naproxen   

GtoPdb Ligand ID: 5230

Synonyms: (S)-naproxen | Aleve® | Naprosy®
naproxen is an approved drug (FDA (1976))
Compound class: Synthetic organic
Comment: Naproxen is one of the 2-arylpropionic acid ('profen') family of nonsteroidal anti-inflammatory drugs (NSAIDs), like ibuprofen.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 46.53
Molecular weight 230.09
XLogP 2.84
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES COc1ccc2c(c1)ccc(c2)C(C(=O)O)C
Isomeric SMILES COc1ccc2c(c1)ccc(c2)[C@@H](C(=O)O)C
InChI InChI=1S/C14H14O3/c1-9(14(15)16)10-3-4-12-8-13(17-2)6-5-11(12)7-10/h3-9H,1-2H3,(H,15,16)/t9-/m0/s1
InChI Key CMWTZPSULFXXJA-VIFPVBQESA-N
References
1. Kolasa T, Brooks CD, Rodriques KE, Summers JB, Dellaria JF, Hulkower KI, Bouska J, Bell RL, Carter GW. (1997)
Nonsteroidal anti-inflammatory drugs as scaffolds for the design of 5-lipoxygenase inhibitors.
J. Med. Chem., 40 (5): 819-24. [PMID:9057869]
2. Reyes-Uribe L, Wu W, Gelincik O, Bommi PV, Francisco-Cruz A, Solis LM, Lynch PM, Lim R, Stoffel EM, Kanth P et al.. (2020)
Naproxen chemoprevention promotes immune activation in Lynch syndrome colorectal mucosa.
Gut, [Epub ahead of print]. DOI: 10.1136/gutjnl-2020-320946 [PMID:32641470]