Heptelidic acid , CAS No.57710-57-3

CAS: 57710-57-3 Cat. No.: H646838 Molecular Weight: 280.32
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Synonyms
Avocettin | SCHEMBL20199901 | (5aS,6R,9S,9aS)-1-oxo-6-propan-2-ylspiro[3,5a,6,7,8,9a-hexahydro-2-benzoxepine-9,2'-oxirane]-4-carboxylic acid | DTXSID901105608 | (5aS,6R,9S,9aS)-1-Oxo-6-(propan-2-yl)-3,5a,6,7,8,9a-hexahydro-1H-spiro[2-benzoxepine-9,2'-oxir
Storage
Store at -20°C
Shipped In
Ice chest + Ice pads
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Size
Status
Price
Qty
1mg
H646838-1mg
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$2,080.90
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Why this grade

for sensitive chromatographic and analytical workflows requiring minimal baseline interference.

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Storage & shipping

Store at -20°C Ships Ice chest + Ice pads Check lot-specific COA for exact specifications.

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Quality documents

SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.

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Literature proof

Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.

Overview

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).

Form:Solid

Specifications

Synonyms
Avocettin | SCHEMBL20199901 | (5aS, 6R, 9S, 9aS)-1-oxo-6-propan-2-ylspiro[3, 5a, 6, 7, 8, 9a-hexahydro-2-benzoxepine-9, 2'-oxirane]-4-carboxylic acid | DTXSID901105608 | (5aS, 6R, 9S, 9aS)-1-Oxo-6-(propan-2-yl)-3, 5a, 6, 7, 8, 9a-hexahydro-1H-spiro[2-benzoxepine-9, 2'-oxir
Biochemical and Physiological Mechanisms
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 .
Storage
Store at -20°C
Shipped In
Ice chest + Ice pads
This product requires cold chain shipping. Ground and other economy services are not available.
Action Type
INHIBITOR
Names and Identifiers
Canonical SmilesCC(C)C1CCC2(CO2)C3C1C=C(COC3=O)C(=O)O
IUPAC Name(5aS,6R,9S,9aS)-1-oxo-6-propan-2-ylspiro[3,5a,6,7,8,9a-hexahydro-2-benzoxepine-9,2'-oxirane]-4-carboxylic acid
InChIKeyJESMSCGUTIEROV-RTWAVKEYSA-N
INCHI1S/C15H20O5/c1-8(2)10-3-4-15(7-20-15)12-11(10)5-9(13(16)17)6-19-14(12)18/h5,8,10-12H,3-4,6-7H2,1-2H3,(H,16,17)/t10-,11-,12-,15-/m1/s1
Isomeric SMILES CC(C)[C@H]1CC[C@@]2(CO2)[C@@H]3[C@@H]1C=C(COC3=O)C(=O)O
Molecular Weight 280.32
Reaxy-Rn 30085085
Reaxys-RN_link_address https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=30085085&ln=

Documentation

📋 Safety Data Sheet (SDS)

Comprehensive hazard, handling, storage, and regulatory compliance document.

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✅ Certificate of Analysis (COA)

Lot-specific quality data. Enter your lot number to retrieve the exact COA.

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📊 Datasheet

Quick-reference summary of product specifications and applications.

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🔬 Specification Sheet

Full quality attributes and acceptance criteria for this grade.

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Advanced Data

Taxonomic Classification

Taxonomy Tree

KingdomOrganic compounds
SuperclassLipids and lipid-like molecules
ClassPrenol lipids
SubclassTerpene lactones
Intermediate Tree Nodes Not available
Direct ParentTerpene lactones
Alternative Parents Sesquiterpenoids  Dicarboxylic acids and derivatives  Lactones  Carboxylic acid esters  Oxacyclic compounds  Epoxides  Dialkyl ethers  Carboxylic acids  Organic oxides  Hydrocarbon derivatives  Carbonyl compounds  
Molecular FrameworkAliphatic heteropolycyclic compounds
Substituents Terpene lactone - Sesquiterpenoid - Dicarboxylic acid or derivatives - Carboxylic acid ester - Lactone - Carboxylic acid derivative - Carboxylic acid - Dialkyl ether - Oxirane - Ether - Oxacycle - Organoheterocyclic compound - Organic oxygen compound - Carbonyl group - Hydrocarbon derivative - Organooxygen compound - Organic oxide - Aliphatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
External Descriptors Not available
3D Structure
Interactive Chemical Structure Model





Associated Targets(Human)
A-375 (9258 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DU-145 (51482 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HL-60 (67320 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HT-29 (80576 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KM12 (47707 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OVCAR-3 (48710 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PANC-1 (6144 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-OV-3 (52876 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TK-10 (45540 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A549 (127892 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
T47D (39041 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCT-116 (91556 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HEK293 (82097 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI-H460 (60772 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HOP-62 (47048 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Associated Targets(non-human)
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PC-12 (7051 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mechanisms of Action
Certificates(CoA,COO,BSE/TSE and Analysis Chart)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemical and Physical Properties
Molecular Weight280.320 g/mol
XLogP31.400
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Exact Mass280.131 Da
Monoisotopic Mass280.131 Da
Topological Polar Surface Area76.100 Ų
Heavy Atom Count20
Formal Charge0
Complexity481.000
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
The total count of all stereochemical bonds0
Covalently-Bonded Unit Count1
Solution Calculators
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