Kanamycin A - Moligand™, ≥97% , CAS No.59-01-8

CAS: 59-01-8 Cat. No.: K275316 Molecular Weight: 484.5

GRADE & PURITY Moligand™, ≥97%

Synonyms

Kantrex (1:1 sulfate) | SBUJHOSQTJFQJX-NOAMYHISSA-N | D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1-4))-2-deoxy- | A07AA08 | UNII-EQK9Q303C5 | Kanamycine [INN-French] | SMP2_000007 | NINDS_00002

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Description
Kanamycin is isolated from the bacterium Streptomyces kanamyceticus and its most commonly used form is kanamycin sulfate. Kanamycin is an aminoglycoside bacteriocidal antibiotic and used to treat a wide variety of infections. Kanamycin interacts with the 30S subunit of prokaryotic ribosomes.

Specifications

Synonyms

Kantrex (1:1 sulfate) | SBUJHOSQTJFQJX-NOAMYHISSA-N | D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1-4))-2-deoxy- | A07AA08 | UNII-EQK9Q303C5 | Kanamycine [INN-French] | SMP2_000007 | NINDS_00002

Specifications & Purity

Moligand™, ≥97%

Biochemical and Physiological Mechanisms

Aminoglycoside antibiotic. Inhibits translocation by binding to the 70S ribosomal subunit. Effective against Gram-negative and Gram-positive bacteria and mycoplasma.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Refer to SDS for further information Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥97%

Names and Identifiers

• Pubchem Sid: 504750989
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504750989
• Canonical Smiles: C1C(C(C(C(C1N)OC2C(C(C(C(O2)CN)O)O)O)O)OC3C(C(C(C(O3)CO)O)N)O)N
• IUPAC Name: (2R,3S,4S,5R,6R)-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3,4,5-triol
• InChIKey: SBUJHOSQTJFQJX-NOAMYHISSA-N
• INCHI: 1S/C18H36N4O11/c19-2-6-10(25)12(27)13(28)18(30-6)33-16-5(21)1-4(20)15(14(16)29)32-17-11(26)8(22)9(24)7(3-23)31-17/h4-18,23-29H,1-3,19-22H2/t4-,5+,6-,7-,8+,9-,10-,11-,12+,13-,14-,15+,16-,17-,18-/m1/s1
• Isomeric SMILES: C1[C@H]([C@@H]([C@H]([C@@H]([C@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CN)O)O)O)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)N)O)N
• Molecular Weight: 484.5
• Reaxy-Rn: 10788856
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=10788856&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Aminosaccharides
          • Level6 Aminoglycosides
            • Level7 Aminocyclitol glycosides
              • Level8 2-deoxystreptamine aminoglycosides
                • Level9 4,6-disubstituted 2-deoxystreptamines

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Aminosaccharides - Aminoglycosides - Aminocyclitol glycosides - 2-deoxystreptamine aminoglycosides
• Direct Parent: 4,6-disubstituted 2-deoxystreptamines
• Alternative Parents: O-glycosyl compounds Aminocyclitols and derivatives Cyclohexylamines Cyclohexanols Oxanes Monosaccharides 1,2-aminoalcohols Polyols Oxacyclic compounds Acetals Primary alcohols Organopnictogen compounds Monoalkylamines Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: 4,6-disubstituted 2-deoxystreptamine - Glycosyl compound - O-glycosyl compound - Aminocyclitol or derivatives - Cyclohexanol - Cyclohexylamine - Cyclitol or derivatives - Monosaccharide - Oxane - Cyclic alcohol - Secondary alcohol - 1,2-aminoalcohol - Polyol - Organoheterocyclic compound - Acetal - Oxacycle - Alcohol - Hydrocarbon derivative - Organopnictogen compound - Primary aliphatic amine - Organonitrogen compound - Organic nitrogen compound - Amine - Primary alcohol - Primary amine - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as 4,6-disubstituted 2-deoxystreptamines. These are 2-deoxystreptamine aminoglycosides that a glycosidically linked to a pyranose of furanose unit at the C4- and C6-positions.
• External Descriptors: kanamycins

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

PDE5A Tclin Phosphodiesterase 5A (5113 Activities)

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EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)

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CA2 Tclin Carbonic anhydrase II (17698 Activities)

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ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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HMGCR Tclin HMG-CoA reductase (2475 Activities)

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NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

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INSR Tclin Insulin receptor (5558 Activities)

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PGR Tclin Progesterone receptor (8562 Activities)

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ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)

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CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

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ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)

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HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

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ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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AR Tclin Androgen Receptor (11781 Activities)

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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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ACE Tclin Angiotensin-converting enzyme (1423 Activities)

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DRD2 Tclin Dopamine D2 receptor (23596 Activities)

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GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

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MAOA Tclin Monoamine oxidase A (11911 Activities)

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CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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DRD4 Tchem Dopamine D4 receptor (7907 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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HRH2 Tclin Histamine H2 receptor (5428 Activities)

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ADRA1D Tclin Alpha-1d adrenergic receptor (4171 Activities)

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HTR1B Tclin Serotonin 1b (5-HT1b) receptor (2801 Activities)

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HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)

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HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)

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AVPR2 Tclin Vasopressin V2 receptor (2912 Activities)

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ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)

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CALCR Tclin Calcitonin receptor (2215 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

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HRH1 Tclin Histamine H1 receptor (7573 Activities)

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ADRA1B Tclin Alpha-1b adrenergic receptor (2912 Activities)

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OPRM1 Tclin Mu opioid receptor (19785 Activities)

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DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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AVPR1A Tclin Vasopressin V1a receptor (5412 Activities)

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OPRD1 Tclin Delta opioid receptor (15096 Activities)

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OPRK1 Tclin Kappa opioid receptor (16155 Activities)

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HTR3A Tclin Serotonin 3a (5-HT3a) receptor (3366 Activities)

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SLC6A3 Tclin Dopamine transporter (10535 Activities)

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GRIN1 Tclin Glutamate (NMDA) receptor subunit zeta 1 (122 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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HTR4 Tclin Serotonin 4 (5-HT4) receptor (2068 Activities)

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CACNA1C Tclin Voltage-gated L-type calcium channel alpha-1C subunit (766 Activities)

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Associated Targets(non-human)

Agtr2 Angiotensin II type 2 (AT-2) receptor (803 Activities)

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Mc4r Melanocortin receptor 4 (1205 Activities)

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Ltc4s Leukotriene C4 synthase (1 Activities)

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Sigmar1 Sigma opioid receptor (160 Activities)

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Npy1r Neuropeptide Y receptor type 1 (8 Activities)

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Cckar Cholecystokinin A receptor (90 Activities)

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Pde4d Phosphodiesterase 4D (4 Activities)

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Nos2 Nitric oxide synthase, inducible (3573 Activities)

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Mapk1 MAP kinase ERK2 (650 Activities)

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Mmp9 Matrix metalloproteinase 9 (38 Activities)

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Pla1a Phosphatidylserine-specific phospholipase A1 (10 Activities)

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Lypla1 Lysosomal phospholipase A1 (40 Activities)

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Streptococcus pneumoniae (31063 Activities)

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Enterococcus (1748 Activities)

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Campylobacter jejuni (634 Activities)

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Pseudomonas (460 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Burkholderia cepacia (649 Activities)

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Pseudomonas fluorescens (1630 Activities)

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Pseudomonas putida (467 Activities)

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Legionella pneumophila (143 Activities)

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Enterobacter cloacae (7976 Activities)

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Klebsiella (302 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Proteus (150 Activities)

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Proteus vulgaris (5823 Activities)

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Providencia rettgeri (925 Activities)

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Salmonella typhimurium (15756 Activities)

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Shigella boydii (323 Activities)

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Shigella flexneri (1836 Activities)

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Micrococcus luteus (7463 Activities)

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Staphylococcus aureus (210822 Activities)

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Staphylococcus epidermidis (22802 Activities)

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Staphylococcus haemolyticus (1695 Activities)

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Acinetobacter baumannii (41033 Activities)

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Neisseria gonorrhoeae (1461 Activities)

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Citrobacter freundii (1864 Activities)

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Klebsiella aerogenes (4963 Activities)

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Dickeya chrysanthemi (75 Activities)

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Escherichia coli (133304 Activities)

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Klebsiella oxytoca (929 Activities)

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Proteus mirabilis (3894 Activities)

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Providencia stuartii (425 Activities)

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Salmonella (646 Activities)

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Salmonella enteritidis (727 Activities)

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Salmonella typhi (4293 Activities)

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Serratia (189 Activities)

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Serratia marcescens (3237 Activities)

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Shigella dysenteriae (933 Activities)

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Haemophilus influenzae (8812 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water to 100 mM
• Molecular Weight: 484.500 g/mol
• XLogP3: -6.900
• Hydrogen Bond Donor Count: 11
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 6
• Exact Mass: 484.238 Da
• Monoisotopic Mass: 484.238 Da
• Topological Polar Surface Area: 283.000 Ų
• Heavy Atom Count: 33
• Formal Charge: 0
• Complexity: 638.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 15
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Qian Wang, Li Zhu, Yi Yu, Huashi Guan, Zhe Xu.  (2021)  Microbial Screening of Marine Natural Product Inhibitors for the 6′-Aminoglycoside Acetyltransferase 2″-Aminoglycoside Phosphotransferase [AAC(6′)-APH(2″)] Bifunctional Enzyme by Ultra-High Performance Liquid Chromatography–Mass Spectrometry (UHPLC-MS).  ANALYTICAL LETTERS,      [PMID:] [10.1080/00032719.2021.1903025]

2. Li Zhu, Ruonan Liu, Tangrong Liu, Xuan Zou, Zhe Xu, Huashi Guan.  (2018)  A novel strategy to screen inhibitors of multiple aminoglycoside-modifying enzymes with ultra-high performance liquid chromatography-quadrupole-time-of-flight mass spectrometry.  JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS,      [PMID:30458385] [10.1016/j.jpba.2018.11.021]

3. Yanhua He, Xiaoye Wen, Bingyan Zhang, Zhefeng Fan.  (2018)  Novel aptasensor for the ultrasensitive detection of kanamycin based on grapheneoxide quantum-dot-linked single-stranded DNA-binding protein.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2018.03.029]