ID: ALA108766

Max Phase: Preclinical

Molecular Formula: C12H24O2

Molecular Weight: 200.32

Molecule Type: Small molecule

Representations

Synonyms (3): Dodecanoic Acid | Dodecanoic Acid Anion | Lauric Acid
Synonyms from Alternative Forms(3):

Canonical SMILES:  CCCCCCCCCCCC(=O)O

Standard InChI:  InChI=1S/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14)

Standard InChI Key:  POULHZVOKOAJMA-UHFFFAOYSA-N

Molecule Features

Natural Product: Yes

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

Properties

Molecular Weight: 200.32

Molecular Weight (Monoisotopic): 200.1776

AlogP: 3.99

#Rotatable Bonds: 10

Polar Surface Area: 37.30

Molecular Species: ACID

HBA: 1

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 4.95

CX Basic pKa:

CX LogP: 4.48

CX LogD: 2.06

Aromatic Rings: 0

Heavy Atoms: 14

QED Weighted: 0.54

Np Likeness Score: 0.50

References

1. Hirsch RF, Rachlin EM..  (1983)  Ion-sensitive electrode potentiometry of organic anions: application to quantitative structure-activity relationships.,  26  (9): [PMID:6887198] [10.1021/jm00363a006]

2. 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]

3. Bodor N, Kaminski JJ, Selk S..  (1980)  Soft drugs. 1. Labile quaternary ammonium salts as soft antimicrobials.,  23  (5): [PMID:7381846] [10.1021/jm00179a001]

4. Kubo I, Muroi H, Kubo A..  (1994)  Naturally occurring antiacne agents.,  57  (1): [PMID:8158169] [10.1021/np50103a002]

5. Chen FC, Peng CF, Tsai IL, Chen IS..  (2005)  Antitubercular constituents from the stem wood of Cinnamomum kotoense.,  68  (9): [PMID:16180806] [10.1021/np0580210]

6. Bera S, Zhanel GG, Schweizer F..  (2008)  Design, synthesis, and antibacterial activities of neomycin-lipid conjugates: polycationic lipids with potent gram-positive activity.,  51  (19): [PMID:18778047] [10.1021/jm800345u]

7. Himejima M, Kubo I..  (1992)  Antimicrobial agents from Licaria puchuri-major and their synergistic effect with polygodial.,  55  (5): [PMID:1517735] [10.1021/np50083a010]

8. Liu Y, Nair MG..  (2010)  An efficient and economical MTT assay for determining the antioxidant activity of plant natural product extracts and pure compounds.,  73  (7): [PMID:20565070] [10.1021/np1000945]

9. PubChem BioAssay data set, 

10. PubChem BioAssay data set, 

11.  (2008)  Casarett and Doull's Toxicology The Basic Science of Poisons, 7th edition, 

12. 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]

13. PubChem BioAssay data set, 

14. Tukey RH, Strassburg CP..  (2000)  Human UDP-glucuronosyltransferases: metabolism, expression, and disease.,  40  (1): [PMID:10836148] [10.1146/annurev.pharmtox.40.1.581]

15. Maruo S, Kuriyama I, Kuramochi K, Tsubaki K, Yoshida H, Mizushina Y..  (2011)  Inhibitory effect of novel 5-O-acyl juglones on mammalian DNA polymerase activity, cancer cell growth and inflammatory response.,  19  (19): [PMID:21903399] [10.1016/j.bmc.2011.08.023]

16. Seo SM, Kim J, Kim E, Park HM, Kim YJ, Park IK..  (2010)  Structure-activity relationship of aliphatic compounds for nematicidal activity against pine wood nematode (Bursaphelenchus xylophilus).,  58  (3): [PMID:20055406] [10.1021/jf902575f]

17. 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]

18. 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]

19. Yamamoto H, Oda M, Nakano M, Watanabe N, Yabiku K, Shibutani M, Inoue M, Imagawa H, Nagahama M, Himeno S, Setsu K, Sakurai J, Nishizawa M..  (2013)  Development of vizantin, a safe immunostimulant, based on the structure-activity relationship of trehalose-6,6'-dicorynomycolate.,  56  (1): [PMID:23210481] [10.1021/jm3016443]

20. PubChem BioAssay data set, 

21. PubChem BioAssay data set, 

22. 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]

23. Christiansen E, Hudson BD, Hansen AH, Milligan G, Ulven T..  (2016)  Development and Characterization of a Potent Free Fatty Acid Receptor 1 (FFA1) Fluorescent Tracer.,  59  (10): [PMID:27074625] [10.1021/acs.jmedchem.6b00202]

24. Kaspersen MH, Jenkins L, Dunlop J, Milligan G, Ulven T..  (2017)  Succinct synthesis of saturated hydroxy fatty acids and in vitro evaluation of all hydroxylauric acids on FFA1, FFA4 and GPR84.,  8  (6): [PMID:30108848] [10.1039/C7MD00130D]

25. 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]

26. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek.  (2020)  Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection,  [10.21203/rs.3.rs-23951/v1]

27. Köse M, Pillaiyar T, Namasivayam V, De Filippo E, Sylvester K, Ulven T, von Kügelgen I, Müller CE..  (2020)  An Agonist Radioligand for the Proinflammatory Lipid-Activated G Protein-Coupled Receptor GPR84 Providing Structural Insights.,  63  (5): [PMID:31721581] [10.1021/acs.jmedchem.9b01339]

28. 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]

29. 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]

30. 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]

31. 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]

32. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

33. Chen LH,Zhang Q,Xie X,Nan FJ.  (2020)  Modulation of the G-Protein-Coupled Receptor 84 (GPR84) by Agonists and Antagonists.,  63  (24.0): [PMID:33267584] [10.1021/acs.jmedchem.0c01378]

34. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

Source

Source(5):

• Scientific Literature
• PubChem BioAssays
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6