Pironetin , CAS No.151519-02-7

CAS: 151519-02-7 Cat. No.: P651011 Molecular Weight: 324.45 PubChem CID: 6438891
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Synonyms
CHEBI:189353 | 2H-Pyran-2-one, 5-ethyl-5,6-dihydro-6-(2-hydroxy-4-methoxy-3,5-dimethyl-7-nonenyl)-, (5R-(5alpha,6alpha(2R*,3S*,4R*,5S*,7E)))- | SCHEMBL8940434 | DTXSID601037185 | (5R,6R)-5-Ethyl-5,6-dihydro-6-[(2R,3S,4R,5S,7E)-2-hydroxy-4-methoxy-3,5-dime
Storage
Store at -20°C
Shipped In
Ice chest + Ice pads
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Size
Status
Price
Qty
1mg
P651011-1mg
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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

Pironetin is an α/β unsaturated lactone isolated from Streptomyces species. Pironetin binds to α-tubulin and is a potent inhibitor of microtubule polymerization, and has cell cycle arrest and antitumor activity

In Vitro

Pironetin (20-100 ng/mL; 24 hours; 3Y1 cells) treatment arrests the cell cycle progression at G2/M in 3Y1 cells. Pironetin (1-10000 ng/mL; 3 days; HeLa, A2780 and K-NRK cells) treatment inhibits the cell proliferation. IC 50 values against these cell lines are almost 10 ng/mL. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Cell Cycle AnalysisCell Line: 3Y1 cells Concentration: 20 ng/mL, 50 ng/mL, 100 ng/mL Incubation Time: 24 hours Result: Arrested the cell cycle progression at G2/M in3Y1 cells. Cell Proliferation AssayCell Line: HeLa, A2780 and K-NRK cells Concentration: 1 ng/mL, 10 ng/mL, 100 ng/mL, 1000 ng/mL and 10000 ng/mL Incubation Time: 3 days Result: Inhibited the cell proliferation.

In Vivo

Pironetin (0.78-6.25 mg/kg; intraperitoneal injection; daily; for 5 days; female CDF1-SLC mice) treatment shows a moderate antitumor effect, however, a severe weight loss is observed as a side effect . MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: Female CDF1-SLC mice (10 weeks) injected with P388 murine leukemia cells Dosage: 0.78 mg/kg, 1.56 mg/kg, 3.13 mg/kg, 6.25 mg/kg Administration: Intraperitoneal injection; daily; for 5 days Result: Showed a moderate antitumor effect.

Form:Oil

IC50& Target:Microtubule

Specifications

Synonyms
CHEBI:189353 | 2H-Pyran-2-one, 5-ethyl-5, 6-dihydro-6-(2-hydroxy-4-methoxy-3, 5-dimethyl-7-nonenyl)-, (5R-(5alpha, 6alpha(2R*, 3S*, 4R*, 5S*, 7E)))- | SCHEMBL8940434 | DTXSID601037185 | (5R, 6R)-5-Ethyl-5, 6-dihydro-6-[(2R, 3S, 4R, 5S, 7E)-2-hydroxy-4-methoxy-3, 5-dime
Biochemical and Physiological Mechanisms
Pironetin is an α/β unsaturated lactone isolated from Streptomyces species. Pironetin binds to α-tubulin and is a potent inhibitor of microtubule polymerization, and has cell cycle arrest and antitumor activity.
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 SmilesCCC1C=CC(=O)OC1CC(C(C)C(C(C)CC=CC)OC)O
IUPAC Name(2R,3R)-3-ethyl-2-[(E,2R,3S,4R,5S)-2-hydroxy-4-methoxy-3,5-dimethylnon-7-enyl]-2,3-dihydropyran-6-one
InChIKeyXIHGDBYGUWEHCV-FSEPSNHWSA-N
INCHI1S/C19H32O4/c1-6-8-9-13(3)19(22-5)14(4)16(20)12-17-15(7-2)10-11-18(21)23-17/h6,8,10-11,13-17,19-20H,7,9,12H2,1-5H3/b8-6+/t13-,14-,15+,16+,17+,19+/m0/s1
Isomeric SMILES CC[C@@H]1C=CC(=O)O[C@@H]1C[C@H]([C@H](C)[C@@H]([C@@H](C)C/C=C/C)OC)O
Alternate CAS 151519-02-7
PubChem CID 6438891
MeSH Entry Terms 5-ethyl-5,6-dihydro-6-(2-hydroxy-4-methoxy-3,5-dimethyl-7-nonenyl)-2H-pyran-2-one;PA 48153C;PA-48153C;pironetin
Molecular Weight 324.45

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
ClassFatty Acyls
SubclassFatty alcohols
Intermediate Tree Nodes Not available
Direct ParentFatty alcohols
Alternative Parents Dihydropyranones  Enoate esters  Secondary alcohols  Lactones  Oxacyclic compounds  Monocarboxylic acids and derivatives  Dialkyl ethers  Organic oxides  Hydrocarbon derivatives  Carbonyl compounds  
Molecular FrameworkAliphatic heteromonocyclic compounds
Substituents Fatty alcohol - Dihydropyranone - Pyran - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Carboxylic acid ester - Lactone - Secondary alcohol - Carboxylic acid derivative - Dialkyl ether - Ether - Oxacycle - Monocarboxylic acid or derivatives - Organoheterocyclic compound - Organic oxide - Carbonyl group - Hydrocarbon derivative - Alcohol - Organic oxygen compound - Organooxygen compound - Aliphatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.
External Descriptors Not available
3D Structure
Interactive Chemical Structure Model





Associated Targets(Human)
CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 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
K562 (73714 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
T98G (1524 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A549 (127892 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI-H69 (709 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HEK293 (82097 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A2780 (11979 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HeLa (62764 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-MB-231 (73002 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCT-15 (51914 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TUBA3C Tchem Tubulin alpha (84 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Associated Targets(non-human)
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DC3F (23 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EL4 (235 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
P388 (20296 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TUBB2B Tubulin (2175 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 Weight324.500 g/mol
XLogP34.000
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count9
Exact Mass324.23 Da
Monoisotopic Mass324.23 Da
Topological Polar Surface Area55.800 Ų
Heavy Atom Count23
Formal Charge0
Complexity416.000
Isotope Atom Count0
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
The total count of all stereochemical bonds1
Covalently-Bonded Unit Count1
Solution Calculators
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