2750dibData in BriefData BriefElsevierPMC6198130619813061981303036464810.1016/j.dib.2018.09.0691H-NMR and 13C-NMR dataset for some oxidative metabolites of CRA13 and their analogsHassanAhmed HEabChoMin ChangcKimHye IncYangJi SeulcParkKyung TaecLeeYong Supacd⁎Medicinal Chemistry Laboratory, Department of Pharmacy, College of Pharmacy, Kyung Hee University, Seoul 02447, Republic of KoreaDepartment of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, EgyptDepartment of Life and Nanopharmaceutical Sciences, Kyung Hee University, Seoul 02447, Republic of KoreaKHU-KIST Department of Converging Science and Technology, Kyung Hee University, Seoul 02447, Republic of Korea
Corresponding author at: Medicinal Chemistry Laboratory, Department of Pharmacy, College of Pharmacy, Kyung Hee University, Seoul 02447, Republic of Korea. kyslee@khu.ac.kr
CRA13 (CB-13; SAB-378) is a dual CB1R/CB2R agonist cannabinoid agent developed by Novartis Pharma. Upon administration, it undergoes metabolism to oxidative metabolites. Herein, the 1H-NMR and 13C-NMR dataset of some oxidative metabolites and analogs thereof are presented for further analysis and comparison purposes, for whom may be interested.
Received 2018 Sep 7; Accepted 2018 Sep 26; Collection date 2018 Dec.
Specifications table
Table
Subject area
Chemistry
More specific subject area
Structural characterization
Type of data
Figures
How data was acquired
Nuclear magnetic resonance (NMR) spectral analyses were performed using a Brucker Avance 400 spectrometer (400 MHz for 1H-NMR) or Agilent 500 spectrometer (125 MHz for 13C-NMR).
Data format
Raw
Experimental factors
Sample solutions were prepared with deuterated CDCl3 or CD3OD.
Experimental features
Detection temperature was set at 25 °C. Samples were scanned 16 times for 1H-NMR spectra measurement, and scanned 1 h for 13C-NMR measurement
Data source location
Kyung Hee University, Seoul, Republic of Korea
Data accessibility
Data is provided in the article
Related research article
A.H.E. Hassan, M.C. Cho, H.I. Kim, J.S. Yang, K.T. Park, J.Y. Hwang, C.G. Jang, K.D. Park, Y.S. Lee, Synthesis of oxidative metabolites of CRA13 and their analogs: Identification of CRA13 active metabolites and analogs thereof with selective CB2R affinity, Bioorg. Med. Chem.26, 2018, 5069–5078, doi:10.1016/j.bmc.2018.09.007.
Value of the data
CRA13 (CB-13; SAB-378) is a controlled cannabinoid substance in China and therefore a reference data for its metabolites are required.
The presented data provides reference that might be useful for detection of metabolites of CRA13 and related cannabinoids in biological samples.
In addition. It might be helpful in the assignment of signals of molecules containing di(naphthalen-1-yl)methanone moiety.
Also, the shown splitting and chemical shifts is helpful to structural analysis of related cannabinoids.
Data
The data presented herein describe the acquired for 1H-NMR and 13C-NMR spectra of hydroxy and carboxy metabolites of CRA13, as well as, methyl ester and analogs of the hydroxy, carboxy and methyl ester [1], [2]. Thus, a total of eight compounds were chemically synthesized and NMR data of pure samples were acquired in deuterated chloroform or deuterated methanol. These data might be useful for detection of metabolites of these controlled cannabinoids compounds and for structural assignment of compounds possessing di(naphthalen-1-yl)methanone moiety. The data are presented as figures with enlargement of proton peaks to clarify their splitting pattern.
Experimental design, materials, and methods
The compounds were chemically synthesized and purified by column chromatography as described in [1]. The samples were dissolved in CDCl3 or CD3OD then NMR spectra were acquired using a Brucker Avance 400 spectrometer (400 MHz) for 1H-NMR or Agilent 500 spectrometer (125 MHz) for 13C-NMR at 25 °C. The NMR peaks of the acquired NMR spectra are shown in Fig. 1, Fig. 2, Fig. 3, Fig. 4, Fig. 5, Fig. 6, Fig. 7, Fig. 8, Fig. 9, Fig. 10, Fig. 11, Fig. 12, Fig. 13, Fig. 14, Fig. 15, Fig. 16.
1H-NMR spectrum of four carbons alkyl chain analog of methyl ester of terminally oxidized carboxylic acid metabolite of CRA13 (CDCl3, 400 MHz).
Fig. 1
13C-NMR spectrum of four carbons alkyl chain analog of methyl ester of terminally oxidized carboxylic acid metabolite of CRA13 (CDCl3, 125 MHz).
Fig. 2
1H-NMR spectrum of methyl ester of terminally oxidized carboxylic acid metabolite of CRA13 (CDCl3, 400 MHz).
Fig. 3
13C-NMR spectrum of methyl ester of terminally oxidized carboxylic acid metabolite of CRA13 (CDCl3, 125 MHz).
Fig. 4
1H-NMR spectrum of four carbons alkyl chain analog of terminally oxidized carboxylic acid metabolite of CRA13 (CD3OD, 400 MHz).
Fig. 5
13C-NMR spectrum of four carbons alkyl chain analog of terminally oxidized carboxylic acid metabolite of CRA13 (CD3OD, 125 MHz).
Fig. 6
1H-NMR spectrum of terminally oxidized carboxylic acid metabolite of CRA13 (CD3OD, 400 MHz).
Fig. 7
13C-NMR spectrum of terminally oxidized carboxylic acid metabolite of CRA13 (CD3OD, 125 MHz).
Fig. 8
1H-NMR spectrum of three carbons alkyl chain analog of terminally oxidized alcoholic metabolite of CRA13 (CDCl3, 400 MHz).
Fig. 9
13C-NMR spectrum of three carbons alkyl chain analog of terminally oxidized alcoholic metabolite of CRA13 (CDCl3, 125 MHz).
Fig. 10
1H-NMR spectrum of four carbons alkyl chain analog of terminally oxidized alcoholic metabolite of CRA13 (CDCl3, 400 MHz).
Fig. 11
13C-NMR spectrum of four carbons alkyl chain analog of terminally oxidized alcoholic metabolite of CRA13 (CDCl3, 125 MHz).
Fig. 12
1H-NMR spectrum of terminally oxidized alcoholic metabolite of CRA13 (CDCl3, 400 MHz).
Fig. 13
13C-NMR spectrum of terminally oxidized alcoholic metabolite of CRA13 (CDCl3, 125 MHz).
Fig. 14
1H-NMR spectrum of six carbons alkyl chain analog of terminally oxidized alcoholic metabolite of CRA13 (CDCl3, 400 MHz).
Fig. 15
13C-NMR spectrum of six carbons alkyl chain analog of terminally oxidized alcoholic metabolite of CRA13 (CDCl3, 125 MHz).
Fig. 16Acknowledgments
This work was supported by Korea Institute of Science and Technology (2Z05140-17-148).
Footnotes
Transparency document associated with this article can be found in the online version at 10.1016/j.dib.2018.09.069.
Contributor Information
Ahmed H.E. Hassan, Email: ahmed_hassan@mans.edu.eg, ahmed_hassan@khu.ac.kr.
Yong Sup Lee, Email: kyslee@khu.ac.kr.
Supplementary material
Supplementary material
ReferencesA.H.E. Hassan, M.C. Cho, H.I. Kim, J.S. Yang, K.T. Park, J.Y. Hwang, C.G. Jang, K.D. Park, Y.S. Lee, Synthesis of oxidative metabolites of CRA13 and their analogs: Identification of CRA13 active metabolites and analogs thereof with selective CB2R affinity, Bioorg. Med. Chem.26 (2018) 5069–5078, 10.1016/j.bmc.2018.09.007.A. Gardin, K. Kucher, B. Kiese S. Appel-Dingemanse, Cannabinoid receptor agonist 13, a novel cannabinoid agonist: first in human pharmacokinetics and safety, Drug Metab Dispos. 37 (2009) 827–833, 10.1124/dmd.108.024000Associated DataSupplementary Materials