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W1020

Sigma-Aldrich

W146 hydrate

≥98% (HPLC)

Synonym(s):

ML056, R-3-amino-4-(3-hexylphenylamino)-4-oxobutylphosphonic acid hydrate, [(3R)-3-amino-4-[(3-hexylphenyl)amino]-4-oxobutyl]-phosphonic acid

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About This Item

Empirical Formula (Hill Notation):
C16H27N2O4P · xH2O
CAS Number:
909725-61-7
Molecular Weight:
342.37 (anhydrous basis)
MDL number:
MFCD16875441
UNSPSC Code:
12352211
PubChem Substance ID:
329830425
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

off-white

solubility

methanol: soluble (with 0.1% TFA)

originator

Novartis

storage temp.

2-8°C

SMILES string

O.CCCCCCc1cccc(NC(=O)[C@H](N)CCP(O)(O)=O)c1

InChI

1S/C16H27N2O4P.H2O/c1-2-3-4-5-7-13-8-6-9-14(12-13)18-16(19)15(17)10-11-23(20,21)22;/h6,8-9,12,15H,2-5,7,10-11,17H2,1H3,(H,18,19)(H2,20,21,22);1H2/t15-;/m1./s1

InChI key

DQKSZHVSROOTFY-XFULWGLBSA-N

General description

W146 hydrate functions as an orthosteric antagonist. It is associated with blood lymphopenia and lung edema in mice.

Application

W146 hydrate has been used to assess vascular permeability in mice.

Biochem/physiol Actions

Potent S1P(1) competitive antagonist; Ki = 10-77 nM.

Features and Benefits

This compound is featured on the Lysophospholipid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Novartis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sphingosine-1-Phosphate Signaling in Immunology and Infectious Diseases (2014)
Impaired endothelial barrier function in apolipoprotein M-deficient mice is dependent on sphingosine-1-phosphate receptor 1
Christensen PM, et al.
Faseb Journal, 30(6), 2351-2359 (2016)
María V Simón et al.
Investigative ophthalmology & visual science, 56(10), 5808-5815 (2015-09-02)
Migration of Müller glial cells is enhanced in proliferative retinopathies, but the mechanisms involved are ill defined. Sphingosine-1-phosphate (S1P) is a bioactive sphingolipid synthesized by sphingosine kinase (SphK), which promotes proliferation, migration, and inflammation, acting as an intracellular mediator and
The sphingosine-1-phosphate receptor-1 antagonist, W146, causes early and short-lasting peripheral blood lymphopenia in mice
Tarrason G, et al.
International Immunopharmacology, 11(11), 1773-1779 (2011)
Shahzad Nawaz Syed et al.
International journal of molecular sciences, 21(13) (2020-07-08)
Recent studies suggested an important contribution of sphingosine-1-phospate (S1P) signaling via its specific receptors (S1PRs) in the production of pro-inflammatory mediators such as Interleukin (IL)-1β in cancer and inflammation. In an inflammation-driven cancer setting, we previously reported that myeloid S1PR1

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