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SML2410

Sigma-Aldrich

ABC99

≥98% (HPLC)

Synonym(s):

7-(4-Chlorobenzyl)-1,3-dioxohexahydroimidazo[1,5-a]pyrazin-2(3H)-yl 2,3-dihydro-4Hbenzo[b][1,4]oxazine-4-carboxylate

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About This Item

Empirical Formula (Hill Notation):
C22H21ClN4O5
CAS Number:
2331255-53-7
Molecular Weight:
456.88
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

O=C(ON(C(N1C2CN(CC1)CC3=CC=C(C=C3)Cl)=O)C2=O)N4C5=CC=CC=C5OCC4

Biochem/physiol Actions

ABC99 is an N-hydroxyhydantoin (NHH) carbamate-based irreversible, potent and selective inhibitor against the serine hydrolase activity of the Wnt-deacylating enzyme NOTUM (IC50 = 13 nM against NOTUM-mediated labeling of fluorophosphonate (FP) probe), an enzyme that reverses the posttranslational O-linked palmitoleate modification of Wnt proteins. ABC99 prevents NOTUM-mediated negative regulation against Wnt3A-dependent cellular signaling (EC50 = 89 nM by HEK293T TOPflash reporter assay) with excellent selectivity over 65 other serine hydrolases, including PPT1.
Inhibition of NOTUM has therapeutic use in treating degenerative diseases including osteopenia and osteoporosis.

Storage Class Code

11 - Combustible Solids

WGK

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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Selective irreversible inhibitors of the Wnt-deacylating enzyme NOTUM developed by activity-based protein profiling
Suciu RM, et al.
ACS Medicinal Chemistry Letters, 9(6), 563-568 (2018)
Radu M Suciu et al.
ACS medicinal chemistry letters, 9(6), 563-568 (2018-06-26)
Wnt proteins are secreted morphogens that play critical roles in embryonic development and tissue remodeling in adult organisms. Aberrant Wnt signaling contributes to diseases such as cancer. Wnts are modified by an unusual O-fatty acylation event (O-linked palmitoleoylation of a
Mariyan J Jeyarajah et al.
Proceedings of the National Academy of Sciences of the United States of America, 119(49), e2203071119-e2203071119 (2022-11-29)
Remodeling of the uterine vasculature by invasive extravillous trophoblasts (EVTs) is a critical aspect of human placentation. Insufficient EVT invasion can lead to severe obstetrical complications like preeclampsia, intrauterine growth restriction, and preterm birth. Glial cells missing-1 (GCM1) is a

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