HA155
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MedKoo CAT#: 530383

CAS#: 1229652-22-5

Description: HA155, also known as Autotaxin Inhibitor IV, is a boronic acid-based compound that inhibits autotaxin (IC50 = 5.7 nM) by selectively binding to its catalytic threonine.


Chemical Structure

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HA155
CAS# 1229652-22-5

Theoretical Analysis

MedKoo Cat#: 530383
Name: HA155
CAS#: 1229652-22-5
Chemical Formula: C24H19BFNO5S
Exact Mass: 463.11
Molecular Weight: 463.286
Elemental Analysis: C, 62.22; H, 4.13; B, 2.33; F, 4.10; N, 3.02; O, 17.27; S, 6.92

Price and Availability

Size Price Availability Quantity
25mg USD 350 2 Weeks
50mg USD 550 2 Weeks
100mg USD 950 2 Weeks
200mg USD 1450 2 Weeks
500mg USD 2450 2 Weeks
1g USD 3450 2 Weeks
2g USD 5450 2 Weeks
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Related CAS #: 1312201-00-5  

Synonym: HA155; HA-155; HA 155. Autotaxin Inhibitor IV.

IUPAC/Chemical Name: B-[4-[[4-[[3-[(4-fluorophenyl)methyl]-2,4-dioxo-5-thiazolidinylidene]methyl]phenoxy]methyl]phenyl]-boronic acid

InChi Key: BRWUZCBSWABPMR-XKZIYDEJSA-N

InChi Code: InChI=1S/C24H19BFNO5S/c26-20-9-3-17(4-10-20)14-27-23(28)22(33-24(27)29)13-16-5-11-21(12-6-16)32-15-18-1-7-19(8-2-18)25(30)31/h1-13,30-31H,14-15H2/b22-13-

SMILES Code: OB(C1=CC=C(COC2=CC=C(/C=C(SC(N3CC4=CC=C(F)C=C4)=O)/C3=O)C=C2)C=C1)O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Biological target: (E/Z)-HA155 is a potent autotaxin (ATX) type I inhibitor.
In vitro activity: The thrombin-mediated increase in platelet-derived LPA was completely attenuated in a dose-dependent manner by the ATX inhibitor HA155 (Fig. 1A). Reference: J Biol Chem. 2011 Oct 7;286(40):34654-63. https://pubmed.ncbi.nlm.nih.gov/21832043/
In vivo activity: Compound 40 (HA155) was also able to decrease the plasma LPA levels upon oral administration to rats. Reference: J Med Chem. 2017 Sep 14;60(17):7371-7392. https://pubmed.ncbi.nlm.nih.gov/28731719/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 50.0 107.92
DMSO 30.0 64.75

Preparing Stock Solutions

The following data is based on the product molecular weight 463.29 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Fulkerson Z, Wu T, Sunkara M, Kooi CV, Morris AJ, Smyth SS. Binding of autotaxin to integrins localizes lysophosphatidic acid production to platelets and mammalian cells. J Biol Chem. 2011 Oct 7;286(40):34654-63. doi: 10.1074/jbc.M111.276725. Epub 2011 Aug 10. PMID: 21832043; PMCID: PMC3186383. 2. Joncour A, Desroy N, Housseman C, Bock X, Bienvenu N, Cherel L, Labeguere V, Peixoto C, Annoot D, Lepissier L, Heiermann J, Hengeveld WJ, Pilzak G, Monjardet A, Wakselman E, Roncoroni V, Le Tallec S, Galien R, David C, Vandervoort N, Christophe T, Conrath K, Jans M, Wohlkonig A, Soror S, Steyaert J, Touitou R, Fleury D, Vercheval L, Mollat P, Triballeau N, van der Aar E, Brys R, Heckmann B. Discovery, Structure-Activity Relationship, and Binding Mode of an Imidazo[1,2-a]pyridine Series of Autotaxin Inhibitors. J Med Chem. 2017 Sep 14;60(17):7371-7392. doi: 10.1021/acs.jmedchem.7b00647. Epub 2017 Aug 18. Erratum in: J Med Chem. 2018 May 10;61(9):4270. PMID: 28731719.
In vitro protocol: 1. Fulkerson Z, Wu T, Sunkara M, Kooi CV, Morris AJ, Smyth SS. Binding of autotaxin to integrins localizes lysophosphatidic acid production to platelets and mammalian cells. J Biol Chem. 2011 Oct 7;286(40):34654-63. doi: 10.1074/jbc.M111.276725. Epub 2011 Aug 10. PMID: 21832043; PMCID: PMC3186383.
In vivo protocol: 1. Joncour A, Desroy N, Housseman C, Bock X, Bienvenu N, Cherel L, Labeguere V, Peixoto C, Annoot D, Lepissier L, Heiermann J, Hengeveld WJ, Pilzak G, Monjardet A, Wakselman E, Roncoroni V, Le Tallec S, Galien R, David C, Vandervoort N, Christophe T, Conrath K, Jans M, Wohlkonig A, Soror S, Steyaert J, Touitou R, Fleury D, Vercheval L, Mollat P, Triballeau N, van der Aar E, Brys R, Heckmann B. Discovery, Structure-Activity Relationship, and Binding Mode of an Imidazo[1,2-a]pyridine Series of Autotaxin Inhibitors. J Med Chem. 2017 Sep 14;60(17):7371-7392. doi: 10.1021/acs.jmedchem.7b00647. Epub 2017 Aug 18. Erratum in: J Med Chem. 2018 May 10;61(9):4270. PMID: 28731719.

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1: Katsamakas S, Papadopoulos AG, Hadjipavlou-Litina D. Boronic Acid Group: A
Cumbersome False Negative Case in the Process of Drug Design. Molecules. 2016 Sep
7;21(9). pii: E1185. doi: 10.3390/molecules21091185. PubMed PMID: 27617984.


2: Albers HM, Hendrickx LJ, van Tol RJ, Hausmann J, Perrakis A, Ovaa H.
Structure-based design of novel boronic acid-based inhibitors of autotaxin. J Med
Chem. 2011 Jul 14;54(13):4619-26. doi: 10.1021/jm200310q. PubMed PMID: 21615078;
PubMed Central PMCID: PMC3131786.