C10H12N2O
Cotinine
176.09496
8395266
ChemSpider
17215925
ChemSpider
7722-84-1
CAS
937
ChemSpider
HMDB0003125
HMDB
C9H10N2O
Norcotinine
162.07932
439153
PubChem-compound
SMILES
[H][C@]1(CCCN1C)C1=CC=CN=C1
SMILES
O
SMILES
OO
1.0
61192-50-5
CAS
NICOTINE
BioCyc
2616-64-0
CAS
Cytochrome P450 2B6
NADPH
CPD-3186
BioCyc
CPD-3185
BioCyc
Uridine diphosphate glucuronic acid
Neuronal acetylcholine receptor subunit alpha-3
1.0
Water
PW000604
PathWhiz
Dimethylaniline monooxygenase [N-oxide-forming] 3
CHEBI:15846
ChEBI
P32297
UniProt
1.0
CHEBI:17688
ChEBI
Cotinine glucuronide
C16H20N2O7
Cotinine glucuronide
352.12704
1.0
53-59-8
CAS
Cytochrome P450 2A6
BTO:0000759
BRENDA TISSUE ONTOLOGY
1.0
1038
PubChem-compound
CHEBI:17200
ChEBI
1.0
CHEBI:16474
ChEBI
Hydrogen Ion
SMILES
CN1[C@@H](CCC1=O)C1=C[N+]([O-])=CC=C1
952
ChemSpider
Norcotinine
Dimethylaniline monooxygenase [N-oxide-forming] 3
396
ChemSpider
CH2O
Formaldehyde
30.010565
Neuronal acetylcholine receptor subunit beta-2
395
ChemSpider
C10H12N2O2
5'-Hydroxycotinine
192.08987
1.0
54-11-5
CAS
Nicotine activation of Nicotinic Acetylcholine Receptor
ActivatingSubPathway
Nicotine activation of Neuronal acetylcholine receptor 2
ActivatingSubPathway
CHEBI:16908
ChEBI
7991264
ChemSpider
UDP-GLUCURONATE
BioCyc
6031
PubChem-compound
1.0
1.0
SMILES
C[N+]1=CCCC1C1=CC=CN=C1
CHEBI:16240
ChEBI
C16H20N2O8
trans-3-Hydroxycotinine glucuronide
368.12198
Cotinine
1010
ChemSpider
HMDB0001411
HMDB
139427-57-9
CAS
SMILES
O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O
C21H30N7O17P3
NADPH
745.0911
C21H29N7O17P3
NADP
744.08325
7991265
ChemSpider
NADPH
BioCyc
C15H22N2O18P2
Uridine diphosphate glucuronic acid
580.0343
1.0
FORMALDEHYDE
BioCyc
C16H22N2O6
Nicotine glucuronide
338.1478
494-97-3
CAS
CPD-6641
BioCyc
152306-59-7
CAS
SMILES
CN1C(CCC1=O)C1=C[N+](=CC=C1)C1OC(C(O)C(O)C1O)C([O-])=O
58-68-4
CAS
Reaction2021
false
Cotinine → Cotinine N-oxide
LEFT_TO_RIGHT
UDP-glucuronosyltransferase 1-9
Reaction2022
false
Cotinine → 5'-Hydroxycotinine
LEFT_TO_RIGHT
UDP-glucuronosyltransferase 1-4
P17787
UniProt
Reaction2020
false
Hydroxycotinine → trans-3-Hydroxycotinine glucuronide
LEFT_TO_RIGHT
SMILES
CN1C(=O)CC[C@@]1(O)C1=CN=CC=C1
HMDB0001427
HMDB
HMDB0000217
HMDB
SMILES
C=O
HMDB0001426
HMDB
692
ChemSpider
CHEBI:127762
ChEBI
1.0
GO:0005886
GENE ONTOLOGY
132929-88-5
CAS
BiologicalState73
Homo sapiens, Neuron
Hydroxycotinine
2.0
Nicotine-1'-N-oxide
NADH
SMILES
[H][C@@]1(O[C@@H]2CC(N(C)C2=O)C2=CC=CN=C2)O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O
1.0
C00007
KEGG Compound
Oxygen
C00006
KEGG Compound
2.0
CHEBI:18009
ChEBI
Formaldehyde
2642613
ChemSpider
C00001
KEGG Compound
C00005
KEGG Compound
Nicotine imine
431
PubChem-compound
C00004
KEGG Compound
1.0
C00003
KEGG Compound
Liver
SMILES
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O
2.4.1.17
false
2.4.1.17
Nicotine + Uridine diphosphate glucuronic acid → Nicotine glucuronide + Uridine 5'-diphosphate
LEFT_TO_RIGHT
Reaction2013
false
Nicotine → Nornicotine
LEFT_TO_RIGHT
HMDB0000221
HMDB
Reaction2011
false
Hydrogen Ion + NADPH + Nicotine + Oxygen → NADP + Nicotine-1'-N-oxide + Water
LEFT_TO_RIGHT
1.0
SMILES
NC(=O)C1=CN(C=CC1)[C@H]1O[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2O[C@@H]([C@@H](OP(O)(O)=O)[C@H]2O)N2C=NC3=C(N)N=CN=C23)[C@H](O)[C@@H]1O
Nornicotine
17473
PubChem-compound
1.14.13.-
false
1.14.13.-
Cotinine + NADH + Oxygen → Formaldehyde + NAD + Norcotinine + Water
LEFT_TO_RIGHT
C9H12N2
Nornicotine
148.10005
1.14.13.-
false
1.14.13.-
Cotinine + Hydrogen Ion + NADPH + Oxygen → Hydroxycotinine + NADP + Water
LEFT_TO_RIGHT
Reaction2016
false
Nornicotine → Norcotinine
LEFT_TO_RIGHT
2.4.1.17
false
2.4.1.17
Cotinine + Uridine diphosphate glucuronic acid → Cotinine glucuronide + Uridine 5'-diphosphate
LEFT_TO_RIGHT
1.14.13.-
false
1.14.13.-
Nicotine → Hydrogen Ion + Nicotine imine
LEFT_TO_RIGHT
Reaction2015
false
Nicotine imine + Oxygen + Water → Cotinine + Hydrogen Ion + Hydrogen peroxide
LEFT_TO_RIGHT
53-57-6
CAS
Oxygen
SMP0000628
SMPDB
P31513
UniProt
CPD-2743
BioCyc
CPD-2744
BioCyc
C21H28N7O14P2
NAD
664.11694
Neuronal acetylcholine receptor subunit alpha-4
CPD-2742
BioCyc
CL:0000540
CELL TYPE ONTOLOGY
Neuron
Neuronal acetylcholine receptor subunit beta-2
1.0
HMDB0000902
HMDB
C00015
KEGG Compound
1.0
NAD(P)
BioCyc
Hydrogen peroxide
C21H29N7O14P2
NADH
665.12476
HMDB0001204
HMDB
Aldehyde oxidase
1.0
1.0
CPD-2747
BioCyc
CPD-2748
BioCyc
CPD-2749
BioCyc
Cytochrome P450 2B6
1.0
BTO:0000049
BRENDA TISSUE ONTOLOGY
CPD-2750
BioCyc
CPD-2751
BioCyc
H
Hydrogen Ion
1.007825
CHEBI:16842
ChEBI
Neuronal acetylcholine receptor subunit alpha-3
CPD-2752
BioCyc
89594
PubChem-compound
53-84-9
CAS
C00027
KEGG Compound
C10H14N2O
Nicotine-1'-N-oxide
178.11061
Cytochrome P450 2A6
GO:0005737
GENE ONTOLOGY
3035848
PubChem-compound
BiologicalState24
Homo sapiens, Adrenal Medulla
Endoplasmic Reticulum Membrane
SMILES
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O
418
ChemSpider
2299987
ChemSpider
UDP
BioCyc
5682
ChemSpider
SMILES
NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O
C10H12N2O2
Cotinine N-oxide
192.08987
O60656
UniProt
Nicotine
SubPathwayActivator
HYDROGEN-PEROXIDE
BioCyc
409
PubChem-compound
2.0
Nicotine imine
34834-67-8
CAS
408
PubChem-compound
Cotinine
UDP-glucuronosyltransferase 1-4
74710-78-4
CAS
C10H13N2
Nicotine imine
161.10788
SubPathwayControl532
SubPathway532Control
ActivatingSubPathwayControl
SubPathwayControl533
SubPathway533Control
ActivatingSubPathwayControl
5675
ChemSpider
HMDB0000935
HMDB
1.0
C00167
KEGG Compound
SMILES
C[N+]1([O-])CCCC1C1=CN=CC=C1
400
ChemSpider
763
ChemSpider
NAD
C9H14N2O12P2
Uridine 5'-diphosphate
404.0022
17114-40-8
CAS
Cytoplasm
784
PubChem-compound
53477725
PubChem-compound
Nicotine glucuronide
Homo sapiens
7732-18-5
CAS
388299
ChemSpider
SMILES
CN1C(CCC1=O)C1=CN=CC=C1
1.0
SMILES
O=C1CCC(N1)C1=CN=CC=C1
Water
HMDB0001487
HMDB
Cotinine N-oxide
Hydrogen Ion
Nicotinic Acetylcholine Receptor
SubPathwayActivation
HMDB0001126
HMDB
O2
Oxygen
31.98983
GO:0005789
GENE ONTOLOGY
ReactionCatalysis1869
ACTIVATION
ReactionCatalysis1868
ACTIVATION
Adrenal Medulla
1.0
16522
ChemSpider
1.0
412
PubChem-compound
C00745
KEGG Compound
413
PubChem-compound
BiologicalState10
Homo sapiens, Liver
C00067
KEGG Compound
Aldehyde oxidase
7782-44-7
CAS
10219774
PubChem-compound
HMDB0001377
HMDB
ReactionCatalysis1874
ACTIVATION
Neuronal acetylcholine receptor subunit alpha-4
C10H12N2O2
Hydroxycotinine
192.08987
36508-80-2
CAS
HMDB0001497
HMDB
ReactionCatalysis1873
ACTIVATION
HMDB0001013
HMDB
ReactionCatalysis1876
ACTIVATION
ReactionCatalysis1875
ACTIVATION
1.0
P22310
UniProt
ReactionCatalysis1877
ACTIVATION
Hydroxycotinine
1.0
ReactionCatalysis1870
ACTIVATION
HMDB0001010
HMDB
UDP-glucuronosyltransferase 1-9
ReactionCatalysis1872
ACTIVATION
ReactionCatalysis1871
ACTIVATION
P20813
UniProt
9606
TAXONOMY
Nicotine
962
PubChem-compound
1.0
1.0
Nicotine Metabolism Pathway
trans-3-Hydroxycotinine glucuronide
58-98-0
CAS
HMDB0001934
HMDB
5'-Hydroxycotinine
1.0
P43681
UniProt
1.0
5893
PubChem-compound
C00080
KEGG Compound
1.0
SMILES
O=O
1.0
HMDB0002111
HMDB
HMDB0000295
HMDB
5809
ChemSpider
1.0
CHEBI:15377
ChEBI
Cell Membrane
80863
ChemSpider
CHEBI:15379
ChEBI
CHEBI:15378
ChEBI
SMILES
[H+]
712
PubChem-compound
5886
PubChem-compound
Q06278
UniProt
CHEBI:28313
ChEBI
SMILES
CN1[C@@H](CC(O)C1=O)C1=CN=CC=C1
21108497
ChemSpider
9815514
PubChem-compound
9815515
PubChem-compound
HMDB0001390
HMDB
63551-14-4
CAS
HMDB0001272
HMDB
CHEBI:63860
ChEBI
486-56-6
CAS
SMILES
CN1CCC[C@H]1C1=C[N+](=CC=C1)[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C([O-])=O
P11509
UniProt
SMILES
O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)O[C@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)O[C@H]([C@@H]1O)N1C=CC(=O)NC1=O
HMDB0001046
HMDB
22833512
PubChem-compound
C10H14N2
Nicotine
162.11569
H2O
Water
18.010565
H2O2
Hydrogen peroxide
34.005478
CHEBI:30734
ChEBI
Uridine 5'-diphosphate
NADH
BioCyc
NADP
NAD
BioCyc
977
PubChem-compound
CHEBI:17659
ChEBI
HMDB0059597
HMDB
3398121
PubChem-compound
50-00-0
CAS
C06524
KEGG Compound
Cotinine
SMILES
C1CNC(C1)C1=CC=CN=C1
Norcotinine
Neuronal acetylcholine receptor 2
SubPathwayActivation
HMDB0001297
HMDB