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
C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2[C@H]1C)C(O)=O
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: 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 |
---|---|---|---|
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 |
---|---|---|---|---|
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 |
---|---|---|---|---|
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 |
|
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 |
|
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 |
|
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 |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
|
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 |
|
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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
|
4.46 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 |
|
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 |
Doses
Dose | Population | Adverse events |
---|---|---|
130 mg/m2 single, intravenous Highest studied dose Dose: 130 mg/m2 Route: intravenous Route: single Dose: 130 mg/m2 Sources: |
unhealthy |
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 MTD Dose: 94 mg/m2 Route: intravenous Route: single Dose: 94 mg/m2 Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN 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 Studied dose Dose: 74 mg/m2 Route: intravenous Route: single Dose: 74 mg/m2 Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN 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 Highest studied dose Dose: 130 mg/m2 Route: intravenous Route: single Dose: 130 mg/m2 Sources: |
unhealthy |
ALT increased | grade 3, 2 patients DLT |
130 mg/m2 single, intravenous Highest studied dose Dose: 130 mg/m2 Route: intravenous Route: single Dose: 130 mg/m2 Sources: |
unhealthy |
AST increased | grade 3, 2 patients DLT |
130 mg/m2 single, intravenous Highest studied dose Dose: 130 mg/m2 Route: intravenous Route: single Dose: 130 mg/m2 Sources: |
unhealthy |
Direct bilirubin increased | grade 3, 2 patients DLT |
130 mg/m2 single, intravenous Highest studied dose Dose: 130 mg/m2 Route: intravenous Route: single Dose: 130 mg/m2 Sources: |
unhealthy |
AST increased | grade 2, 2 patients | 94 mg/m2 single, intravenous MTD Dose: 94 mg/m2 Route: intravenous Route: single Dose: 94 mg/m2 Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
ALT increased | grade 3, 1 pt DLT |
94 mg/m2 single, intravenous MTD Dose: 94 mg/m2 Route: intravenous Route: single Dose: 94 mg/m2 Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
GGT increased | grade 3, 1 pt DLT |
94 mg/m2 single, intravenous MTD Dose: 94 mg/m2 Route: intravenous Route: single Dose: 94 mg/m2 Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
ALT increased | grade 3, 1 pt DLT |
74 mg/m2 single, intravenous Studied dose Dose: 74 mg/m2 Route: intravenous Route: single Dose: 74 mg/m2 Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
AST increased | grade 3, 1 pt DLT |
74 mg/m2 single, intravenous Studied dose Dose: 74 mg/m2 Route: intravenous Route: single Dose: 74 mg/m2 Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
diarrhea | grade 3, 1 pt DLT |
74 mg/m2 single, intravenous Studied dose Dose: 74 mg/m2 Route: intravenous Route: single Dose: 74 mg/m2 Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Oleanolic acid from cranberries. | 1953 Oct |
|
[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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[Studies on the triterpenoidal saponins from flowers of Eriobotrya japonica]. | 2001 Jun |
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[Isolation and elucidation of chemical constituents of Shandanshaoyao Decoction(I)]. | 2001 Jun |
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[The research on the chemical components of Schizonepeta tenuifolia Briq]. | 2001 Mar |
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[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 |
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[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 |
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Inhibitory activity of minor polyphenolic and nonpolyphenolic constituents of olive oil against in vitro low-density lipoprotein oxidation. | 2002 Spring |
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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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The triterpenoid CDDO inhibits expression of matrix metalloproteinase-1, matrix metalloproteinase-13 and Bcl-3 in primary human chondrocytes. | 2003 |
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Antileukemic activity of selected natural products in Taiwan. | 2003 |
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New ursolic and betulinic derivatives as potential cytotoxic agents. | 2003 Apr |
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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 |
|
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 |
|
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 |
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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 |
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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 |
|
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 |
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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 |
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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 |
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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 |
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Antiplasmodial triterpenes from twigs of Gardenia saxatilis. | 2003 Oct |
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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 |
|
A new pentacyclic triterpenoid glucoside from Prunus serrulata var. spontanea. | 2004 Jan |
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:23:16 GMT 2025
by
admin
on
Mon Mar 31 19:23:16 GMT 2025
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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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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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100000090272
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DB15588
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Related Record | Type | Details | ||
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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 |