23-hydroxyursolic acid: from medicinal plants of the Rubiaceae family; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
23-hydroxyursolic acid : A pentacyclic triterpenoid that is ursolic acid substituted by an additional hydroxy group at position 23. It has been isolated from Lagerstroemia speciosa and Juglans sinensis. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
| Flora | Rank | Flora Definition | Family | Family Definition |
|---|---|---|---|---|
| Juglans | genus | A plant genus of the family JUGLANDACEAE that provides the familiar walnut.[MeSH] | Juglandaceae | The walnut plant family of the order Juglandales, subclass Hamamelidae, class Magnoliopsida. They are mainly temperate zone trees.[MeSH] |
| Lagerstroemia | genus | A plant genus of the family LYTHRACEAE. Members contain lagertannin and have hypoglycemic effects.[MeSH] | Lythraceae | The loosestrife plant family of the order Myrtales, subclass Rosidae, class Magnoliopsida. Members are mainly herbs and many of them contain ALKALOIDS.[MeSH] |
| Rubiaceae | family | The Madder plant family of the order Gentianales (formerly Rubiales), subclass Asteridae, class Magnoliopsida includes important medicinal plants that provide QUININE; IPECAC; and COFFEE. They have opposite leaves and interpetiolar stipules.[MeSH] | Rubiaceae | The Madder plant family of the order Gentianales (formerly Rubiales), subclass Asteridae, class Magnoliopsida includes important medicinal plants that provide QUININE; IPECAC; and COFFEE. They have opposite leaves and interpetiolar stipules.[MeSH] |
| Lagerstroemia speciosa | species | [no description available] | Lythraceae | The loosestrife plant family of the order Myrtales, subclass Rosidae, class Magnoliopsida. Members are mainly herbs and many of them contain ALKALOIDS.[MeSH] |
| ID Source | ID |
|---|---|
| PubMed CID | 14136881 |
| CHEMBL ID | 523622 |
| CHEBI ID | 67896 |
| MeSH ID | M0444175 |
| Synonym |
|---|
| bdbm50250341 |
| CHEMBL523622 , |
| 23-hydroxyursolic acid |
| chebi:67896 , |
| 2-deoxyasiatic acid |
| 3beta,23-dihydroxyurs-12-en-28-oic acid |
| 94414-19-4 |
| (3.beta.,4.alpha.)-3,23-dihydroxyurs-12-en-28-oic acid |
| 3.beta.,23-dihydroxyurs-12-ene-28-oic acid |
| 1I1MDP27ZG , |
| urs-12-en-28-oic acid, 3,23-dihydroxy-, (3.beta.,4.alpha.)- |
| (+)-23-hydroxyursolic acid |
| Q27136370 |
| urs-12-en-28-oic acid, 3,23-dihydroxy-, (3beta,4alpha)- |
| 3beta,23-dihydroxyurs-12-ene-28-oic acid |
| (3beta,4alpha)-3,23-dihydroxyurs-12-en-28-oic acid |
| unii-1i1mdp27zg |
| (1s,2r,4as,6ar,6as,6br,8ar,9r,10s,12ar,14bs)-10-hydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1h-picene-4a-carboxylic acid |
| (1s,2r,4as,6as,6br,8ar,9r,10s,12ar,12br,14bs)-10-hydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid |
| DTXSID101314493 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " Based on structure-function analyses of naturally occurring UA analogs, we synthesized 23-hydroxy ursolic acid (23-OHUA), a compound with structural features predicted to enhance its bioavailability and anti-atherogenic properties compared to UA." | ( Dietary 23-hydroxy ursolic acid protects against atherosclerosis and obesity by preventing dyslipidemia-induced monocyte priming and dysfunction. Ahn, YJ; Asmis, R; Medina, EA; Nguyen, HN, 2018) | 0.48 |
| Role | Description |
|---|---|
| plant metabolite | Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. |
| [role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Class | Description |
|---|---|
| pentacyclic triterpenoid | |
| dihydroxy monocarboxylic acid | Any hydroxy monocarboxylic acid carrying at least two hydroxy groups. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Sterol O-acyltransferase 1 | Rattus norvegicus (Norway rat) | IC50 (µMol) | 64.0000 | 0.0058 | 0.6626 | 6.0000 | AID380812 |
| Tyrosine-protein phosphatase non-receptor type 1 | Homo sapiens (human) | IC50 (µMol) | 7.4000 | 0.0005 | 3.4984 | 9.7600 | AID1634795; AID683328 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1436763 | Anticomplement activity in sheep erythrocytes assessed as concentration required for 50% hemolytic inhibition by classic pathway preincubated for 10 mins with guinea pig serum followed by erythrocyte addition measured after 30 mins by spectrophotometer | 2017 | Bioorganic & medicinal chemistry letters, 02-15, Volume: 27, Issue:4 | Anticomplement triterpenoids from the roots of Ilex asprella. |
| AID38498 | In vitro percent protective effect against Amyloid Beta(A beta)-induced neurotoxicity in B103 cells | 2000 | Bioorganic & medicinal chemistry letters, Jan-17, Volume: 10, Issue:2 | Structure-activity relationship study of asiatic acid derivatives against beta amyloid (A beta)-induced neurotoxicity. |
| AID356480 | Cytotoxicity against LPS-stimulated mouse RAW264.7 cells by Griess method | 2003 | Journal of natural products, Sep, Volume: 66, Issue:9 | Saponins from Cussonia bancoensis and their inhibitory effects on nitric oxide production. |
| AID683328 | Inhibition of human recombinant PTP1B using p-nitrophenyl phosphate as substrate assessed as p-nitrophenol release after 30 mins | 2012 | Bioorganic & medicinal chemistry letters, Oct-01, Volume: 22, Issue:19 | Rhododendric acid A, a new ursane-type PTP1B inhibitor from the endangered plant Rhododendron brachycarpum G. Don. |
| AID595306 | Antiproliferative activity against rat HSC-T6 cells at 100 uM after 48 hrs by MTT assay | 2011 | Journal of natural products, Apr-25, Volume: 74, Issue:4 | Antiproliferative triterpenes from the leaves and twigs of Juglans sinensis on HSC-T6 cells. |
| AID1436764 | Anticomplement activity in New Zealand White rabbit erythrocytes assessed as concentration required for 50% hemolytic inhibition by alternative pathway preincubated for 10 mins with normal human serum followed by erythrocyte addition measured after 30 min | 2017 | Bioorganic & medicinal chemistry letters, 02-15, Volume: 27, Issue:4 | Anticomplement triterpenoids from the roots of Ilex asprella. |
| AID1651606 | Cytoprotective activity against LPS-induced NRK-52E cells assessed as reduction in cell death measured every 5 min for 72 hrs by xCELLigence based RTCA analysis | 2020 | Journal of natural products, 04-24, Volume: 83, Issue:4 | Renoprotective Mono- and Triterpenoids from the Fruit of |
| AID356479 | Inhibition of LPS-induced nitric oxide production in mouse RAW264.7 cells by Griess method | 2003 | Journal of natural products, Sep, Volume: 66, Issue:9 | Saponins from Cussonia bancoensis and their inhibitory effects on nitric oxide production. |
| AID1634795 | Inhibition of GST-tagged human PTP1B expressed in Escherichia coli using pNPP substrate assessed as reduction in p-nitrophenol release | 2016 | Journal of natural products, Apr-22, Volume: 79, Issue:4 | Identification of PTP1B and α-Glucosidase Inhibitory Serrulatanes from Eremophila spp. by Combined use of Dual High-Resolution PTP1B and α-Glucosidase Inhibition Profiling and HPLC-HRMS-SPE-NMR. |
| AID380812 | Inhibition of rat liver microsomal ACAT | 1999 | Journal of natural products, Jul, Volume: 62, Issue:7 | Activity-guided isolation of triterpenoid acyl CoA cholesteryl acyl transferase (ACAT) inhibitors from Ilex kudincha. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 1 (6.25) | 18.2507 |
| 2000's | 6 (37.50) | 29.6817 |
| 2010's | 6 (37.50) | 24.3611 |
| 2020's | 3 (18.75) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.
| This Compound (12.05) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 16 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||