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Pironetin , CAS No.151519-02-7

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P651011
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P651011-1mg
1mg
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$1,080.90

Basic Description

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 Temp Store at -20°C
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Product Description

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

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
Superclass Lipids and lipid-like molecules
Class Fatty Acyls
Subclass Fatty alcohols
Intermediate Tree Nodes Not available
Direct Parent Fatty alcohols
Alternative Parents Dihydropyranones  Enoate esters  Secondary alcohols  Lactones  Oxacyclic compounds  Monocarboxylic acids and derivatives  Dialkyl ethers  Organic oxides  Hydrocarbon derivatives  Carbonyl compounds  
Molecular Framework Aliphatic 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
Description This 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

Associated Targets(Human)

CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HL-60 (67320 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HT-29 (80576 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
K562 (73714 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
MCF7 (126967 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
T98G (1524 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
A549 (127892 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
NCI-H69 (709 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HEK293 (82097 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
A2780 (11979 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HeLa (62764 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
MDA-MB-231 (73002 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HCT-15 (51914 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
TUBA3C Tchem Tubulin alpha (84 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID

Associated Targets(non-human)

Mus musculus (284745 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
DC3F (23 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
EL4 (235 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
P388 (20296 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
TUBB2B Tubulin (2175 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID

Mechanisms of Action

Mechanism of Action Action Type target ID Target Name Target Type Target Organism Binding Site Name References

Names and Identifiers

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
INCHI InChI=1S/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
InChIKey XIHGDBYGUWEHCV-FSEPSNHWSA-N
Smiles CCC1C=CC(=O)OC1CC(C(C)C(C(C)CC=CC)OC)O
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

Certificates(CoA,COO,BSE/TSE and Analysis Chart)

C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:

Chemical and Physical Properties

Molecular Weight 324.500 g/mol
XLogP3 4.000
Hydrogen Bond Donor Count 1
Hydrogen Bond Acceptor Count 4
Rotatable Bond Count 9
Exact Mass 324.23 Da
Monoisotopic Mass 324.23 Da
Topological Polar Surface Area 55.800 Ų
Heavy Atom Count 23
Formal Charge 0
Complexity 416.000
Isotope Atom Count 0
Defined Atom Stereocenter Count 6
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 1
Undefined Bond Stereocenter Count 0
The total count of all stereochemical bonds 1
Covalently-Bonded Unit Count 1

Solution Calculators

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