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Ligand (S)-nicotine

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

KEGG

Biosynthesis of alkaloids derived from ornithine, lysine and nicotinic acid, Biosynthesis of secondary metabolites, Chemical carcinogenesis - receptor activation, Metabolism of xenobiotics by cytochrome P450, Nicotine addiction, Thermogenesis, Tropane, piperidine and pyridine alkaloid biosynthesis more

MetaCyc

nicotine biosynthesis, nicotine degradation I (pyridine pathway), nicotine degradation II (pyrrolidine pathway), nicotine degradation III (VPP pathway), nicotine degradation IV, nicotine degradation V, superpathway of nicotine biosynthesis more

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (10 results)

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Show Natural Substrate (10 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.13.8

(S)-nicotine + NADPH + O2 = (S)-nicotine N1-oxide + NADP+ + H2O

671729

-

1.14.14.B11

(S)-nicotine + [reduced NADPH-hemoprotein reductase] + O2 = (S)-nornicotine + formaldehyde + [oxidized NADPH-hemoprotein reductase] + H2O

728461, 727654, 727935

-

1.14.14.B11

nicotine + NADPH + H+ = nornicotine + NADP+

746003, 746124

-

1.14.14.B11

nicotine + NADPH + O2 + H+ = nornicotine + formaldehyde + NADP+ + H2O

700634

-

1.14.14.B11

nicotine + O2 + [reduced NADPH-hemoprotein reductase] + O2 = nornicotine + formaldehyde + [oxidized NADPH-hemoprotein reductase] + H2O

726648, 728555

-

1.14.14.B11

nicotine + [reduced NADPH-hemoprotein reductase] + O2 = nornicotine + formaldehyde + [oxidized NADPH-hemoprotein reductase] + H2O

746124, 676779

-

1.5.99.4

(S)-nicotine + acceptor + H2O = pseudooxynicotine + reduced acceptor

724032

-

1.5.99.4

L-nicotine + acceptor + H2O = (S)-6-hydroxynicotine + reduced acceptor

656187

-

1.5.99.4

nicotine + acceptor + H2O = 6-hydroxynicotine + reduced acceptor

741709, 392440, 392537

-

1.14.14.B11

5 entries

1.5.99.4

3 entries

2.4.1.17

UDP-D-glucuronate + nicotine = UDP + ?

694256

-

Substrate in Enzyme-catalyzed Reactions (28 results)

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Show Substrate (28 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.13.101

nicotine + NADPH + H+ + O2 = nicotine N-oxide + NADP+ + H2O

728567

-

1.14.13.8

(S)-nicotine + NADPH + H+ + O2 = ?

743616

-

1.14.13.8

(S)-nicotine + NADPH + O2 = (S)-nicotine N1-oxide + NADP+ + H2O

671729

-

1.14.13.8

nicotine + NADPH + H+ + O2 = (S)-nicotine N1-oxide + NADP+ + H2O

742463

-

1.14.13.8

nicotine + NADPH + H+ + O2 = nicotine N-oxide + NADP+ + H2O

689806, 686276

-

1.14.13.8

4 entries

1.14.13.92

(S)-nicotine + NADPH + O2 = ?

677171

-

1.14.14.1

(S)-nicotine + [reduced NADPH-hemoprotein reductase] + O2 = ?

671729

4ejg, 3D-view

1.14.14.1

(S)-nicotine + [reduced NADPH-hemoprotein reductase] + O2 = ?

671729

4ejj, 3D-view

1.14.14.B11

(S)-nicotine + [reduced NADPH-hemoprotein reductase] + O2 = (S)-nornicotine + formaldehyde + [oxidized NADPH-hemoprotein reductase] + H2O

728461, 727654, 727935

-

1.14.14.B11

nicotine + NADPH + H+ = nornicotine + NADP+

746003, 746124

-

1.14.14.B11

nicotine + NADPH + O2 + H+ = nornicotine + formaldehyde + NADP+ + H2O

700634

-

1.14.14.B11

nicotine + O2 + [reduced NADPH-hemoprotein reductase] + O2 = nornicotine + formaldehyde + [oxidized NADPH-hemoprotein reductase] + H2O

726648, 728555

-

1.14.14.B11

nicotine + [reduced NADPH-hemoprotein reductase] + O2 = nornicotine + formaldehyde + [oxidized NADPH-hemoprotein reductase] + H2O

686348, 746124, 687594, 689241, 689487, 676779

-

1.5.3.5

(S)-nicotine + H2O + O2 = N-methylmyosmine + H2O2

764029, 741686, 764183

-

1.5.3.5

nicotine + H2O + O2 = N-methylmyosmine + H2O2

765711

-

1.5.99.4

(S)-nicotine + 2,6-dichlorophenolindophenol + H2O = (S)-6-hydroxynicotine + reduced 2,6-dichlorophenolindophenol

741698, 763949, 392538

-

1.5.99.4

(S)-nicotine + acceptor + H2O = nicotine-N-oxide + reduced acceptor

392540

-

1.5.99.4

(S)-nicotine + acceptor + H2O = nornicotine + reduced acceptor + ?

392540

-

1.5.99.4

(S)-nicotine + acceptor + H2O = pseudooxynicotine + reduced acceptor

724032

-

1.5.99.4

(S)-nicotine + acceptor = (S)-nicotine delta1',5'-iminium ion + reduced acceptor

392540

-

1.5.99.4

(S)-nicotine + brilliant cresyl blue + H2O = (S)-6-hydroxynicotine + reduced brilliant cresyl blue

392538

-

1.5.99.4

(S)-nicotine + menadione + H2O = (S)-6-hydroxynicotine + menadiol

392538

-

1.5.99.4

(S)-nicotine + methylene blue + H2O = (S)-6-hydroxynicotine + reduced methylene blue

392538

-

1.5.99.4

(S)-nicotine + pseudoazurin + H2O = (S)-6-hydroxynicotine + reduced pseudoazurin

763949

-

1.5.99.4

(S)-nicotine + vitamin K5 + H2O = (S)-6-hydroxynicotine + reduced vitamin K5

392538

-

1.5.99.4

L-nicotine + acceptor + H2O = (S)-6-hydroxynicotine + reduced acceptor

684760, 656187

-

1.5.99.4

nicotine + acceptor + H2O = 6-hydroxynicotine + reduced acceptor

392541, 741709, 392440, 392538, 392537, 391423

-

1.14.14.1

2 entries

1.14.14.B11

5 entries

1.5.3.5

2 entries

1.5.99.4

12 entries

2.4.1.17

UDP-D-glucuronate + nicotine = UDP + ?

735649, 694256

-

Activator in Enzyme-catalyzed Reactions (5 results)

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Show Activating Compound (5 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.13.11.34

treatment with 0.01 mM nicotine activates 5-lipoxygenase gastric cancer cell lines from 36-72 h

711661

-

1.21.99.4

stimulates isozyme type II

644806

-

1.8.1.7

0.5 mg/kg, 11.8% enhancement of enzymatic activity in brain

673460

-

2.4.1.17

slightly activating with substrate amitriptyline

736005

-

4.6.1.1

nicotine treatment in adulthood produces an immediate increase in adenylate cyclase activity in males that disappears upon withdrawal, nicotine increases the activating effect of forskolin, especially in males, overview

691561

-

Inhibitor in Enzyme-catalyzed Reactions (10 results)

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Show Inhibitors (10 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.49

inhibits the enzyme from lung, testis, kidney, stomach, and brain, in concert with vitamin E the enzyme from testis brain and liver is inhibited, tissue-specific inhibition of 12.5-48%, overview, nicotine has no effect on enzyme from muscle, heart, and liver

675105

-

1.1.3.17

ability of nicotine to inhibit catalytic activity of choline oxidase used for biosensorial detection of

686373

-

1.8.1.7

0.5 mg/kg, significant inhibition of enzymatic activity in liver (61.5%), lung (65%), heart (70.5%), stomach (72.5%), kidney (64%) and testicle (71.5%)

673460

-

2.1.1.37

decreases glutamic acid decarboxylase 67 promoter methylation by DMT1 in GABAergic interneurons

700956

-

2.4.1.17

-

736012

-

2.4.1.17

-

736005

-

2.4.1.17

2 entries

2.5.1.18

about 16% inhibition at 0.01 mM

759335

-

2.7.11.26

attenuates beta-amyloid peptide 1-42-induced activation of GSK-3beta

693729

-

3.2.1.26

-

136129

-

3.5.3.18

50% decrease in DDAH-2 mRNA

697831

-

3D Structure of Enzyme-Ligand-Complex (PDB) (17 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (17 entries)

EC NUMBER

ENZYME 3D STRUCTURE

1.14.14.1

4ejg, 3D-view

1.14.14.1

4ejj, 3D-view

1.14.14.1

4ejg, 3D-view

1.14.14.1

4ejj, 3D-view

1.14.14.1

4ejg, 3D-view

1.14.14.1

4ejj, 3D-view

1.14.14.1

4ejg, 3D-view

1.14.14.1

4ejj, 3D-view

1.14.15.1

1p2y, 3D-view

1.14.15.1

1p7r, 3D-view

1.14.15.1

1p2y, 3D-view

1.14.15.1

1p7r, 3D-view

1.14.15.1

1p2y, 3D-view

1.14.15.1

1p7r, 3D-view

1.14.15.1

1p2y, 3D-view

1.14.15.1

1p7r, 3D-view

1.14.14.1

8 entries

1.14.15.1

8 entries

3.1.1.98

7bne, 3D-view

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (8 results)

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Show Turnover Number (8 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.14.13.8

3

-

pH 8.5, 25°C

689806

1.5.3.5

0.1

-

wild-type, pH 7.4, 22°C

764029

1.5.3.5

1.14

-

mutant R274A/Y311W/C417W, pH 7.4, 37°C

764029

1.5.3.5

1.44

-

mutant Y311W, pH 7.4, 22°C

764029

1.5.3.5

2.03

-

pH 7.0, 40°C

741686

1.5.3.5

2.65

-

mutant R274A/Y311W/C417W, pH 7.4, 22°C

764029

1.5.99.4

0.468

-

respiratory

392540

1.5.99.4

0.597

-

olfactory

392540

1.5.3.5

5 entries

1.5.99.4

2 entries

K_M Value (26 results)

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Show KM Value (26 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.14.13.8

0.13

-

pH 8.5, 25°C

689806

1.14.14.B11

0.0039

-

-

700634

1.14.14.B11

0.0039

-

at 25°C, pH 6.25

700634

1.14.14.B11

0.0091

-

23°C, pH 7.1

687594

1.14.14.B11

0.015

-

pH 7.1, 23°C

689241

1.14.14.B11

0.0203

-

isoform CYP82E1, in 50 mM Tris-HCl (pH 7.5), at 25°C

728461

1.14.14.B11

0.0481

-

23°C, pH 7.1

687594

1.14.14.B11

0.049

-

isoform CYP2A6, pH 7.4, 37°C

686348

1.14.14.B11

0.054

-

isoform CYP82E2, in 50 mM Tris-HCl (pH 7.5), at 25°C

728461

1.14.14.B11

0.056

-

pH 7.1, 23°C

689487

1.14.14.B11

0.0619

-

isoform CYP82E4, in 50 mM Tris-HCl (pH 7.5), at 25°C

728461

1.14.14.B11

0.0684

-

isoform CYP82E1, in 50 mM Tris-HCl (pH 7.5), at 25°C

728461

1.14.14.B11

0.1186

-

isoform CYP82E3, in 50 mM Tris-HCl (pH 7.5), at 25°C

728461

1.14.14.B11

0.55

-

isoform CYP2B6, pH 7.4, 37°C

686348

1.5.3.5

0.000114

-

pH and temperature not specified in the publication

764183

1.5.3.5

0.225

-

37°C, pH not specified in the publication

765711

1.5.3.5

0.346

-

37°C, pH not specified in the publication

765711

1.5.3.5

0.396

-

pH 7.0, 40°C

741686

1.5.3.5

13

-

mutant R274A/Y311W/C417W, pH 7.4, 37°C

764029

1.5.3.5

13

-

wild-type, pH 7.4, 22°C

764029

1.5.3.5

16

-

mutant R274A/Y311W/C417W, pH 7.4, 22°C

764029

1.5.3.5

19

-

mutant Y311W, pH 7.4, 22°C

764029

1.5.99.4

0.00087

-

cosubstrate 2,6-dichlorophenolindophenol, pH 7, 30°C

763949

1.5.99.4

0.00167

-

cosubstrate pseudoazurin, pH 7, 30°C

763949

1.5.99.4

0.035

-

-

392540

1.5.99.4

0.037

-

-

392538

1.14.14.B11

13 entries

1.5.3.5

8 entries

1.5.99.4

4 entries

IC₅₀ Value (1 result)

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Show IC50 Value (1 entry)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

2.4.1.17

0.214

-

pH 7.4, 37°C

736012

References & Links

Literature References (51)

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Show Reference (51 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

136129

-

Nicotiana glauca invertase: characterization and effects of endogenous alkaloids

1998

Rojo, H.P.; Quiroga, E.N.; Vattuone, M.A.; Sampietro, A.R.

Phytochemistry

49

965-969

391423

-

Bactopterin as component of eubacterial dehydrogenases involved in hydroxylation reactions initiating the degradation of nicotine, nicotinate, and 2-furancarboxylate

1989

Nagel, M.; Koenig, K.; Andreesen, J.R.

FEMS Microbiol. Lett.

60

323-326

392440

5849820

Induction and purification of stereospecific nicotine oxidizing enzymes from Arthrobacter oxidans

1965

Decker, K.; Bleeg, H.

Biochim. Biophys. Acta

105

313-324

392537

-

Nicotine dehydrogenase from Arthrobacter oxidans: A molybdenum-containing hydroxylase

1988

Freudenberg, W.; Koenig, K.; Andreesen, J.R.

FEMS Microbiol. Lett.

52

13-18

392538

4962139

The purification and properties of nicotine oxidase

1967

Hochstein, L.L.; Dalton, B.P.

Biochim. Biophys. Acta

139

56-68

392540

2302249

Rabbit nasal cytochrome P-450 NMa has high activity as a nicotine oxidase

1990

Williams, D.E.; Ding, X.; Coon, M.J.

Biochem. Biophys. Res. Commun.

166

945-952

392541

7074142

Heterogeneity of hepatic nicotine oxidase

1982

Nakayama, H.; Nakashima, T.; Kurogochi, Y.

Biochim. Biophys. Acta

715

254-257

644806

11898402

Iodothyronine deiodinases

2002

Koehrle, J.

Methods Enzymol.

347

125-167

656187

14534317

Characterization of HdnoR, the transcriptional repressor of the 6-hydroxy-D-nicotine oxidase gene of Arthrobacter nicotinovorans pAO1, and its DNA-binding activity in response to L- and D-nicotine Derivatives

2003

Sandu, C.; Chiribau, C.B.; Brandsch, R.

J. Biol. Chem.

278

51307-51315

671729

16112078

Some distinctions between flavin-containing and cytochrome P450 monooxygenases

2005

Cashman, J.R.

Biochem. Biophys. Res. Commun.

338

599-604

673460

17113070

Effects of nicotine and vitamin E on glutathione reductase activity in some rat tissues in vivo and in vitro

2007

Erat, M.; Ciftci, M.; Gumustekin, K.; Gul, M.

Eur. J. Pharmacol.

554

92-97

675105

16335059

Effects of nicotine and vitamin E on glucose 6-phosphate dehydrogenase activity in some rat tissues in vivo and in vitro

2005

Gumustekin, K.; Ciftci, M.; Coban, A.; Altikat, S.; Aktas, O.; Gul, M.; Timur, H.; Dane, S.

J. Enzyme Inhib. Med. Chem.

20

497-502

676779

16192354

Conversion of nicotine to nornicotine in Nicotiana tabacum is mediated by CYP82E4, a cytochrome P450 monooxygenase

2005

Siminszky, B.; Gavilano, L.; Bowen, S.W.; Dewey, R.E.

Proc. Natl. Acad. Sci. USA

102

14919-14924

677171

-

Oxidations catalyzed by phenylacetone monooxygenase from Thermobifida fusca

2005

de Gonzalo, G.; Torres Pazmino, D.E.; Ottolina, G.; Fraaije, M.W.; Carrea, G.

Tetrahedron

16

3077-3083

684760

18071673

Two closely related pathways of nicotine catabolism in Arthrobacter nicotinovorans and Nocardioides sp. strain JS614

2008

Ganas, P.; Sachelaru, P.; Mihasan, M.; Igloi, G.L.; Brandsch, R.

Arch. Microbiol.

189

511-517

686276

-

The flavin-containing monooxygenases (FMOs): genetic variation and its consequences for the metabolism of therapeutic drugs

2007

Phillips, I.R.; Francois, A.A.; Shephard, E.A.

Curr. Pharmacogenomics

5

292-313

686348

16135656

CYP2A6 AND CYP2B6 are involved in nornicotine formation from nicotine in humans: interindividual differences in these contributions

2005

Yamanaka, H.; Nakajima, M.; Fukami, T.; Sakai, H.; Nakamura, A.; Katoh, M.; Takamiya, M.; Aoki, Y.; Yokoi, T.

Drug Metab. Dispos.

33

1811-1818

686373

-

Amperometric biosensors based on choline oxidase entrapped in polyacrylamide microgels

2007

Lopez, M.S.; Perez, J.P.; Lopez-Cabarcos, E.; Lopez-Ruiz, B.

Electroanalysis

19

370-378

687594

17102129

Functional analysis of nicotine demethylase genes reveals insights into the evolution of modern tobacco

2007

Gavilano, L.B.; Coleman, N.P.; Bowen, S.W.; Siminszky, B.

J. Biol. Chem.

282

249-256

689241

17635231

Inactivation of the cytochrome P450 gene CYP82E2 by degenerative mutations was a key event in the evolution of the alkaloid profile of modern tobacco

2007

Chakrabarti, M.; Meekins, K.M.; Gavilano, L.B.; Siminszky, B.

New Phytol.

175

565-574

689487

17923451

Isolation and characterization of the cytochrome P450 gene CYP82E5v2 that mediates nicotine to nornicotine conversion in the green leaves of tobacco

2007

Gavilano, L.B.; Siminszky, B.

Plant Cell Physiol.

48

1567-1574

689806

18443301

Revealing the moonlighting role of NADP in the structure of a flavin-containing monooxygenase

2008

Alfieri, A.; Malito, E.; Orru, R.; Fraaije, M.W.; Mattevi, A.

Proc. Natl. Acad. Sci. USA

105

6572-6577

691561

18534261

Adolescent nicotine administration changes the responses to nicotine given subsequently in adulthood: adenylyl cyclase cell signaling in brain regions during nicotine administration and withdrawal, and lasting effects

2008

Slotkin, T.A.; Ryde, I.T.; Mackillop, E.A.; Bodwell, B.E.; Seidler, F.J.

Brain Res. Bull.

76

522-530

693729

18485099

Role of GSK-3beta activation and alpha7 nAChRs in Abeta(1-42)-induced tau phosphorylation in PC12 cells

2008

Hu, M.; Waring, J.F.; Gopalakrishnan, M.; Li, J.

J. Neurochem.

106

1371-1377

694256

17576790

Nicotine glucuronidation and the human UDP-glucuronosyltransferase UGT2B10

2007

Kaivosaari, S.; Toivonen, P.; Hesse, L.M.; Koskinen, M.; Court, M.H.; Finel, M.

Mol. Pharmacol.

72

761-768

697831

19331593

Dimethylarginine dimethylaminohydrolase regulation: a novel therapeutic target in cardiovascular disease

2009

Wadham, C.; Mangoni, A.A.

Expert. Opin. Drug Metab. Toxicol.

5

303-319

700634

100103560

Biochemical and molecular characterizations of nicotine demethylase in tobacco

2007

Xu, D.; Shen, Y.; Chappell, J.; Cui, M.; Nielsen, M.T.

Physiol. Plant.

129

307-319

700956

18852456

Nicotine decreases DNA methyltransferase 1 expression and glutamic acid decarboxylase 67 promoter methylation in GABAergic interneurons

2008

Satta, R.; Maloku, E.; Zhubi, A.; Pibiri, F.; Hajos, M.; Costa, E.; Guidotti, A.

Proc. Natl. Acad. Sci. USA

105

16356-16361

711661

20061081

Activation of 5-lipoxygenase is required for nicotine mediated epithelial-mesenchymal transition and tumor cell growth

2010

Shin, V.Y.; Jin, H.C.; Ng, E.K.; Sung, J.J.; Chu, K.M.; Cho, C.H.

Cancer Lett.

292

237-245

724032

23335761

Cloning of a novel nicotine oxidase gene from Pseudomonas sp. strain HZN6 whose product nonenantioselectively degrades nicotine to pseudooxynicotine

2013

Qiu, J.; Ma, Y.; Zhang, J.; Wen, Y.; Liu, W.

Appl. Environ. Microbiol.

79

2164-2171

726648

-

Data mining of nicotine demethylase genes in modern tobacoo

2013

Lian, J.; Wang, D.; Xie, J.

Adv. Mater. Res.

787

356-360

727654

23116221

Variable nornicotine enantiomeric composition caused by nicotine demethylase CYP82E4 in tobacco leaf

2012

Cai, B.; Bush, L.

J. Agric. Food Chem.

60

11586-11591

727935

23100254

Enantioselective demethylation of nicotine as a mechanism for variable nornicotine composition in tobacco leaf

2012

Cai, B.; Siminszky, B.; Chappell, J.; Dewey, R.; Bush, L.

J. Biol. Chem.

287

42804-42811

728461

23034878

Non-functionalization of two CYP82E nicotine N-demethylase genes abolishes nornicotine formation in nicotiana langsdorffii

2012

Pakdeechanuan, P.; Teoh, S.; Shoji, T.; Hashimoto, T.

Plant Cell Physiol.

53

2038-2046

728555

21858078

Molecular dynamics analysis reveals structural insights into mechanism of nicotine N-demethylation catalyzed by tobacco cytochrome P450 mono-oxygenase

2011

Wang, S.; Yang, S.; An, B.; Wang, S.; Yin, Y.; Lu, Y.; Xu, Y.; Hao, D.

PLoS ONE

6

e23342

728567

22363737

Independent recruitment of a flavin-dependent monooxygenase for safe accumulation of sequestered pyrrolizidine alkaloids in grasshoppers and moths

2012

Wang, L.; Beuerle, T.; Timbilla, J.; Ober, D.

PLoS ONE

7

e31796

735649

25937523

Roles of human UDP-glucuronosyltransferases in clearance and homeostasis of endogenous substrates, and functional implications

2015

Bock, K.W.

Biochem. Pharmacol.

96

77-82

736005

23611809

Human UDP-glucuronosyltransferase (UGT) 2B10 in drug N-glucuronidation: substrate screening and comparison with UGT1A3 and UGT1A4

2013

Kato, Y.; Izukawa, T.; Oda, S.; Fukami, T.; Finel, M.; Yokoi, T.; Nakajima, M.

Drug Metab. Dispos.

41

1389-1397

736012

26669329

Human UDP-glucuronosyltransferase (UGT) 2B10: validation of cotinine as a selective probe substrate, inhibition by UGT enzyme-selective inhibitors and antidepressant and antipsychotic drugs, and structural determinants of enzyme inhibition

2016

Pattanawongsa, A.; Nair, P.C.; Rowland, A.; Miners, J.O.

Drug Metab. Dispos.

44

378-388

741686

25002425

A novel (S)-6-hydroxynicotine oxidase gene from Shinella sp. strain HZN7

2014

Qiu, J.; Wei, Y.; Ma, Y.; Wen, R.; Wen, Y.; Liu, W.

Appl. Environ. Microbiol.

80

5552-5560

741698

26729714

Nicotine dehydrogenase complexed with 6-hydroxypseudooxynicotine oxidase involved in the hybrid nicotine-degrading pathway in Agrobacterium tumefaciens S33

2016

Li, H.; Xie, K.; Yu, W.; Hu, L.; Huang, H.; Xie, H.; Wang, S.

Appl. Environ. Microbiol.

82

1745-1755

741709

27568381

Conversion of nornicotine to 6-hydroxy-nornicotine and 6-hydroxy-myosmine by Shinella sp. strain HZN7

2016

Qiu, J.; Li, N.; Lu, Z.; Yang, Y.; Ma, Y.; Niu, L.; He, J.; Liu, W.

Appl. Microbiol. Biotechnol.

100

10019-10029

742463

27678284

Drug metabolism by flavin-containing monooxygenases of human and mouse

2017

Phillips, I.R.; Shephard, E.A.

Expert. Opin. Drug Metab. Toxicol.

13

167-181

743616

28072829

Predicting the metabolic sites by flavin-containing monooxygenase on drug molecules using SVM classification on computed quantum mechanics and circular fingerprints molecular descriptors

2017

Fu, C.W.; Lin, T.H.

PLoS ONE

12

e0169910

746003

27596288

Identification of CYP82E21 as a functional nicotine N-demethylase in tobacco flowers

2016

Liedschulte, V.; Schwaar, J.D.; Laparra, H.; Vuarnoz, A.; Philippon, B.; Bakaher, N.; Sierro, N.; Bovet, L.; Lang, G.; Goepfert, S.

Phytochemistry

131

9-16

746124

27314515

RNA interference of the nicotine demethylase gene CYP82E4v1 reduces nornicotine content and enhances Myzus persicae resistance in Nicotiana tabacum L

2016

Zhao, D.; Qin, L.J.; Zhao, D.G.

Plant Physiol. Biochem.

107

214-221

759335

29578047

Characterization of a Drosophila glutathione transferase involved in isothiocyanate detoxification

2018

Gonzalez, D.; Fraichard, S.; Grassein, P.; Delarue, P.; Senet, P.; Nicolai, A.; Chavanne, E.; Mucher, E.; Artur, Y.; Ferveur, J.F.; Heydel, J.M.; Briand, L.; Neiers, F.

Insect Biochem. Mol. Biol.

95

33-43

763949

28625985

Periplasmic nicotine dehydrogenase NdhAB utilizes pseudoazurin as its physiological electron acceptor in Agrobacterium tumefaciens S33

2017

Yu, W.; Wang, R.; Huang, H.; Xie, H.; Wang, S.

Appl. Environ. Microbiol.

83

e01050

764029

32750321

An active site mutation in 6-hydroxy-L-nicotine oxidase from Arthrobacter nicotinovorans changes the substrate specificity in favor of (S)-nicotine

2020

Deay, D.I.; Colvert, K.; Gao, F.; Seibold, S.; Goyal, P.; Aillon, D.; Petillo, P.; Richter, M.

Arch. Biochem. Biophys.

692

108520

764183

33464876

Fast kinetics reveals rate-limiting oxidation and the role of the aromatic cage in the mechanism of the nicotine-degrading enzyme NicA2

2021

Tararina, M.A.; Dam, K.K.; Dhingra, M.; Janda, K.D.; Palfey, B.A.; Allen, K.N.

Biochemistry

60

259-273

765711

32987121

Expression and functional identification of two homologous nicotine dehydrogenases, NicA2 and Nox, from Pseudomonas sp. JY-Q

2021

Li, J.; Shen, M.; Chen, Z.; Pan, F.; Yang, Y.; Shu, M.; Chen, G.; Jiao, Y.; Zhang, F.; Linhardt, R.; Zhong, W.

Protein Expr. Purif.

178

105767

Links to other databases for (S)-nicotine

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