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Stoccaggio e spedizione
Store at -20°C Spedizione Ice chest + Ice pads. Consultare il COA specifico del lotto per le specifiche esatte.
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Documenti di qualità
SDS, COA, scheda tecnica e scheda delle specifiche disponibili per il download. COA specifico del lotto accessibile tramite ricerca per numero di lotto.
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Prova documentale
Citato in 0 pubblicazioni peer-reviewed su cromatografia, sintesi organica e reazioni di accoppiamento incrociato.
Panoramica
Heptelidic acid (Koningic acid) is a sesquiterpene antibiotic. Heptelidic acid inhibits Etoposide-induced apoptosis via downregulation of caspases . Koningic acid (KA) is a specific GAPDH inhibitor with an IC 50 of 90 μM .
In Vitro
Heptelidic acid is a sesquiterpene antibiotic, found in the culture filtrate of three different strains of fungi isolated from soil samples. Heptelidic acid produces organisms, fermentation, isolation and characterization. Heptelidic acid inhibits Etoposide-induced apoptosis in human leukemia U937 cells.Heptelidic acid inhibits caspase- 3 induction in U937 cells with an IC 50 value of 40 μM after 8 h of Etoposide treatment. Heptelidic acid (Koningic acid; KA), a natural product obtained from the Trichoderma fungus, can directly bind to the active site of human GAPDH. The expression of T. koningii KAr-GAPDH successfully rescued cell viability in human cells treated with Heptelidic acid. HEK293T cells expressing T. koningii KAr-GAPDH exhibited complete cell viability after treatment with 0-200 μM Heptelidic acid with the IC 50 =5 μM. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Cell Viability AssayCell Line: HEK293T cells expressing KAr-GAPDH or EV (top left) Concentration: 0.1, 1, 10, 100, 1000 μM Incubation Time: 24 hours Result: IC 50 =5 μM.
In Vivo
Heptelidic acid (Koningic acid; KA) is bioavailable and induces dynamic changes to glycolysis in vivo. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: 6-week old female Foxn1 nu mice bearing BT-474 tumorDosage: 1, 2.5, 5, and 10 mg/kg Administration: Daily intraperitoneal (IP) injections, 24 hours Result: 1 mg/kg was determined to be the maximum tolerated dose (MTD) based upon behavioral monitoring and adverse events at higher doses (hemolysis, hematuria, and anemia).
Heptelidic acid (Koningic acid) is a sesquiterpene antibiotic. Heptelidic acid inhibits Etoposide-induced apoptosis via downregulation of caspases. Koningic acid (KA) is a specific GAPDH inhibitor with an IC 50 of 90 μM .
Condizioni di conservazione di stoccaggio
Store at -20°C
Spedito in
Ice chest + Ice pads
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This compound belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
External Descriptors
Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
280.320 g/mol
XLogP3
1.400
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
2
Exact Mass
280.131 Da
Monoisotopic Mass
280.131 Da
Topological Polar Surface Area
76.100 Ų
Heavy Atom Count
20
Formal Charge
0
Complexity
481.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
4
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
Calcolatori di soluzioni
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Recensioni
Recensioni dei clienti
Application Protocols
Item-specific, tested protocols and recommended dilutions are not provided in the Product Data.
General research-use guidance (non-validated, literature-informed):
Stock preparation: dissolve in anhydrous DMSO to prepare a concentrated stock. Filter if sterility is required (PTFE/PVDF). Record exact concentration by gravimetry or quantitative NMR if needed.
Working solutions: dilute into assay buffer immediately before use; maintain low organic cosolvent (e.g., ≤1–2% v/v DMSO) unless your assay tolerates more.
Controls: include vehicle controls, time-course controls, and, where relevant, inactive analogs or thiol scavengers to probe covalency.
Storage of working solutions: avoid long storage in aqueous media; prepare fresh to preserve epoxide/lactone integrity.
For detailed, validated protocols (e.g., WB, IHC, IF, FC), please refer to primary literature or develop in-house SOPs.
Biological Roles
Literature-based overview (for research context; not a medical claim):
Origin: Heptelidic acid (koningic acid) is a fungal polyketide metabolite.
Primary biochemical activity: potent, irreversible inhibition of glyceraldehyde-3-phosphate dehydrogenase (GAPDH), attributed to covalent modification via its epoxide. This disrupts glycolytic flux in cell-free and cellular models and is used to interrogate glycolysis-dependent phenotypes.
Selectivity considerations: literature reports relative selectivity for GAPDH among glycolytic enzymes, though off-target alkylation of other nucleophilic proteins can occur at higher concentrations or prolonged exposure due to the inherent reactivity of epoxides.
Cellular consequences (research observations): altered NAD+/NADH balance, accumulation of upstream glycolytic intermediates, and metabolic reprogramming. These effects are context dependent and should be validated in the relevant system.
Probe development: the scaffold has been derivatized to attach reporter tags (e.g., biotin/fluorophores) for activity-based protein profiling, leveraging the electrophilic center while retaining binding determinants.
Best practices:
Use appropriate controls (inactive analogs, rescue experiments with substrate or thiol scavengers) to confirm on-target GAPDH engagement.
Validate concentration–response relationships and exposure times to balance potency with potential non-specific reactivity.
Buffer Applications
Not typically used as a buffering agent. As an acidic small-molecule tool compound, heptelidic acid is introduced into existing biological buffers for assays rather than serving as the buffer itself.
Practical notes (general):
Prepare concentrated stock solutions in DMSO and dilute into assay buffer immediately before use.
Avoid high-pH buffers (≥8.5–9) or nucleophile-rich media for extended periods to minimize epoxide/lactone degradation.
If increased aqueous solubility is required, limited titration with base can form the carboxylate, but monitor for decomposition and revert to neutral pH promptly.
Green Alternatives
Scope: This section addresses greener choices for solvents and workflow when handling heptelidic acid; the compound itself is a specific natural product and not typically replaced in studies probing its unique mode of action.
Greener solvent choices (general guidance):
Preferable diluents for stock preparation: water with minimal DMSO cosolvent where feasible. If organic solvent is needed, ethanol is generally considered more benign than DMF/DMF-like solvents.
For chromatography: shift from chlorinated eluents to alcohol/water or acetonitrile/water systems on reversed-phase columns. Use buffered aqueous mobile phases at near-neutral pH to limit degradation.
Comparison (general sustainability view):
DMSO vs DMF: DMSO has a better EHS profile and lower volatility; choose DMSO over DMF for stocks when compatible.
Ethanol vs acetonitrile: ethanol is greener but can broaden peaks; acetonitrile offers performance but has higher environmental burden.
Process considerations:
Minimize solvent volumes by using concentrated DMSO stocks and immediate dilution into assay buffers.
Reduce waste by adopting microscale assay formats (384/1536-well plates) and inline analytical methods.
Note: There is no direct “green substitute” for heptelidic acid’s biochemical role; consider alternative GAPDH modulators only if aligned with your study design and safety objectives.
Pharmaceutical Uses
No item-specific pharmacopeial status or excipient role is provided for this product.
General context (non-clinical, for research and manufacturing insights only):
Heptelidic acid is primarily a research tool compound and natural product standard. It is not commonly employed as a pharmaceutical excipient.
Potential roles in R&D workflows include: reference standard for analytical method development (e.g., LC–MS), positive control for target engagement assays, and starting point for medicinal chemistry exploration of covalent modulators.
Regulatory considerations: if used in regulated environments (e.g., GLP analytical labs), ensure traceability via CoA, validated analytical methods, and documented storage conditions.
Statement of use: For research use only (per Product Data). Not for human or veterinary use.
Physical Properties
Item-specific specifications:
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature and general reference values (for context only; not item specifications):
Molecular formula (literature): C16H22O7
Molecular weight (literature): ~326.34 g/mol
Acidic functionality: contains a carboxylic acid (expected to be deprotonated at basic pH; pKa for similar polyoxygenated carboxylic acids often ~3–5, literature generalization)
Polarity/solubility (typical):
Soluble in polar aprotic organic solvents (e.g., DMSO) and alcohols; limited aqueous solubility at neutral pH due to hydrophobic scaffold; increased solubility in basic aqueous media via carboxylate formation.
Hygroscopic tendencies are not widely reported; handle under dry conditions to protect epoxide and lactone moieties.
LogP: Not readily available in standard references; expect moderate polarity due to multiple oxygens (literature expectation).
MP/BP/Refractive index/Density: Not specified for this item; consult primary literature or CoA.
Practical notes:
The epoxide and lactone functionalities are sensitive to strong acid/base and nucleophiles; prolonged exposure to high pH or nucleophilic buffers may induce ring opening or hydrolysis (literature behavior of epoxylactones).
Quality and Grades
Item-specific:
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grades (general):
Research/Biochemical grade typically emphasizes structural identity and purity appropriate for mechanistic enzymology or chemical biology screens. When purity is specified (e.g., ≥95% HPLC), it reflects the main component area by HPLC/UPLC with controlled residual solvents/metals.
For small-molecule tool compounds like heptelidic acid, low-level stereochemical or oxidative impurities can impact activity. Review chromatograms and NMR where available.
UV-Vis background and residual water/peroxides are generally not specified for non-solvent reagents; if your application is sensitive (e.g., enzyme kinetics), request full analytical data (1H/13C NMR, HRMS, HPLC purity, water by Karl Fischer) from the CoA.
Stabilizer/additives:
None specified for this item. If stabilizers or salts are used, they should be declared on the CoA; absence typically indicates the free acid form.
Fit-for-purpose recommendations:
For quantitative biochemical assays, verify: stereochemical integrity (chiroptical or chiral HPLC), absence of hydrolysis products (lactone/epoxide opening), and confirm counterion content (free acid vs. salt).
Reaction and Applications
Context: Heptelidic acid is primarily used as a biochemical tool compound rather than as a reagent or solvent. Its notable reactivity derives from its epoxide and lactone functionalities.
Research applications (literature):
Enzyme mechanistic studies: widely used as a covalent, irreversible probe of glycolytic glyceraldehyde-3-phosphate dehydrogenase (GAPDH), reacting with active-site nucleophiles (e.g., Cys) via epoxide opening.
Chemical biology: applied in target engagement assays, activity-based profiling, and pathway perturbation studies in carbohydrate metabolism. It can serve as a positive control for GAPDH inhibition in cell-free systems.
Natural products and biosynthesis: reference standard for polyketide biosynthetic investigations and stereochemical assignment protocols.
Chemical reactivity considerations (general):
Epoxide: susceptible to nucleophilic ring opening (thiols, amines, alkoxides). Rate and regioselectivity are solvent and pH dependent.
Lactone: vulnerable to hydrolysis under base or acid, producing hydroxyacids; transesterification possible in alcohols with acid/base catalysis.
Carboxylic acid: enables salt formation (for solubility) and coupling chemistry (amide/ester formation) if derivatization is desired for probe development.
Practical tips:
Maintain neutral to slightly acidic conditions during handling to preserve the epoxide/lactone.
For biochemical testing, prepare fresh dilutions and minimize exposure to high pH or nucleophile-rich buffers to retain activity.
Reaction Conditions
Item-specific, validated reaction conditions are not provided for this product.
General guidance drawn from literature chemistry of epoxylactone natural products:
Stability window: neutral, anhydrous organic solvents at ambient temperature; avoid extended exposure to pH >8 or strong acids.
Epoxide opening: proceeds with soft nucleophiles (e.g., thiols, amines) in polar protic or aprotic solvents (MeOH, EtOH, DMF, DMSO) at 0–25°C; catalysts (Lewis acids/bases) modulate regioselectivity. Reaction times: minutes to hours depending on nucleophile strength.
Esterification/Amidation (carboxylic acid): typical peptide-coupling conditions (EDCI or HATU, base such as DIPEA) in DMF/DCM at 0–25°C, 0.5–12 h. Monitor carefully to avoid unintended epoxide opening; add coupling reagents at low temperature.
Lactone hydrolysis: aqueous THF/MeOH with mild base (e.g., NaHCO3) at 0–25°C yields hydroxyacid; stronger base (NaOH) accelerates but risks epoxide loss.
Analytical monitoring:
LC–MS (ESI negative) and 1H NMR are preferred for tracking integrity of the epoxide/lactone.
Note: Conditions above are general literature practices for related scaffolds and should be re-optimized for heptelidic acid; perform small-scale trials and confirm structure by NMR/MS.
Safety and Handling
Item-specific hazard information:
Signal Word: Not specified for this item; refer to SDS.
H-Statements: Not specified for this item; refer to SDS.
GHS Classification/Pictograms: Not specified for this item; refer to SDS.
General safety guidance (literature/precautionary, not a substitute for SDS):
Likely hazards: organic acids with epoxide/lactone motifs can be irritating to skin/eyes and harmful if swallowed; epoxides are generally reactive toward biological nucleophiles.
PPE: lab coat, nitrile gloves, safety glasses or splash goggles; work in a chemical fume hood to avoid inhalation of dust/aerosols.
Handling: minimize exposure to strong bases/acids and nucleophiles which can trigger decomposition; avoid heat and prolonged light.
Incompatibilities: strong bases (epoxide/lactone opening), strong acids (hydrolysis), strong nucleophiles (e.g., amines, thiols), reducing agents targeting epoxides, and oxidants that may over-oxidize polyols.
First aid (overview):
Skin/eye contact: rinse with plenty of water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
Inhalation: move to fresh air; seek medical attention if symptoms occur.
Ingestion: rinse mouth; do not induce vomiting; obtain medical advice.
Storage and shipping (item-specific):
Storage Conditions: Store at -20°C (per Product Data). Keep container tightly closed, desiccated, and protected from light.
Always consult the SDS for authoritative hazard classifications and response measures.
Solvent Selection
Applicability: Heptelidic acid is a polyoxygenated small molecule (carboxylic acid, lactone, epoxide, alcohols). It is not a bulk solvent; this section addresses solvents suitable for dissolving/handling it.
General solvent behavior (literature-informed):
Preferred stock-solution solvents: DMSO (typical for screening libraries), DMF, and alcohols (MeOH, EtOH). These balance polarity and stability.
Aqueous media: Limited solubility at neutral pH; solubility improves in basic buffers by forming the carboxylate, but strong base increases risk of epoxide/lactone opening. If aqueous delivery is needed, prepare a concentrated DMSO stock and dilute into buffer immediately before use (maintain final DMSO ≤1–2% v/v for biochemical assays as needed).
Nonpolar solvents (EtOAc, dichloromethane, toluene): variable solubility; EtOAc often acceptable. Chlorinated solvents and strong nucleophilic solvents may accelerate decomposition if warmed.
Selection tips:
For bioassays: DMSO stocks (e.g., 10–50 mM) are common; filter-sterilize if required using PTFE or PVDF membranes.
For purification/analytical work: MeOH/H2O or ACN/H2O (0.1% acid modifier) systems often give sharp HPLC peaks for polyoxygenated natural products; avoid high-pH eluents.
Quick comparison (general):
DMSO: highest solvating power; best for stable freezer stocks.
MeOH/EtOH: good solvency; easier evaporation; can participate in transesterification at high pH/temperature.
Aqueous basic buffers: increase solubility but risk functional group degradation; use minimally and briefly.
Storage and Reconstitution
Item-specific conditions (from Product Data):
Storage: Store at -20°C.
Shipping: Ice chest + Ice pads.
General best practices (supplemental, not item specifications):
Container: store in airtight, light-protective vials with desiccant. If supplied as a solid, equilibrate to room temperature before opening to prevent condensation.
Stability: avoid repeated freeze–thaw and prolonged exposure to moisture, base, or strong nucleophiles to protect epoxide and lactone.
Reconstitution: prepare concentrated stock solutions in anhydrous DMSO. If aqueous formulations are required, dilute immediately before use into neutral buffers; minimize time at elevated pH.
Aliquoting: prepare single-use aliquots to reduce freeze–thaw cycles. Clearly label concentration, solvent, and date of preparation.
Working concentration range: Not specified for this item; determine empirically for your assay.
Always consult the product’s CoA/Spec Sheet for any additional, lot-specific handling or stability information.
Structure and Identity
Item-specific (from Product Data):
CAS: 57710-57-3
PubChem CID: 10945834
InChIKey: 158472 (as listed; note this is not in standard 27-character format)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature identity (general reference information):
Core structural motifs (literature description): bicyclic framework featuring a γ-lactone fused to a tetrahydrofuran-like ring, with an electrophilic epoxide and multiple hydroxyl substituents; one free carboxylic acid. Multiple stereogenic centers define its absolute configuration.
2D structure (verbal description, literature): a compact, oxygen-rich bicyclic system; an epoxide ring is embedded adjacent to the lactone carbonyl, with hydroxyl groups arrayed around the fused ring system and a pendant carboxylate-bearing side chain. Stereochemistry is fixed at several contiguous chiral centers.
Notes:
When definitive identifiers (SMILES/InChI) are required, consult authoritative databases (e.g., PubChem CID 10945834) or the product CoA to avoid stereochemical ambiguity.
Synthetic Utility
Perspective: Heptelidic acid is more often the target of synthesis than a reagent. Nevertheless, its functional groups offer derivatization opportunities for probe and SAR development.
Functional-group reactivity (general):
Carboxylic acid: amenable to amidation/esterification (e.g., EDCI/HOBt, HATU, or Steglich conditions) to install handles (alkynes, azides, biotin) for conjugation.
Epoxide: can be opened regioselectively by soft nucleophiles (e.g., thiols) under mild conditions to generate adducts; however, such modifications typically abolish GAPDH inhibition.
Lactone: under controlled conditions, hydrolysis affords hydroxyacid derivatives; re-lactonization may be feasible for analog synthesis.
Alcohols: selective protection (e.g., silyl ethers, acylation) enables stepwise modification without compromising the core.
Applications:
Synthesis of activity-based probes: introduce reporter tags via the acid functionality while preserving the electrophilic epoxide.
Isotopic labeling: incorporation of 13C/2H-labeled fragments through late-stage coupling for metabolic tracing or quantitative LC–MS.
Cautions:
Multicenter stereochemistry necessitates protecting-group strategies and mild conditions to avoid epimerization or undesired ring opening.
Maintain near-neutral conditions when possible to preserve the native epoxide/lactone during manipulations.
Target Specificity
Item-specific target and validation data are not provided in the Product Data for this catalog entry.
General note:
While literature discusses heptelidic acid as a covalent inhibitor of GAPDH, Aladdin Scientific provides this compound for research use without a guaranteed target profile. Users should perform their own target engagement and selectivity assays suitable for their system.
Domande frequenti
How should this product be stored?
Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.
How is this product shipped?
This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 57710-57-3, the molecular formula is C15H20O5, and the molecular weight is 280.32 g/mol. InChIKey JESMSCGUTIEROV-RTWAVKEYSA-N.
What documentation is provided?
Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.
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