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Pironetin

CAT: 0804-HY-116446-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-116446-01Size:1 mg
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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[1][2].
CAS Number
151519-02-7
Product Name Alternative
3,3',4,4'-Benzophenonetetracarboxylic acid
UNSPSC
12352005
Hazard Statement
H315-H319-H335
Target
Microtubule/Tubulin
Type
Reference compound
Related Pathways
Cell Cycle/DNA Damage; Cytoskeleton
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/pironetin.html
Purity
97.94
Solubility
DMSO : < 1 mg/mL (ultrasonic; warming; heat to 60°C)
Smiles
O=C1C=C[C@H]([C@H](O1)C[C@H]([C@@H]([C@@H]([C@H](C/C=C/C)C)OC)C)O)CC
Molecular Formula
C19H32O4
Molecular Weight
324.45
Precautions
P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P362+P364-P403+P233-P405-P501
References & Citations
[1]Kondoh M, et al. Cell cycle arrest and antitumor activity of pironetin and its derivatives. Cancer Lett. 1998 Apr 10;126 (1) :29-32.|[2]Yang J, et al. Pironetin reacts covalently with cysteine-316 of α-tubulin to destabilize microtubule. ] Nat Commun. 2016 Jun 30;7:12103.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C, 3 years (Powder)
Scientific Category
Reference compound1
Clinical Information
No Development Reported

Chemical Information

Pironetin

Pironetin is an aliphatic alcohol.

CAS Number151519-02-7
PubChem CID6438891
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
Molecular FormulaC19H32O4
Molecular Weight324.5
XLogP4
Topological Polar Surface Area55.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count9
Heavy Atom Count23
Formal Charge0
Complexity416
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
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
Chemical Structure
2D Structure
2D structure of Pironetin
CAS: 151519-02-7
CID: 6438891
Formula: C19H32O4
MW: 324.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight324.5
XLogP34
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count9
Exact Mass324.23005950
Monoisotopic Mass324.23005950
Topological Polar Surface Area55.8 Ų
Heavy Atom Count23
Formal Charge0
Complexity416
Isotope Atom Count0
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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CatalogName
561750Pironetin

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