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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (18) Show 18 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:18:07 UTC

HMDB ID

HMDB0001204

Secondary Accession Numbers

HMDB01204

Metabolite Identification

Common Name

trans-3-Hydroxycotinine glucuronide

Description

trans-3-Hydroxycotinine glucuronide, also known as 3HC-gluc, belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond. trans-3-Hydroxycotinine glucuronide is a strong basic compound (based on its pKa). In humans, trans-3-hydroxycotinine glucuronide is involved in nicotine action pathway.

Structure

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


  Mrv0541 02231218592D          

 27 29  0  0  1  0            999 V2000
    8.6657  -15.3156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6657  -16.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3802  -16.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0947  -16.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0947  -15.3156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3802  -14.9031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8091  -16.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8954  -17.3736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7023  -17.5451    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.1148  -16.8306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5628  -16.2175    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9354  -16.7444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7343  -15.4106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0379  -18.2988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5530  -18.9662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.7325  -18.8800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2476  -19.5475    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.5831  -20.3011    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4036  -20.3874    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.8885  -19.7199    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.7090  -19.8061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7392  -21.1410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4271  -19.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0982  -20.9686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0915  -18.7075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9421  -20.1287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3735  -19.0525    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11  7  1  0  0  0  0
 10 12  2  0  0  0  0
 11 13  1  0  0  0  0
  9 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 15  1  0  0  0  0
 20 21  1  6  0  0  0
 19 22  1  1  0  0  0
 17 23  1  1  0  0  0
 18 24  1  6  0  0  0
 23 25  2  0  0  0  0
 23 26  1  0  0  0  0
 15 27  1  6  0  0  0
M  END

HMDB0001204
     RDKit          3D
trans-3-Hydroxycotinine glucuronide
 46 48  0  0  0  0  0  0  0  0999 V2000
    3.0119   -2.6975   -0.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2991   -1.4163   -0.5031 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2912   -1.0036    0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1105   -1.5663    1.5281 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5256    0.1278   -0.1697 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8082   -0.3033   -0.2697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6704    0.4920    0.4878 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1909   -0.2970    1.4790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5486   -0.3531    1.5461 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0107   -1.1745    2.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2155   -1.3917    2.9437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0677   -1.7773    3.4814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0554   -0.8113    0.2007 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3765   -1.2200    0.2262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9028    0.4329   -0.6853 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0333    0.0312   -2.0162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6423    1.1557   -0.4139 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9397    2.4357    0.0555 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1490    0.3102   -1.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5118   -0.3141   -1.4235 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5648    0.6052   -0.9834 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4981    1.0448   -1.8979 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5185    1.9223   -1.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5661    2.3357   -0.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6464    1.8975    0.6853 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6660    1.0536    0.3140 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8858   -2.5786    0.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3016   -2.9587   -1.5814 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3591   -3.5244   -0.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6241    1.0044    0.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0354    1.2650    0.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9241    0.6928    1.7195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0203   -1.4595    4.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3596   -1.5846   -0.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4248   -2.0766    0.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7829    1.0644   -0.4477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5889   -0.8702   -2.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1340    1.3246   -1.4100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4060    2.9543   -0.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5279   -0.1531   -2.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2551    1.4124   -1.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7543   -0.7952   -2.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5087    0.7554   -2.9341 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2543    2.2727   -2.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3659    3.0239    0.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9418    0.7128    1.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 20  2  1  0
 26 21  1  0
 17  7  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  5 30  1  1
  7 31  1  1
  9 32  1  1
 12 33  1  0
 13 34  1  6
 14 35  1  0
 15 36  1  1
 16 37  1  0
 17 38  1  6
 18 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  1  0
 22 43  1  0
 23 44  1  0
 24 45  1  0
 26 46  1  0
M  END


  Mrv0541 02231218592D          

 27 29  0  0  1  0            999 V2000
    8.6657  -15.3156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6657  -16.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3802  -16.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0947  -16.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0947  -15.3156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3802  -14.9031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8091  -16.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8954  -17.3736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7023  -17.5451    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.1148  -16.8306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5628  -16.2175    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9354  -16.7444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7343  -15.4106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0379  -18.2988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5530  -18.9662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.7325  -18.8800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2476  -19.5475    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.5831  -20.3011    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4036  -20.3874    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.8885  -19.7199    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.7090  -19.8061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7392  -21.1410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4271  -19.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0982  -20.9686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0915  -18.7075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9421  -20.1287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3735  -19.0525    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11  7  1  0  0  0  0
 10 12  2  0  0  0  0
 11 13  1  0  0  0  0
  9 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 15  1  0  0  0  0
 20 21  1  6  0  0  0
 19 22  1  1  0  0  0
 17 23  1  1  0  0  0
 18 24  1  6  0  0  0
 23 25  2  0  0  0  0
 23 26  1  0  0  0  0
 15 27  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0001204

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(O[C@@H]2CC(N(C)C2=O)C2=CC=CN=C2)O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H20N2O8/c1-18-8(7-3-2-4-17-6-7)5-9(14(18)22)25-16-12(21)10(19)11(20)13(26-16)15(23)24/h2-4,6,8-13,16,19-21H,5H2,1H3,(H,23,24)/t8?,9-,10+,11+,12-,13+,16-/m1/s1

> <INCHI_KEY>
WALNNKZUGHYSCT-QBYCBOKUSA-N

> <FORMULA>
C16H20N2O8

> <MOLECULAR_WEIGHT>
368.3386

> <EXACT_MASS>
368.121965626

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
35.294882038769614

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(3R)-1-methyl-2-oxo-5-(pyridin-3-yl)pyrrolidin-3-yl]oxy}oxane-2-carboxylic acid

> <ALOGPS_LOGP>
-1.70

> <JCHEM_LOGP>
-3.288512647477155

> <ALOGPS_LOGS>
-0.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.226886899472197

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2272433205673607

> <JCHEM_PKA_STRONGEST_BASIC>
4.800834381183043

> <JCHEM_POLAR_SURFACE_AREA>
149.65

> <JCHEM_REFRACTIVITY>
83.00979999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.89e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(3R)-1-methyl-2-oxo-5-(pyridin-3-yl)pyrrolidin-3-yl]oxy}oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001204
     RDKit          3D
trans-3-Hydroxycotinine glucuronide
 46 48  0  0  0  0  0  0  0  0999 V2000
    3.0119   -2.6975   -0.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2991   -1.4163   -0.5031 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2912   -1.0036    0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1105   -1.5663    1.5281 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5256    0.1278   -0.1697 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8082   -0.3033   -0.2697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6704    0.4920    0.4878 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1909   -0.2970    1.4790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5486   -0.3531    1.5461 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0107   -1.1745    2.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2155   -1.3917    2.9437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0677   -1.7773    3.4814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0554   -0.8113    0.2007 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3765   -1.2200    0.2262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9028    0.4329   -0.6853 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0333    0.0312   -2.0162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6423    1.1557   -0.4139 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9397    2.4357    0.0555 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1490    0.3102   -1.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5118   -0.3141   -1.4235 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5648    0.6052   -0.9834 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4981    1.0448   -1.8979 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5185    1.9223   -1.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5661    2.3357   -0.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6464    1.8975    0.6853 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6660    1.0536    0.3140 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8858   -2.5786    0.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3016   -2.9587   -1.5814 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3591   -3.5244   -0.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6241    1.0044    0.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0354    1.2650    0.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9241    0.6928    1.7195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0203   -1.4595    4.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3596   -1.5846   -0.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4248   -2.0766    0.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7829    1.0644   -0.4477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5889   -0.8702   -2.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1340    1.3246   -1.4100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4060    2.9543   -0.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5279   -0.1531   -2.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2551    1.4124   -1.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7543   -0.7952   -2.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5087    0.7554   -2.9341 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2543    2.2727   -2.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3659    3.0239    0.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9418    0.7128    1.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 20  2  1  0
 26 21  1  0
 17  7  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  5 30  1  1
  7 31  1  1
  9 32  1  1
 12 33  1  0
 13 34  1  6
 14 35  1  0
 15 36  1  1
 16 37  1  0
 17 38  1  6
 18 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  1  0
 22 43  1  0
 23 44  1  0
 24 45  1  0
 26 46  1  0
M  END

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      16.176 -28.589   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.176 -30.129   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.510 -30.899   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.843 -30.129   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      18.843 -28.589   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      17.510 -27.819   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      20.177 -30.899   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.338 -32.431   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.844 -32.751   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.614 -31.417   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      21.584 -30.273   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0      24.146 -31.256   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      21.904 -28.766   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      22.471 -34.158   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      21.566 -35.404   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      20.034 -35.243   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      19.129 -36.489   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.755 -37.895   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.287 -38.056   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.192 -36.810   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      23.723 -36.971   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      21.913 -39.463   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      17.597 -36.328   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      18.850 -39.141   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      16.971 -34.921   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      16.692 -37.574   0.000  0.00  0.00           O+0
HETATM   27  H   UNK     0      23.097 -35.565   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    7   13                                                  
CONECT   12   10                                                            
CONECT   13   11                                                            
CONECT   14    9   15                                                       
CONECT   15   14   16   20   27                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19   24                                                  
CONECT   19   18   20   22                                                  
CONECT   20   19   15   21                                                  
CONECT   21   20                                                            
CONECT   22   19                                                            
CONECT   23   17   25   26                                                  
CONECT   24   18                                                            
CONECT   25   23                                                            
CONECT   26   23                                                            
CONECT   27   15                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

COMPND    HMDB0001204
HETATM    1  C1  UNL     1       3.012  -2.697  -0.531  1.00  0.00           C  
HETATM    2  N1  UNL     1       2.299  -1.416  -0.503  1.00  0.00           N  
HETATM    3  C2  UNL     1       1.291  -1.004   0.396  1.00  0.00           C  
HETATM    4  O1  UNL     1       1.110  -1.566   1.528  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.526   0.128  -0.170  1.00  0.00           C  
HETATM    6  O2  UNL     1      -0.808  -0.303  -0.270  1.00  0.00           O  
HETATM    7  C4  UNL     1      -1.670   0.492   0.488  1.00  0.00           C  
HETATM    8  O3  UNL     1      -2.191  -0.297   1.479  1.00  0.00           O  
HETATM    9  C5  UNL     1      -3.549  -0.353   1.546  1.00  0.00           C  
HETATM   10  C6  UNL     1      -4.011  -1.174   2.657  1.00  0.00           C  
HETATM   11  O4  UNL     1      -5.215  -1.392   2.944  1.00  0.00           O  
HETATM   12  O5  UNL     1      -3.068  -1.777   3.481  1.00  0.00           O  
HETATM   13  C7  UNL     1      -4.055  -0.811   0.201  1.00  0.00           C  
HETATM   14  O6  UNL     1      -5.376  -1.220   0.226  1.00  0.00           O  
HETATM   15  C8  UNL     1      -3.903   0.433  -0.685  1.00  0.00           C  
HETATM   16  O7  UNL     1      -4.033   0.031  -2.016  1.00  0.00           O  
HETATM   17  C9  UNL     1      -2.642   1.156  -0.414  1.00  0.00           C  
HETATM   18  O8  UNL     1      -2.940   2.436   0.056  1.00  0.00           O  
HETATM   19  C10 UNL     1       1.149   0.310  -1.524  1.00  0.00           C  
HETATM   20  C11 UNL     1       2.512  -0.314  -1.423  1.00  0.00           C  
HETATM   21  C12 UNL     1       3.565   0.605  -0.983  1.00  0.00           C  
HETATM   22  C13 UNL     1       4.498   1.045  -1.898  1.00  0.00           C  
HETATM   23  C14 UNL     1       5.518   1.922  -1.514  1.00  0.00           C  
HETATM   24  C15 UNL     1       5.566   2.336  -0.198  1.00  0.00           C  
HETATM   25  N2  UNL     1       4.646   1.897   0.685  1.00  0.00           N  
HETATM   26  C16 UNL     1       3.666   1.054   0.314  1.00  0.00           C  
HETATM   27  H1  UNL     1       3.886  -2.579   0.134  1.00  0.00           H  
HETATM   28  H2  UNL     1       3.302  -2.959  -1.581  1.00  0.00           H  
HETATM   29  H3  UNL     1       2.359  -3.524  -0.172  1.00  0.00           H  
HETATM   30  H4  UNL     1       0.624   1.004   0.485  1.00  0.00           H  
HETATM   31  H5  UNL     1      -1.035   1.265   0.970  1.00  0.00           H  
HETATM   32  H6  UNL     1      -3.924   0.693   1.719  1.00  0.00           H  
HETATM   33  H7  UNL     1      -3.020  -1.460   4.462  1.00  0.00           H  
HETATM   34  H8  UNL     1      -3.360  -1.585  -0.183  1.00  0.00           H  
HETATM   35  H9  UNL     1      -5.425  -2.077   0.698  1.00  0.00           H  
HETATM   36  H10 UNL     1      -4.783   1.064  -0.448  1.00  0.00           H  
HETATM   37  H11 UNL     1      -3.589  -0.870  -2.073  1.00  0.00           H  
HETATM   38  H12 UNL     1      -2.134   1.325  -1.410  1.00  0.00           H  
HETATM   39  H13 UNL     1      -3.406   2.954  -0.655  1.00  0.00           H  
HETATM   40  H14 UNL     1       0.528  -0.153  -2.331  1.00  0.00           H  
HETATM   41  H15 UNL     1       1.255   1.412  -1.697  1.00  0.00           H  
HETATM   42  H16 UNL     1       2.754  -0.795  -2.402  1.00  0.00           H  
HETATM   43  H17 UNL     1       4.509   0.755  -2.934  1.00  0.00           H  
HETATM   44  H18 UNL     1       6.254   2.273  -2.222  1.00  0.00           H  
HETATM   45  H19 UNL     1       6.366   3.024   0.104  1.00  0.00           H  
HETATM   46  H20 UNL     1       2.942   0.713   1.026  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3   20
CONECT    3    4    4    5
CONECT    5    6   19   30
CONECT    6    7
CONECT    7    8   17   31
CONECT    8    9
CONECT    9   10   13   32
CONECT   10   11   11   12
CONECT   12   33
CONECT   13   14   15   34
CONECT   14   35
CONECT   15   16   17   36
CONECT   16   37
CONECT   17   18   38
CONECT   18   39
CONECT   19   20   40   41
CONECT   20   21   42
CONECT   21   22   22   26
CONECT   22   23   43
CONECT   23   24   24   44
CONECT   24   25   45
CONECT   25   26   26
CONECT   26   46
END

HMDB0001204
     RDKit          3D
trans-3-Hydroxycotinine glucuronide
 46 48  0  0  0  0  0  0  0  0999 V2000
    3.0119   -2.6975   -0.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2991   -1.4163   -0.5031 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2912   -1.0036    0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1105   -1.5663    1.5281 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5256    0.1278   -0.1697 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8082   -0.3033   -0.2697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6704    0.4920    0.4878 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1909   -0.2970    1.4790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5486   -0.3531    1.5461 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0107   -1.1745    2.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2155   -1.3917    2.9437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0677   -1.7773    3.4814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0554   -0.8113    0.2007 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3765   -1.2200    0.2262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9028    0.4329   -0.6853 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0333    0.0312   -2.0162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6423    1.1557   -0.4139 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9397    2.4357    0.0555 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1490    0.3102   -1.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5118   -0.3141   -1.4235 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5648    0.6052   -0.9834 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4981    1.0448   -1.8979 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5185    1.9223   -1.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5661    2.3357   -0.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6464    1.8975    0.6853 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6660    1.0536    0.3140 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8858   -2.5786    0.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3016   -2.9587   -1.5814 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3591   -3.5244   -0.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6241    1.0044    0.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0354    1.2650    0.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9241    0.6928    1.7195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0203   -1.4595    4.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3596   -1.5846   -0.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4248   -2.0766    0.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7829    1.0644   -0.4477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5889   -0.8702   -2.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1340    1.3246   -1.4100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4060    2.9543   -0.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5279   -0.1531   -2.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2551    1.4124   -1.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7543   -0.7952   -2.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5087    0.7554   -2.9341 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2543    2.2727   -2.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3659    3.0239    0.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9418    0.7128    1.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 20  2  1  0
 26 21  1  0
 17  7  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  5 30  1  1
  7 31  1  1
  9 32  1  1
 12 33  1  0
 13 34  1  6
 14 35  1  0
 15 36  1  1
 16 37  1  0
 17 38  1  6
 18 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  1  0
 22 43  1  0
 23 44  1  0
 24 45  1  0
 26 46  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3'-Hydroxycotnine-glucuronide	HMDB
3HC-Gluc	HMDB
trans-3-Hydroxycotinine-glucuronide	HMDB

Chemical Formula

C₁₆H₂₀N₂O₈

Average Molecular Weight

368.3386

Monoisotopic Molecular Weight

368.121965626

IUPAC Name

(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(3R)-1-methyl-2-oxo-5-(pyridin-3-yl)pyrrolidin-3-yl]oxy}oxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(3R)-1-methyl-2-oxo-5-(pyridin-3-yl)pyrrolidin-3-yl]oxy}oxane-2-carboxylic acid

CAS Registry Number

132929-88-5

SMILES

[H][C@@]1(O[C@@H]2CC(N(C)C2=O)C2=CC=CN=C2)O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C16H20N2O8/c1-18-8(7-3-2-4-17-6-7)5-9(14(18)22)25-16-12(21)10(19)11(20)13(26-16)15(23)24/h2-4,6,8-13,16,19-21H,5H2,1H3,(H,23,24)/t8?,9-,10+,11+,12-,13+,16-/m1/s1

InChI Key

WALNNKZUGHYSCT-QBYCBOKUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glucuronides

Alternative Parents

Substituents

1-o-glucuronide
O-glucuronide
Glycosyl compound
O-glycosyl compound
Pyrrolidinylpyridine
Alkaloid or derivatives
Beta-hydroxy acid
Hydroxy acid
Monosaccharide
Oxane
Pyran
Pyridine
Pyrrolidone
2-pyrrolidone
N-alkylpyrrolidine
Pyrrolidine
Tertiary carboxylic acid amide
Heteroaromatic compound
Secondary alcohol
Carboxamide group
Lactam
Azacycle
Organoheterocyclic compound
Carboxylic acid
Oxacycle
Carboxylic acid derivative
Polyol
Acetal
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Alcohol
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Non-excretory biofluid

Blood (HMDB: HMDB0001204)

Excreta

Urine (HMDB: HMDB0001204)

Organ

Liver (HMDB: HMDB0001204)
Kidney (HMDB: HMDB0001204)

Cellular substructure

Cytoplasm (HMDB: HMDB0001204)

Source

Endogenous

Endogenous (HMDB: HMDB0001204)

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

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Venison

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

Bovine

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Nicotine Action Pathway (HMDB: HMDB0001204)

Drug action pathway

Nicotine Action Pathway (PathBank: SMP0000431)

Metabolic pathway

Nicotine Metabolism Pathway (PathBank: SMP0000628)

Role

Biological role

Drug metabolite (HMDB: HMDB0001204)

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	38.9 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-3.3	ChemAxon
logS	-0.98	ALOGPS
pKa (Strongest Acidic)	3.23	ChemAxon
pKa (Strongest Basic)	4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	149.65 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	83.01 m³·mol⁻¹	ChemAxon
Polarizability	35.29 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	188.113	31661259
DarkChem	[M-H]-	177.663	31661259
AllCCS	[M+H]+	186.453	32859911
AllCCS	[M-H]-	184.156	32859911
DeepCCS	[M+H]+	180.322	30932474
DeepCCS	[M-H]-	177.927	30932474
DeepCCS	[M-2H]-	211.087	30932474
DeepCCS	[M+Na]+	187.448	30932474
AllCCS	[M+H]+	186.5	32859911
AllCCS	[M+H-H2O]+	183.6	32859911
AllCCS	[M+NH4]+	189.1	32859911
AllCCS	[M+Na]+	189.8	32859911
AllCCS	[M-H]-	184.2	32859911
AllCCS	[M+Na-2H]-	184.0	32859911
AllCCS	[M+HCOO]-	183.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
trans-3-Hydroxycotinine glucuronide	[H][C@@]1(O[C@@H]2CC(N(C)C2=O)C2=CC=CN=C2)O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O	4249.4	Standard polar	33892256
trans-3-Hydroxycotinine glucuronide	[H][C@@]1(O[C@@H]2CC(N(C)C2=O)C2=CC=CN=C2)O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O	2976.0	Standard non polar	33892256
trans-3-Hydroxycotinine glucuronide	[H][C@@]1(O[C@@H]2CC(N(C)C2=O)C2=CC=CN=C2)O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O	3374.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
trans-3-Hydroxycotinine glucuronide,1TMS,isomer #1	CN1C(=O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O)CC1C1=CC=CN=C1	2961.9	Semi standard non polar	33892256
trans-3-Hydroxycotinine glucuronide,1TMS,isomer #2	CN1C(=O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O)CC1C1=CC=CN=C1	2948.6	Semi standard non polar	33892256
trans-3-Hydroxycotinine glucuronide,1TMS,isomer #3	CN1C(=O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C)CC1C1=CC=CN=C1	2930.8	Semi standard non polar	33892256
trans-3-Hydroxycotinine glucuronide,1TMS,isomer #4	CN1C(=O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]2O)CC1C1=CC=CN=C1	2954.2	Semi standard non polar	33892256
trans-3-Hydroxycotinine glucuronide,2TMS,isomer #1	CN1C(=O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O)CC1C1=CC=CN=C1	2972.4	Semi standard non polar	33892256
trans-3-Hydroxycotinine glucuronide,2TMS,isomer #2	CN1C(=O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O)CC1C1=CC=CN=C1	2969.1	Semi standard non polar	33892256
trans-3-Hydroxycotinine glucuronide,2TMS,isomer #3	CN1C(=O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C)CC1C1=CC=CN=C1	2951.6	Semi standard non polar	33892256
trans-3-Hydroxycotinine glucuronide,2TMS,isomer #4	CN1C(=O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O)CC1C1=CC=CN=C1	2950.0	Semi standard non polar	33892256
trans-3-Hydroxycotinine glucuronide,2TMS,isomer #5	CN1C(=O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)CC1C1=CC=CN=C1	2942.0	Semi standard non polar	33892256
trans-3-Hydroxycotinine glucuronide,2TMS,isomer #6	CN1C(=O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C)CC1C1=CC=CN=C1	2937.5	Semi standard non polar	33892256
trans-3-Hydroxycotinine glucuronide,3TMS,isomer #1	CN1C(=O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O)CC1C1=CC=CN=C1	2970.2	Semi standard non polar	33892256
trans-3-Hydroxycotinine glucuronide,3TMS,isomer #2	CN1C(=O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C)CC1C1=CC=CN=C1	2963.8	Semi standard non polar	33892256
trans-3-Hydroxycotinine glucuronide,3TMS,isomer #3	CN1C(=O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)CC1C1=CC=CN=C1	2947.5	Semi standard non polar	33892256
trans-3-Hydroxycotinine glucuronide,3TMS,isomer #4	CN1C(=O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)CC1C1=CC=CN=C1	2939.6	Semi standard non polar	33892256
trans-3-Hydroxycotinine glucuronide,4TMS,isomer #1	CN1C(=O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)CC1C1=CC=CN=C1	2985.9	Semi standard non polar	33892256
trans-3-Hydroxycotinine glucuronide,1TBDMS,isomer #1	CN1C(=O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O)CC1C1=CC=CN=C1	3195.1	Semi standard non polar	33892256
trans-3-Hydroxycotinine glucuronide,1TBDMS,isomer #2	CN1C(=O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)CC1C1=CC=CN=C1	3196.3	Semi standard non polar	33892256
trans-3-Hydroxycotinine glucuronide,1TBDMS,isomer #3	CN1C(=O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)CC1C1=CC=CN=C1	3182.6	Semi standard non polar	33892256
trans-3-Hydroxycotinine glucuronide,1TBDMS,isomer #4	CN1C(=O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]2O)CC1C1=CC=CN=C1	3208.5	Semi standard non polar	33892256
trans-3-Hydroxycotinine glucuronide,2TBDMS,isomer #1	CN1C(=O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O)CC1C1=CC=CN=C1	3411.2	Semi standard non polar	33892256
trans-3-Hydroxycotinine glucuronide,2TBDMS,isomer #2	CN1C(=O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)CC1C1=CC=CN=C1	3390.7	Semi standard non polar	33892256
trans-3-Hydroxycotinine glucuronide,2TBDMS,isomer #3	CN1C(=O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)CC1C1=CC=CN=C1	3389.0	Semi standard non polar	33892256
trans-3-Hydroxycotinine glucuronide,2TBDMS,isomer #4	CN1C(=O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)CC1C1=CC=CN=C1	3394.8	Semi standard non polar	33892256
trans-3-Hydroxycotinine glucuronide,2TBDMS,isomer #5	CN1C(=O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)CC1C1=CC=CN=C1	3375.7	Semi standard non polar	33892256
trans-3-Hydroxycotinine glucuronide,2TBDMS,isomer #6	CN1C(=O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)CC1C1=CC=CN=C1	3393.0	Semi standard non polar	33892256
trans-3-Hydroxycotinine glucuronide,3TBDMS,isomer #1	CN1C(=O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)CC1C1=CC=CN=C1	3575.2	Semi standard non polar	33892256
trans-3-Hydroxycotinine glucuronide,3TBDMS,isomer #2	CN1C(=O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)CC1C1=CC=CN=C1	3597.1	Semi standard non polar	33892256
trans-3-Hydroxycotinine glucuronide,3TBDMS,isomer #3	CN1C(=O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)CC1C1=CC=CN=C1	3554.8	Semi standard non polar	33892256
trans-3-Hydroxycotinine glucuronide,3TBDMS,isomer #4	CN1C(=O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)CC1C1=CC=CN=C1	3563.3	Semi standard non polar	33892256
trans-3-Hydroxycotinine glucuronide,4TBDMS,isomer #1	CN1C(=O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)CC1C1=CC=CN=C1	3746.6	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 - trans-3-Hydroxycotinine glucuronide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0k96-9073000000-a76eb98dd2fd62dd0584	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-3-Hydroxycotinine glucuronide GC-MS (4 TMS) - 70eV, Positive	splash10-0006-4201179000-9254404b076d74eeae1c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-3-Hydroxycotinine glucuronide 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 - trans-3-Hydroxycotinine glucuronide 10V, Positive-QTOF	splash10-00mo-0905000000-7038294c68496223be60	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Hydroxycotinine glucuronide 20V, Positive-QTOF	splash10-002f-0900000000-e54057ee0f0d26f3f378	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Hydroxycotinine glucuronide 40V, Positive-QTOF	splash10-00ac-1900000000-00b8bf1411dcaf0caf62	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Hydroxycotinine glucuronide 10V, Negative-QTOF	splash10-00r6-2907000000-30422e965692a971b41a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Hydroxycotinine glucuronide 20V, Negative-QTOF	splash10-0006-1902000000-11066820c76bbb6636dc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Hydroxycotinine glucuronide 40V, Negative-QTOF	splash10-06wd-4900000000-4188e8db1462ca96d24e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Hydroxycotinine glucuronide 10V, Positive-QTOF	splash10-014i-0009000000-f1fda6b1d975224b623d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Hydroxycotinine glucuronide 20V, Positive-QTOF	splash10-004l-0903000000-05352da20e71cb23d0ca	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Hydroxycotinine glucuronide 40V, Positive-QTOF	splash10-0002-1900000000-a1583b9a514b1fe49564	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Hydroxycotinine glucuronide 10V, Negative-QTOF	splash10-014i-0409000000-4e639ab1f3da97839083	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Hydroxycotinine glucuronide 20V, Negative-QTOF	splash10-05bf-4903000000-0beee16561bfd1bc86f5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Hydroxycotinine glucuronide 40V, Negative-QTOF	splash10-0pdl-5910000000-1226b09b79453fef7cb4	2021-09-22	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

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

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

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022490

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6080

PubChem Compound

53477725

PDB ID

Not Available

ChEBI ID

Not Available

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

Rop PP, Grimaldi F, Oddoze C, Viala A: Determination of nicotine and its main metabolites in urine by high-performance liquid chromatography. J Chromatogr. 1993 Feb 26;612(2):302-9. [PubMed:8468389 ]

Only showing the first 10 proteins. There are 18 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 2B28

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 has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
Gene Name:: UGT2B28
Uniprot ID:: Q9BY64
Molecular weight:: 38742.9

Enzyme Details

2. 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

Enzyme Details

3. 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

Kuehl GE, Murphy SE: N-glucuronidation of nicotine and cotinine by human liver microsomes and heterologously expressed UDP-glucuronosyltransferases. Drug Metab Dispos. 2003 Nov;31(11):1361-8. [PubMed:14570768 ]

Enzyme Details

4. 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

Enzyme Details

5. UDP-glucuronosyltransferase 2B15

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 displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
Gene Name:: UGT2B15
Uniprot ID:: P54855
Molecular weight:: 61035.815

Enzyme Details

6. UDP-glucuronosyltransferase 2A1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
Gene Name:: UGT2A1
Uniprot ID:: Q9Y4X1
Molecular weight:: 60771.605

Enzyme Details

7. UDP-glucuronosyltransferase 1-1

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. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Enzyme Details

8. 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

Enzyme Details

9. UDP-glucuronosyltransferase 1-3

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.
Gene Name:: UGT1A3
Uniprot ID:: P35503
Molecular weight:: 60337.835

Enzyme Details

10. UDP-glucuronosyltransferase 2B17

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. The major substrates of this isozyme are eugenol > 4-methylumbelliferone > dihydrotestosterone (DHT) > androstane-3-alpha,17-beta-diol (3-alpha-diol) > testosterone > androsterone (ADT).
Gene Name:: UGT2B17
Uniprot ID:: O75795
Molecular weight:: 61094.915

Only showing the first 10 proteins. There are 18 proteins in total.

Show all enzymes and transporters

Showing metabocard for trans-3-Hydroxycotinine glucuronide (HMDB0001204)

MOL for HMDB0001204 (trans-3-Hydroxycotinine glucuronide)

3D MOL for HMDB0001204 (trans-3-Hydroxycotinine glucuronide)

3D SDF for HMDB0001204 (trans-3-Hydroxycotinine glucuronide)

3D-SDF for HMDB0001204 (trans-3-Hydroxycotinine glucuronide)

PDB for HMDB0001204 (trans-3-Hydroxycotinine glucuronide)

3D PDB for HMDB0001204 (trans-3-Hydroxycotinine glucuronide)

SMILES for HMDB0001204 (trans-3-Hydroxycotinine glucuronide)

INCHI for HMDB0001204 (trans-3-Hydroxycotinine glucuronide)

Structure for HMDB0001204 (trans-3-Hydroxycotinine glucuronide)

3D Structure for HMDB0001204 (trans-3-Hydroxycotinine glucuronide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References