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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 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

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

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

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
Oleanolic acid from cranberries.
1953 Oct
Topical anti-inflammatory activity of Thymus willdenowii.
2001 Dec
Proposed active constituents of Dipladenia martiana.
2001 Dec
Ursolic acid enhances nitric oxide and tumor necrosis factor-alpha production via nuclear factor-kappaB activation in the resting macrophages.
2001 Dec 7
[Studies on the triterpenoidal saponins from flowers of Eriobotrya japonica].
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
Influence of the parasite Viscum cruciatum Sieber on the chemical constituents of Crataegus monogyna Jacq.
2001 Nov-Dec
[HPLC determination of oleanolic acid and llrolic acid in Chinese medicinal herbs].
2001 Sep
Activation of caspase-3 protease during the process of ursolic acid and its derivative-induced apoptosis.
2001 Sep-Oct
[Chemical composition of fructus Liquidambaris--lulutong].
2002 Apr
[Studies on chemical constituents in fruit of Eucalyptus globulus].
2002 Aug
Partial synthesis of 23-hydroxyursolic acid isolated from medicinal plants of the Rubiaceae family.
2002 Aug
[Determination of ursolic acid in herba of Verbena officinalis by HPLC].
2002 Dec
Antithrombin activity of some constituents from Origanum vulgare.
2002 Dec
Alysinol--a new triterpene from Alysicarpus monolifer.
2002 Dec
Triterpenes and saponins from Ilex psammophila.
2002 Dec
Quinovic acid glycosides from Mitragyna stipulosa--first examples of natural inhibitors of snake venom phosphodiesterase I.
2002 Dec
Abietane diterpenoids and triterpenoic acids from Salvia cilicica and their antileishmanial activities.
2002 Dec
Constituents of Gnetum montanum.
2002 Feb
Production of bioactive triterpenes by Eriobotrya japonica calli.
2002 Feb
Ursolic acid of Origanum majorana L. reduces Abeta-induced oxidative injury.
2002 Feb 28
Liposome-encapsulated ursolic acid increases ceramides and collagen in human skin cells.
2002 Jan
New prenylated benzoic acid and other constituents from almond hulls (Prunus amygdalus Batsch).
2002 Jan 30
Effects of ursolic acid and oleanolic acid on human colon carcinoma cell line HCT15.
2002 Jun
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
Phosphoinositide 3-OH kinase/protein kinase B inhibits apoptotic cell death induced by reactive oxygen species in Saccharomyces cerevisiae.
2002 May
Synthesis of combinatorial libraries based on terpenoid scaffolds.
2002 May
Screening of ubiquitous plant constituents for COX-2 inhibition with a scintillation proximity based assay.
2002 Nov
Ursolic acid as a trypanocidal constituent in rosemary.
2002 Nov
Brine shrimp lethality of the compounds from Phryma leptostachya L.
2002 Oct
Sessiline, a new nitrogenous compound from the fruits of Acanthopanax sessiliflorus.
2002 Oct
Cytotoxic ent-kaurane diterpenoids from Isodon sculponeata.
2002 Oct
Antimicrobial and anti-inflammatory activity of folklore: Mallotus peltatus leaf extract.
2002 Oct
Extract and identify ingredient from Ligustrum Lucidum Ait and study its effect to periodontal pathogen.
2002 Sep
Effect of naturally occurring triterpenoids glycyrrhizic acid, ursolic acid, oleanolic acid and nomilin on the immune system.
2003
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
Inhibition of ultraviolet-A-modulated signaling pathways by asiatic acid and ursolic acid in HaCaT human keratinocytes.
2003 Aug 29
Antihypertensive, antiatherosclerotic and antioxidant activity of triterpenoids isolated from Olea europaea, subspecies africana leaves.
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
Ursolic acid induces apoptosis through caspase-3 activation and cell cycle arrest in HaCat cells.
2003 Jul
Ursolic acid inhibits proliferation and stimulates apoptosis in HT29 cells following activation of alkaline sphingomyelinase.
2003 Jul-Aug
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
Sterol and triterpenoid constituents of Verbena littoralis with NGF-potentiating activity.
2003 May
Sterols and triterpenes in cell culture of Hyssopus officinalis L.
2003 May-Jun
A new pentacyclic triterpenoid glucoside from Prunus serrulata var. spontanea.
2004 Jan
Patents

Sample Use Guides

In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 17 12:54:03 UTC 2022
Edited
by admin
on Sat Dec 17 12:54:03 UTC 2022
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 17 12:54:03 UTC 2022 , Edited by admin on Sat Dec 17 12:54:03 UTC 2022
PRIMARY
RXCUI
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
PRIMARY RxNorm
DAILYMED
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
PRIMARY
EPA CompTox
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
PRIMARY
FDA UNII
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
PRIMARY
CAS
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
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE