Page last updated: 2024-12-08
secalonic acid
Description
Research Excerpts
Clinical Trials
Roles
Classes
Pathways
Study Profile
Bioassays
Related Drugs
Related Conditions
Protein Interactions
Research Growth
Market Indicators
Description
secalonic acid: consists of 4 acids (A,C,D,E) differing only in their stereochemistry; RN given is for parent cpd; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
Cross-References
| ID Source | ID |
|---|---|
| PubMed CID | 423972 |
| CHEMBL ID | 30050 |
| MeSH ID | M0053735 |
Synonyms (31)
| Synonym |
|---|
| NSC159631 , |
| nsc-268921 |
| [7,4'a-dicarboxylic acid, 2,2',3,3',4,4',9,9'-octahydro-1,1',4,4',8,8'-hexahydroxy-3,3'-dimethyl-9,9'-dioxo-, dimethyl ester, [3s-[3.alpha.,4.beta.,4a.beta.,7(3'r*,4's*,4'as*)]]- |
| secalonsaure d |
| nsc268920 |
| (7,4'a-dicarboxylic acid, 2,2',3,3',4,4',9,9'-octahydro-1,1',4,4',8,8'-hexahydroxy-3,3'-dimethyl-9,9'-dioxo-, dimethyl ester, [3s-[3.alpha.,4.beta.,4a.beta.,7(3'r*,4's*,4'as*)]]- |
| SAD , |
| (7,4'a-dicarboxylic acid, 2,2',3,3',4,4',9,9'-octahydro-1,1',4,4',8,8'-hexahydroxy-3,3'-dimethyl-9,9'-dioxo-, dimethyl ester, [3s-[3-.alpha.,4-.beta.,4a-.beta.,7(3'r,4's,4'as)]] |
| secalonsaure b |
| nsc268921 |
| ergochrome aa (2,6-.alpha.,10-.beta.-5',6'-.alpha.,10'-.beta. |
| secalonsaure a |
| 35287-69-5 |
| nsc-268922 |
| nsc-268920 |
| nsc268922 |
| CHEMBL30050 |
| secalonic acid |
| 56283-72-8 |
| (7,7'-bi-4ah-xanthene)-4a,4'a-dicarboxylic acid, 2,2',3,3',4,4',9,9'-octahydro-1,1',4,4',8,8'-hexahydroxy-3,3'-dimethyl-9,9'-dioxo-, dimethyl ester, (3s-(3-.alpha.,4-.beta.,4a-.beta.,7(3'r,4's,4'as))) |
| ergochrome aa (2,2')-5-.beta.,6-.alpha.,10-.beta.-5',6'-.alpha.,10'-.beta. |
| ergochrome aa(2,2'), (5.beta.,6.alpha.,10.beta.)-(5'.beta.,6'.alpha.,10'.beta.)- |
| [7,7'-bi-4ah-xanthene]-4a,4'a-dicarboxylic acid, 2,2',3,3',4,4',9,9'-octahydro-1,1',4,4',8,8'-hexahydroxy-3,3'-dimethyl-9,9'-dioxo-, dimethyl ester, [3s-[3.alpha.,4.beta.,4a.beta.,7(3'r*,4's*,4'as*)]]- |
| DRYDKQOPVBDZMQ-UHFFFAOYSA-N |
| methyl(3s,4r,4ar)-7-[(5r,6s,10ar)-1,5,9-trihydroxy-10a-methoxycarbonyl-6-methyl-8-oxo-6,7-dihydro-5h-xanthen-2-yl]-4,8,9-trihydroxy-3-methyl-1-oxo-3,4-dihydro-2h-xanthene-4a-carboxylate |
| dimethyl 1,1',5,5',9,9'-hexahydroxy-6,6'-dimethyl-8,8'-dioxo-5,5',6,6',7,7',8,8'-octahydro-10ah,10a'h-2,2'-bixanthene-10a,10a'-dicarboxylate |
| secalonic acid d from penicillium*oxalicum |
| DTXSID001017604 |
| dimethyl 1,1',5,5',8,8'-hexahydroxy-6,6'-dimethyl-9,9'-dioxo-5,5',6,6',7,7',9,9'-octahydro-10ah,10'ah-[2,2'-bixanthene]-10a,10'a-dicarboxylate |
| DTXSID50956725 |
| (3s,3's,4s,4'r,4ar,4'ar)-2,2',3,3',4,4',9,9'-octahydro-1,1',4,4',8,8'-hexahydroxy-3,3'-dimethyl-9,9'-dioxo-7,7'-bi(4ah-xanthene)-4a,4'a-dicarboxylic acid dimethyl ester |
Research Excerpts
Overview
Secalonic acid D (SAD) is an acutely toxic and teratogenic fungal metabolite produced by Penicillium oxalium in corn. It causes cleft palate in the offspring of treated pregnant mice.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Secalonic acid A (SAA) is a natural compound found in marine fungi. " | ( Secalonic acid A protects dopaminergic neurons from 1-methyl-4-phenylpyridinium (MPP⁺)-induced cell death via the mitochondrial apoptotic pathway. Chen, R; Wang, H; Wang, X; Zhai, A; Zhu, X, 2013) | 3.28 |
| "Secalonic acid-D (SAD) is a teratogenic mycotoxin inducing cleft palate (CP) in the offspring of the exposed mice by reducing palatal shelf size secondary to reduced proliferation of the palatal mesenchymal (PM) cells. " | ( Relevance of the palatal protein kinase A pathway to the pathogenesis of cleft palate by secalonic acid D in mice. Balasubramanian, G; Dhulipala, VC; Hanumegowda, UM; Reddy, CS, 2004) | 1.99 |
| "Secalonic acid D (SAD) is an acutely toxic and teratogenic fungal metabolite produced by Penicillium oxalium in corn and other cereal grains. " | ( Interaction of secalonic acid D with phenobarbital, 3-methyl cholanthrene, and SKF-525A in mice. Hayes, AW; Reddy, CS; Reddy, RV, ) | 1.93 |
| "Secalonic acid D is an acutely toxic and teratogenic mycotoxin, produced by Penicillium oxalicum in corn. " | ( Mutagenicity of secalonic acid D in mice. Chan, PK; Hayes, AW; Reddy, CS; Reddy, RV, 1980) | 2.05 |
| "Secalonic acid D (SAD) is an acutely toxic, teratogenic and possibly mutagenic fungal metabolite produced in corn by Penicillium oxalicum. " | ( High-performance liquid chromatographic analysis of the mycotoxin secalonic acid D and its application to biological fluids. Hayes, AW; Reddy, CS; Reddy, RV, 1981) | 1.94 |
| "Secalonic acid D (SAD) is a teratogenic mycotoxin that causes cleft palate in the offspring of treated pregnant mice. " | ( Role of maternal plasma corticosterone elevation in the teratogenicity of secalonic acid D in mice. Eldeib, MM; Reddy, CS, 1990) | 1.95 |
Effects
| Excerpt | Reference | Relevance |
|---|---|---|
| "Secalonic acid F (SAF) has been previously identified, however, little is known about its cytotoxic activity and related cytotoxic mechanism. " | ( Differential proteomic analysis of HL60 cells treated with secalonic acid F reveals caspase 3-induced cleavage of Rho GDP dissociation inhibitor 2. Li, N; Qiu, Y; Tang, X; Wang, Y; Wu, Z; Yi, Z; Zhang, Q; Zhong, T, 2012) | 1.82 |
Toxicity
| Excerpt | Reference | Relevance |
|---|---|---|
| " The ip LD50 values of 37, 31, and 27 mg/kg were obtained for Charles River CD-1, Texas (ICR), and Sprague-Dawley (CF-1) strains of mice, respectively." | ( Toxicity of Secalonic acid D. Ciegler, A; Hayes, AW; Reddy, CS; Williams, WL, 1979) | 0.64 |
| " Body weights, toxic signs, and mortality were used to arrive at no observable effect level (NOEL)." | ( Neurotoxic effects of secalonic acid D in mice during subchronic postnatal exposure. Montella, PG; Reddy, CS, 1991) | 0.6 |
| " Dose response was studied by intragastric and intratracheal instillation, and SAD was given in suspension in Krebs-Ringer phosphate solution at doses well below the reported LD50 values for both rats and mice." | ( Secalonic acid D toxicity in rat lung. Ciegler, A; Green, FH; Sorenson, WG; Vallyathan, V, 1982) | 1.71 |
Dosage Studied
| Excerpt | Relevance | Reference |
|---|---|---|
| "To establish a dose-response of neurotoxic effects to daily oral doses of the mycotoxin secalonic acid D (SAD), as well as to correlate the neonatal behavioral responses to smaller doses of SAD with the attendant neurochemical effects in mice, 5 neonates of each sex were placed with each mother and 4 litters were treated orally with 0 to 5 mg/kg of SAD daily from postnatal day (PND) 3 through 35." | ( Neurotoxic effects of secalonic acid D in mice during subchronic postnatal exposure. Montella, PG; Reddy, CS, 1991) | 0.82 |
| "01) elevations in plasma corticosterone concentrations were seen 24 and 48 hr following dosing of SAD in NaHCO3 with concentrations reaching a peak just prior to the onset of shelf elevation and fusion." | ( Role of maternal plasma corticosterone elevation in the teratogenicity of secalonic acid D in mice. Eldeib, MM; Reddy, CS, 1990) | 0.51 |
| " A significant dose-response effect in olfactory discrimination existed between the groups exposed to postnatal SAD." | ( Behavioral and developmental effects in suckling mice following maternal exposure to the mycotoxin secalonic acid D. Bolon, B; St Omer, VE, 1989) | 0.49 |
| " In experimental mouse models of breast cancer, SAD dosing produced no apparent toxicities (either orally or intraperitoneal) at levels that yielded antitumor effects." | ( Secalonic Acid-D Represses HIF1α/VEGF-Mediated Angiogenesis by Regulating the Akt/mTOR/p70S6K Signaling Cascade. Bhushan, S; Chandan, BK; Faruk, A; Guru, SK; Jaglan, S; Kumar, A; Kumar, M; Kumar, S; Lattoo, SK; Malik, F; Pathania, AS; Ramesh, D; Rana, S; Saxena, AK; Shah, BA; Sharma, JP; Sharma, PR; Tasduq, SA; Vishwakarma, RA, 2015) | 1.86 |
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
Bioassays (1)
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID69132 | Inhibitory activity against tetracycline uptake in everted membrane vesicles derived from Tc-resistant Escherichia coli bearing class B tetracycline resistance efflux protein (Tet) | 1994 | Journal of medicinal chemistry, Apr-29, Volume: 37, Issue:9 | Molecular requirements for the inhibition of the tetracycline antiport protein and the effect of potent inhibitors on the growth of tetracycline-resistant bacteria. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
Research
Studies (71)
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 21 (29.58) | 18.7374 |
| 1990's | 8 (11.27) | 18.2507 |
| 2000's | 18 (25.35) | 29.6817 |
| 2010's | 17 (23.94) | 24.3611 |
| 2020's | 7 (9.86) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
Market Indicators
Research Demand Index: 26.05
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 (26.05) All Compounds (24.57) |
Study Types
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 5 (6.41%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 73 (93.59%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||