An endogenous N-acyl amine
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N-Oleoyl Glutamine

Item No. 28922

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N2-[(9Z)-1-oxo-9-octadecen-1-yl]-L-glutamine
CAS Number
247150-73-8
Synonyms
  • N-Oleoyl Gln
Molecular Formula
C23H42N2O4
Formula Weight
410.6
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 1 mg/ml
SMILES
O=C(CCCCCCC/C=C\CCCCCCCC)N[C@H](C(O)=O)CCC(N)=O
InChi Code
InChI=1S/C23H42N2O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-22(27)25-20(23(28)29)18-19-21(24)26/h9-10,20H,2-8,11-19H2,1H3,(H2,24,26)(H,25,27)(H,28,29)/b10-9-/t20-/m0/s1
InChi Key
ZHVSXWCIYWYBQP-QJRAZLAKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $63

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    5 mg

    $257

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    10 mg

    $481

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    25 mg

    $1,053

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    Product Description

    N-Oleoyl glutamine is an endogenous N-acyl amine.1,2 It is both formed and degraded by peptidase M20 domain-containing 1 (PM20D1), a factor secreted by thermogenic adipose cells. N-Oleoyl glutamine (50 µM) induces mitochondrial uncoupling to increase respiration in C2C12 cells by 64%.3 It inhibits capsaicin-induced calcium flux in HEK293A cells co-transfected with transient receptor potential vanilloid 1 (TRPV1) and red fluorescent protein (RFP).2 N-Oleoyl glutamine (100 mg/kg) reduces the number of acetic acid-induced abdominal constrictions, as well as formalin-induced paw licking in mice.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Long, J.Z., Svensson, K.J., Bateman, L.A., et al. The secreted enzyme PM20D1 regulates lipidated amino acid uncouplers of mitochondria. Cell 166(2), 1-12 (2016).

    2. Long, J.Z., Roche, A.M., Berdan, C.A., et al. Ablation of PM20D1 reveals N-acyl amino acid control of metabolism and nociception. Proc. Natl. Acad. Sci. USA 115(29), E6937-E6945 (2018).

    3. Lin, H., Long, J.Z., Roche, A.M., et al. Discovery of hydrolysis-resistant isoindoline N-acyl amino acid analogues that stimulate mitochondrial respiration. J. Med. Chem. 61(7), 3224-3230 (2018).