zaragozic acid C: structure given in first source; a fungal metabolite [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
zaragozic acid C : A polyketide isolated from fungi that is a potent inhibitor of fungal and mammalian squalene synthase. [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]
| ID Source | ID |
|---|---|
| PubMed CID | 11814656 |
| CHEMBL ID | 505374 |
| CHEBI ID | 83934 |
| MeSH ID | M0211816 |
| Synonym |
|---|
| (1s,3s,4s,5r,6r,7r)-1-[(4r,5r)-4-(acetyloxy)-5-benzylhexyl]-4,7-dihydroxy-6-{[(4e,6r)-6-methyl-9-phenylnon-4-enoyl]oxy}-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid |
| gtpl3073 |
| zaragozic acid c |
| bdbm50292333 |
| l-697350 |
| chebi:83934 , |
| CHEMBL505374 , |
| 04isx24t1b , |
| l-erythro-l-glycero-d-altro-7-trideculo-7,4-furanosonic acid, 2,7-anhydro-3,4-di-c-carboxy-8,9,10,12,13-pentadeoxy-12-(phenylmethyl)-, 11-acetate 5-((4e,6r)-6-methyl-9-phenyl-4-nonenoate), (7s)- |
| unii-04isx24t1b |
| (+)-zaragozic acid |
| zaragozic acid c [mi] |
| 146389-62-0 |
| (1s,3s,4s,5r,6r,7r)-1-[(4r,5r)-4-acetoxy-5-methyl-6-phenylhexyl]-4,7-dihydroxy-6-{[(4e,6r)-6-methyl-9-phenylnon-4-enoyl]oxy}-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid |
| (1s,3s,4s,5r,6r,7r)-1-((4r,5r)-4-acetoxy-5-methyl-6-phenylhexyl)-4,7-dihydroxy-6-(((r,e)-6-methyl-9-phenylnon-4-enoyl)oxy)-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid |
| Q27089281 |
| (1s,3s,4s,5r,6r,7r)-1-[(4r,5r)-4-acetyloxy-5-methyl-6-phenylhexyl]-4,7-dihydroxy-6-[(e,6r)-6-methyl-9-phenylnon-4-enoyl]oxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid |
| l-erythro-l-glycero-d-altro-7-trideculo-7,4-furanosonic acid, 2,7-anhydro-3,4-di-c-carboxy-8,9,10,12,13-pentadeoxy-12-(phenylmethyl)-, 11-acetate 5-[(4e,6r)-6-methyl-9-phenyl-4-nonenoate], (7s)- |
| DTXSID901098471 |
| AKOS040746286 |
Zaragozic acid C was found to be a competitive inhibitor with respect to farnesyl pyrophosphate and has a Kis value of 250 pM.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Zaragozic acid C was found to be a competitive inhibitor with respect to farnesyl pyrophosphate and has a Kis value of 250 pM (@ [NADPH] = 5 mM)." | ( Expression, purification, and characterization of the human squalene synthase: use of yeast and baculoviral systems. Caplan, SL; Chamberlin, HA; Cornell-Kennon, SA; Dottavio, D; Dudas, DA; Engstrom, RG; McMahon, G; Rucker, ML; Soltis, DA; Vattay, A, 1995) | 1.01 |
| Role | Description |
|---|---|
| EC 2.5.1.21 (squalene synthase) inhibitor | An EC 2.5.1.* (non-methyl-alkyl or aryl transferase) inhibitor that interferes with the action of squalene synthase (EC 2.5.1.21). |
| fungal metabolite | Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds. |
| [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 |
|---|---|
| acetate ester | Any carboxylic ester where the carboxylic acid component is acetic acid. |
| cyclic ketal | A ketal in the molecule of which the ketal carbon and one or both oxygen atoms thereon are members of a ring. |
| oxabicycloalkane | |
| polyketide | Natural and synthetic compounds containing alternating carbonyl and methylene groups ('beta-polyketones'), biogenetically derived from repeated condensation of acetyl coenzyme A (via malonyl coenzyme A), and usually the compounds derived from them by further condensations, etc. Considered by many to be synonymous with the less frequently used terms acetogenins and ketides. |
| tertiary alcohol | A tertiary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has three other carbon atoms attached to it. |
| tricarboxylic acid | An oxoacid containing three carboxy 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] | |
| Pathway | Proteins | Compounds |
|---|---|---|
| Mevalonate arm of cholesterol biosynthesis pathway with inhibitors | 2 | 14 |
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Adenosine receptor A1 | Rattus norvegicus (Norway rat) | IC50 (µMol) | 0.0004 | 0.0002 | 0.5521 | 10.0000 | AID336318 |
| Squalene synthase | Rattus norvegicus (Norway rat) | IC50 (µMol) | 0.0004 | 0.0002 | 0.4543 | 4.2000 | AID336318 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID336093 | Inhibition of bovine Ras FPTase | 1993 | Journal of natural products, Nov, Volume: 56, Issue:11 | Zaragozic acids D and D2: potent inhibitors of squalene synthase and of Ras farnesyl-protein transferase. |
| AID336318 | Inhibition of rat liver squalene synthase by liqiud scintillation counting | 1993 | Journal of natural products, Nov, Volume: 56, Issue:11 | Zaragozic acids D and D2: potent inhibitors of squalene synthase and of Ras farnesyl-protein transferase. |
| AID1346813 | Rat squalene synthase (Lanosterol biosynthesis pathway) | 1993 | Proceedings of the National Academy of Sciences of the United States of America, Jan-01, Volume: 90, Issue:1 | Zaragozic acids: a family of fungal metabolites that are picomolar competitive inhibitors of squalene synthase. |
| [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 | 5 (31.25) | 18.2507 |
| 2000's | 7 (43.75) | 29.6817 |
| 2010's | 4 (25.00) | 24.3611 |
| 2020's | 0 (0.00) | 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 moderate demand-to-supply ratio for research on this compound.
| This Compound (16.77) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 3 (18.75%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 13 (81.25%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||