Synonym
N-palmitoylglycine; palmitoyl glycine
IUPAC/Chemical Name
2-(hexadecanoylamino)acetic acid
InChi Key
KVTFEOAKFFQCCX-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H35NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-17(20)19-16-18(21)22/h2-16H2,1H3,(H,19,20)(H,21,22)
SMILES Code
O=C(CCCCCCCCCCCCCCC)NCC(O)=O
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
>3 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
Biological target:
Palmitoylglycine (N-palmitoyl glycine), an endogenous lipid that acts as a modulator of calcium influx and nitric oxide (NO) production in sensory neurons.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
313.48
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.
| 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:
TBD
1: Foster JR, Ueno S, Chen MX, Harvey J, Dowell SJ, Irving AJ, Brown AJ. N-Palmitoylglycine and other N-acylamides activate the lipid receptor G2A/GPR132. Pharmacol Res Perspect. 2019 Nov 21;7(6):e00542. doi: 10.1002/prp2.542. PMID: 31768260; PMCID: PMC6868653.
2: Anderson RL, Merkler DJ. N-FATTY ACYLGLYCINES: UNDERAPPRECIATED ENDOCANNABINOID-LIKE FATTY ACID AMIDES? J Biol Nat. 2017;8(4):156-165. Epub 2018 Mar 3. PMID: 29607420; PMCID: PMC5878051.
3: Bradshaw HB, Rimmerman N, Hu SS, Burstein S, Walker JM. Novel endogenous N-acyl glycines identification and characterization. Vitam Horm. 2009;81:191-205. doi: 10.1016/S0083-6729(09)81008-X. PMID: 19647113.
4: Ravindranathan KP, Gallicchio E, Friesner RA, McDermott AE, Levy RM. Conformational equilibrium of cytochrome P450 BM-3 complexed with N-palmitoylglycine: a replica exchange molecular dynamics study. J Am Chem Soc. 2006 May 3;128(17):5786-91. doi: 10.1021/ja058465i. PMID: 16637647; PMCID: PMC2533527.
5: Brenner S, Hay S, Girvan HM, Munro AW, Scrutton NS. Conformational dynamics of the cytochrome P450 BM3/N-palmitoylglycine complex: the proposed "proximal- distal" transition probed by temperature-jump spectroscopy. J Phys Chem B. 2007 Jul 12;111(27):7879-86. doi: 10.1021/jp073036n. Epub 2007 Jun 16. PMID: 17571881.
6: Hegde A, Haines DC, Bondlela M, Chen B, Schaffer N, Tomchick DR, Machius M, Nguyen H, Chowdhary PK, Stewart L, Lopez C, Peterson JA. Interactions of substrates at the surface of P450s can greatly enhance substrate potency. Biochemistry. 2007 Dec 11;46(49):14010-7. doi: 10.1021/bi701667m. Epub 2007 Nov 16. PMID: 18004886.
7: Baumann J, Kokabee M, Wong J, Balasubramaniyam R, Sun Y, Conklin DS. Global metabolite profiling analysis of lipotoxicity in HER2/neu-positive breast cancer cells. Oncotarget. 2018 Jun 5;9(43):27133-27150. doi: 10.18632/oncotarget.25500. PMID: 29930756; PMCID: PMC6007458.
8: Catalano J, Sadre-Bazzaz K, Amodeo GA, Tong L, McDermott A. Structural evidence: a single charged residue affects substrate binding in cytochrome P450 BM-3. Biochemistry. 2013 Oct 1;52(39):6807-15. doi: 10.1021/bi4000645. Epub 2013 Sep 16. PMID: 23829560; PMCID: PMC5945292.
9: Haines DC, Tomchick DR, Machius M, Peterson JA. Pivotal role of water in the mechanism of P450BM-3. Biochemistry. 2001 Nov 13;40(45):13456-65. doi: 10.1021/bi011197q. PMID: 11695892.
10: Bradshaw HB, Lee SH, McHugh D. Orphan endogenous lipids and orphan GPCRs: a good match. Prostaglandins Other Lipid Mediat. 2009 Sep;89(3-4):131-4. doi: 10.1016/j.prostaglandins.2009.04.006. Epub 2009 Apr 18. PMID: 19379823; PMCID: PMC2740803.
