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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:45:00 UTC

HMDB ID

HMDB0001390

Secondary Accession Numbers

HMDB01390

Metabolite Identification

Common Name

Hydroxycotinine

Description

Hydroxycotinine 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. It is also excreted as a glucuronide conjugate (3HC-Gluc). Hydroxycotinine is a strong basic compound (based on its pKa). hydroxycotinine can be biosynthesized from cotinine through its interaction with the enzyme cytochrome P450 2A6. In humans, hydroxycotinine is involved in nicotine metabolism pathway. Hydroxycotinine (3HC) is the main nicotine metabolite detected in smokers urine. Quantitatively, the most important metabolite of nicotine in most mammalian species is cotinine. 3HC and 3HC-Gluc account for 40-60% of the nicotine dose in urine.

Structure

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


  Mrv0541 02231219062D          

 14 15  0  0  1  0            999 V2000
    9.2615   -4.7254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7851   -5.3878    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0516   -4.9810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2615   -6.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9601   -5.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0516   -5.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7140   -4.4930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7168   -4.6789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0058   -3.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5418   -4.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5418   -6.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3101   -5.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7168   -6.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6301   -6.3045    0.0000 O   0  0  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  6  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001390

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1[C@@H](CC(O)C1=O)C1=CN=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N2O2/c1-12-8(5-9(13)10(12)14)7-3-2-4-11-6-7/h2-4,6,8-9,13H,5H2,1H3/t8-,9?/m0/s1

> <INCHI_KEY>
XOKCJXZZNAUIQN-IENPIDJESA-N

> <FORMULA>
C10H12N2O2

> <MOLECULAR_WEIGHT>
192.2145

> <EXACT_MASS>
192.089877638

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
19.4808912153036

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S)-3-hydroxy-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one

> <ALOGPS_LOGP>
-0.32

> <JCHEM_LOGP>
-0.7332253989999996

> <ALOGPS_LOGS>
-0.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.107323140437018

> <JCHEM_PKA_STRONGEST_BASIC>
4.788748646548031

> <JCHEM_POLAR_SURFACE_AREA>
53.43000000000001

> <JCHEM_REFRACTIVITY>
50.7291

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.77e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydroxycotinine

> <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      17.288  -8.821   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      16.399 -10.057   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.763  -9.298   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.288 -11.315   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.859 -10.057   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.763 -10.838   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      19.999  -8.387   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      12.538  -8.734   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      16.811  -7.346   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.078  -8.734   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.078 -11.402   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.779 -10.057   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.538 -11.402   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      19.843 -11.768   0.000  0.00  0.00           O+0
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   14                                                  
CONECT    7    3                                                            
CONECT    8   10   12                                                       
CONECT    9    1                                                            
CONECT   10    5    8                                                       
CONECT   11    5   13                                                       
CONECT   12    8   13                                                       
CONECT   13   11   12                                                       
CONECT   14    6                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

COMPND    HMDB0001390
HETATM    1  C1  UNL     1      -0.829   2.183   0.320  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.143   0.793   0.411  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.489   0.293   0.588  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.477   0.927   1.078  1.00  0.00           O  
HETATM    5  C3  UNL     1      -2.557  -1.111   0.099  1.00  0.00           C  
HETATM    6  O2  UNL     1      -2.592  -1.995   1.187  1.00  0.00           O  
HETATM    7  C4  UNL     1      -1.188  -1.250  -0.583  1.00  0.00           C  
HETATM    8  C5  UNL     1      -0.349  -0.408   0.362  1.00  0.00           C  
HETATM    9  C6  UNL     1       1.029  -0.252  -0.063  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.818   0.739   0.465  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.150   0.901   0.061  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.688   0.057  -0.882  1.00  0.00           C  
HETATM   13  N2  UNL     1       2.903  -0.908  -1.389  1.00  0.00           N  
HETATM   14  C10 UNL     1       1.603  -1.077  -1.003  1.00  0.00           C  
HETATM   15  H1  UNL     1      -0.002   2.408  -0.408  1.00  0.00           H  
HETATM   16  H2  UNL     1      -1.687   2.794  -0.071  1.00  0.00           H  
HETATM   17  H3  UNL     1      -0.606   2.623   1.313  1.00  0.00           H  
HETATM   18  H4  UNL     1      -3.381  -1.256  -0.600  1.00  0.00           H  
HETATM   19  H5  UNL     1      -2.296  -2.878   0.827  1.00  0.00           H  
HETATM   20  H6  UNL     1      -0.860  -2.285  -0.649  1.00  0.00           H  
HETATM   21  H7  UNL     1      -1.309  -0.749  -1.578  1.00  0.00           H  
HETATM   22  H8  UNL     1      -0.442  -0.935   1.358  1.00  0.00           H  
HETATM   23  H9  UNL     1       1.466   1.430   1.204  1.00  0.00           H  
HETATM   24  H10 UNL     1       3.759   1.686   0.485  1.00  0.00           H  
HETATM   25  H11 UNL     1       4.724   0.150  -1.225  1.00  0.00           H  
HETATM   26  H12 UNL     1       1.068  -1.882  -1.476  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    8
CONECT    3    4    4    5
CONECT    5    6    7   18
CONECT    6   19
CONECT    7    8   20   21
CONECT    8    9   22
CONECT    9   10   10   14
CONECT   10   11   23
CONECT   11   12   12   24
CONECT   12   13   25
CONECT   13   14   14
CONECT   14   26
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(3R-trans)-3-Hydroxy-1-methyl-5-(3-pyridinyl)-2-pyrrolidinone	HMDB
3-Hydroxy-1-methyl-5-(3-pyridinyl)-2-pyrrolidinone	HMDB
3-Hydroxycotinine	HMDB
trans-3'-Hydroxycotinine	HMDB
trans-3-Hydroxycotinine	HMDB
1-Methyl-3-hydroxy-5-(3-pyridyl)-2-pyrrolidinone	HMDB
3'-Hydroxycotinine	HMDB

Chemical Formula

C₁₀H₁₂N₂O₂

Average Molecular Weight

192.2145

Monoisotopic Molecular Weight

192.089877638

IUPAC Name

(5S)-3-hydroxy-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one

Traditional Name

hydroxycotinine

CAS Registry Number

34834-67-8

SMILES

CN1[C@@H](CC(O)C1=O)C1=CN=CC=C1

InChI Identifier

InChI=1S/C10H12N2O2/c1-12-8(5-9(13)10(12)14)7-3-2-4-11-6-7/h2-4,6,8-9,13H,5H2,1H3/t8-,9?/m0/s1

InChI Key

XOKCJXZZNAUIQN-IENPIDJESA-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
Pyrrolidone
2-pyrrolidone
N-alkylpyrrolidine
Pyrrolidine
Tertiary carboxylic acid amide
Heteroaromatic compound
Carboxamide group
Lactam
Secondary alcohol
Carboxylic acid derivative
Azacycle
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

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	-1.45	LI,NY & GORROD,JW (1992)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	47.7 g/L	ALOGPS
logP	-0.32	ALOGPS
logP	-0.73	ChemAxon
logS	-0.61	ALOGPS
pKa (Strongest Acidic)	13.11	ChemAxon
pKa (Strongest Basic)	4.79	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	53.43 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	50.73 m³·mol⁻¹	ChemAxon
Polarizability	19.48 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]+	142.227	31661259
DarkChem	[M-H]-	140.77	31661259
AllCCS	[M+H]+	143.02	32859911
AllCCS	[M-H]-	143.554	32859911
DeepCCS	[M+H]+	145.966	30932474
DeepCCS	[M-H]-	143.57	30932474
DeepCCS	[M-2H]-	177.051	30932474
DeepCCS	[M+Na]+	151.9	30932474
AllCCS	[M+H]+	143.0	32859911
AllCCS	[M+H-H2O]+	138.6	32859911
AllCCS	[M+NH4]+	147.1	32859911
AllCCS	[M+Na]+	148.3	32859911
AllCCS	[M-H]-	143.6	32859911
AllCCS	[M+Na-2H]-	143.9	32859911
AllCCS	[M+HCOO]-	144.4	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.	2.25 minutes	32390414
Predicted by Siyang on May 30, 2022	8.4514 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.43 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	128.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	530.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	243.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	78.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	156.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	38.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	229.2 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	251.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	246.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	563.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	41.7 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	716.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	174.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	179.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	482.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	425.2 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	192.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hydroxycotinine	CN1[C@@H](CC(O)C1=O)C1=CN=CC=C1	2713.8	Standard polar	33892256
Hydroxycotinine	CN1[C@@H](CC(O)C1=O)C1=CN=CC=C1	1837.3	Standard non polar	33892256
Hydroxycotinine	CN1[C@@H](CC(O)C1=O)C1=CN=CC=C1	1814.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hydroxycotinine,1TMS,isomer #1	CN1C(=O)C(O[Si](C)(C)C)C[C@H]1C1=CC=CN=C1	1831.1	Semi standard non polar	33892256
Hydroxycotinine,1TBDMS,isomer #1	CN1C(=O)C(O[Si](C)(C)C(C)(C)C)C[C@H]1C1=CC=CN=C1	2039.5	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 - Hydroxycotinine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kgy-3900000000-f4341e07a5c7a80b7536	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxycotinine GC-MS (1 TMS) - 70eV, Positive	splash10-0kmv-7920000000-c5ea44b12e63e343fb9a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxycotinine 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hydroxycotinine 0V, Positive-QTOF	splash10-0006-0900000000-eb516ddd256ff613e87d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hydroxycotinine 30V, Positive-QTOF	splash10-053r-9300000000-f280be49213ae3a13079	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hydroxycotinine 0V, Positive-QTOF	splash10-0006-0900000000-7bda1053fba136e84796	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hydroxycotinine 10V, Positive-QTOF	splash10-0006-0900000000-1c333f7a47d4c50ba147	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hydroxycotinine 30V, Positive-QTOF	splash10-001i-9200000000-764ed8e56080570ebb2b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hydroxycotinine 10V, Positive-QTOF	splash10-000l-2900000000-bb4782c424b825499da9	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycotinine 10V, Positive-QTOF	splash10-0006-0900000000-e71a8aefcc63f8da573f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycotinine 20V, Positive-QTOF	splash10-002f-0900000000-9c8836e76f228880b9ef	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycotinine 40V, Positive-QTOF	splash10-0006-9700000000-ac3865df5f81a068cc89	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycotinine 10V, Negative-QTOF	splash10-0006-0900000000-422cb094c7d4df4e9032	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycotinine 20V, Negative-QTOF	splash10-0006-1900000000-455cd9052e09eb5156d2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycotinine 40V, Negative-QTOF	splash10-004i-9800000000-dbdfb504e7cdb984dc83	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycotinine 10V, Positive-QTOF	splash10-0006-0900000000-0827985d284ee4847587	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycotinine 20V, Positive-QTOF	splash10-002f-0900000000-b7907c9e2b16530e9636	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycotinine 40V, Positive-QTOF	splash10-0a5c-5900000000-aeeff361755465a46a0a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycotinine 10V, Negative-QTOF	splash10-0006-0900000000-0bb6b33191167fa82f57	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycotinine 20V, Negative-QTOF	splash10-0fi3-3900000000-94e7e72f592f380dfd37	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycotinine 40V, Negative-QTOF	splash10-0ufr-8900000000-343920275b5ee98bf6ac	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

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Saliva
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	0.25 +/- 0.045 uM	Adult (>18 years old)	Both	Normal	12194923	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Saliva	Detected and Quantified	<1.00 uM	Adult (>18 years old)	Both	Normal	10080645	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.35 +/- 0.15 uM	Adult (>18 years old)	Both	Smoking	8294547	details
Blood	Detected and Quantified	1.5 (0.52-2.6) uM	Adult (>18 years old)	Both	Active tobacco user	12194923	details
Urine	Detected and Quantified	4.5 (1.0-8.5) umol/mmol creatinine	Adult (>18 years old)	Both	Active tobacco user	12194923	details

Associated Disorders and Diseases

Disease References

Smoking

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 ]
Moyer TP, Charlson JR, Enger RJ, Dale LC, Ebbert JO, Schroeder DR, Hurt RD: Simultaneous analysis of nicotine, nicotine metabolites, and tobacco alkaloids in serum or urine by tandem mass spectrometry, with clinically relevant metabolic profiles. Clin Chem. 2002 Sep;48(9):1460-71. [PubMed:12194923 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022597

KNApSAcK ID

Not Available

Chemspider ID

8395266

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6210

PubChem Compound

10219774

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000320

Good Scents ID

Not Available

References

Synthesis Reference

Jacob, Peyton, III; Shulgin, Alexander T.; Benowitz, Neal L. Synthesis of (3'R,5'S)-trans-3'-hydroxycotinine, a major metabolite of nicotine. Metabolic formation of 3'-hydroxycotinine in humans is highly stereoselective. J. Med. Chem. (1990), 33 (7), pp 1888–1891

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Bentley MC, Abrar M, Kelk M, Cook J, Phillips K: Validation of an assay for the determination of cotinine and 3-hydroxycotinine in human saliva using automated solid-phase extraction and liquid chromatography with tandem mass spectrometric detection. J Chromatogr B Biomed Sci Appl. 1999 Feb 19;723(1-2):185-94. [PubMed:10080645 ]
Moyer TP, Charlson JR, Enger RJ, Dale LC, Ebbert JO, Schroeder DR, Hurt RD: Simultaneous analysis of nicotine, nicotine metabolites, and tobacco alkaloids in serum or urine by tandem mass spectrometry, with clinically relevant metabolic profiles. Clin Chem. 2002 Sep;48(9):1460-71. [PubMed:12194923 ]
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 ]
Kim I, Huestis MA: A validated method for the determination of nicotine, cotinine, trans-3'-hydroxycotinine, and norcotinine in human plasma using solid-phase extraction and liquid chromatography-atmospheric pressure chemical ionization-mass spectrometry. J Mass Spectrom. 2006 Jun;41(6):815-21. [PubMed:16705667 ]
Pacifici R, Pichini S, Altieri I, Rosa M, Bacosi A, Caronna A, Zuccaro P: Determination of nicotine and two major metabolites in serum by solid-phase extraction and high-performance liquid chromatography, and high-performance liquid chromatography-particle beam mass spectrometry. J Chromatogr. 1993 Feb 26;612(2):209-13. [PubMed:8468378 ]
Tuomi T, Johnsson T, Reijula K: Analysis of nicotine, 3-hydroxycotinine, cotinine, and caffeine in urine of passive smokers by HPLC-tandem mass spectrometry. Clin Chem. 1999 Dec;45(12):2164-72. [PubMed:10585349 ]
Lerman C, Tyndale R, Patterson F, Wileyto EP, Shields PG, Pinto A, Benowitz N: Nicotine metabolite ratio predicts efficacy of transdermal nicotine for smoking cessation. Clin Pharmacol Ther. 2006 Jun;79(6):600-8. Epub 2006 May 11. [PubMed:16765148 ]

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 2B4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:: UGT2B4
Uniprot ID:: P06133
Molecular weight:: 60512.035

References

Yamanaka H, Nakajima M, Katoh M, Kanoh A, Tamura O, Ishibashi H, Yokoi T: Trans-3'-hydroxycotinine O- and N-glucuronidations in human liver microsomes. Drug Metab Dispos. 2005 Jan;33(1):23-30. Epub 2004 Oct 6. [PubMed:15470160 ]

Enzyme Details

2. UDP-glucuronosyltransferase 1-4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:: UGT1A4
Uniprot ID:: P22310
Molecular weight:: 60024.535

References

Yamanaka H, Nakajima M, Katoh M, Kanoh A, Tamura O, Ishibashi H, Yokoi T: Trans-3'-hydroxycotinine O- and N-glucuronidations in human liver microsomes. Drug Metab Dispos. 2005 Jan;33(1):23-30. Epub 2004 Oct 6. [PubMed:15470160 ]

Enzyme Details

3. UDP-glucuronosyltransferase 2B7

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:: UGT2B7
Uniprot ID:: P16662
Molecular weight:: 60720.15

References

Yamanaka H, Nakajima M, Katoh M, Kanoh A, Tamura O, Ishibashi H, Yokoi T: Trans-3'-hydroxycotinine O- and N-glucuronidations in human liver microsomes. Drug Metab Dispos. 2005 Jan;33(1):23-30. Epub 2004 Oct 6. [PubMed:15470160 ]

Enzyme Details

4. UDP-glucuronosyltransferase 1-9

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:: UGT1A9
Uniprot ID:: O60656
Molecular weight:: 59940.495

References

Yamanaka H, Nakajima M, Katoh M, Kanoh A, Tamura O, Ishibashi H, Yokoi T: Trans-3'-hydroxycotinine O- and N-glucuronidations in human liver microsomes. Drug Metab Dispos. 2005 Jan;33(1):23-30. Epub 2004 Oct 6. [PubMed:15470160 ]

Showing metabocard for Hydroxycotinine (HMDB0001390)

MOL for HMDB0001390 (Hydroxycotinine)

3D MOL for HMDB0001390 (Hydroxycotinine)

3D SDF for HMDB0001390 (Hydroxycotinine)

3D-SDF for HMDB0001390 (Hydroxycotinine)

PDB for HMDB0001390 (Hydroxycotinine)

3D PDB for HMDB0001390 (Hydroxycotinine)

SMILES for HMDB0001390 (Hydroxycotinine)

INCHI for HMDB0001390 (Hydroxycotinine)

Structure for HMDB0001390 (Hydroxycotinine)

3D Structure for HMDB0001390 (Hydroxycotinine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

References

References