U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of SODIUM URSOLATE

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

HIDE SMILES / InChI

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

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

Description
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

Sources: Trommsdorff, H., Arch. Pharm., 80, 273 (1854)

Approval Year

TargetsConditions

Conditions

Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1835 μg/mL
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
4203 ng × h/mL
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
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
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
4.59 h
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
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
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
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

Doses

DosePopulationAdverse 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)
AST increased (grade 3, 2 patients)
Direct bilirubin increased (grade 3, 2 patients)
Other AEs:
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)
GGT increased (grade 3, 1 pt)
Other AEs:
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)
ALT increased (grade 3, 1 pt)
diarrhea (grade 3, 1 pt)
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
[Lipid chemical constituents of Salvia sochifolia C. Y. Wu].
2001 Apr
[Studies on chemical constituents of Gaultheria leucocarpa var. Yunnanensis (Franch.) T. Z. Hsu & R. C. Fang].
2001 Dec
[Studies on the triterpenoidal saponins from flowers of Eriobotrya japonica].
2001 Jun
[Isolation and elucidation of chemical constituents of Shandanshaoyao Decoction(I)].
2001 Jun
[The research on the chemical components of Schizonepeta tenuifolia Briq].
2001 Mar
Triterpenes and sterols in the flowers and leaves of Prunus spinosa L. (Rosaceae).
2001 Nov-Dec
[HPLC determination of oleanolic acid and llrolic acid in Chinese medicinal herbs].
2001 Sep
[Chemical composition of fructus Liquidambaris--lulutong].
2002 Apr
[Studies on chemical constituents in fruit of Eucalyptus globulus].
2002 Aug
[Comparative study of the spectral characteristics of ursolic acid between laser Raman spectra and IR spectrum].
2002 Dec
[Determination of ursolic acid in herba of Verbena officinalis by HPLC].
2002 Dec
Biosynthesis of sterols and triterpenes in cell suspension cultures of Uncaria tomentosa.
2002 Dec
Antithrombin activity of some constituents from Origanum vulgare.
2002 Dec
Screening of ubiquitous plant constituents for COX-2 inhibition with a scintillation proximity based assay.
2002 Nov
Antimicrobial triterpenes from Debregeasia salicifolia.
2002 Oct
Sessiline, a new nitrogenous compound from the fruits of Acanthopanax sessiliflorus.
2002 Oct
Effect of naturally occurring triterpenoids glycyrrhizic acid, ursolic acid, oleanolic acid and nomilin on the immune system.
2003
The triterpenoid CDDO inhibits expression of matrix metalloproteinase-1, matrix metalloproteinase-13 and Bcl-3 in primary human chondrocytes.
2003
Antileukemic activity of selected natural products in Taiwan.
2003
New ursolic and betulinic derivatives as potential cytotoxic agents.
2003 Apr
Eremophilenolides and other constituents from the roots of Ligularia sagitta.
2003 Apr
A new in vitro tissue factor inhibitory triterpene from the fruits of Chaenomeles sinensis.
2003 Apr
Development of LC-MS method for determination of ursolic acid: application to the analysis of ursolic acid in Staphylea holocarpa Hemsl.
2003 Apr 1
[Effects of ursolic acid on liver-protection and bile secretion].
2003 Aug
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
High-performance liquid chromatographic analysis of bioactive triterpenes in Perilla frutescens.
2003 Aug 21
Inhibition of ultraviolet-A-modulated signaling pathways by asiatic acid and ursolic acid in HaCaT human keratinocytes.
2003 Aug 29
Epicuticular waxes from caatinga and cerrado species and their efficiency against water loss.
2003 Dec
Antihypertensive, antiatherosclerotic and antioxidant activity of triterpenoids isolated from Olea europaea, subspecies africana leaves.
2003 Feb
In vivo anti-nociceptive and anti-inflammatory effect of the two triterpenes, ursolic acid and 23-hydroxyursolic acid, from Cussonia bancoensis.
2003 Feb
Natural anti-HIV agents. Part IV. Anti-HIV constituents from Vatica cinerea.
2003 Feb
Isolation, characterization and biological activity of betulinic acid and ursolic acid from Vitex negundo L.
2003 Feb
Biomass segregation in sage cell suspension culture.
2003 Jan
The role of hydrogen peroxide produced by polychlorinated biphenyls in PMR1-deficient yeast cells.
2003 Jul
In vitro TGF-beta1 antagonistic activity of ursolic and oleanolic acids isolated from Clerodendranthus spicatus.
2003 Jul
Immunomodulatory activities of flavonoids, monoterpenoids, triterpenoids, iridoid glycosides and phenolic compounds of Plantago species.
2003 Jul
Ursolic acid induces apoptosis through caspase-3 activation and cell cycle arrest in HaCat cells.
2003 Jul
MECC determination of oleanolic acid and ursolic acid isomers in Ligustrum lucidum Ait.
2003 Jul 14
Ursolic acid inhibits proliferation and stimulates apoptosis in HT29 cells following activation of alkaline sphingomyelinase.
2003 Jul-Aug
Cardiovascular, antihyperlipidemic and antioxidant effects of oleanolic and ursolic acids in experimental hypertension.
2003 Mar
New cytotoxic lupane triterpenoids from the twigs of Coussarea paniculata.
2003 Mar
CNS activity of the methanol extract of Mallotus peltatus (Geist) Muell Arg. leaf: an ethnomedicine of Onge.
2003 Mar
Antifeedant activity of some pentacyclic triterpene acids and their fatty acid ester analogues.
2003 Mar 26
[Chemical constituents in the roots of Salvia przewalskii Maxim].
2003 May
Sterol and triterpenoid constituents of Verbena littoralis with NGF-potentiating activity.
2003 May
Biological activity of some naturally occurring resins, gums and pigments against in vitro LDL oxidation.
2003 May
Sterols and triterpenes in cell culture of Hyssopus officinalis L.
2003 May-Jun
Antiplasmodial triterpenes from twigs of Gardenia saxatilis.
2003 Oct
A review of natural and modified betulinic, ursolic and echinocystic acid derivatives as potential antitumor and anti-HIV agents.
2003 Sep
A new pentacyclic triterpenoid glucoside from Prunus serrulata var. spontanea.
2004 Jan
Patents

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
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 Sat Dec 16 01:48:52 GMT 2023
Edited
by admin
on Sat Dec 16 01:48:52 GMT 2023
Record UNII
NV5D25VL1O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SODIUM URSOLATE
INCI  
INCI  
Official Name English
URS-12-EN-28-OIC ACID, 3-HYDROXY-, SODIUM SALT (1:1), (3.BETA.)-
Common Name English
URS-12-3EN-28-OIC ACID, 3-HYDROXY-, MONOSODIUM SALT, (3-.BETA.)-
Common Name English
SODIUM URSOLATE [INCI]
Common Name English
DUBOISIA URSOLIC ACID, SODIUM SALT, PREMIER
Brand Name English
Code System Code Type Description
PUBCHEM
71587647
Created by admin on Sat Dec 16 01:48:53 GMT 2023 , Edited by admin on Sat Dec 16 01:48:53 GMT 2023
PRIMARY
RXCUI
1366935
Created by admin on Sat Dec 16 01:48:53 GMT 2023 , Edited by admin on Sat Dec 16 01:48:53 GMT 2023
PRIMARY RxNorm
DAILYMED
NV5D25VL1O
Created by admin on Sat Dec 16 01:48:53 GMT 2023 , Edited by admin on Sat Dec 16 01:48:53 GMT 2023
PRIMARY
EPA CompTox
DTXSID90176521
Created by admin on Sat Dec 16 01:48:53 GMT 2023 , Edited by admin on Sat Dec 16 01:48:53 GMT 2023
PRIMARY
FDA UNII
NV5D25VL1O
Created by admin on Sat Dec 16 01:48:53 GMT 2023 , Edited by admin on Sat Dec 16 01:48:53 GMT 2023
PRIMARY
CAS
220435-39-2
Created by admin on Sat Dec 16 01:48:53 GMT 2023 , Edited by admin on Sat Dec 16 01:48:53 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE