Hexadecanoic acid anion

ID: ALA82293

Chembl Id: CHEMBL82293

Cas Number: 57-10-3

PubChem CID: 985

Product Number: P101057

Max Phase: Unknown

Molecular Formula: C16H32O2

Molecular Weight: 256.43

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: Cetyl acid | Cetylic acid | N-hexadecanoic acid | Palmitate | Palmitic acid | Prifac-2960 | Pristerene-4934 | FEMA NO. 2832 | IMEX C 1498 | KORTACID 1698 | LOXIOL EP 278 | NSC-5030 | palmitic acid|Hexadecanoic acid|57-10-3|Cetylic acid|palmitate|n-Hexadecanoic acid|Hexadecylic acid|Hydrofol|n-Hexadecoic acid|1-Pentadecanecarboxylic acid|Palmitinic acid|hexaectylic acid|Pentadecanecarboxylic acid|hexadecoic acid|1-Hexyldecanoic Acid|Industrene 4516|Emersol 140|Emersol 143|Hystrene 8016|Hystrene 9Show More

Canonical SMILES:  CCCCCCCCCCCCCCCC(=O)O

Standard InChI:  InChI=1S/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18)

Standard InChI Key:  IPCSVZSSVZVIGE-UHFFFAOYSA-N

Alternative Forms

  1. Parent:

Associated Targets(Human)

FABP4 Tchem Fatty acid binding protein adipocyte (764 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FABP2 Tchem Fatty acid binding protein intestinal (28 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FABP3 Tchem Fatty acid binding protein muscle (214 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FABP5 Tchem Fatty acid binding protein epidermal (323 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TLR2 Tchem Toll-like receptor 2 (975 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TOP1 Tclin DNA topoisomerase I (7553 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP19A1 Tclin Cytochrome P450 19A1 (6099 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HepG2 (196354 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-MEL (619 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KB (17409 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BT-549 (31254 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-OV-3 (52876 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SW1353 (113 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SP1 Tbio Transcription factor Sp1 (37 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ESR1 Tclin Estrogen receptor alpha (17718 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AR Tclin Androgen Receptor (11781 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NR3C1 Tclin Glucocorticoid receptor (14987 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NR1H4 Tclin Bile acid receptor FXR (6228 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ABCB1 Tchem P-glycoprotein 1 (14716 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GMNN Tbio Geminin (128009 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PPARA Tclin Peroxisome proliferator-activated receptor alpha (9197 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PPARD Tchem Peroxisome proliferator-activated receptor delta (6293 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BXPC-3 (2997 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RBP4 Tchem Plasma retinol-binding protein (718 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A549 (127892 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RXRA Tclin Retinoid X receptor alpha (3637 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OR51E2 Tchem Olfactory receptor 51E2 (144 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTPN1 Tchem Protein-tyrosine phosphatase 1B (8528 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TEAD4 Tchem Transcriptional enhancer factor TEF-3 (237 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SF-268 (49410 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Caco-2 (12174 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MONO-MAC-6 (495 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Bacillus subtilis (32866 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Escherichia coli (133304 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Staphylococcus aureus (210822 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Enterococcus faecalis (29875 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Pseudomonas aeruginosa (123386 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTGS2 Cyclooxygenase-2 (1953 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTGS1 Cyclooxygenase-1 (167 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Streptococcus mutans (2687 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cutibacterium acnes (887 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Klebsiella aerogenes (4963 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Saccharomyces cerevisiae (19171 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cyberlindnera jadinii (900 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Proteus vulgaris (5823 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Malassezia (23 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Penicillium chrysogenum (1593 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trichophyton mentagrophytes (4846 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Corynebacterium ammoniagenes (75 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Vero (26788 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Neisseria meningitidis (411 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium yoelii (6656 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
fabI Enoyl-acyl-carrier protein reductase (415 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
fabZ Fatty acid synthase (82 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
fabG 3-oxoacyl-acyl-carrier protein reductase (70 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypanosoma brucei rhodesiense (7991 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypanosoma cruzi (99888 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Leishmania donovani (89745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
L6 (7924 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Pmp22 Peripheral myelin protein 22 (1279 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mycolicibacterium smegmatis (8003 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Meloidogyne incognita (862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Heterodera zeae (651 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Colletotrichum gloeosporioides (560 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Colletotrichum fragariae (147 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Colletotrichum acutatum (300 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
S49 (59 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium berghei (192651 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Danio rerio (3092 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trichomonas vaginalis (2376 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ALB Serum albumin (1163 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trpv2 Transient receptor potential cation channel subfamily V member 2 (148 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ache Acetylcholinesterase (12221 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BCHE Cholinesterase (8742 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Staphylococcus epidermidis (22802 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Enterococcus hirae (484 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
rep Replicase polyprotein 1ab (11336 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SARS-CoV-2 (38078 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
COS-1 (266 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: YesAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 256.43Molecular Weight (Monoisotopic): 256.2402AlogP: 5.55#Rotatable Bonds: 14
Polar Surface Area: 37.30Molecular Species: ACIDHBA: 1HBD: 1
#RO5 Violations: 1HBA (Lipinski): 2HBD (Lipinski): 1#RO5 Violations (Lipinski): 1
CX Acidic pKa: 4.95CX Basic pKa: CX LogP: 6.26CX LogD: 3.84
Aromatic Rings: Heavy Atoms: 18QED Weighted: 0.41Np Likeness Score: 0.39

References

1. Cozzini P, Fornabaio M, Marabotti A, Abraham DJ, Kellogg GE, Mozzarelli A..  (2002)  Simple, intuitive calculations of free energy of binding for protein-ligand complexes. 1. Models without explicit constrained water.,  45  (12): [PMID:12036355] [10.1021/jm0200299]
2. Buckman BO, VanBrocklin HF, Dence CS, Bergmann SR, Welch MJ, Katzenellenbogen JA..  (1994)  Synthesis and tissue biodistribution of [omega-11C]palmitic acid. A novel PET imaging agent for cardiac fatty acid metabolism.,  37  (15): [PMID:8057294] [10.1021/jm00041a028]
3. Buckman BO, VanBrocklin HF, Dence CS, Bergmann SR, Welch MJ, Katzenellenbogen JA..  (1994)  Synthesis and tissue biodistribution of [omega-11C]palmitic acid. A novel PET imaging agent for cardiac fatty acid metabolism.,  37  (15): [PMID:8057294] [10.1021/jm00041a028]
4. Ishchenko AV, Shakhnovich EI..  (2002)  SMall Molecule Growth 2001 (SMoG2001): an improved knowledge-based scoring function for protein-ligand interactions.,  45  (13): [PMID:12061879] [10.1021/jm0105833]
5. Yasuda Y, Tochikubo K, Hachisuka Y, Tomida H, Ikeda K..  (1982)  Quantitative structure-inhibitory activity relationships of phenols and fatty acids for Bacillus subtilis spore germination.,  25  (3): [PMID:6802973] [10.1021/jm00345a016]
6. Lehmann F, Haile S, Axen E, Medina C, Uppenberg J, Svensson S, Lundbäck T, Rondahl L, Barf T..  (2004)  Discovery of inhibitors of human adipocyte fatty acid-binding protein, a potential type 2 diabetes target.,  14  (17): [PMID:15357969] [10.1016/j.bmcl.2004.06.057]
7. Seyberth T, Voss S, Brock R, Wiesmüller KH, Jung G..  (2006)  Lipolanthionine peptides act as inhibitors of TLR2-mediated IL-8 secretion. Synthesis and structure-activity relationships.,  49  (5): [PMID:16509590] [10.1021/jm050585d]
8. McDonnell PA, Constantine KL, Goldfarb V, Johnson SR, Sulsky R, Magnin DR, Robl JA, Caulfield TJ, Parker RA, Taylor DS, Adam LP, Metzler WJ, Mueller L, Farmer BT..  (2006)  NMR structure of a potent small molecule inhibitor bound to human keratinocyte fatty acid-binding protein.,  49  (16): [PMID:16884313] [10.1021/jm060360i]
9. Sulsky R, Magnin DR, Huang Y, Simpkins L, Taunk P, Patel M, Zhu Y, Stouch TR, Bassolino-Klimas D, Parker R, Harrity T, Stoffel R, Taylor DS, Lavoie TB, Kish K, Jacobson BL, Sheriff S, Adam LP, Ewing WR, Robl JA..  (2007)  Potent and selective biphenyl azole inhibitors of adipocyte fatty acid binding protein (aFABP).,  17  (12): [PMID:17502136] [10.1016/j.bmcl.2006.12.044]
10. Kubo A, Kubo I.  (1995)  Antimicrobial Agents from Tanacetum balsamita,  58  (10): [10.1021/np50124a013]
11. Ringbom T, Huss U, Stenholm A, Flock S, Skattebøl L, Perera P, Bohlin L..  (2001)  Cox-2 inhibitory effects of naturally occurring and modified fatty acids.,  64  (6): [PMID:11421736] [10.1021/np000620d]
12. Carballeira NM, Betancourt JE, Orellano EA, González FA..  (2002)  Total synthesis and biological evaluation of (5Z,9Z)-5,9-hexadecadienoic acid, an inhibitor of human topoisomerase I.,  65  (11): [PMID:12444712] [10.1021/np0202576]
13. Balunas MJ, Su B, Landini S, Brueggemeier RW, Kinghorn AD..  (2006)  Interference by naturally occurring fatty acids in a noncellular enzyme-based aromatase bioassay.,  69  (4): [PMID:16643058] [10.1021/np050513p]
14. Hamburger MO, Cordell GA..  (1987)  A direct bioautographic tlc assay for compounds possessing antibacterial activity.,  50  (1): [PMID:3110376] [10.1021/np50049a003]
15. Chatterjee A, Chowdhury R..  (2008)  Bile and unsaturated fatty acids inhibit the binding of cholera toxin and Escherichia coli heat-labile enterotoxin to GM1 receptor.,  52  (1): [PMID:17954701] [10.1128/aac.01009-07]
16. Li J, Ding Y, Li XC, Ferreira D, Khan S, Smillie T, Khan IA..  (2009)  Scuteflorins A and B, dihydropyranocoumarins from Scutellaria lateriflora.,  72  (6): [PMID:19555121] [10.1021/np900068t]
17. Kamal N, Shafer WM..  (2010)  Biologic activities of the TolC-like protein of Neisseria meningitidis as assessed by functional complementation in Escherichia coli.,  54  (1): [PMID:19884363] [10.1128/aac.01168-09]
18. Tasdemir D, Sanabria D, Lauinger IL, Tarun A, Herman R, Perozzo R, Zloh M, Kappe SH, Brun R, Carballeira NM..  (2010)  2-Hexadecynoic acid inhibits plasmodial FAS-II enzymes and arrests erythrocytic and liver stage Plasmodium infections.,  18  (21): [PMID:20855214] [10.1016/j.bmc.2010.08.055]
19. Maisuria BB, Actis ML, Hardrict SN, Falkinham JO, Cole MF, Cihlar RL, Peters SM, Macri RV, Sugandhi EW, Williams AA, Poppe MA, Esker AR, Gandour RD..  (2011)  Comparing micellar, hemolytic, and antibacterial properties of di- and tricarboxyl dendritic amphiphiles.,  19  (9): [PMID:21493076] [10.1016/j.bmc.2011.03.036]
20. PubChem BioAssay data set, 
21. Gröblacher B, Kunert O, Bucar F..  (2012)  Compounds of Alpinia katsumadai as potential efflux inhibitors in Mycobacterium smegmatis.,  20  (8): [PMID:22459211] [10.1016/j.bmc.2012.02.039]
22. Konishi T, Satsu H, Hatsugai Y, Aizawa K, Inakuma T, Nagata S, Sakuda SH, Nagasawa H, Shimizu M..  (2004)  Inhibitory effect of a bitter melon extract on the P-glycoprotein activity in intestinal Caco-2 cells.,  143  (1): [PMID:15351776] [10.1038/sj.bjp.0705804]
23. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 
24. PubChem BioAssay data set, 
25. Carballeira NM, Cartagena M, Sanabria D, Tasdemir D, Prada CF, Reguera RM, Balaña-Fouce R..  (2012)  2-Alkynoic fatty acids inhibit topoisomerase IB from Leishmania donovani.,  22  (19): [PMID:22932312] [10.1016/j.bmcl.2012.08.019]
26. Faizi S, Fayyaz S, Bano S, Iqbal EY, Lubna, Siddiqi H, Naz A..  (2011)  Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.,  59  (17): [PMID:21780738] [10.1021/jf201611b]
27. Ntalli NG, Vargiu S, Menkissoglu-Spiroudi U, Caboni P..  (2010)  nematicidal carboxylic acids and aldehydes from Melia azedarach fruits.,  58  (21): [PMID:20925380] [10.1021/jf1025345]
28. Zhang WP, Ruan WB, Deng YY, Gao YB..  (2012)  Potential antagonistic effects of nine natural fatty acids against Meloidogyne incognita.,  60  (46): [PMID:23121218] [10.1021/jf3036885]
29. Aoudia H, Ntalli N, Aissani N, Yahiaoui-Zaidi R, Caboni P..  (2012)  Nematotoxic phenolic compounds from Melia azedarach against Meloidogyne incognita.,  60  (47): [PMID:23136941] [10.1021/jf3038874]
30. Tabanca N, Demirci B, Crockett SL, Başer KH, Wedge DE..  (2007)  Chemical composition and antifungal activity of Arnica longifolia, Aster hesperius, and Chrysothamnus nauseosus essential oils.,  55  (21): [PMID:17894463] [10.1021/jf071379c]
31. Maltarollo VG, Honorio KM.  (2013)  Molecular properties of fatty acids related to PPAR binding and metabolic diseases,  22  (7): [10.1007/s00044-012-0285-6]
32. Marshall AJ, Lin JM, Grey A, Reid IR, Cornish J, Denny WA..  (2013)  Long-chain triazolyl acids as inhibitors of osteoclastogenesis.,  21  (14): [PMID:23726411] [10.1016/j.bmc.2013.05.013]
33. PubChem BioAssay data set, 
34. PubChem BioAssay data set, 
35. Meyer RB, Stone TE, Ullman B..  (1979)  2'-O-Acyl-6-thioinosine cyclic 3',5'-phosphates as prodrugs of thioinosinic acid.,  22  (7): [PMID:221658] [10.1021/jm00193a012]
36. Carballeira NM, Bwalya AG, Itoe MA, Andricopulo AD, Cordero-Maldonado ML, Kaiser M, Mota MM, Crawford AD, Guido RV, Tasdemir D..  (2014)  2-Octadecynoic acid as a dual life stage inhibitor of Plasmodium infections and plasmodial FAS-II enzymes.,  24  (17): [PMID:25103602] [10.1016/j.bmcl.2014.07.050]
37. Fako VE, Wu X, Pflug B, Liu JY, Zhang JT..  (2015)  Repositioning proton pump inhibitors as anticancer drugs by targeting the thioesterase domain of human fatty acid synthase.,  58  (2): [PMID:25513712] [10.1021/jm501543u]
38. Honda T, Takakusa H, Murai T, Izumi T..  (2013)  Tissue distribution and identification of radioactivity components at elimination phase after oral administration of [¹⁴C]CS-1036, an α-amylase inhibitor, to rats.,  41  (5): [PMID:23454829] [10.1124/dmd.112.050617]
39. PubChem BioAssay data set, 
40. Sanabria-Ríos DJ, Rivera-Torres Y, Rosario J, Gutierrez R, Torres-García Y, Montano N, Ortíz-Soto G, Ríos-Olivares E, Rodríguez JW, Carballeira NM..  (2015)  Chemical conjugation of 2-hexadecynoic acid to C5-curcumin enhances its antibacterial activity against multi-drug resistant bacteria.,  25  (22): [PMID:26483137] [10.1016/j.bmcl.2015.10.022]
41. Tagami U, Takahashi K, Igarashi S, Ejima C, Yoshida T, Takeshita S, Miyanaga W, Sugiki M, Tokumasu M, Hatanaka T, Kashiwagi T, Ishikawa K, Miyano H, Mizukoshi T..  (2016)  Interaction Analysis of FABP4 Inhibitors by X-ray Crystallography and Fragment Molecular Orbital Analysis.,  (4): [PMID:27096055] [10.1021/acsmedchemlett.6b00040]
42. Bala V, Chhonker YS..  (2018)  Recent developments in anti-Trichomonas research: An update review.,  143  [PMID:29175675] [10.1016/j.ejmech.2017.11.029]
43. Gutiérrez-García K, Neira-González A, Pérez-Gutiérrez RM, Granados-Ramírez G, Zarraga R, Wrobel K, Barona-Gómez F, Flores-Cotera LB..  (2017)  Phylogenomics of 2,4-Diacetylphloroglucinol-Producing Pseudomonas and Novel Antiglycation Endophytes from Piper auritum.,  80  (7): [PMID:28704049] [10.1021/acs.jnatprod.6b00823]
44. Schiano Moriello A, López Chinarro S, Novo Fernández O, Eras J, Amodeo P, Canela-Garayoa R, Vitale RM, Di Marzo V, De Petrocellis L..  (2018)  Elongation of the Hydrophobic Chain as a Molecular Switch: Discovery of Capsaicin Derivatives and Endogenous Lipids as Potent Transient Receptor Potential Vanilloid Channel 2 Antagonists.,  61  (18): [PMID:30176215] [10.1021/acs.jmedchem.8b00734]
45. Loesche A, Wiemann J, Al Halabi Z, Karasch J, Sippl W, Csuk R..  (2018)  Unexpected AChE inhibitory activity of (2E)α,β-unsaturated fatty acids.,  28  (20): [PMID:30220607] [10.1016/j.bmcl.2018.09.013]
46. Cioffi CL, Racz B, Varadi A, Freeman EE, Conlon MP, Chen P, Zhu L, Kitchen DB, Barnes KD, Martin WH, Pearson PG, Johnson G, Blaner WS, Petrukhin K..  (2019)  Design, Synthesis, and Preclinical Efficacy of Novel Nonretinoid Antagonists of Retinol-Binding Protein 4 in the Mouse Model of Hepatic Steatosis.,  62  (11): [PMID:31079449] [10.1021/acs.jmedchem.9b00352]
47. Chrzanowska A, Roszkowski P, Bielenica A, Olejarz W, Stępień K, Struga M..  (2020)  Anticancer and antimicrobial effects of novel ciprofloxacin fatty acids conjugates.,  185  [PMID:31678743] [10.1016/j.ejmech.2019.111810]
48. Liang X, Wu Q, Luan S, Yin Z, He C, Yin L, Zou Y, Yuan Z, Li L, Song X, He M, Lv C, Zhang W..  (2019)  A comprehensive review of topoisomerase inhibitors as anticancer agents in the past decade.,  171  [PMID:30917303] [10.1016/j.ejmech.2019.03.034]
49. Yamada S, Kawasaki M, Fujihara M, Watanabe M, Takamura Y, Takioku M, Nishioka H, Takeuchi Y, Makishima M, Motoyama T, Ito S, Tokiwa H, Nakano S, Kakuta H..  (2019)  Competitive Binding Assay with an Umbelliferone-Based Fluorescent Rexinoid for Retinoid X Receptor Ligand Screening.,  62  (19): [PMID:31483660] [10.1021/acs.jmedchem.9b00995]
50.  (2013)  Method for treating skin with retinoids and retinoid boosters, 
51.  (2018)  Modulators of Prostate-Specific G-Protein Receptor (PSGR/OR51E2) and Methods of Using Same, 
52. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]
53. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]
54. Pedersen HA, Ndi C, Semple SJ, Buirchell B, Møller BL, Staerk D..  (2020)  PTP1B-Inhibiting Branched-Chain Fatty Acid Dimers from Eremophila oppositifolia subsp. angustifolia Identified by High-Resolution PTP1B Inhibition Profiling and HPLC-PDA-HRMS-SPE-NMR Analysis.,  83  (5): [PMID:32255628] [10.1021/acs.jnatprod.0c00070]
55. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]
56. Karatas H,Akbarzadeh M,Adihou H,Hahne G,Pobbati AV,Yihui Ng E,Guéret SM,Sievers S,Pahl A,Metz M,Zinken S,Dötsch L,Nowak C,Thavam S,Friese A,Kang C,Hong W,Waldmann H.  (2020)  Discovery of Covalent Inhibitors Targeting the Transcriptional Enhanced Associate Domain Central Pocket.,  63  (20.0): [PMID:32907324] [10.1021/acs.jmedchem.0c01275]
57. Kokotou MG,Kokotos AC,Gkikas D,Mountanea OG,Mantzourani C,Almutairi A,Lei X,Ramanadham S,Politis PK,Kokotos G.  (2020)  Saturated Hydroxy Fatty Acids Exhibit a Cell Growth Inhibitory Activity and Suppress the Cytokine-Induced β-Cell Apoptosis.,  63  (21): [PMID:33124824] [10.1021/acs.jmedchem.0c00844]
58. Sæther T,Paulsen SM,Tungen JE,Vik A,Aursnes M,Holen T,Hansen TV,Nebb HI.  (2018)  Synthesis and biological evaluations of marine oxohexadecenoic acids: PPARα/γ dual agonism and anti-diabetic target gene effects.,  155  [PMID:29940464] [10.1016/j.ejmech.2018.06.034]
59. Batsika CS, Mantzourani C, Gkikas D, Kokotou MG, Mountanea OG, Kokotos CG, Politis PK, Kokotos G..  (2021)  Saturated Oxo Fatty Acids (SOFAs): A Previously Unrecognized Class of Endogenous Bioactive Lipids Exhibiting a Cell Growth Inhibitory Activity.,  64  (9.0): [PMID:33881857] [10.1021/acs.jmedchem.0c02058]
60. Baranyai Z, Krátký M, Vosátka R, Szabó E, Senoner Z, Dávid S, Stolaříková J, Vinšová J, Bősze S..  (2017)  In vitro biological evaluation of new antimycobacterial salicylanilide-tuftsin conjugates.,  133  [PMID:28384546] [10.1016/j.ejmech.2017.03.047]
61. Floresta G, Pistarà V, Amata E, Dichiara M, Marrazzo A, Prezzavento O, Rescifina A..  (2017)  Adipocyte fatty acid binding protein 4 (FABP4) inhibitors. A comprehensive systematic review.,  138  [PMID:28738306] [10.1016/j.ejmech.2017.07.022]
62. Chen J, Lu Y, Ye X, Emam M, Zhang H, Wang H..  (2020)  Current advances in Vibrio harveyi quorum sensing as drug discovery targets.,  207  [PMID:32871343] [10.1016/j.ejmech.2020.112741]