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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:32 UTC

HMDB ID

HMDB0001240

Secondary Accession Numbers

HMDB01240

Metabolite Identification

Common Name

Pseudooxynicotine

Description

Nicorette is a branded over-the-counter palliative treatment which is used to ameliorate the withdrawal effects involved in quitting smoking. Originally available as a patch for topical application, it was later made available as a nicotine gum (composed of nicotine polacrilex)lozenge, inhaler, and nasal spray. All these products contain nicotine as the active ingredient and work by delivering this into the bloodstream.

Structure

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

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  C   UNK     0       9.347 -20.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.117 -21.668   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.347 -23.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.807 -23.001   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       7.037 -21.668   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       7.807 -20.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.117 -19.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.347 -17.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.117 -16.333   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.347 -14.999   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      10.117 -13.666   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       9.347 -12.332   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.657 -19.000   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    1    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    7                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    HMDB0001240
HETATM    1  C1  UNL     1      -3.785   0.641  -0.483  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.557   0.750  -1.207  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.035  -0.512  -1.683  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.571  -1.407  -0.581  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.489  -0.863   0.286  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.735  -0.594  -0.491  1.00  0.00           C  
HETATM    7  O1  UNL     1       0.754  -0.897  -1.705  1.00  0.00           O  
HETATM    8  C6  UNL     1       1.919   0.024   0.154  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.073   0.282  -0.549  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.149   0.863   0.104  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.122   1.199   1.444  1.00  0.00           C  
HETATM   12  N2  UNL     1       2.972   0.928   2.091  1.00  0.00           N  
HETATM   13  C10 UNL     1       1.908   0.366   1.488  1.00  0.00           C  
HETATM   14  H1  UNL     1      -4.422  -0.132  -0.916  1.00  0.00           H  
HETATM   15  H2  UNL     1      -3.659   0.430   0.593  1.00  0.00           H  
HETATM   16  H3  UNL     1      -4.294   1.650  -0.524  1.00  0.00           H  
HETATM   17  H4  UNL     1      -1.841   1.337  -0.735  1.00  0.00           H  
HETATM   18  H5  UNL     1      -2.924  -1.039  -2.152  1.00  0.00           H  
HETATM   19  H6  UNL     1      -1.295  -0.294  -2.467  1.00  0.00           H  
HETATM   20  H7  UNL     1      -2.482  -1.704  -0.003  1.00  0.00           H  
HETATM   21  H8  UNL     1      -1.264  -2.372  -1.083  1.00  0.00           H  
HETATM   22  H9  UNL     1      -0.849   0.057   0.811  1.00  0.00           H  
HETATM   23  H10 UNL     1      -0.293  -1.620   1.092  1.00  0.00           H  
HETATM   24  H11 UNL     1       3.084   0.015  -1.595  1.00  0.00           H  
HETATM   25  H12 UNL     1       5.063   1.065  -0.457  1.00  0.00           H  
HETATM   26  H13 UNL     1       4.968   1.652   1.946  1.00  0.00           H  
HETATM   27  H14 UNL     1       1.014   0.175   2.067  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   17
CONECT    3    4   18   19
CONECT    4    5   20   21
CONECT    5    6   22   23
CONECT    6    7    7    8
CONECT    8    9    9   13
CONECT    9   10   24
CONECT   10   11   11   25
CONECT   11   12   26
CONECT   12   13   13
CONECT   13   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(Methylamino)-1-(3-pyridinyl)-1-butanone	ChEBI
4-(Methylamino)-1-(3-pyridyl)-1-butanone	ChEBI
4-(Methylamino)-1-(pyridin-3-yl)butan-1-one	Kegg

Chemical Formula

C₁₀H₁₄N₂O

Average Molecular Weight

178.231

Monoisotopic Molecular Weight

178.11061308

IUPAC Name

4-(methylamino)-1-(pyridin-3-yl)butan-1-one

Traditional Name

pseudooxynicotine

CAS Registry Number

2055-23-4

SMILES

CNCCCC(=O)C1=CC=CN=C1

InChI Identifier

InChI=1S/C10H14N2O/c1-11-6-3-5-10(13)9-4-2-7-12-8-9/h2,4,7-8,11H,3,5-6H2,1H3

InChI Key

SGDIDUFQYHRMPR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl alkyl ketones

Alternative Parents

Substituents

Aryl alkyl ketone
Pyridine
Gamma-aminoketone
Heteroaromatic compound
Azacycle
Organoheterocyclic compound
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyridine alkaloid (CHEBI:37753 )
aminoacylpyridine (CHEBI:37753 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cell membrane (HMDB: HMDB0001240)
Membrane (HMDB: HMDB0001240)

Source

Endogenous

Endogenous (HMDB: HMDB0001240)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

Process

Not Available

Role

Not Available

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	7.2 g/L	ALOGPS
logP	0.36	ALOGPS
logP	0.35	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	15.84	ChemAxon
pKa (Strongest Basic)	10.28	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	51.89 m³·mol⁻¹	ChemAxon
Polarizability	20.2 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	142.491	31661259
DarkChem	[M-H]-	139.03	31661259
AllCCS	[M+H]+	139.717	32859911
AllCCS	[M-H]-	143.324	32859911
DeepCCS	[M+H]+	141.124	30932474
DeepCCS	[M-H]-	137.293	30932474
DeepCCS	[M-2H]-	174.872	30932474
DeepCCS	[M+Na]+	150.468	30932474
AllCCS	[M+H]+	139.7	32859911
AllCCS	[M+H-H2O]+	135.5	32859911
AllCCS	[M+NH4]+	143.7	32859911
AllCCS	[M+Na]+	144.8	32859911
AllCCS	[M-H]-	143.3	32859911
AllCCS	[M+Na-2H]-	144.3	32859911
AllCCS	[M+HCOO]-	145.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pseudooxynicotine	CNCCCC(=O)C1=CC=CN=C1	2282.8	Standard polar	33892256
Pseudooxynicotine	CNCCCC(=O)C1=CC=CN=C1	1695.2	Standard non polar	33892256
Pseudooxynicotine	CNCCCC(=O)C1=CC=CN=C1	1643.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pseudooxynicotine,1TMS,isomer #1	CN(CCCC(=O)C1=CC=CN=C1)[Si](C)(C)C	1800.4	Semi standard non polar	33892256
Pseudooxynicotine,1TMS,isomer #1	CN(CCCC(=O)C1=CC=CN=C1)[Si](C)(C)C	1814.4	Standard non polar	33892256
Pseudooxynicotine,1TMS,isomer #1	CN(CCCC(=O)C1=CC=CN=C1)[Si](C)(C)C	2206.9	Standard polar	33892256
Pseudooxynicotine,1TBDMS,isomer #1	CN(CCCC(=O)C1=CC=CN=C1)[Si](C)(C)C(C)(C)C	2027.2	Semi standard non polar	33892256
Pseudooxynicotine,1TBDMS,isomer #1	CN(CCCC(=O)C1=CC=CN=C1)[Si](C)(C)C(C)(C)C	2063.5	Standard non polar	33892256
Pseudooxynicotine,1TBDMS,isomer #1	CN(CCCC(=O)C1=CC=CN=C1)[Si](C)(C)C(C)(C)C	2328.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Pseudooxynicotine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-8900000000-a51d7230ba64ee05b9bf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pseudooxynicotine 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 - Pseudooxynicotine 10V, Positive-QTOF	splash10-004i-0900000000-864e3a7b118c43c28ab9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudooxynicotine 20V, Positive-QTOF	splash10-0a4i-2900000000-aa5527fd5a4939d5db96	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudooxynicotine 40V, Positive-QTOF	splash10-0a4i-9400000000-6e453ee4f5fffb43f0f3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudooxynicotine 10V, Negative-QTOF	splash10-004i-1900000000-3d5c5ae2acb462ff372e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudooxynicotine 20V, Negative-QTOF	splash10-004i-2900000000-772a8d554e7586b358c6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudooxynicotine 40V, Negative-QTOF	splash10-004i-9400000000-1eb60cdce5693a6699c5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudooxynicotine 10V, Positive-QTOF	splash10-0002-0900000000-ba736bf097495f199225	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudooxynicotine 20V, Positive-QTOF	splash10-006t-3900000000-51e47f5c6d14a31b8725	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudooxynicotine 40V, Positive-QTOF	splash10-001i-9400000000-6b4f5e53b780312a852c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudooxynicotine 10V, Negative-QTOF	splash10-004i-0900000000-403f45bf7fa583376662	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudooxynicotine 20V, Negative-QTOF	splash10-004i-5900000000-64491dac933fd429afa6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudooxynicotine 40V, Negative-QTOF	splash10-00ou-9100000000-f2b7446f5c11b5b26757	2021-09-22	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+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

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB022506

KNApSAcK ID

Not Available

Chemspider ID

421

KEGG Compound ID

C20361

BioCyc ID

CPD-14092

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6100

PubChem Compound

434

PDB ID

Not Available

ChEBI ID

37753

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Kisaki, Takuro; Maeda, Susumu; Sasaki, So; Mikami, Yoichi; Uchida, Setsuko. Pseudooxynicotine. Jpn. Kokai Tokkyo Koho (1977), 6 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Pseudooxynicotine (HMDB0001240)

MOL for HMDB0001240 (Pseudooxynicotine)

3D MOL for HMDB0001240 (Pseudooxynicotine)

3D SDF for HMDB0001240 (Pseudooxynicotine)

3D-SDF for HMDB0001240 (Pseudooxynicotine)

PDB for HMDB0001240 (Pseudooxynicotine)

3D PDB for HMDB0001240 (Pseudooxynicotine)

SMILES for HMDB0001240 (Pseudooxynicotine)

INCHI for HMDB0001240 (Pseudooxynicotine)

Structure for HMDB0001240 (Pseudooxynicotine)

3D Structure for HMDB0001240 (Pseudooxynicotine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra