An automated framework for NMR chemical shift calculations of small organic molecules

Yesiltepe, Yasemin; Nuñez, Jamie R.; Colby, Sean M.; Thomas, Dennis G.; Borkum, Mark I.; Reardon, Patrick N.; Washton, Nancy M.; Metz, Thomas O.; Teeguarden, Justin G.; Govind, Niranjan; Renslow, Ryan S.

doi:10.1186/s13321-018-0305-8

Journal of Cheminformatics

Table 1 Demonstration set sources and details

From: An automated framework for NMR chemical shift calculations of small organic molecules

References	# of molecules	Ave. atoms per molecule	Ave. H per molecule	Ave. C per molecule	Types of molecules
Alver [63]	1	24	11	8	Boron-based compound
Asiri et al. [64]	1	33	12	16	Organic photochromic compound
Bagno et al. [66]	4	44	21	18	Small organic molecules with constrained conformations
Barkowski et al. [67]	15	83	50	31	Pentacyclic terpenoids (fernenes)
Coruh et al. [68]	1	25	8	13	Heterocyclic aromatic compound
Fulmer et al. [69]	33	14	9	4	Commonly used NMR solvents
Hill et al. [70]	1	70	33	30	Complex drug with multiple chemical groups and one stereocenter
Izgi et al. [71]	1	24	15	8	Molecule with cyclohexene (C₆H₁₀) attached to ethylamine (C₂H₇N)
Karabacak et al. [72]	1	17	8	7	Planar benzene ring with attached B(OH)₂ and two F groups
Krishnakumar et al. [74]	2	16	4	6	Agrochemical intermediate compounds with planar rings
Krishnakumar et al. [73]	2	16	7	7	Nitrotoluene derivatives
Krishnakumar et al. [75]	2	17	6	7	Phenol derivatives
Kwan and Liu [45]	1	42	22	18	Natural product
Li et al. [76]	78	11	4	5	Molecules with a large number of connected substituent groups
Lomas [77]	15	18	12	5	Saturated alcohols
Osmialowski et al. [78]	28	28	11	14	Substituted phenacylpyridines (ketimine forms) and tautomers
Parlak et al. [79]	1	26	4	12	Polyfluoroaromatic compound with two rings
Perez et al. [80]	2	22	10	8	Chloropyrimidine species
Rablen et al. [81]	80	6	4	11	Rigid organic compounds with constrained conformations
Sarotti and Pellegrinet [82, 83]	66	15	8	6	Low polarity compounds with constrained conformations
Sebestian et al. [84]	1	26	11	14	Phenyl cyanide compound with two planar phenyl rings
Seca et al. [52]	4	40	24	65	Light petroleum extracts
Senyel et al. [85]	1	23	13	9	A structural element of many pharmaceutical drugs
Senyel et al. [86]	1	28	18	8	3-Piperidino-propylamine molecule
Sridevi et al. [87]	1	21	8	10	Chromene, a two ringed planar compound
Tormena and da Silva [88]	3	17	8	8	Para-X-sub’ed (X=H, CH₃O, & NO₂) aromatic carbonyl compounds
Vijaja and Sankaran [89]	1	47	24	20	Azine
Watts et al. [53]	6	45	21	18	Coniferol, a building block of lignin, stereoisomers and conformers
Wiitala et al. [90]	43	11	6	3	Organic compounds
Wiitala et al. [91]	7	24	14	8	Cis-/trans-forms of 2-, 3-, and 4-methylcyclohexanols
Willoughby et al. [92]	2	22	14	7	Cis-/trans-diastereomers of 3-methylcyclohexanol
Yang et al. [93]	2	57	28	23	Complex natural products
This study’s demonstration set	312	20	10	8	Small- to medium-sized organic molecules with constrained conformations

Details (i.e. experimental conditions, total and average number of nuclei, molecule types and classes) for each molecule set are given in Additional file 1 (S3)

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ISSN: 1758-2946

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