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Win 18446 (Standard)

CAT: 0804-HY-W011094R-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-W011094R-01Size:5 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Win 18446 is an orally active testes-specific enzyme ALDH1a2 inhibitor, with an IC50 of 0.3 μM. Win 18446 reversibly inhibits spermatogenesis in many species and inhibits Retinoic acid biosynthesis from Retinol (HY-B1342) within the testes[1][2].
CAS Number
1477-57-2
UNSPSC
12352211
Target
Aldehyde Dehydrogenase (ALDH)
Related Pathways
Metabolic Enzyme/Protease
Field of Research
Endocrinology
Smiles
O=C(NCCCCCCCCNC(C(Cl)Cl)=O)C(Cl)Cl
Molecular Formula
C12H20Cl4N2O2
Molecular Weight
366.11
References & Citations
[1]John K Amory, et al. Suppression of spermatogenesis by bisdichloroacetyldiamines is mediated by inhibition of testicular retinoic acid biosynthesis. J Androl. Jan-Feb 2011;32 (1) :111-9.|[2]Cathryn A Hogarth, et al. Suppression of Stra8 expression in the mouse gonad by WIN 18,446. Biol Reprod. 2011 May;84 (5) :957-65.
Shipping Conditions
Room temperature
Scientific Category
Reference Standards

Chemical Information

N,N'-1,8-Octanediylbis(2,2-dichloroacetamide)

WIN 18446 is a carboxamide that is 1,8-diaminooctane in which a hydrogen attached to each of the amino groups has been replaced by a dichloroacetyl group. Inhibitor of aldehyde dehydrogenase 1a2 (ALDH1a2). Inhibits the biosynthesis of retinoic acid from retinol in neonatal and adult murine testis. It down-regulates sex related genes in zebrafish. It has a role as an EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor. It is a secondary carboxamide and an organochlorine compound. It is functionally related to a dichloroacetic acid and a 1,8-diaminooctane.

CAS Number1477-57-2
PubChem CID15134
IUPAC Name2,2-dichloro-N-[8-[(2,2-dichloroacetyl)amino]octyl]acetamide
Molecular FormulaC12H20Cl4N2O2
Molecular Weight366.1
XLogP4.1
Topological Polar Surface Area58.2
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count11
Heavy Atom Count20
Formal Charge0
Complexity261
SMILES
C(CCCCNC(=O)C(Cl)Cl)CCCNC(=O)C(Cl)Cl
InChI
InChI=1S/C12H20Cl4N2O2/c13-9(14)11(19)17-7-5-3-1-2-4-6-8-18-12(20)10(15)16/h9-10H,1-8H2,(H,17,19)(H,18,20)
InChIKey
FAOMZVDZARKPFJ-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of N,N'-1,8-Octanediylbis(2,2-dichloroacetamide)
CAS: 1477-57-2
CID: 15134
Formula: C12H20Cl4N2O2
MW: 366.1
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight366.1
XLogP34.1
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count11
Exact Mass366.024939
Monoisotopic Mass364.027889
Topological Polar Surface Area58.2 Ų
Heavy Atom Count20
Formal Charge0
Complexity261
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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