NP-MRD: Showing NP-Card for Nicotine glucuronide (NP0086743)

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Record Information

Version

2.0

Created at

2022-05-11 16:29:46 UTC

Updated at

2022-05-11 16:29:46 UTC

NP-MRD ID

NP0086743

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Nicotine glucuronide

Description

Nicotine glucuronide belongs to the class of organic compounds known as purine ribonucleoside triphosphates. These are purine ribobucleotides with a triphosphate group linked to the ribose moiety. Nicotine glucuronide is a very strong basic compound (based on its pKa). Nicotine glucuronide and uridine 5'-diphosphate can be biosynthesized from nicotine and uridine diphosphate glucuronic acid; which is mediated by the enzymes UDP-glucuronosyltransferase 1-4 and UDP-glucuronosyltransferase 1-9. In humans, nicotine glucuronide is involved in nicotine metabolism pathway. Nicotine glucuronide was first documented in 1993 (PMID: 7902257). An N-glycosylpyridine that is the N-alpha-D-glucosiduronyl derivative of (S)-nicotine (PMID: 15894687) (PMID: 11201307) (PMID: 11846386) (PMID: 15265511) (PMID: 21497036).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 46 48  0  0  0  0  0  0  0  0999 V2000
   -5.1677   -1.1179   -0.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0290   -0.3243    0.2587 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4728    1.0147    0.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5475    1.9701   -0.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9992    1.1110   -1.3104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0042   -0.2642   -0.7820 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7698   -0.7758   -0.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8801   -1.9455    0.5670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7588   -2.4922    1.1534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4786   -1.8734    0.9790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5788   -0.7534    0.2457 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.8465   -0.1195    0.0671 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4862    0.1137    1.2673 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5504    0.9742    1.1632 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1131    2.3920    0.9445 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2692    2.9688   -0.1678 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5168    3.1335    1.9562 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.5632    0.5647    0.1314 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3919   -0.4035    0.7072 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9670    0.0190   -1.1215 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5239    1.0381   -1.9576 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7704   -0.8812   -0.8524 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2486   -2.0466   -0.2960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5222   -0.2452   -0.3109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6443   -1.4973    0.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8561   -0.4519   -0.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8913   -1.9488   -0.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4569    1.2046    1.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4923    1.1761    0.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0318    2.8317   -0.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6711    2.2426    0.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0624    1.5498   -1.6264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6941    1.1540   -2.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3285   -1.0016   -1.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8348   -2.4328    0.7081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7857   -3.3966    1.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480   -2.2933    1.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7012    0.8908   -0.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0767    0.9715    2.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1411    1.4944   -0.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7690   -1.0024    0.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7701   -0.5340   -1.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2907    1.3911   -2.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2821   -1.1039   -1.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6236   -1.9519    0.6014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4065    0.6504   -0.8907 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7 24  2  0
 24 11  1  0
 11 10  2  0
 10  9  1  0
  9  8  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 14 15  1  0
 15 17  1  0
 15 16  2  0
  6  2  1  0
  8  7  1  0
 22 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  6
 24 46  1  0
 10 37  1  0
  9 36  1  0
  8 35  1  0
 12 38  1  6
 14 39  1  1
 18 40  1  6
 19 41  1  0
 20 42  1  6
 21 43  1  0
 22 44  1  6
 23 45  1  0
M  CHG  2  11   1  17  -1
M  END


  Mrv0541 02231219012D          

 24 26  0  0  1  0            999 V2000
   11.6189   -6.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0023   -8.6391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7168   -8.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0023   -9.4641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4313   -9.4641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4515   -7.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8995   -8.5622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0390   -7.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4313   -8.6391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1457   -8.2266    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0023  -11.9392    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7168  -12.3517    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0023  -11.1142    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4313  -11.9392    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7168  -10.7017    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1457  -12.3517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7168   -9.8767    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   12.2320   -7.4061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2878  -12.3517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7168  -13.1767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2878  -10.7017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1457  -13.1767    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   12.8603  -11.9392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4313  -11.1142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  3  9  1  0  0  0  0
  4 17  2  0  0  0  0
  5  9  2  0  0  0  0
  5 17  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8 18  1  0  0  0  0
 10  9  1  1  0  0  0
 10 18  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 19  1  6  0  0  0
 12 14  1  0  0  0  0
 12 20  1  1  0  0  0
 13 15  1  0  0  0  0
 13 21  1  1  0  0  0
 14 16  1  6  0  0  0
 14 24  1  0  0  0  0
 15 17  1  1  0  0  0
 15 24  1  0  0  0  0
 16 22  1  0  0  0  0
 16 23  2  0  0  0  0
M  CHG  2  17   1  22  -1
M  END
> <DATABASE_ID>
NP0086743

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CCC[C@H]1C1=C[N+](=CC=C1)[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H22N2O6/c1-17-6-3-5-10(17)9-4-2-7-18(8-9)15-13(21)11(19)12(20)14(24-15)16(22)23/h2,4,7-8,10-15,19-21H,3,5-6H2,1H3/t10-,11-,12-,13+,14-,15-/m0/s1

> <INCHI_KEY>
SAWAIULJDYFLPD-SOAFEQHCSA-N

> <FORMULA>
C16H22N2O6

> <MOLECULAR_WEIGHT>
338.3557

> <EXACT_MASS>
338.147786446

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
33.41630530952722

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[(2S,3R,4S,5S,6S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-3-[(2S)-1-methylpyrrolidin-2-yl]-1λ⁵-pyridin-1-ylium

> <ALOGPS_LOGP>
-1.65

> <JCHEM_LOGP>
-7.262402522114074

> <ALOGPS_LOGS>
-1.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
11.709548854847307

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.5186103009766083

> <JCHEM_PKA_STRONGEST_BASIC>
7.4181638395435066

> <JCHEM_POLAR_SURFACE_AREA>
117.17

> <JCHEM_REFRACTIVITY>
94.17699999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.02e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nicotine glucuronide

> <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  C   UNK     0      21.689 -12.794   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.671 -16.126   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.005 -15.356   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.671 -17.666   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.338 -17.666   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.109 -14.838   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.079 -15.983   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.339 -13.505   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.338 -16.126   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.672 -15.356   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.671 -22.287   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.005 -23.057   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.671 -20.747   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      21.338 -22.287   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.005 -19.977   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.672 -23.057   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      20.005 -18.437   0.000  0.00  0.00           N+1
HETATM   18  N   UNK     0      22.833 -13.825   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      17.337 -23.057   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      20.005 -24.597   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      17.337 -19.977   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      22.672 -24.597   0.000  0.00  0.00           O-1
HETATM   23  O   UNK     0      24.006 -22.287   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      21.338 -20.747   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2    3    4                                                       
CONECT    3    2    9                                                       
CONECT    4    2   17                                                       
CONECT    5    9   17                                                       
CONECT    6    7    8                                                       
CONECT    7    6   10                                                       
CONECT    8    6   18                                                       
CONECT    9    3    5   10                                                  
CONECT   10    7    9   18                                                  
CONECT   11   12   13   19                                                  
CONECT   12   11   14   20                                                  
CONECT   13   11   15   21                                                  
CONECT   14   12   16   24                                                  
CONECT   15   13   17   24                                                  
CONECT   16   14   22   23                                                  
CONECT   17    4    5   15                                                  
CONECT   18    1    8   10                                                  
CONECT   19   11                                                            
CONECT   20   12                                                            
CONECT   21   13                                                            
CONECT   22   16                                                            
CONECT   23   16                                                            
CONECT   24   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
(S)-1-alpha-D-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)pyridinium inner salt	ChEBI
3,4,5-Trihydroxy-6-[5-(1-methylpyrrolidin-2-yl)pyridin-1-yl]-oxane-2-carboxylate	ChEBI
Nicotine N-glucuronide	ChEBI
(S)-1-a-D-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)pyridinium inner salt	Generator
(S)-1-Α-D-glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)pyridinium inner salt	Generator
3,4,5-Trihydroxy-6-[5-(1-methylpyrrolidin-2-yl)pyridin-1-yl]-oxane-2-carboxylic acid	Generator
(S)-1-alpha-D-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)-pyridinium inner salt	HMDB
(S)-1-alpha-delta-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)-pyridinium inner salt	HMDB
(S)-1-alpha-delta-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)pyridinium inner salt	HMDB
1-alpha-D-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)-(S)-pyridinium	HMDB
1-alpha-D-Glucopyranuronosyl-3-[(2S)-1-methyl-2-pyrrolidinyl]-pyridinium	HMDB
1-alpha-delta-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)-(S)-pyridinium	HMDB
1-alpha-delta-Glucopyranuronosyl-3-[(2S)-1-methyl-2-pyrrolidinyl]-pyridinium	HMDB
Nicotine-glucuronide	HMDB

Chemical Formula

C₁₆H₂₂N₂O₆

Average Mass

338.3557 Da

Monoisotopic Mass

338.14779 Da

IUPAC Name

1-[(2S,3R,4S,5S,6S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-3-[(2S)-1-methylpyrrolidin-2-yl]-1λ⁵-pyridin-1-ylium

Traditional Name

nicotine glucuronide

CAS Registry Number

Not Available

SMILES

CN1CCC[C@H]1C1=C[N+](=CC=C1)[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C([O-])=O

InChI Identifier

InChI=1S/C16H22N2O6/c1-17-6-3-5-10(17)9-4-2-7-18(8-9)15-13(21)11(19)12(20)14(24-15)16(22)23/h2,4,7-8,10-15,19-21H,3,5-6H2,1H3/t10-,11-,12-,13+,14-,15-/m0/s1

InChI Key

SAWAIULJDYFLPD-SOAFEQHCSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine ribonucleoside triphosphates. These are purine ribobucleotides with a triphosphate group linked to the ribose moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine ribonucleotides

Direct Parent

Purine ribonucleoside triphosphates

Alternative Parents

Substituents

Purine ribonucleoside triphosphate
Purine ribonucleoside monophosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Imidazopyrimidine
Purine
Monoalkyl phosphate
Hydroxypyrimidine
Alkyl phosphate
Pyrimidine
Monosaccharide
Phosphoric acid ester
N-substituted imidazole
Organic phosphoric acid derivative
Heteroaromatic compound
Azole
Imidazole
Tetrahydrofuran
Secondary alcohol
1,2-diol
Oxacycle
Organoheterocyclic compound
Azacycle
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

guanosine 5'-phosphate (CHEBI:15996 )
purine ribonucleoside 5'-triphosphate (CHEBI:15996 )
Ribonucleotides (C00044 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	-1.6	ALOGPS
logP	-7.3	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	2.52	ChemAxon
pKa (Strongest Basic)	7.42	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	117.17 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	94.18 m³·mol⁻¹	ChemAxon
Polarizability	33.42 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0001272

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022526

KNApSAcK ID

Not Available

Chemspider ID

2299987

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6127

PubChem Compound

3035848

PDB ID

Not Available

ChEBI ID

63860

Good Scents ID

Not Available

References

General References

Tulunay OE, Hecht SS, Carmella SG, Zhang Y, Lemmonds C, Murphy S, Hatsukami DK: Urinary metabolites of a tobacco-specific lung carcinogen in nonsmoking hospitality workers. Cancer Epidemiol Biomarkers Prev. 2005 May;14(5):1283-6. doi: 10.1158/1055-9965.EPI-04-0570. [PubMed:15894687 ]
Byrd GD, Caldwell WS, Bhatti BS, Ravard A, Crooks PA: Determination of nicotine N-1-glucuronide, a quaternary N-glucuronide conjugate, in human biological samples. Drug Metabol Drug Interact. 2000;16(4):281-97. doi: 10.1515/dmdi.2000.16.4.281. [PubMed:11201307 ]
Nakajima M, Kwon JT, Tanaka E, Yokoi T: High-performance liquid chromatographic assay for N-glucuronidation of nicotine and cotinine in human liver microsomes. Anal Biochem. 2002 Mar 1;302(1):131-5. doi: 10.1006/abio.2001.5528. [PubMed:11846386 ]
Yamanaka H, Nakajima M, Nishimura K, Yoshida R, Fukami T, Katoh M, Yokoi T: Metabolic profile of nicotine in subjects whose CYP2A6 gene is deleted. Eur J Pharm Sci. 2004 Aug;22(5):419-25. doi: 10.1016/j.ejps.2004.04.012. [PubMed:15265511 ]
Guo J, Zhou D, Grimm SW: Liquid chromatography-tandem mass spectrometry method for measurement of nicotine N-glucuronide: a marker for human UGT2B10 inhibition. J Pharm Biomed Anal. 2011 Jul 15;55(5):964-71. doi: 10.1016/j.jpba.2011.03.034. Epub 2011 Mar 29. [PubMed:21497036 ]
Seaton MJ, Kyerematen GA, Vesell ES: Rates of excretion of cotinine, nicotine glucuronide, and 3-hydroxycotinine glucuronide in rat bile. Drug Metab Dispos. 1993 Sep-Oct;21(5):927-32. [PubMed:7902257 ]

Showing NP-Card for Nicotine glucuronide (NP0086743)

MOL for NP0086743 (Nicotine glucuronide)

3D MOL for NP0086743 (Nicotine glucuronide)

3D SDF for NP0086743 (Nicotine glucuronide)

3D-SDF for NP0086743 (Nicotine glucuronide)

PDB for NP0086743 (Nicotine glucuronide)

3D PDB for NP0086743 (Nicotine glucuronide)

SMILES for NP0086743 (Nicotine glucuronide)

INCHI for NP0086743 (Nicotine glucuronide)

Structure for NP0086743 (Nicotine glucuronide)

3D Structure for NP0086743 (Nicotine glucuronide)