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

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
Structure of URSOLIC ACID

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

HIDE SMILES / InChI

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

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
[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
[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
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
Screening of ubiquitous plant constituents for COX-2 inhibition with a scintillation proximity based assay.
2002 Nov
Antimicrobial triterpenes from Debregeasia salicifolia.
2002 Oct
Brine shrimp lethality of the compounds from Phryma leptostachya L.
2002 Oct
Extract and identify ingredient from Ligustrum Lucidum Ait and study its effect to periodontal pathogen.
2002 Sep
Inhibitory activity of minor polyphenolic and nonpolyphenolic constituents of olive oil against in vitro low-density lipoprotein oxidation.
2002 Spring
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
[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
Biomass segregation in sage cell suspension culture.
2003 Jan
Cytotoxic triterpenes from the twigs of Celtis philippinensis.
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
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 Fri Dec 15 18:51:59 GMT 2023
Edited
by admin
on Fri Dec 15 18:51:59 GMT 2023
Record UNII
P3M2575F3F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
URSOLIC ACID
HSDB   INCI   MI   USP-RS   WHO-DD  
INCI  
Official Name English
URS-12-EN-28-OIC ACID, 3-HYDROXY-, (3.BETA.)-
Common Name English
NSC-4060
Code English
URSOLIC ACID [INCI]
Common Name English
URSOLIC ACID [MI]
Common Name English
PRUNOL
Common Name English
Ursolic acid [WHO-DD]
Common Name English
URSOLIC ACID (CONSTITUENT OF HOLY BASIL LEAF) [DSC]
Common Name English
MICROMEROL
Common Name English
URSON
Common Name English
(3.BETA.)-3-HYDROXYURS-12-EN-28-OIC ACID
Common Name English
URSOLIC ACID [USP-RS]
Common Name English
NSC-167406
Code English
URSOLIC ACID [HSDB]
Common Name English
MALOL
Common Name English
Classification Tree Code System Code
DSLD 2413 (Number of products:7)
Created by admin on Fri Dec 15 18:51:59 GMT 2023 , Edited by admin on Fri Dec 15 18:51:59 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID70883221
Created by admin on Fri Dec 15 18:51:59 GMT 2023 , Edited by admin on Fri Dec 15 18:51:59 GMT 2023
PRIMARY
CAS
77-52-1
Created by admin on Fri Dec 15 18:51:59 GMT 2023 , Edited by admin on Fri Dec 15 18:51:59 GMT 2023
PRIMARY
CHEBI
9908
Created by admin on Fri Dec 15 18:51:59 GMT 2023 , Edited by admin on Fri Dec 15 18:51:59 GMT 2023
PRIMARY
RXCUI
1426931
Created by admin on Fri Dec 15 18:52:00 GMT 2023 , Edited by admin on Fri Dec 15 18:52:00 GMT 2023
PRIMARY RxNorm
HSDB
7685
Created by admin on Fri Dec 15 18:51:59 GMT 2023 , Edited by admin on Fri Dec 15 18:51:59 GMT 2023
PRIMARY
DAILYMED
P3M2575F3F
Created by admin on Fri Dec 15 18:51:59 GMT 2023 , Edited by admin on Fri Dec 15 18:51:59 GMT 2023
PRIMARY
PUBCHEM
64945
Created by admin on Fri Dec 15 18:52:00 GMT 2023 , Edited by admin on Fri Dec 15 18:52:00 GMT 2023
PRIMARY
NSC
4060
Created by admin on Fri Dec 15 18:52:00 GMT 2023 , Edited by admin on Fri Dec 15 18:52:00 GMT 2023
PRIMARY
RXCUI
1370661
Created by admin on Fri Dec 15 18:52:00 GMT 2023 , Edited by admin on Fri Dec 15 18:52:00 GMT 2023
PRIMARY
ECHA (EC/EINECS)
201-034-0
Created by admin on Fri Dec 15 18:51:59 GMT 2023 , Edited by admin on Fri Dec 15 18:51:59 GMT 2023
PRIMARY
RS_ITEM_NUM
1707770
Created by admin on Fri Dec 15 18:52:00 GMT 2023 , Edited by admin on Fri Dec 15 18:52:00 GMT 2023
PRIMARY
FDA UNII
P3M2575F3F
Created by admin on Fri Dec 15 18:51:59 GMT 2023 , Edited by admin on Fri Dec 15 18:51:59 GMT 2023
PRIMARY
NCI_THESAURUS
C172843
Created by admin on Fri Dec 15 18:51:59 GMT 2023 , Edited by admin on Fri Dec 15 18:51:59 GMT 2023
PRIMARY
MERCK INDEX
m11345
Created by admin on Fri Dec 15 18:51:59 GMT 2023 , Edited by admin on Fri Dec 15 18:51:59 GMT 2023
PRIMARY Merck Index
EVMPD
SUB27186
Created by admin on Fri Dec 15 18:51:59 GMT 2023 , Edited by admin on Fri Dec 15 18:51:59 GMT 2023
PRIMARY
MESH
C005466
Created by admin on Fri Dec 15 18:51:59 GMT 2023 , Edited by admin on Fri Dec 15 18:51:59 GMT 2023
PRIMARY
WIKIPEDIA
URSOLIC ACID
Created by admin on Fri Dec 15 18:52:00 GMT 2023 , Edited by admin on Fri Dec 15 18:52:00 GMT 2023
PRIMARY
NSC
167406
Created by admin on Fri Dec 15 18:52:00 GMT 2023 , Edited by admin on Fri Dec 15 18:52:00 GMT 2023
PRIMARY
SMS_ID
100000090272
Created by admin on Fri Dec 15 18:52:00 GMT 2023 , Edited by admin on Fri Dec 15 18:52:00 GMT 2023
PRIMARY
DRUG BANK
DB15588
Created by admin on Fri Dec 15 18:51:59 GMT 2023 , Edited by admin on Fri Dec 15 18:51:59 GMT 2023
PRIMARY
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