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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:41 UTC

HMDB ID

HMDB0001411

Secondary Accession Numbers

HMDB01411

Metabolite Identification

Common Name

Cotinine N-oxide

Description

Cotinine N-oxide is a minor metabolite of nicotine, cotinine formation being the major pathway of nicotine metabolism in smokers. Cotinine N-oxide accounts for less than 5% of the nicotine dose. Cotinine N-oxide can be reduced back to the parent amine in vivo. Nicotine is a naturally occurring alkaloid found in many plants. The principal sources of nicotine exposure are through the use of tobacco, nicotine containing gum and nicotine replacement therapies. Nicotine is an amine composed of pyridine and pyrrolidine rings. It has been shown that nicotine crosses biological membranes and the blood brain barrier easily. The absorbed nicotine is extensively metabolized in the liver to form a wide variety of metabolites including and cotinine N-oxide. Nicotine has been shown to affect a wide variety of biological functions ranging from gene expression, regulation of hormone secretion and enzyme activities. (PMID: 16359169 , 15109883 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02231219072D          

 14 15  0  0  1  0            999 V2000
    8.7332   -6.3752    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2569   -7.0375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.5233   -6.6308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7332   -7.7113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4319   -7.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5233   -7.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1855   -6.1429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1888   -6.3287    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    8.4777   -5.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0137   -6.3287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0137   -7.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7822   -7.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1888   -7.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6274   -5.4982    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  9  1  1  0  0  0  0
  4  2  1  0  0  0  0
  2  5  1  1  0  0  0
  6  3  1  0  0  0  0
  7  3  2  0  0  0  0
  6  4  1  0  0  0  0
 10  5  2  0  0  0  0
 11  5  1  0  0  0  0
 10  8  1  0  0  0  0
 12  8  2  0  0  0  0
 13 11  2  0  0  0  0
 13 12  1  0  0  0  0
 14  8  1  0  0  0  0
M  CHG  2   8   1  14  -1
M  END
> <DATABASE_ID>
HMDB0001411

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1[C@@H](CCC1=O)C1=C[N+]([O-])=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N2O2/c1-11-9(4-5-10(11)13)8-3-2-6-12(14)7-8/h2-3,6-7,9H,4-5H2,1H3/t9-/m0/s1

> <INCHI_KEY>
CIPULDKLIIVIER-VIFPVBQESA-N

> <FORMULA>
C10H12N2O2

> <MOLECULAR_WEIGHT>
192.2145

> <EXACT_MASS>
192.089877638

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
19.49733863167793

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(2S)-1-methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olate

> <ALOGPS_LOGP>
-0.66

> <JCHEM_LOGP>
-1.0495223999999999

> <ALOGPS_LOGS>
-1.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
0.8049121441667914

> <JCHEM_POLAR_SURFACE_AREA>
45.77

> <JCHEM_REFRACTIVITY>
52.970000000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.10e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(2S)-1-methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0      16.302 -11.900   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      15.413 -13.137   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.777 -12.378   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.302 -14.394   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.873 -13.137   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.777 -13.917   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      19.013 -11.467   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      11.552 -11.814   0.000  0.00  0.00           N+1
HETATM    9  C   UNK     0      15.825 -10.426   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.092 -11.814   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.092 -14.481   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.793 -13.137   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.552 -14.481   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.505 -10.263   0.000  0.00  0.00           O-1
CONECT    1    2    3    9                                                  
CONECT    2    1    4    5                                                  
CONECT    3    1    6    7                                                  
CONECT    4    2    6                                                       
CONECT    5    2   10   11                                                  
CONECT    6    3    4                                                       
CONECT    7    3                                                            
CONECT    8   10   12   14                                                  
CONECT    9    1                                                            
CONECT   10    5    8                                                       
CONECT   11    5   13                                                       
CONECT   12    8   13                                                       
CONECT   13   11   12                                                       
CONECT   14    8                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(-)-Cotinine N-oxide	ChEBI
(5S)-1-Methyl-5-(1-oxido-3-pyridinyl)-2-pyrrolidinone	ChEBI
(S)-1-Methyl-5-(1-oxido-3-pyridinyl)-2-pyrrolidinone	ChEBI
(S)-1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone N-oxide	ChEBI
3-[(2S)-1-Methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olate	ChEBI
Cotinine-N-oxide	ChEBI
3-[(2S)-1-Methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olic acid	Generator
Cotinine-1-N-oxide	MeSH, HMDB

Chemical Formula

C₁₀H₁₂N₂O₂

Average Molecular Weight

192.2145

Monoisotopic Molecular Weight

192.089877638

IUPAC Name

3-[(2S)-1-methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olate

Traditional Name

3-[(2S)-1-methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olate

CAS Registry Number

36508-80-2

SMILES

CN1[C@@H](CCC1=O)C1=C[N+]([O-])=CC=C1

InChI Identifier

InChI=1S/C10H12N2O2/c1-11-9(4-5-10(11)13)8-3-2-6-12(14)7-8/h2-3,6-7,9H,4-5H2,1H3/t9-/m0/s1

InChI Key

CIPULDKLIIVIER-VIFPVBQESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyrrolidinylpyridines

Direct Parent

Pyrrolidinylpyridines

Alternative Parents

Substituents

Pyrrolidinylpyridine
Alkaloid or derivatives
Pyridinium
Pyrrolidone
2-pyrrolidone
N-alkylpyrrolidine
Pyrrolidine
Tertiary carboxylic acid amide
Heteroaromatic compound
Lactam
Carboxamide group
Carboxylic acid derivative
Azacycle
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 8294547)

Organ

Liver (HMDB: HMDB0001411)
Kidney (HMDB: HMDB0001411)

Excreta

Biofluid or Excreta

Urine (PMID: 8294547)

Cellular substructure

Cytoplasm (HMDB: HMDB0001411)

Source

Endogenous

Endogenous (HMDB: HMDB0001411)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Nicotine Metabolism Pathway (HMDB: HMDB0001411)
Nicotine Metabolism Pathway (PathBank: SMP0000628)

Drug action pathway

Nicotine Action Pathway (HMDB: HMDB0001411)
Nicotine Action Pathway (PathBank: SMP0000431)

Role

Biological role

Drug metabolite (HMDB: HMDB0001411)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	11 g/L	ALOGPS
logP	-0.66	ALOGPS
logP	-1	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Basic)	0.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	45.77 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	52.97 m³·mol⁻¹	ChemAxon
Polarizability	19.5 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	143.883	31661259
DarkChem	[M-H]-	142.305	31661259
AllCCS	[M+H]+	142.259	32859911
AllCCS	[M-H]-	144.166	32859911
DeepCCS	[M+H]+	146.752	30932474
DeepCCS	[M-H]-	144.87	30932474
DeepCCS	[M-2H]-	178.11	30932474
DeepCCS	[M+Na]+	152.777	30932474
AllCCS	[M+H]+	142.3	32859911
AllCCS	[M+H-H2O]+	137.8	32859911
AllCCS	[M+NH4]+	146.4	32859911
AllCCS	[M+Na]+	147.6	32859911
AllCCS	[M-H]-	144.2	32859911
AllCCS	[M+Na-2H]-	144.5	32859911
AllCCS	[M+HCOO]-	144.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.69 minutes	32390414
Predicted by Siyang on May 30, 2022	8.8448 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.63 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	824.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	249.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	86.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	161.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	54.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	238.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	275.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	462.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	596.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	40.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	739.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	157.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	184.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	502.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	371.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	130.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cotinine N-oxide	CN1[C@@H](CCC1=O)C1=C[N+]([O-])=CC=C1	2713.3	Standard polar	33892256
Cotinine N-oxide	CN1[C@@H](CCC1=O)C1=C[N+]([O-])=CC=C1	1748.7	Standard non polar	33892256
Cotinine N-oxide	CN1[C@@H](CCC1=O)C1=C[N+]([O-])=CC=C1	2272.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cotinine N-oxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-007c-2900000000-b21511ca6ae8481af0e8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cotinine N-oxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cotinine N-oxide 10V, Positive-QTOF	splash10-0006-0900000000-c4eef2387e9f2b62d330	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cotinine N-oxide 20V, Positive-QTOF	splash10-0006-0900000000-fef784f029be5b488c33	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cotinine N-oxide 40V, Positive-QTOF	splash10-0kmj-4900000000-68e5ea5e4ec111232d7d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cotinine N-oxide 10V, Negative-QTOF	splash10-0006-0900000000-2aae58a0b3f0a1cfff7e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cotinine N-oxide 20V, Negative-QTOF	splash10-0006-1900000000-8a7a6a4c3590431d80ba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cotinine N-oxide 40V, Negative-QTOF	splash10-0a4l-9400000000-db8d337314f54fbc6087	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cotinine N-oxide 10V, Negative-QTOF	splash10-0006-0900000000-18fc00c031adb8129b3a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cotinine N-oxide 20V, Negative-QTOF	splash10-0006-0900000000-18d8f25ee061190ca3b4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cotinine N-oxide 40V, Negative-QTOF	splash10-00di-5900000000-e69e4e58d2b626f4e06b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cotinine N-oxide 10V, Positive-QTOF	splash10-0006-0900000000-db2f5cc959f8b671bd15	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cotinine N-oxide 20V, Positive-QTOF	splash10-0006-0900000000-32cfe0677b371918de71	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cotinine N-oxide 40V, Positive-QTOF	splash10-01bc-2900000000-ffd6d9f4ac3b44e62d61	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Nicotine Action Pathway		Not Available
Nicotine Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000017 +/- 0.000006 uM	Adult (>18 years old)	Both	Normal	8294547	details
Urine	Detected and Quantified	0.24 +/- 0.19 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	8294547	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022606

KNApSAcK ID

Not Available

Chemspider ID

7991264

KEGG Compound ID

Not Available

BioCyc ID

CPD-3185

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6227

PubChem Compound

9815514

PDB ID

Not Available

ChEBI ID

89087

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Riah, Omar; Dousset, Jean Claude; Courriere, Philippe; Baziard-Mouysset, Genevieve; Ecalle, Rene. Synthesis of cotinine and cotinine N-oxide. Evaluation of their interaction with nicotine in the insecticidal activity. Natural Product Letters (1997), 11(1), 37-45.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Xu X, Iba MM, Weisel CP: Simultaneous and sensitive measurement of anabasine, nicotine, and nicotine metabolites in human urine by liquid chromatography-tandem mass spectrometry. Clin Chem. 2004 Dec;50(12):2323-30. Epub 2004 Oct 7. [PubMed:15472033 ]
Zuccaro P, Altieri I, Rosa M, Passa AR, Pichini S, Ricciarello G, Pacifici R: Determination of nicotine and four metabolites in the serum of smokers by high-performance liquid chromatography with ultraviolet detection. J Chromatogr. 1993 Nov 24;621(2):257-61. [PubMed:8294547 ]
Jacob P 3rd, Shulgin AT, Yu L, Benowitz NL: Determination of the nicotine metabolite trans-3'-hydroxycotinine in urine of smokers using gas chromatography with nitrogen-selective detection or selected ion monitoring. J Chromatogr. 1992 Dec 2;583(2):145-54. [PubMed:1478978 ]
Brown KM, von Weymarn LB, Murphy SE: Identification of N-(hydroxymethyl) norcotinine as a major product of cytochrome P450 2A6, but not cytochrome P450 2A13-catalyzed cotinine metabolism. Chem Res Toxicol. 2005 Dec;18(12):1792-8. [PubMed:16359169 ]
Yildiz D: Nicotine, its metabolism and an overview of its biological effects. Toxicon. 2004 May;43(6):619-32. [PubMed:15109883 ]

Showing metabocard for Cotinine N-oxide (HMDB0001411)

MOL for HMDB0001411 (Cotinine N-oxide)

3D MOL for HMDB0001411 (Cotinine N-oxide)

3D SDF for HMDB0001411 (Cotinine N-oxide)

3D-SDF for HMDB0001411 (Cotinine N-oxide)

PDB for HMDB0001411 (Cotinine N-oxide)

3D PDB for HMDB0001411 (Cotinine N-oxide)

SMILES for HMDB0001411 (Cotinine N-oxide)

INCHI for HMDB0001411 (Cotinine N-oxide)

Structure for HMDB0001411 (Cotinine N-oxide)

3D Structure for HMDB0001411 (Cotinine N-oxide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra