NP-MRD: Showing NP-Card for [(e)-(4-methanesulfinyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}butylidene)amino]oxysulfonic acid (NP0329544)

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Record Information

Version

2.0

Created at

2022-09-12 14:01:58 UTC

Updated at

2022-09-12 14:01:58 UTC

NP-MRD ID

NP0329544

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Glucoiberin belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain. [(e)-(4-methanesulfinyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}butylidene)amino]oxysulfonic acid is found in Brassica macrocarpa, Brassica oleracea and Brassica tournefortii. [(e)-(4-methanesulfinyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}butylidene)amino]oxysulfonic acid was first documented in 2016 (PMID: 28231170). Glucoiberin is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 32316621) (PMID: 31889076) (PMID: 31336993) (PMID: 31328127) (PMID: 30920356) (PMID: 30827654).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652305142022542D          

 25 25  0  0  0  0            999 V2000
    3.9296    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0716    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    1.2374    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3572    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7861    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0717    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0717    1.2374    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3572    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9296    1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.6500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151    1.2374    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3569   -1.2421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0714   -0.8296    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4827   -1.5446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0716    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8952   -0.8301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  1  0  0  0
  7  3  1  0  0  0  0
  8  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12  7  2  0  0  0  0
 13  5  1  0  0  0  0
  8 14  1  6  0  0  0
  9 15  1  1  0  0  0
 10 16  1  6  0  0  0
 18  6  1  0  0  0  0
 18 11  1  0  0  0  0
 19  7  1  0  0  0  0
 11 19  1  1  0  0  0
 20  1  1  0  0  0  0
 20  4  1  0  0  0  0
 20 17  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 22 25  2  0  0  0  0
 24 12  1  0  0  0  0
M  END

     RDKit          3D

 46 46  0  0  0  0  0  0  0  0999 V2000
    5.2406   -1.2585   -0.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7615   -2.1925   -0.4113 S   0  0  0  0  0  4  0  0  0  0  0  0
    3.2541   -2.4118   -1.7857 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5656   -1.9581    0.8669 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1732   -0.4936    0.8994 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5914   -0.1616   -0.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1358    1.2228   -0.5981 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0479    2.1481   -0.5961 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3813    1.8514   -0.4694 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5402    3.0226   -0.0981 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.7607    2.8814   -0.9899 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0089    2.9082    1.3199 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8278    4.5327   -0.3956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5645    1.6316   -0.7730 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6762    0.2075   -0.8050 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9513    0.7343   -1.0400 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9457   -0.2154   -0.8370 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2431    0.3056   -1.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2867   -0.6036   -1.2259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0800   -0.5035    0.6424 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2466   -1.8743    0.7911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8022   -0.0743    1.3370 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7228    1.3145    1.4451 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5832   -0.4928    0.5089 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4919   -1.8714    0.4171 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6801   -1.0519   -1.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9956   -0.2642    0.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9857   -1.7496    0.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6286   -2.5291    0.6653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9486   -2.2863    1.8548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1455    0.0834    1.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5354   -0.2498    1.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7709   -0.8417   -0.7172 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3978   -0.3508   -1.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7555    5.0525    0.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4498   -0.4800   -1.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6973   -1.1442   -1.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1781    0.5246   -2.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5727    1.2411   -0.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1561   -1.3254   -1.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9253    0.0590    1.1052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0548   -2.1045    1.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7132   -0.5594    2.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8481    1.6240    2.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7078   -0.1164    1.0646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2351   -2.1806   -0.4849 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 13  1  0
 10 11  2  0
 10 12  2  0
 24 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
 15 36  1  6
 17 37  1  6
 18 38  1  0
 18 39  1  0
 19 40  1  0
 20 41  1  1
 21 42  1  0
 22 43  1  1
 23 44  1  0
 24 45  1  1
 25 46  1  0
 13 35  1  0
M  END


  Mrv1652305142022542D          

 25 25  0  0  0  0            999 V2000
    3.9296    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0716    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    1.2374    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3572    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7861    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0717    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0717    1.2374    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3572    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9296    1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.6500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151    1.2374    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3569   -1.2421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0714   -0.8296    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4827   -1.5446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0716    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8952   -0.8301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  1  0  0  0
  7  3  1  0  0  0  0
  8  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12  7  2  0  0  0  0
 13  5  1  0  0  0  0
  8 14  1  6  0  0  0
  9 15  1  1  0  0  0
 10 16  1  6  0  0  0
 18  6  1  0  0  0  0
 18 11  1  0  0  0  0
 19  7  1  0  0  0  0
 11 19  1  1  0  0  0
 20  1  1  0  0  0  0
 20  4  1  0  0  0  0
 20 17  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 22 25  2  0  0  0  0
 24 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0329544

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CS(=O)CCC\C(S[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)=N/OS(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H21NO10S3/c1-24(17)4-2-3-7(12-22-25(18,19)20)23-11-10(16)9(15)8(14)6(5-13)21-11/h6,8-11,13-16H,2-5H2,1H3,(H,18,19,20)/b12-7+/t6-,8-,9+,10-,11+,24?/m1/s1

> <INCHI_KEY>
PHYYADMVYQURSX-WWFIZPDBSA-N

> <FORMULA>
C11H21NO10S3

> <MOLECULAR_WEIGHT>
423.47

> <EXACT_MASS>
423.032759402

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
38.191377069396204

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.50

> <JCHEM_LOGP>
-5.130768098874457

> <ALOGPS_LOGS>
-1.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.447674453512157

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.679235365764975

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5072423700546337

> <JCHEM_POLAR_SURFACE_AREA>
183.18

> <JCHEM_REFRACTIVITY>
89.01799999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.16e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-MAY-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAY-20         0                                  
HETATM    1  C   UNK     0       7.335   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.000   3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.668   3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.002   3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.667   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.668   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.334   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.001   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       0.667   0.770   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0      -7.335   2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -6.002   0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -3.334  -1.540   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -0.667   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.002   0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -3.334   3.080   0.000  0.00  0.00           O+0
HETATM   19  S   UNK     0      -0.667   3.080   0.000  0.00  0.00           S+0
HETATM   20  S   UNK     0       6.002   2.310   0.000  0.00  0.00           S+0
HETATM   21  O   UNK     0       0.666  -2.319   0.000  0.00  0.00           O+0
HETATM   22  S   UNK     0       2.000  -1.549   0.000  0.00  0.00           S+0
HETATM   23  O   UNK     0       2.768  -2.883   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.000   0.000   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       3.538  -1.550   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2    3    4                                                       
CONECT    3    2    7                                                       
CONECT    4    2   20                                                       
CONECT    5    6   13                                                       
CONECT    6    5    8   18                                                  
CONECT    7    3   12   19                                                  
CONECT    8    6    9   14                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10   18   19                                                  
CONECT   12    7   24                                                       
CONECT   13    5                                                            
CONECT   14    8                                                            
CONECT   15    9                                                            
CONECT   16   10                                                            
CONECT   17   20                                                            
CONECT   18    6   11                                                       
CONECT   19    7   11                                                       
CONECT   20    1    4   17                                                  
CONECT   21   22                                                            
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22   12                                                       
CONECT   25   22                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

View in JSmol

Synonyms

Value	Source
3-(Methylsulfinyl)propyl glucosinolate	HMDB
Glucoiberin	HMDB
3-Methylsulfinylpropyl glucosinolate	HMDB

Chemical Formula

C₁₁H₂₁NO₁₀S₃

Average Mass

423.4700 Da

Monoisotopic Mass

423.03276 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CS(=O)CCC\C(S[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)=N/OS(O)(=O)=O

InChI Identifier

InChI=1S/C11H21NO10S3/c1-24(17)4-2-3-7(12-22-25(18,19)20)23-11-10(16)9(15)8(14)6(5-13)21-11/h6,8-11,13-16H,2-5H2,1H3,(H,18,19,20)/b12-7+/t6-,8-,9+,10-,11+,24?/m1/s1

InChI Key

PHYYADMVYQURSX-WWFIZPDBSA-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 macrocarpa	LOTUS Database	35616633
Brassica oleracea	LOTUS Database	35616633
Brassica tournefortii	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
Sulfoxide
Sulfinyl compound
Oxacycle
Polyol
Sulfenyl compound
Organoheterocyclic compound
Alcohol
Primary alcohol
Hydrocarbon derivative
Organosulfur compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic nitrogen compound
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	-1.5	ALOGPS
logP	-5.1	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	-3.7	ChemAxon
pKa (Strongest Basic)	-0.51	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	183.18 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	89.02 m³·mol⁻¹	ChemAxon
Polarizability	38.19 Å³	ChemAxon
Number of Rings	1	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

HMDB0038406

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

3-METHYLSULFINYLPROPYL-GLUCOSINOLATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9548622

PDB ID

Not Available

ChEBI ID

5406

Good Scents ID

Not Available

References

General References

Bhandari SR, Rhee J, Choi CS, Jo JS, Shin YK, Lee JG: Profiling of Individual Desulfo-Glucosinolate Content in Cabbage Head (Brassica oleracea var. capitata) Germplasm. Molecules. 2020 Apr 17;25(8):1860. doi: 10.3390/molecules25081860. [PubMed:32316621 ]
Chang J, Wang M, Jian Y, Zhang F, Zhu J, Wang Q, Sun B: Health-promoting phytochemicals and antioxidant capacity in different organs from six varieties of Chinese kale. Sci Rep. 2019 Dec 30;9(1):20344. doi: 10.1038/s41598-019-56671-w. [PubMed:31889076 ]
Baenas N, Marhuenda J, Garcia-Viguera C, Zafrilla P, Moreno DA: Influence of Cooking Methods on Glucosinolates and Isothiocyanates Content in Novel Cruciferous Foods. Foods. 2019 Jul 12;8(7):257. doi: 10.3390/foods8070257. [PubMed:31336993 ]
Hwang ES: Effect of Cooking Method on Antioxidant Compound Contents in Cauliflower. Prev Nutr Food Sci. 2019 Jun;24(2):210-216. doi: 10.3746/pnf.2019.24.2.210. Epub 2019 Jun 30. [PubMed:31328127 ]
Madloo P, Lema M, Francisco M, Soengas P: Role of Major Glucosinolates in the Defense of Kale Against Sclerotinia sclerotiorum and Xanthomonas campestris pv. campestris. Phytopathology. 2019 Jul;109(7):1246-1256. doi: 10.1094/PHYTO-09-18-0340-R. Epub 2019 Jun 3. [PubMed:30920356 ]
Ye JH, Huang LY, Terefe NS, Augustin MA: Fermentation-based biotransformation of glucosinolates, phenolics and sugars in retorted broccoli puree by lactic acid bacteria. Food Chem. 2019 Jul 15;286:616-623. doi: 10.1016/j.foodchem.2019.02.030. Epub 2019 Feb 14. [PubMed:30827654 ]
Novotny C, Schulzova V, Krmela A, Hajslova J, Svobodova K, Koudela M: Ascorbic Acid and Glucosinolate Levels in New Czech Cabbage Cultivars: Effect of Production System and Fungal Infection. Molecules. 2018 Jul 25;23(8):1855. doi: 10.3390/molecules23081855. [PubMed:30046026 ]
Luang-In V, Deeseenthum S, Udomwong P, Saengha W, Gregori M: Formation of Sulforaphane and Iberin Products from Thai Cabbage Fermented by Myrosinase-Positive Bacteria. Molecules. 2018 Apr 19;23(4):955. doi: 10.3390/molecules23040955. [PubMed:29671807 ]
Oliviero T, Lamers S, Capuano E, Dekker M, Verkerk R: Bioavailability of Isothiocyanates From Broccoli Sprouts in Protein, Lipid, and Fiber Gels. Mol Nutr Food Res. 2018 Sep;62(18):e1700837. doi: 10.1002/mnfr.201700837. Epub 2018 Apr 14. [PubMed:29532635 ]
Singh J, Jayaprakasha GK, Patil BS: Rapid and Efficient Desulfonation Method for the Analysis of Glucosinolates by High-Resolution Liquid Chromatography Coupled with Quadrupole Time-of-Flight Mass Spectrometry. J Agric Food Chem. 2017 Dec 20;65(50):11100-11108. doi: 10.1021/acs.jafc.7b04662. Epub 2017 Dec 5. [PubMed:29161816 ]
Yang H, Liu F, Li Y, Yu B: Reconstructing Biosynthetic Pathway of the Plant-Derived Cancer Chemopreventive-Precursor Glucoraphanin in Escherichia coli. ACS Synth Biol. 2018 Jan 19;7(1):121-131. doi: 10.1021/acssynbio.7b00256. Epub 2017 Nov 29. [PubMed:29149798 ]
Nugrahedi PY, Oliviero T, Heising JK, Dekker M, Verkerk R: Stir-Frying of Chinese Cabbage and Pakchoi Retains Health-Promoting Glucosinolates. Plant Foods Hum Nutr. 2017 Dec;72(4):439-444. doi: 10.1007/s11130-017-0646-x. [PubMed:29134463 ]
Cui H, Guo L, Wang S, Xie W, Jiao X, Wu Q, Zhang Y: The ability to manipulate plant glucosinolates and nutrients explains the better performance of Bemisia tabaci Middle East-Asia Minor 1 than Mediterranean on cabbage plants. Ecol Evol. 2017 Jun 30;7(16):6141-6150. doi: 10.1002/ece3.2921. eCollection 2017 Aug. [PubMed:28861220 ]
Robin AHK, Hossain MR, Park JI, Kim HR, Nou IS: Glucosinolate Profiles in Cabbage Genotypes Influence the Preferential Feeding of Diamondback Moth (Plutella xylostella). Front Plant Sci. 2017 Jul 18;8:1244. doi: 10.3389/fpls.2017.01244. eCollection 2017. [PubMed:28769953 ]
Montaut S, Guido BS, Grison C, Rollin P: Identification of Glucosinolates in Seeds of Three Brassicaceae Species Known to Hyperaccumulate Heavy Metals. Chem Biodivers. 2017 Mar;14(3). doi: 10.1002/cbdv.201600311. Epub 2017 Mar 4. [PubMed:27981800 ]
Hanschen FS, Schreiner M: Isothiocyanates, Nitriles, and Epithionitriles from Glucosinolates Are Affected by Genotype and Developmental Stage in Brassica oleracea Varieties. Front Plant Sci. 2017 Jun 22;8:1095. doi: 10.3389/fpls.2017.01095. eCollection 2017. [PubMed:28690627 ]
Sahamishirazi S, Zikeli S, Fleck M, Claupein W, Graeff-Hoenninger S: Development of a near-infrared spectroscopy method (NIRS) for fast analysis of total, indolic, aliphatic and individual glucosinolates in new bred open pollinating genotypes of broccoli (Brassica oleracea convar. botrytis var. italica). Food Chem. 2017 Oct 1;232:272-277. doi: 10.1016/j.foodchem.2017.04.025. Epub 2017 Apr 6. [PubMed:28490075 ]
Jaiswal AK, Abu-Ghannam N: Fermentation-Assisted Extraction of Isothiocyanates from Brassica Vegetable Using Box-Behnken Experimental Design. Foods. 2016 Nov 4;5(4):75. doi: 10.3390/foods5040075. [PubMed:28231170 ]
Yi GE, Robin AH, Yang K, Park JI, Hwang BH, Nou IS: Exogenous Methyl Jasmonate and Salicylic Acid Induce Subspecies-Specific Patterns of Glucosinolate Accumulation and Gene Expression in Brassica oleracea L. Molecules. 2016 Oct 24;21(10):1417. doi: 10.3390/molecules21101417. [PubMed:27783045 ]
LOTUS database [Link]

Showing NP-Card for [(e)-(4-methanesulfinyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}butylidene)amino]oxysulfonic acid (NP0329544)

MOL for NP0329544 ([(e)-(4-methanesulfinyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}butylidene)amino]oxysulfonic acid)

3D MOL for NP0329544 ([(e)-(4-methanesulfinyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}butylidene)amino]oxysulfonic acid)

3D SDF for NP0329544 ([(e)-(4-methanesulfinyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}butylidene)amino]oxysulfonic acid)

3D-SDF for NP0329544 ([(e)-(4-methanesulfinyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}butylidene)amino]oxysulfonic acid)

PDB for NP0329544 ([(e)-(4-methanesulfinyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}butylidene)amino]oxysulfonic acid)

3D PDB for NP0329544 ([(e)-(4-methanesulfinyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}butylidene)amino]oxysulfonic acid)

SMILES for NP0329544 ([(e)-(4-methanesulfinyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}butylidene)amino]oxysulfonic acid)

INCHI for NP0329544 ([(e)-(4-methanesulfinyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}butylidene)amino]oxysulfonic acid)

Structure for NP0329544 ([(e)-(4-methanesulfinyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}butylidene)amino]oxysulfonic acid)

3D Structure for NP0329544 ([(e)-(4-methanesulfinyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}butylidene)amino]oxysulfonic acid)