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SML0177

Sigma-Aldrich

AUDA

≥98% (HPLC)

Synonym(s):

12-[[(tricyclo[3.3.1.13,7]dec-1-ylamino)carbonyl]amino]-dodecanoic acid

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About This Item

Empirical Formula (Hill Notation):
C23H40N2O3
CAS Number:
479413-70-2
Molecular Weight:
392.58
MDL number:
MFCD12912267
UNSPSC Code:
12352200
PubChem Substance ID:
329825206
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: ≥10 mg/mL at warmed to 60 °C

storage temp.

−20°C

SMILES string

OC(=O)CCCCCCCCCCCNC(=O)NC12C[C@@H]3C[C@@H](C[C@@H](C3)C1)C2

InChI

1S/C23H40N2O3/c26-21(27)10-8-6-4-2-1-3-5-7-9-11-24-22(28)25-23-15-18-12-19(16-23)14-20(13-18)17-23/h18-20H,1-17H2,(H,26,27)(H2,24,25,28)/t18-,19+,20-,23-

InChI key

XLGSEOAVLVTJDH-UKBVAGSOSA-N

Application

AUDA has been used in the inhibition of epoxide hydrolase in human macrophages and in inhibition of tumor necrosis factor α (TNF-α)- induced phosphorylation in human aortic smooth muscle cells.
AUDA may be used in soluble epoxide hydrolase-mediated cell signaling studies.

Biochem/physiol Actions

Inhibition of soluble epoxide hydrolase by AUDA inhibits the metabolism of epoxyeicosatrienoic acids (EETs) and protects end-organs against the damaging effects of salt-sensitive hypertension. AUDA also renders protection against myocardial ischemia-reperfusion injury and cerebral ischemia.
AUDA is a potent inhibitor of soluble epoxide hydrolase

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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You-Yang Qu et al.
Neurochemical research, 40(1), 1-14 (2014-11-05)
Epoxyeicosatrienoic acids (EETs), the cytochrome P450 epoxygenase metabolite of arachidonic acid, have been demonstrated to have neuroprotective effect. Phosphatidylinositol 3-kinase (PI3K)/Akt and ATP-sensitive potassium (KATP) channels are thought to be important factors that mediate neuroprotection. However, little is known about
Chun-Hu Wu et al.
Journal of neuroinflammation, 14(1), 230-230 (2017-11-28)
Inflammatory responses significantly contribute to neuronal damage and poor functional outcomes following intracerebral hemorrhage (ICH). Soluble epoxide hydrolase (sEH) is known to induce neuroinflammatory responses via degradation of anti-inflammatory epoxyeicosatrienoic acids (EET), and sEH is upregulated in response to brain
PD n-3 DPA Pathway Regulates Human Monocyte Differentiation and Macrophage Function
Pistorius K, et al.
Cell Chemical Biology, 25(6), 749-760 (2018)
Alexis N Simpkins et al.
The American journal of pathology, 174(6), 2086-2095 (2009-05-14)
Inhibition of soluble epoxide hydrolase (SEH), the enzyme responsible for degradation of vasoactive epoxides, protects against cerebral ischemia in rats. However, the molecular and biological mechanisms that confer protection in normotension and hypertension remain unclear. Here we show that 6
Jang Hoon Kim et al.
Biomolecules, 10(2) (2020-01-30)
: Three flavonoids derived from the leaves of Capsicum chinense Jacq. were identified as chrysoeriol (1), luteolin-7-O-glucopyranoside (2), and isorhamnetin-7-O-glucopyranoside (3). They had IC50 values of 11.6±2.9, 14.4±1.5, and 42.7±3.5 µg/mL against soluble epoxide hydrolase (sEH), respectively. The three inhibitors
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