Cat. No.: HY-120838

Heptelidic acid

Name: Heptelidic acid
Brand: MedChemExpress
SKU: HY-120838
Price: 810.00 USD
Availability: InStock
Rating: 5 (1 reviews)

(Synonyms: Koningic acid)

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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 IC₅₀of 90 μM.

For research use only. We do not sell to patients.

Purity : 97.5%
CAS No.: 57710-57-3
Formula: C₁₅H₂₀O₅
Molecular Weight:280.32

Storage:

Powder -20°C, 3 years ; In solvent -80°C, 6 months , -20°C, 1 month

Heptelidic acid Chemical Structure

CAS No.: 57710-57-3

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Biological Activity
- Description
- IC₅₀ & Target
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
Publications (1)
Solvent & Solubility
- In Vitro
Protocols (4)
Purity & Documentation
References
Help & FAQs
Classifications
Bioz

Biological Activity

Description

Heptelidic acid (Koningic acid) is a sesquiterpene antibiotic^[1]. Heptelidic acid inhibits Etoposide-induced apoptosis via downregulation of caspases^[2]. Koningic acid (KA) is a specific GAPDH inhibitor with an IC₅₀of 90 μM^[3].

IC₅₀ & Target

^[2]

Caspase-3

All Caspase Isoforms :

Cellular Effect

Cell Line	Type	Value	Description	References
A-375	IC₅₀	1.26 μM Compound: 1, KA, heptelidic acid	Antiproliferative activity against human A375 cells assessed as inhibition of cell proliferation incubated for 24 hrs by conventional ATP quantification method Antiproliferative activity against human A375 cells assessed as inhibition of cell proliferation incubated for 24 hrs by conventional ATP quantification method	[PMID: 25937235]
A-375	IC₅₀	1.34 μM Compound: 1, KA, heptelidic acid	Antiproliferative activity against human A375 cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method Antiproliferative activity against human A375 cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method	[PMID: 25937235]
BXPC-3	IC₅₀	0.76 μM Compound: 1, KA, heptelidic acid	Antiproliferative activity against human BxPC3 cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method Antiproliferative activity against human BxPC3 cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method	[PMID: 25937235]
COLO 205	IC₅₀	0.63 μM Compound: 1, KA, heptelidic acid	Antiproliferative activity against human COLO205 cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method Antiproliferative activity against human COLO205 cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method	[PMID: 25937235]
DU-145	IC₅₀	0.89 μM Compound: 1, KA, heptelidic acid	Antiproliferative activity against human DU145 cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method Antiproliferative activity against human DU145 cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method	[PMID: 25937235]
HL-60	IC₅₀	0.76 μM Compound: 1, KA, heptelidic acid	Antiproliferative activity against human HL60 cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method Antiproliferative activity against human HL60 cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method	[PMID: 25937235]
HOP-62	IC₅₀	0.51 μM Compound: 1, KA, heptelidic acid	Antiproliferative activity against human HOP62 cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method Antiproliferative activity against human HOP62 cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method	[PMID: 25937235]
KG-1	IC₅₀	0.4 μM Compound: 1, KA, heptelidic acid	Antiproliferative activity against human KG1 cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method Antiproliferative activity against human KG1 cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method	[PMID: 25937235]
KM12	IC₅₀	0.41 μM Compound: 1, KA, heptelidic acid	Antiproliferative activity against human KM12 cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method Antiproliferative activity against human KM12 cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method	[PMID: 25937235]
MDA-MB-231	IC₅₀	0.45 μM Compound: 1, KA, heptelidic acid	Antiproliferative activity against human MDA-MB-231 cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method Antiproliferative activity against human MDA-MB-231 cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method	[PMID: 25937235]
NAMALVA	IC₅₀	0.302 μM Compound: 1, KA, heptelidic acid	Antiproliferative activity against human NAMALWA cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method Antiproliferative activity against human NAMALWA cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method	[PMID: 25937235]
NCI-H460	IC₅₀	0.49 μM Compound: 1, KA, heptelidic acid	Antiproliferative activity against human NCI-H460 cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method Antiproliferative activity against human NCI-H460 cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method	[PMID: 25937235]
OVCAR-3	IC₅₀	0.69 μM Compound: 1, KA, heptelidic acid	Antiproliferative activity against human OVCAR3 cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method Antiproliferative activity against human OVCAR3 cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method	[PMID: 25937235]
SK-OV-3	IC₅₀	0.34 μM Compound: 1, KA, heptelidic acid	Antiproliferative activity against human SKOV3 cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method Antiproliferative activity against human SKOV3 cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method	[PMID: 25937235]
T47D	IC₅₀	0.21 μM Compound: 1, KA, heptelidic acid	Antiproliferative activity against human T47D cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method Antiproliferative activity against human T47D cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method	[PMID: 25937235]
TK-10	IC₅₀	0.66 μM Compound: 1, KA, heptelidic acid	Antiproliferative activity against human TK10 cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method Antiproliferative activity against human TK10 cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method	[PMID: 25937235]
WM 266-4	IC₅₀	0.509 μM Compound: 1, KA, heptelidic acid	Antiproliferative activity against human WM266.4 cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method Antiproliferative activity against human WM266.4 cells assessed as inhibition of cell proliferation incubated for 72 hrs by conventional ATP quantification method	[PMID: 25937235]

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^[1].
Heptelidic acid inhibits Etoposide-induced apoptosis in human leukemia U937 cells^[2].Heptelidic acid inhibits caspase- 3 induction in U937 cells with an IC₅₀ value of 40 μM after 8 h of Etoposide treatment^[2].
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 IC₅₀=5 μM^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only. Further protocols information, click here.

Cell Viability Assay^[3]

View Protocol

Cell Line:

HEK293T cells expressing KAr-GAPDH or EV (top left)
Concentration:

0.1, 1, 10, 100, 1000 μM
Incubation Time:

24 hours
Result:

IC₅₀=5 μM.

In Vivo

Heptelidic acid (Koningic acid; KA) is bioavailable and induces dynamic changes to glycolysis in vivo^[3].

MedChemExpress (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 tumor^[3]
Dosage:

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).

Chemical Information

CAS No. 57710-57-3
Appearance Solid
Molecular Weight 280.32
Formula C₁₅H₂₀O₅
Color Colorless to off-white
SMILES

O=C(C1=C[C@@]2([H])[C@]([C@@]3(OC3)CC[C@@H]2C(C)C)([H])C(OC1)=O)O
Synonyms

Koningic acid
Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Powder	-20°C	3 years
In solvent	-80°C	6 months
	-20°C	1 month

Publications (1)

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Journal Impact Factor

MedComm (2020)

Dimethyl fumarate alleviate hepatic ischemia-reperfusion injury through suppressing cGAS-STING signaling. [Abstract]

2025 Jan 28;6(2):e70077. PMID: 39877286

Solvent & Solubility

In Vitro:

DMSO : ≥ 30 mg/mL (107.02 mM; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

* "≥" means soluble, but saturation unknown.

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

3.5674 mL

17.8368 mL

35.6735 mL

5 mM

0.7135 mL

3.5674 mL

7.1347 mL

10 mM

0.3567 mL

1.7837 mL

3.5674 mL

Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Molarity Calculator

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

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Molecular Weight Molecular Weight

Dilution Calculator

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Protocols

All Cell Biology Signal Pathway Related

Apoptosis
Apoptosis, also called programmed cell death, is generally characterized by distinct morphological characteristics.
TUNEL staining for apoptotic DNA fragmentation
TUNEL staining detects DNA strand breaks by using terminal deoxynucleotidyl transferase to add labeled nucleotides to exposed 3′-OH DNA termini, generating either microscopic staining in fixed cells or tissue sections, or fluorescence/cytometric signal in cell suspensions. TUNEL positivity reflects DNA fragmentation but should not be interpreted alone as definitive apoptosis, because TUNEL can also label necrotic, autolytic, mechanically damaged, or DNA-repair-associated DNA breaks.
Annexin V plus membrane-impermeant dye apoptosis staining
Annexin V-based apoptosis assays rely on the detection of phosphatidylserine (PS) externalization from the inner leaflet of the plasma membrane to the outer leaflet, an early biochemical hallmark of apoptosis. Fluorescently labeled Annexin V binds PS in a calcium-dependent manner, enabling identification of early apoptotic cells by flow cytometry or fluorescence microscopy. When combined with a membrane-impermeant DNA-binding dye (e. g. , propidium iodide), this approach allows discrimination between viable (Annexin V−/dye−), early apoptotic (Annexin V+/dye−), and late apoptotic or necrotic (Annexin V+/dye+) cell populations by assessing membrane integrity and PS exposure.
Apoptosis Solutions
Apoptosis is a regulated, generally non-lytic cell-death pathway that removes unwanted, damaged, infected, or abnormal cells through coordinated morphological changes, caspase activation, DNA fragmentation, and membrane remodeling. The intrinsic apoptosis pathway is controlled mainly by mitochondrial outer membrane permeabilization, BCL-2 family proteins, cytochrome c release, apoptosome formation, caspase-9 activation, and downstream executioner caspase-3/7 activation. The extrinsic apoptosis pathway is initiated by death receptors such as Fas, TNFR, and TRAIL receptors, which recruit adaptor proteins and activate caspase-8 before engaging executioner caspases or mitochondrial amplification through BID cleavage. Apoptosis is linked to many phenotypes, including cancer cell killing, tissue homeostasis, immune regulation, neurodegeneration, infection response, and treatment-induced cytotoxicity; unresolved questions include how apoptosis interacts with necroptosis, pyroptosis, ferroptos

Purity & Documentation

Select Batch:

Purity: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (285 KB)
SDS (394 KB)
- English - EN (394 KB)
- Français - FR (394 KB)
- Deutsch - DE (394 KB)
- Norwegian - NO (394 KB)
- Español - ES (394 KB)
- Swedish - SV (394 KB)
- Italian - IT (394 KB)
- Korean - KR (394 KB)
- Portuguese - PT (394 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

References

[1]. Y Itoh, et al. A new sesquiterpene antibiotic, heptelidic acid producing organisms, fermentation, isolation and characterization. J Antibiot (Tokyo). 1980 May;33(5):468-73. [Content Brief]

[2]. Jin Hee Kim, et al. Heptelidic acid, a sesquiterpene lactone, inhibits Etoposide-induced apoptosis in human leukemia U937 cells. J Microbiol Biotechnol. 2009 Aug;19(8):787-91. [Content Brief]

[3]. Maria V Liberti, et al. A Predictive Model for Selective Targeting of the Warburg Effect through GAPDH Inhibition with a Natural Product. Cell Metab. 2017 Oct 3;26(4):648-659.e8. [Content Brief]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO	1 mM	3.5674 mL	17.8368 mL	35.6735 mL	89.1838 mL
	5 mM	0.7135 mL	3.5674 mL	7.1347 mL	17.8368 mL
	10 mM	0.3567 mL	1.7837 mL	3.5674 mL	8.9184 mL
	15 mM	0.2378 mL	1.1891 mL	2.3782 mL	5.9456 mL
	20 mM	0.1784 mL	0.8918 mL	1.7837 mL	4.4592 mL
	25 mM	0.1427 mL	0.7135 mL	1.4269 mL	3.5674 mL
	30 mM	0.1189 mL	0.5946 mL	1.1891 mL	2.9728 mL
	40 mM	0.0892 mL	0.4459 mL	0.8918 mL	2.2296 mL
	50 mM	0.0713 mL	0.3567 mL	0.7135 mL	1.7837 mL
	60 mM	0.0595 mL	0.2973 mL	0.5946 mL	1.4864 mL
	80 mM	0.0446 mL	0.2230 mL	0.4459 mL	1.1148 mL
	100 mM	0.0357 mL	0.1784 mL	0.3567 mL	0.8918 mL

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Keywords

Heptelidic acid

1 Cited Publications

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Heptelidic acid

Publications Citing Use of MedChemExpress (MCE) Heptelidic acid

All Caspase Isoforms