Research Article Theoretical Investigation of the Structural, Spectroscopic, Electronic, and Pharmacological Properties of 4-Nerolidylcathecol, an Important Bioactive Molecule RenyerA.Costa , 1 EarleSilvaA.Junior, 2 JaquelinedeA.Bezerra, 2 JosianaMoreiraMar, 1 Emerson S. Lima , 3 Maria Lucia B. Pinheiro, 1 Diego V. C. Mendonça, 1 Guilherme Braule P. Lopes, 1 Adjane Dalvana S. Branches, 1 and Kelson M. T. Oliveira 1 1 Department of Chemistry, Federal University of Amazonas (DQ-UFAM), 69077-000 Manaus, AM, Brazil 2 Federal Institute of Science and Technology of Amazonas (IFAM), 69020-120 Manaus, AM, Brazil 3 Faculty of Pharmaceutical Sciences, Federal University of Amazonas, 69077-000 Manaus, AM, Brazil CorrespondenceshouldbeaddressedtoRenyerA.Costa;renyer.costa@gmail.com Received 30 June 2018; Accepted 18 November 2018; Published 13 January 2019 AcademicEditor:FranckRabilloud Copyright©2019RenyerA.Costaetal.isisanopenaccessarticledistributedundertheCreativeCommonsAttributionLicense, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. 4-Nerolidylcatechol(4NRC),asecondarymetabolitedescribedasapotentantioxidantthatpresentsanti-inflammatory,antimalarial, analgesic,andcytotoxicproperties,hasbeenreceivingprominenceinthecatecholclass.Inthiswork,atheoreticalDFTstudyofthe vibrational,structural,andquantumpropertiesof4-nerolidylcatechol(4NRC)usingtheB3LYP/6-311G(2d,p)levelispresented.e theoretical molecular geometry data were compared with the X-ray data of a similar molecule in the associated literature and a conformational study is presented, with the aim of providing a good comprehension of the 4NRC structural arrangement and stability. Also, HOMO-LUMO energy gap and natural bond orbitals (NBOs) were performed and discussed. e calculated UV spectrumshowedsimilaritytotheexperimentallyobtaineddata,withtransitionsassigned.ecomparativeIRstudiesrevealedthat intermolecular hydrogen bonds that stabilize dimeric forms are plausible and also allowed the assignment of several characteristic vibrations. Molecular docking calculations with DNA topoisomerase I-DNA complex (TOPO-I), glyceraldehyde 3-phospate de- hydrogenase(GAPDH),and Plasmodium falciparum lactatedehydrogenase(PfLDH)showedbindingfreeenergiesof −6.3, −6.5,and −7.6kcal/mol, respectively, which indicates that 4NRC is a good competitive inhibitor for these enzymes. 1.Introduction Catechols are a group of small molecules with physiological importance, acting as effective structural units in many ad- renergic, Parkinson’s disease [1], attention-deficit hyperac- tivity disorder (ADHD) [2], bronchodilator, antidepressants, antihypertensive drugs, perfumes, and agrochemical ingre- diants (for the production of pesticides) [3]. In organic chemistry, catechol (1,2-dihydroxybenzene) and its de- rivatives have widely attracted scientists since decades prin- cipally for the design of mussel-inspired synthetic adhesives andcoatings[4].Withrespecttotheirbiologicalimportance, catechols can occur as metabolites [5, 6] or as endogenous compounds,suchasneurotransmitterandtheirprecursorsas adrenaline, noradrenaline, dopamine, and L-DOPA [1, 5, 6]. Catechols could act as antioxidants, preventing lipid perox- idation, and as pro-oxidant-damaging macromolecules such as DNA [7]. Animportantrepresentativeofthisclassofmoleculesis 4-nerolidylcatechol (4NRC) (Figure 1). Its potent antioxi- dantactivityislargelyestablishedintheliterature[8–12],but other pharmacological properties, such as antimicrobial [13], analgesic, anti-inflammatory [14], cytotoxic [15, 16], andantimalarialactivities[17]arerelatedto4NRC.Itisthe major secondary metabolite of Piper genus plants, tradi- tionally known for their use in the treatment of various diseases [12, 15, 17–20]. However, the therapeutic appli- cabilityof4NRCislimitedbyitsverypoorwatersolubility. Many works in the literature have discussed the phar- macological properties [10, 12, 16, 18–22] of 4NRC, but Hindawi Journal of Chemistry Volume 2019, Article ID 9627404, 14 pages https://doi.org/10.1155/2019/9627404