5-fluorosalicylic acid

ID: ALA229239

Cas Number: 345-16-4

PubChem CID: 67658

Product Number: S64672, Order Now?

Max Phase: Preclinical

Molecular Formula: C7H5FO3

Molecular Weight: 156.11

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 5-Fluorosalicylic Acid | 5-Fluorosalicylic acid|5-Fluoro-2-hydroxybenzoic acid|345-16-4|Benzoic acid, 5-fluoro-2-hydroxy-|2-Hydroxy-5-fluorobenzoic acid|GDQ70COQ4K|CHEMBL229239|MFCD00002456|NSC-46619|5-Fluoro-2-hydroxybenzoicacid|5-fluoro-2-hydroxy-benzoic acid|EINECS 206-455-3|5Fluorosalicylic acid|5-fluoro-salicylic acid|UNII-GDQ70COQ4K|SCHEMBL130520|5-Fluorosalicylic acid, 97%|2-hydroxy-5-fluoro-benzoic acid|5-fluoro-2-hydroxy benzoic acid|TAVABOROLE METABOLITE M6A|DTXSID00188054|JWPRICQKUNODShow More⌵

Canonical SMILES:  O=C(O)c1cc(F)ccc1O

Standard InChI:  InChI=1S/C7H5FO3/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,9H,(H,10,11)

Standard InChI Key:  JWPRICQKUNODPZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 11 11  0  0  0  0  0  0  0  0999 V2000
    3.9409  -23.8620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9397  -24.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6540  -25.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3697  -24.6882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3668  -23.8584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6522  -23.4496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0853  -25.0992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0866  -25.9235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7984  -24.6860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6538  -25.9254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6497  -22.6253    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  2  0
  6  1  1  0
  1  2  2  0
  3  4  2  0
  7  8  1  0
  7  9  2  0
  4  7  1  0
  4  5  1  0
  3 10  1  0
  2  3  1  0
  6 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA229239

   5-Fluorosalicylic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 156.11

Molecular Weight (Monoisotopic): 156.0223

AlogP: 1.23

#Rotatable Bonds: 1

Polar Surface Area: 57.53

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.43

CX Basic pKa: ┄

CX LogP: 2.12

CX LogD: -1.39

Aromatic Rings: 1

Heavy Atoms: 11

QED Weighted: 0.64

Np Likeness Score: -0.69

References

1. Shrestha S, Bhattarai BR, Lee KH, Cho H..  (2007)  Mono- and disalicylic acid derivatives: PTP1B inhibitors as potential anti-obesity drugs.,  15  (20): [PMID:17692525] [10.1016/j.bmc.2007.07.010]

2. Jacobsen JA, Fullagar JL, Miller MT, Cohen SM..  (2011)  Identifying chelators for metalloprotein inhibitors using a fragment-based approach.,  54  (2): [PMID:21189019] [10.1021/jm101266s]

3. Fung SP, Wang H, Tomek P, Squire CJ, Flanagan JU, Palmer BD, Bridewell DJ, Tijono SM, Jamie JF, Ching LM..  (2013)  Discovery and characterisation of hydrazines as inhibitors of the immune suppressive enzyme, indoleamine 2,3-dioxygenase 1 (IDO1).,  21  (24): [PMID:24262887] [10.1016/j.bmc.2013.10.037]

4. Hannah J, Ruyle WV, Jones H, Matzuk AR, Kelly KW, Witzel BE, Holtz WJ, Houser RA, Shen TY, Sarett LH..  (1978)  Novel analgesic-antiinflammatory salicylates.,  21  (11): [PMID:309947] [10.1021/jm00209a001]

5. Katane M, Yamada S, Kawaguchi G, Chinen M, Matsumura M, Ando T, Doi I, Nakayama K, Kaneko Y, Matsuda S, Saitoh Y, Miyamoto T, Sekine M, Yamaotsu N, Hirono S, Homma H..  (2015)  Identification of Novel D-Aspartate Oxidase Inhibitors by in Silico Screening and Their Functional and Structural Characterization in Vitro.,  58  (18): [PMID:26322531] [10.1021/acs.jmedchem.5b00871]

6. Chen CL, Lee CC, Liu FL, Chen TC, Ahmed Ali AA, Chang DM, Huang HS..  (2016)  Design, synthesis and SARs of novel salicylanilides as potent inhibitors of RANKL-induced osteoclastogenesis and bone resorption.,  117  [PMID:27089213] [10.1016/j.ejmech.2016.04.007]

7. Malamas, M S MS and 7 more authors.  2000-03-09  New azolidinediones as inhibitors of protein tyrosine phosphatase 1B with antihyperglycemic properties.  [PMID:10715163]

8. Malamas, M S MS and 10 more authors.  2000-04-06  Novel benzofuran and benzothiophene biphenyls as inhibitors of protein tyrosine phosphatase 1B with antihyperglycemic properties.  [PMID:10753467]

9. Andersen, Henrik Sune HS and 19 more authors.  2002-09-26  Discovery and SAR of a novel selective and orally bioavailable nonpeptide classical competitive inhibitor class of protein-tyrosine phosphatase 1B.  [PMID:12238924]

10. Lee, Kyeong K and 8 more authors.  2003-08-04  Tripeptide inhibitors of Yersinia protein-tyrosine phosphatase.  [PMID:12852970]

11. Dufresne, Claude C and 16 more authors.  2004-02-23  The development of potent non-peptidic PTP-1B inhibitors.  [PMID:15013019]

12. Wilson, Douglas P DP and 20 more authors.  2007-09-20  Structure-based optimization of protein tyrosine phosphatase 1B inhibitors: from the active site to the second phosphotyrosine binding site.  [PMID:17705360]

13. Han, Yongxin Y and 14 more authors.  2008-06-01  Discovery of [(3-bromo-7-cyano-2-naphthyl)(difluoro)methyl]phosphonic acid, a potent and orally active small molecule PTP1B inhibitor.  [PMID:18477508]

14. Hussain, Munawar M, Ahmed, Vanessa V, Hill, Bryan B, Ahmed, Zaheer Z and Taylor, Scott D SD.  2008-07-15  A re-examination of the difluoromethylenesulfonic acid group as a phosphotyrosine mimic for PTP1B inhibition.  [PMID:18555687]

15. Zhang, Yi-Nan YN and 7 more authors.  2008-09-15  Oleanolic acid and its derivatives: new inhibitor of protein tyrosine phosphatase 1B with cellular activities.  [PMID:18707891]

16. Shrestha, Suja S, Bhattarai, Bharat Raj BR, Kafle, Bhooshan B, Lee, Keun-Hyeung KH and Cho, Hyeongjin H.  2008-09-15  Derivatives of 1,4-bis(3-hydroxycarbonyl-4-hydroxyl)styrylbenzene as PTP1B inhibitors with hypoglycemic activity.  [PMID:18722777]

17. Lin, Li L, Shen, Qiang Q, Chen, Guo-Rong GR and Xie, Juan J.  2008-11-15  Synthesis of triazole-linked beta-C-glycosyl dimers as inhibitors of PTP1B.  [PMID:18922697]

18. Forghieri, Marco M and 8 more authors.  2009-04-01  Synthesis, activity and molecular modeling of a new series of chromones as low molecular weight protein tyrosine phosphatase inhibitors.  [PMID:19297174]

19. Vidović, Dusica and Schürer, Stephan C.  2009-11-12  Knowledge-based characterization of similarity relationships in the human protein-tyrosine phosphatase family for rational inhibitor design.  [PMID:19810703]

20. Wu, Shuangding S and 14 more authors.  2009-11-12  Multidentate small-molecule inhibitors of vaccinia H1-related (VHR) phosphatase decrease proliferation of cervix cancer cells.  [PMID:19888758]

21. and Combs, Andrew P AP.  2010-03-25  Recent advances in the discovery of competitive protein tyrosine phosphatase 1B inhibitors for the treatment of diabetes, obesity, and cancer.  [PMID:20000419]

22. Lantz, Kristen A KA and 6 more authors.  2010-08  Inhibition of PTP1B by trodusquemine (MSI-1436) causes fat-specific weight loss in diet-induced obese mice.  [PMID:20075852]

23. Cheng, Yuanhua Y, Zhou, Mei M, Tung, Chen-Ho CH, Ji, Mingjuan M and Zhang, Fushi F.  2010-06-01  Studies on two types of PTP1B inhibitors for the treatment of type 2 diabetes: Hologram QSAR for OBA and BBB analogues.  [PMID:20452766]

24. Xu, Ji-Qing JQ, Shen, Qiang Q, Li, Jia J and Hu, Li-Hong LH.  2010-06-01  Dammaranes from Gynostemma pentaphyllum and synthesis of their derivatives as inhibitors of protein tyrosine phosphatase 1B.  [PMID:20472439]

25. Comeau, Anthony B AB, Critton, David A DA, Page, Rebecca R and Seto, Christopher T CT.  2010-09-23  A focused library of protein tyrosine phosphatase inhibitors.  [PMID:20731359]

26. Vang, Torkel T and 15 more authors.  2011-01-27  Inhibition of lymphoid tyrosine phosphatase by benzofuran salicylic acids.  [PMID:21190368]

27. Scott, Latanya M and 8 more authors.  2011-01-15  Shp2 protein tyrosine phosphatase inhibitor activity of estramustine phosphate and its triterpenoid analogs.  [PMID:21193311]

28. He, Yantao Y and 5 more authors.  2012-03-15  Bicyclic benzofuran and indole-based salicylic acids as protein tyrosine phosphatase inhibitors.  [PMID:22133902]

29. He, Hai-Bing HB and 9 more authors.  2012-12-01  Synthesis and biological evaluation of 4,4-dimethyl lithocholic acid derivatives as novel inhibitors of protein tyrosine phosphatase 1B.  [PMID:23067554]

30. Shi, Dayong D and 6 more authors.  2013-01-30  HPN, a synthetic analogue of bromophenol from red alga Rhodomela confervoides: synthesis and anti-diabetic effects in C57BL/KsJ-db/db mice.  [PMID:23364683]

31. Chen, Yue-Ting YT and 8 more authors.  2013-11  Design, synthesis, and biological evaluation of novel 2-ethyl-5-phenylthiazole-4-carboxamide derivatives as protein tyrosine phosphatase 1B inhibitors with improved cellular efficacy.  [PMID:24090912]

32. Ottanà, Rosaria R and 8 more authors.  2014-01  Synthesis, biological activity and structure-activity relationships of new benzoic acid-based protein tyrosine phosphatase inhibitors endowed with insulinomimetic effects in mouse C2C12 skeletal muscle cells.  [PMID:24287560]

33. Nguyen, Phi-Hung PH and 6 more authors.  2015-01-23  Insulin-mimetic selaginellins from Selaginella tamariscina with protein tyrosine phosphatase 1B (PTP1B) inhibitory activity.  [PMID:25559759]

34. Tautz, Lutz L, Senis, Yotis A YA, Oury, Cécile C and Rahmouni, Souad S.  2015-06-15  Perspective: Tyrosine phosphatases as novel targets for antiplatelet therapy.  [PMID:25921264]

35. Abdjul, Delfly B DB and 6 more authors.  2015-06-26  Structures and Biological Evaluations of Agelasines Isolated from the Okinawan Marine Sponge Agelas nakamurai.  [PMID:26083682]

36. Kozakov, Dima and 5 more authors.  2015-12-10  New Frontiers in Druggability.  [PMID:26230724]

37. Wang, Mei-Yan MY and 9 more authors.  2015-10-20  Synthesis, biological evaluation and 3D-QSAR studies of imidazolidine-2,4-dione derivatives as novel protein tyrosine phosphatase 1B inhibitors.  [PMID:26342135]

38. Liu, Peihong P, Du, Yongli Y, Song, Lianhua L, Shen, Jingkang J and Li, Qunyi Q.  2015-11-01  Novel, potent, selective and cellular active ABC type PTP1B inhibitors containing (methanesulfonyl-phenyl-amino)-acetic acid methyl ester phosphotyrosine mimetic.  [PMID:26481657]

39. Abdjul, Delfly B DB, Kanno, Syu-Ichi SI, Yamazaki, Hiroyuki H, Ukai, Kazuyo K and Namikoshi, Michio M.  2016-01-15  A dimeric urea of the bisabolene sesquiterpene from the Okinawan marine sponge Axinyssa sp. inhibits protein tyrosine phosphatase 1B activity in Huh-7 human hepatoma cells.  [PMID:26711144]

40. Liu, Peihong P, Du, Yongli Y, Song, Lianhua L, Shen, Jingkang J and Li, Qunyi Q.  2016-08-08  Discovery of novel, high potent, ABC type PTP1B inhibitors with TCPTP selectivity and cellular activity.  [PMID:27123900]

41. Li, XiangQian X, Wang, LiJun L and Shi, DaYong D.  2016-08-15  The design strategy of selective PTP1B inhibitors over TCPTP.  [PMID:27353889]

42. Tan, Xue Fei XF and 6 more authors.  2017-04-15  Competitive protein tyrosine phosphatase 1B (PTP1B) inhibitors, prenylated caged xanthones from Garcinia hanburyi and their inhibitory mechanism.  [PMID:28318895]

43. Li, Xiang-Qian XQ and 6 more authors.  2017-08-18  Design, synthesis and biological evaluation of uncharged catechol derivatives as selective inhibitors of PTP1B.  [PMID:28511130]

44. Sun, Wenlong W and 6 more authors.  2017-08-01  Varic acid analogues from fungus as PTP1B inhibitors: Biological evaluation and structure-activity relationships.  [PMID:28642102]

45. Mascarello, Alessandra A and 13 more authors.  2018-01-20  Naturally occurring Diels-Alder-type adducts from Morus nigra as potent inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase B.  [PMID:29275228]

46. Pastor, Miryam M and 13 more authors.  2018-01-20  Development of inhibitors of receptor protein tyrosine phosphatase β/ζ (PTPRZ1) as candidates for CNS disorders.  [PMID:29275231]

47. Du, Yongli Y, Zhang, Yanhui Y, Ling, Hao H, Li, Qunyi Q and Shen, Jingkang J.  2018-01-20  Discovery of novel high potent and cellular active ADC type PTP1B inhibitors with selectivity over TC-PTP via modification interacting with C site.  [PMID:29289892]

48. Xie, Fangzhou F and 10 more authors.  2019-02-15  Investigation of stereoisomeric bisarylethenesulfonic acid esters for discovering potent and selective PTP1B inhibitors.  [PMID:30611982]

49. Li, Xiangqian X and 7 more authors.  2019-03-15  Toward a treatment of diabesity: In vitro and in vivo evaluation of uncharged bromophenol derivatives as a new series of PTP1B inhibitors.  [PMID:30711829]

50. Jin, Jia J and 6 more authors.  2019-08-15  Identification and characterization of potent and selective inhibitors targeting protein tyrosine phosphatase 1B (PTP1B).  [PMID:31221555]

51. Dowarah, Jayanta and Singh, Ved Prakash.  2020-03-01  Anti-diabetic drugs recent approaches and advancements.  [PMID:32008883]

52. Yuan, Xinrui; Bu, Hong; Zhou, Jinpei; Yang, Chao-Yie and Zhang, Huibin.  2020-10-22  Recent Advances of SHP2 Inhibitors in Cancer Therapy: Current Development and Clinical Application.  [PMID:32460492]

Source

Source(1):

• Scientific Literature