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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 17:15:41 UTC

HMDB ID

HMDB0001427

Secondary Accession Numbers

HMDB01427

Metabolite Identification

Common Name

5'-Hydroxycotinine

Description

5'-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. In humans, 5'-hydroxycotinine is involved in the nicotine metabolism pathway. 5'-Hydroxycotinine has been detected, but not quantified in, several different foods, such as mustard spinaches (Brassica perviridis), pepper (capsicum), oats (Avena sativa), black raspberries (Rubus occidentalis), and hazelnuts (Corylus). This could make 5'-hydroxycotinine a potential biomarker for the consumption of these foods. 5'-Hydroxycotinine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on 5'-Hydroxycotinine.

Structure

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

  Mrv0541 02231219082D          

 14 15  0  0  1  0            999 V2000
   10.6322   -3.8895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1560   -4.5518    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4224   -4.1452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6322   -5.2257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3310   -4.5518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4224   -4.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0845   -3.6572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0878   -3.8431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3767   -3.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9127   -3.8431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9127   -5.2721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6812   -4.5518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0878   -5.2721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7536   -5.3491    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
  2 14  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0001427

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C(=O)CC[C@@]1(O)C1=CN=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N2O2/c1-12-9(13)4-5-10(12,14)8-3-2-6-11-7-8/h2-3,6-7,14H,4-5H2,1H3/t10-/m1/s1

> <INCHI_KEY>
BBNHNZGTKSWIHD-SNVBAGLBSA-N

> <FORMULA>
C10H12N2O2

> <MOLECULAR_WEIGHT>
192.2145

> <EXACT_MASS>
192.089877638

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
19.285753743481255

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
-0.31

> <JCHEM_LOGP>
-0.20775097999999995

> <ALOGPS_LOGS>
-0.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.205621012526843

> <JCHEM_PKA_STRONGEST_BASIC>
4.560258040946622

> <JCHEM_POLAR_SURFACE_AREA>
53.43000000000001

> <JCHEM_REFRACTIVITY>
50.8582

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.02e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-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      19.847  -7.260   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      18.958  -8.497   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.322  -7.738   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.847  -9.755   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.418  -8.497   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.322  -9.277   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      22.558  -6.827   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      15.097  -7.174   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      19.370  -5.786   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.637  -7.174   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.637  -9.841   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.338  -8.497   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.097  -9.841   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      18.207  -9.985   0.000  0.00  0.00           O+0
CONECT    1    2    3    9                                                  
CONECT    2    1    4    5   14                                             
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                                                       
CONECT    9    1                                                            
CONECT   10    5    8                                                       
CONECT   11    5   13                                                       
CONECT   12    8   13                                                       
CONECT   13   11   12                                                       
CONECT   14    2                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

COMPND    HMDB0001427
HETATM    1  C1  UNL     1      -1.823   1.727  -0.041  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.513   0.341   0.214  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.540  -0.666   0.108  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.738  -0.478  -0.161  1.00  0.00           O  
HETATM    5  C3  UNL     1      -1.937  -2.005   0.379  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.537  -1.692  -0.195  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.341  -0.363   0.588  1.00  0.00           C  
HETATM    8  O2  UNL     1      -0.499  -0.744   1.932  1.00  0.00           O  
HETATM    9  C6  UNL     1       0.962   0.197   0.315  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.701  -0.218  -0.777  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.975   0.273  -1.027  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.542   1.207  -0.173  1.00  0.00           C  
HETATM   13  N2  UNL     1       2.809   1.600   0.890  1.00  0.00           N  
HETATM   14  C10 UNL     1       1.562   1.125   1.139  1.00  0.00           C  
HETATM   15  H1  UNL     1      -1.885   2.007  -1.105  1.00  0.00           H  
HETATM   16  H2  UNL     1      -2.877   1.946   0.341  1.00  0.00           H  
HETATM   17  H3  UNL     1      -1.172   2.438   0.502  1.00  0.00           H  
HETATM   18  H4  UNL     1      -1.803  -2.083   1.476  1.00  0.00           H  
HETATM   19  H5  UNL     1      -2.409  -2.837  -0.107  1.00  0.00           H  
HETATM   20  H6  UNL     1      -0.646  -1.462  -1.242  1.00  0.00           H  
HETATM   21  H7  UNL     1       0.226  -2.414   0.081  1.00  0.00           H  
HETATM   22  H8  UNL     1      -0.496   0.056   2.522  1.00  0.00           H  
HETATM   23  H9  UNL     1       1.296  -0.940  -1.479  1.00  0.00           H  
HETATM   24  H10 UNL     1       3.548  -0.082  -1.904  1.00  0.00           H  
HETATM   25  H11 UNL     1       4.553   1.587  -0.372  1.00  0.00           H  
HETATM   26  H12 UNL     1       1.042   1.480   2.028  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    7
CONECT    3    4    4    5
CONECT    5    6   18   19
CONECT    6    7   20   21
CONECT    7    8    9
CONECT    8   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
5-Hydroxycotinine	HMDB
Allohydroxycotinine	HMDB

Chemical Formula

C₁₀H₁₂N₂O₂

Average Molecular Weight

192.2145

Monoisotopic Molecular Weight

192.089877638

IUPAC Name

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

Traditional Name

5-hydroxycotinine

CAS Registry Number

61192-50-5

SMILES

CN1C(=O)CC[C@@]1(O)C1=CN=CC=C1

InChI Identifier

InChI=1S/C10H12N2O2/c1-12-9(13)4-5-10(12,14)8-3-2-6-11-7-8/h2-3,6-7,14H,4-5H2,1H3/t10-/m1/s1

InChI Key

BBNHNZGTKSWIHD-SNVBAGLBSA-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
Lactam
Carboxamide group
Alkanolamine
Carboxylic acid derivative
Azacycle
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Liver (HMDB: HMDB0001427)
Kidney (HMDB: HMDB0001427)

Cellular substructure

Cytoplasm (HMDB: HMDB0001427)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001427)

Source

Endogenous

Endogenous (HMDB: HMDB0001427)

Plant

Animal

Animal (HMDB: HMDB0001427)

Exogenous

Food

Food (HMDB: HMDB0001427)

Animal origin

Poultry

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)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Nicotine Metabolism Pathway (HMDB: HMDB0001427)
Nicotine Metabolism Pathway (PathBank: SMP0000628)

Drug action pathway

Nicotine Action Pathway (HMDB: HMDB0001427)
Nicotine Action Pathway (PathBank: SMP0000431)

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	90.2 g/L	ALOGPS
logP	-0.31	ALOGPS
logP	-0.21	ChemAxon
logS	-0.33	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	4.56	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	50.86 m³·mol⁻¹	ChemAxon
Polarizability	19.29 Å³	ChemAxon
Number of Rings	2	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]+	144.72	31661259
DarkChem	[M-H]-	142.443	31661259
AllCCS	[M+H]+	142.564	32859911
AllCCS	[M-H]-	143.773	32859911
DeepCCS	[M+H]+	142.831	30932474
DeepCCS	[M-H]-	140.435	30932474
DeepCCS	[M-2H]-	174.051	30932474
DeepCCS	[M+Na]+	148.785	30932474
AllCCS	[M+H]+	142.6	32859911
AllCCS	[M+H-H2O]+	138.1	32859911
AllCCS	[M+NH4]+	146.7	32859911
AllCCS	[M+Na]+	147.9	32859911
AllCCS	[M-H]-	143.8	32859911
AllCCS	[M+Na-2H]-	144.1	32859911
AllCCS	[M+HCOO]-	144.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5'-Hydroxycotinine	CN1C(=O)CC[C@@]1(O)C1=CN=CC=C1	2741.5	Standard polar	33892256
5'-Hydroxycotinine	CN1C(=O)CC[C@@]1(O)C1=CN=CC=C1	1695.8	Standard non polar	33892256
5'-Hydroxycotinine	CN1C(=O)CC[C@@]1(O)C1=CN=CC=C1	1786.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5'-Hydroxycotinine,1TMS,isomer #1	CN1C(=O)CC[C@@]1(O[Si](C)(C)C)C1=CC=CN=C1	1782.6	Semi standard non polar	33892256
5'-Hydroxycotinine,1TBDMS,isomer #1	CN1C(=O)CC[C@@]1(O[Si](C)(C)C(C)(C)C)C1=CC=CN=C1	2034.9	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 - 5'-Hydroxycotinine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ab9-4900000000-8fdc38303fa2e9d326fb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5'-Hydroxycotinine GC-MS (1 TMS) - 70eV, Positive	splash10-0096-8910000000-5a6063a4febbd48d8de4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5'-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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxycotinine 10V, Positive-QTOF	splash10-0006-0900000000-a2649b94dc708d963d16	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxycotinine 20V, Positive-QTOF	splash10-0006-1900000000-d93e8b5830f8c7b52206	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxycotinine 40V, Positive-QTOF	splash10-0ini-9300000000-09c593e669cadd74a021	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxycotinine 10V, Negative-QTOF	splash10-0006-0900000000-350e405fd056b470d809	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxycotinine 20V, Negative-QTOF	splash10-0006-0900000000-e329ecf023780fbb4b78	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxycotinine 40V, Negative-QTOF	splash10-0a6r-9400000000-be7f33457d59944bfacb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxycotinine 10V, Positive-QTOF	splash10-0006-0900000000-326a8bf022204233521d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxycotinine 20V, Positive-QTOF	splash10-001u-1900000000-bb5c51deec943ef81547	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxycotinine 40V, Positive-QTOF	splash10-0059-9300000000-c7ab8eb53e732eb149b4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxycotinine 10V, Negative-QTOF	splash10-0006-2900000000-dc09a61c7f2c3099543f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxycotinine 20V, Negative-QTOF	splash10-002f-4900000000-725ea1c3192b3356573d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxycotinine 40V, Negative-QTOF	splash10-056u-9600000000-5f4aedc4e9f9fde04d4c	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	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

Cytoplasm (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Kidney
Liver

Pathways

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

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

FDB022616

KNApSAcK ID

Not Available

Chemspider ID

7991265

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6239

PubChem Compound

9815515

PDB ID

Not Available

ChEBI ID

173530

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 5'-Hydroxycotinine (HMDB0001427)

MOL for HMDB0001427 (5'-Hydroxycotinine)

3D MOL for HMDB0001427 (5'-Hydroxycotinine)

3D SDF for HMDB0001427 (5'-Hydroxycotinine)

3D-SDF for HMDB0001427 (5'-Hydroxycotinine)

PDB for HMDB0001427 (5'-Hydroxycotinine)

3D PDB for HMDB0001427 (5'-Hydroxycotinine)

SMILES for HMDB0001427 (5'-Hydroxycotinine)

INCHI for HMDB0001427 (5'-Hydroxycotinine)

Structure for HMDB0001427 (5'-Hydroxycotinine)

3D Structure for HMDB0001427 (5'-Hydroxycotinine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra