os, once a day for 10 days) in adjuvant-induced chronic arthritis model.Animal studies have found benefits with ursolic acid in the diet at 0.05-0.2% of the diet, which is around 10-40mg/kg (based on their weight and food intake) and the estimated human dose equivalent to this is 1.6-6.4mg/kg bodyweight; for a 150lb adult it would be the range of 110-440mg. The lone human study used the higher end of this range, 150mg three times a day with meals totalling 450mg each day, and found some biological acitivty. Until further research arises, thrice daily dosing of 150mg with meals is recommended.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27219337
ursolic acid (5-50 μM) strongly inhibited the viability of human soft tissue sarcoma cells and its proliferation in soft agar, with higher concentrations increasing apoptotic death
Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 02:02:29 UTC 2023
by
admin
on
Thu Jul 06 02:02:29 UTC 2023
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Record UNII |
P3M2575F3F
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Record Status |
Validated (UNII)
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DSLD |
2413 (Number of products:7)
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DTXSID70883221
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77-52-1
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9908
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1426931
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7685
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P3M2575F3F
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1370661
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201-034-0
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1707770
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P3M2575F3F
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C172843
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M11345
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SUB27186
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C005466
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URSOLIC ACID
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167406
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100000090272
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DB15588
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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 |
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ACTIVE MOIETY |