NP-MRD: Showing NP-Card for [(e)-(3-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}hex-5-en-1-ylidene)amino]oxysulfonic acid (NP0146995)

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Record Information

Version

2.0

Created at

2022-09-02 02:30:13 UTC

Updated at

2022-09-02 02:30:14 UTC

NP-MRD ID

NP0146995

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(e)-(3-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}hex-5-en-1-ylidene)amino]oxysulfonic acid

Description

Gluconapoleiferin belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain. [(e)-(3-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}hex-5-en-1-ylidene)amino]oxysulfonic acid is found in Brassica rapa. [(e)-(3-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}hex-5-en-1-ylidene)amino]oxysulfonic acid was first documented in 2013 (PMID: 24014097). Based on a literature review a small amount of articles have been published on Gluconapoleiferin (PMID: 29379360) (PMID: 34685838) (PMID: 28337211).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022204302D          

 25 25  0  0  1  0            999 V2000
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 O   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  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  2  0  0  0  0
 10 13  1  0  0  0  0
  7 14  1  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  1  0  0  0
M  END

     RDKit          3D

 46 46  0  0  0  0  0  0  0  0999 V2000
   -3.1959   -3.5427    1.2404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5735   -2.2819    1.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0054   -1.3835    0.1408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2963   -0.1869    0.7846 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3120   -0.6657    1.6327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7619    0.6501   -0.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0246    1.8495    0.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7015    2.8287    0.6036 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0570    2.8061    0.7617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0171    3.7965   -0.2264 S   0  0  0  0  0  6  0  0  0  0  0  0
   -5.2657    2.9943   -0.5574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3261    4.2207   -1.4723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4903    5.1237    0.6895 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7346    1.9385   -0.0839 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.3313    0.4630   -0.9190 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1612   -0.6356   -0.1508 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2532   -1.1809    0.4673 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6461   -0.3796    1.7136 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7526   -0.9345    2.3336 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4258   -1.4034   -0.4351 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5836   -2.7599   -0.7008 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2791   -0.7067   -1.7677 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4621   -0.6588   -2.4714 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7138    0.6680   -1.4954 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5864    1.4278   -2.6550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4515   -3.9388    0.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5867   -4.2382    1.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3124   -1.9070    1.8455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7468   -0.9821   -0.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2221   -1.9268   -0.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0624    0.3944    1.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9806   -1.5317    1.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5999    1.0075   -0.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1494   -0.0286   -0.9753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0102    5.9605    0.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6621    0.3316   -1.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9473   -2.1740    0.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8257   -0.3914    2.4615 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7945    0.7006    1.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4868   -0.2444    2.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3482   -1.0247    0.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5018   -3.0798   -0.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5327   -1.2506   -2.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0542   -1.3681   -2.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3653    1.2438   -0.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7010    2.4013   -2.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14  7  1  0
  7  6  1  0
  6  4  1  0
  4  5  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 13  1  0
 10 11  2  0
 10 12  2  0
 15 24  1  0
 24 25  1  0
 24 22  1  0
 22 23  1  0
 22 20  1  0
 20 21  1  0
 20 17  1  0
 19 40  1  0
 18 38  1  0
 18 39  1  0
 17 37  1  1
 15 36  1  6
  6 33  1  0
  6 34  1  0
  4 31  1  1
  5 32  1  0
  3 29  1  0
  3 30  1  0
  2 28  1  0
  1 26  1  0
  1 27  1  0
 13 35  1  0
 24 45  1  1
 25 46  1  0
 22 43  1  6
 23 44  1  0
 20 41  1  1
 21 42  1  0
M  END


  Mrv1652309022204302D          

 25 25  0  0  1  0            999 V2000
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 O   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  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  2  0  0  0  0
 10 13  1  0  0  0  0
  7 14  1  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0146995

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](S\C(CC(O)CC=C)=N\OS(O)(=O)=O)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C12H21NO10S2/c1-2-3-6(15)4-8(13-23-25(19,20)21)24-12-11(18)10(17)9(16)7(5-14)22-12/h2,6-7,9-12,14-18H,1,3-5H2,(H,19,20,21)/b13-8+/t6?,7-,9-,10+,11-,12+/m1/s1

> <INCHI_KEY>
ZEGLQSKFSKZGRO-FYRHTRITSA-N

> <FORMULA>
C12H21NO10S2

> <MOLECULAR_WEIGHT>
403.42

> <EXACT_MASS>
403.060688228

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
37.39234645520162

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(E)-(3-hydroxy-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}hex-5-en-1-ylidene)amino]oxy}sulfonic acid

> <ALOGPS_LOGP>
-1.74

> <JCHEM_LOGP>
-3.5182120599905846

> <ALOGPS_LOGS>
-1.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.446325009718041

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.529833489762061

> <JCHEM_PKA_STRONGEST_BASIC>
-0.37542949155162353

> <JCHEM_POLAR_SURFACE_AREA>
186.34

> <JCHEM_REFRACTIVITY>
85.41460000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.78e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(E)-(3-hydroxy-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}hex-5-en-1-ylidene)amino]oxysulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669  -1.540   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      10.669   0.000   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0       9.336   0.770   0.000  0.00  0.00           O+0
HETATM   10  S   UNK     0       9.336   2.310   0.000  0.00  0.00           S+0
HETATM   11  O   UNK     0      10.876   2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       7.796   2.310   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   14  S   UNK     0      12.003  -2.310   0.000  0.00  0.00           S+0
HETATM   15  C   UNK     0      12.003  -3.850   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.337  -4.620   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      13.337  -6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      16.004  -6.160   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.003  -8.470   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.669  -6.160   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.336  -3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
CONECT   14    7   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   15   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₂₁NO₁₀S₂

Average Mass

403.4200 Da

Monoisotopic Mass

403.06069 Da

IUPAC Name

{[(E)-(3-hydroxy-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}hex-5-en-1-ylidene)amino]oxy}sulfonic acid

Traditional Name

[(E)-(3-hydroxy-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}hex-5-en-1-ylidene)amino]oxysulfonic acid

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](S\C(CC(O)CC=C)=N\OS(O)(=O)=O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C12H21NO10S2/c1-2-3-6(15)4-8(13-23-25(19,20)21)24-12-11(18)10(17)9(16)7(5-14)22-12/h2,6-7,9-12,14-18H,1,3-5H2,(H,19,20,21)/b13-8+/t6?,7-,9-,10+,11-,12+/m1/s1

InChI Key

ZEGLQSKFSKZGRO-FYRHTRITSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Brassica rapa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Alkylglucosinolates

Alternative Parents

Substituents

Alkylglucosinolate
Glycosyl compound
S-glycosyl compound
Oxane
Monothioacetal
Organic sulfuric acid or derivatives
Secondary alcohol
Oxacycle
Polyol
Organoheterocyclic compound
Sulfenyl compound
Alcohol
Organosulfur compound
Organonitrogen compound
Hydrocarbon derivative
Primary alcohol
Organic nitrogen compound
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

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	-1.7	ALOGPS
logP	-3.5	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	-3.5	ChemAxon
pKa (Strongest Basic)	-0.38	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	186.34 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	85.41 m³·mol⁻¹	ChemAxon
Polarizability	37.39 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00001477

Chemspider ID

7827559

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9548636

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chun JH, Kim NH, Seo MS, Jin M, Park SU, Arasu MV, Kim SJ, Al-Dhabi NA: Molecular characterization of glucosinolates and carotenoid biosynthetic genes in Chinese cabbage (Brassica rapa L. ssp. pekinensis). Saudi J Biol Sci. 2018 Jan;25(1):71-82. doi: 10.1016/j.sjbs.2016.04.004. Epub 2016 Apr 25. [PubMed:29379360 ]
Kim J, Sohn SI, Sathasivam R, Khaskheli AJ, Kim MC, Kim NS, Park SU: Targeted Metabolic and In-Silico Analyses Highlight Distinct Glucosinolates and Phenolics Signatures in Korean Rapeseed Cultivars. Plants (Basel). 2021 Sep 27;10(10):2027. doi: 10.3390/plants10102027. [PubMed:34685838 ]
Bonasia A, Lazzizera C, Elia A, Conversa G: Nutritional, Biophysical and Physiological Characteristics of Wild Rocket Genotypes As Affected by Soilless Cultivation System, Salinity Level of Nutrient Solution and Growing Period. Front Plant Sci. 2017 Mar 9;8:300. doi: 10.3389/fpls.2017.00300. eCollection 2017. [PubMed:28337211 ]
Hol WH, De Boer W, Termorshuizen AJ, Meyer KM, Schneider JH, Van Der Putten WH, Van Dam NM: Heterodera schachtii nematodes interfere with aphid-plant relations on Brassica oleracea. J Chem Ecol. 2013 Sep;39(9):1193-203. doi: 10.1007/s10886-013-0338-4. Epub 2013 Sep 8. [PubMed:24014097 ]
LOTUS database [Link]

Showing NP-Card for [(e)-(3-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}hex-5-en-1-ylidene)amino]oxysulfonic acid (NP0146995)

MOL for NP0146995 ([(e)-(3-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}hex-5-en-1-ylidene)amino]oxysulfonic acid)

3D MOL for NP0146995 ([(e)-(3-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}hex-5-en-1-ylidene)amino]oxysulfonic acid)

3D SDF for NP0146995 ([(e)-(3-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}hex-5-en-1-ylidene)amino]oxysulfonic acid)

3D-SDF for NP0146995 ([(e)-(3-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}hex-5-en-1-ylidene)amino]oxysulfonic acid)

PDB for NP0146995 ([(e)-(3-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}hex-5-en-1-ylidene)amino]oxysulfonic acid)

3D PDB for NP0146995 ([(e)-(3-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}hex-5-en-1-ylidene)amino]oxysulfonic acid)

SMILES for NP0146995 ([(e)-(3-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}hex-5-en-1-ylidene)amino]oxysulfonic acid)

INCHI for NP0146995 ([(e)-(3-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}hex-5-en-1-ylidene)amino]oxysulfonic acid)

Structure for NP0146995 ([(e)-(3-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}hex-5-en-1-ylidene)amino]oxysulfonic acid)

3D Structure for NP0146995 ([(e)-(3-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}hex-5-en-1-ylidene)amino]oxysulfonic acid)