NP-MRD: Showing NP-Card for (2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-{[(1z)-5-methanesulfinyl-1-(sulfoimino)pent-4-en-1-yl]sulfanyl}oxane-3,4,5-triol (NP0295007)

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Record Information

Version

2.0

Created at

2022-09-10 03:47:50 UTC

Updated at

2022-09-10 03:47:50 UTC

NP-MRD ID

NP0295007

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-{[(1z)-5-methanesulfinyl-1-(sulfoimino)pent-4-en-1-yl]sulfanyl}oxane-3,4,5-triol

Description

Glucoraphenin belongs to the class of organic compounds known as thioglycosides. These are glycoside in which a sugar group is bonded through one carbon to another group via a S-glycosidic bond. (2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-{[(1z)-5-methanesulfinyl-1-(sulfoimino)pent-4-en-1-yl]sulfanyl}oxane-3,4,5-triol is found in Apis cerana. (2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-{[(1z)-5-methanesulfinyl-1-(sulfoimino)pent-4-en-1-yl]sulfanyl}oxane-3,4,5-triol was first documented in 2018 (PMID: 29866995). Based on a literature review a significant number of articles have been published on glucoraphenin (PMID: 36099817) (PMID: 35686604) (PMID: 35112855) (PMID: 33929187) (PMID: 32480264) (PMID: 31042585).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102205472D          

 25 25  0  0  1  0            999 V2000
   -4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 S   0  3  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.9980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  4  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  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
  8 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  CHG  2   2   1   3  -1
M  END

     RDKit          3D

 46 46  0  0  0  0  0  0  0  0999 V2000
    5.1331    2.0180    2.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847    2.3072    0.6143 S   0  0  0  0  0  3  0  0  0  0  0  0
    2.8424    2.8981    0.7289 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.4255    0.8778   -0.4171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6778   -0.1726   -0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7594   -0.2472    1.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3151   -0.4600    0.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0822   -1.7197   -0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0293   -2.5600   -0.2759 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8039   -4.0388   -1.1335 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.1174   -4.5631   -1.6287 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1915   -5.0654   -0.2215 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7731   -3.8206   -2.4385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4979   -2.0975   -0.7862 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7697   -0.8938   -0.5562 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5664    0.3169   -1.2158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6780    1.1150   -1.1860 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3447    2.5445   -0.7410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5636    3.2356   -0.7586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8407    0.6337   -0.4089 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7013   -0.1038   -1.2538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5523   -0.0914    0.8581 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9170    0.5668    2.0029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0804   -0.5351    0.8811 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8597   -1.5538    1.7700 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2385    2.1622    2.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0068    0.9540    2.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7298    2.7290    2.9367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0725    0.8435   -1.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7310   -1.0291   -0.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8086    0.7202    1.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1393   -1.0660    1.6669 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0082    0.4367    0.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6556   -0.4738    1.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0067   -4.4261   -2.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7138   -1.3066   -1.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0160    1.2361   -2.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7041    3.0332   -1.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9212    2.5826    0.2597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4909    4.1594   -0.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4576    1.5394   -0.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6135    0.2416   -2.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1322   -1.0556    0.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2904    1.4543    1.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5234    0.4010    1.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6844   -1.7267    2.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8 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
  8  9  2  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
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 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  6
 23 44  1  0
 24 45  1  1
 25 46  1  0
 13 35  1  0
M  CHG  2   2   1   3  -1
M  END


  Mrv1652309102205472D          

 25 25  0  0  1  0            999 V2000
   -4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 S   0  3  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.9980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  4  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  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
  8 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  CHG  2   2   1   3  -1
M  END
> <DATABASE_ID>
NP0295007

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[S+]([O-])C=CCC\C(S[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)=N\S(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H21NO9S3/c1-24(18)5-3-2-4-8(13-25(19,20)21)23-12-11(17)10(16)9(15)7(6-14)22-12/h3,5,7,9-12,14-17H,2,4,6H2,1H3,(H,19,20,21)/b5-3?,13-8-/t7-,9-,10+,11-,12+,24?/m1/s1

> <INCHI_KEY>
HWABDHHTQMTFMW-OOLORDSESA-N

> <FORMULA>
C12H21NO9S3

> <MOLECULAR_WEIGHT>
419.48

> <EXACT_MASS>
419.037844782

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
39.0513915305897

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{[(1Z)-5-methanesulfinyl-1-(sulfoimino)pent-4-en-1-yl]sulfanyl}oxane-3,4,5-triol

> <JCHEM_LOGP>
-5.0820924819396085

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.451451483506528

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.6886839184571416

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9797628931012756

> <JCHEM_POLAR_SURFACE_AREA>
173.95

> <JCHEM_REFRACTIVITY>
92.19970000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{[(1Z)-5-methanesulfinyl-1-(sulfoimino)pent-4-en-1-yl]sulfanyl}oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0      -6.668   3.850   0.000  0.00  0.00           S+1
HETATM    3  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O-1
HETATM    4  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.000   6.160   0.000  0.00  0.00           N+0
HETATM   10  S   UNK     0       1.334   6.930   0.000  0.00  0.00           S+0
HETATM   11  O   UNK     0       2.667   7.700   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.564   8.264   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.104   5.596   0.000  0.00  0.00           O+0
HETATM   14  S   UNK     0       1.334   3.850   0.000  0.00  0.00           S+0
HETATM   15  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
CONECT   14    8   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

C₁₂H₂₁NO₉S₃

Average Mass

419.4800 Da

Monoisotopic Mass

419.03784 Da

IUPAC Name

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{[(1Z)-5-methanesulfinyl-1-(sulfoimino)pent-4-en-1-yl]sulfanyl}oxane-3,4,5-triol

Traditional Name

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{[(1Z)-5-methanesulfinyl-1-(sulfoimino)pent-4-en-1-yl]sulfanyl}oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

C[S+]([O-])C=CCC\C(S[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)=N\S(O)(=O)=O

InChI Identifier

InChI=1S/C12H21NO9S3/c1-24(18)5-3-2-4-8(13-25(19,20)21)23-12-11(17)10(16)9(15)7(6-14)22-12/h3,5,7,9-12,14-17H,2,4,6H2,1H3,(H,19,20,21)/b5-3?,13-8-/t7-,9-,10+,11-,12+,24?/m1/s1

InChI Key

HWABDHHTQMTFMW-OOLORDSESA-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
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thioglycosides. These are glycoside in which a sugar group is bonded through one carbon to another group via a S-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Thioglycosides

Alternative Parents

Substituents

S-glycosyl compound
Monosaccharide
Oxane
Monothioacetal
Organic sulfuric acid or derivatives
Secondary alcohol
Sulfoxide
Polyol
Oxacycle
Organoheterocyclic compound
Sulfenyl compound
Sulfinyl compound
Alcohol
Hydrocarbon derivative
Organosulfur compound
Organonitrogen compound
Primary alcohol
Organic nitrogen compound
Organopnictogen 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	-5.1	ChemAxon
pKa (Strongest Acidic)	-1.7	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	173.95 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	92.2 m³·mol⁻¹	ChemAxon
Polarizability	39.05 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00001481

Chemspider ID

58827359

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

118797910

PDB ID

Not Available

ChEBI ID

79367

Good Scents ID

Not Available

References

General References

Demir K, Sarikamis G, Cakirer Seyrek G: Effect of LED lights on the growth, nutritional quality and glucosinolate content of broccoli, cabbage and radish microgreens. Food Chem. 2023 Feb 1;401:134088. doi: 10.1016/j.foodchem.2022.134088. Epub 2022 Sep 6. [PubMed:36099817 ]
Oh MJ, Lee HHL, Lee HB, Do MH, Park M, Lee CH, Park HY: A water soluble extract of radish greens ameliorates high fat diet-induced obesity in mice and inhibits adipogenesis in preadipocytes. Food Funct. 2022 Jul 18;13(14):7494-7506. doi: 10.1039/d1fo04152e. [PubMed:35686604 ]
Wang L, Jiang H, Qiu Y, Dong Y, Hamouda HI, Balah MA, Mao X: Biochemical Characterization of a Novel Myrosinase Rmyr from Rahnella inusitata for High-Level Preparation of Sulforaphene and Sulforaphane. J Agric Food Chem. 2022 Feb 23;70(7):2303-2311. doi: 10.1021/acs.jafc.1c07646. Epub 2022 Feb 3. [PubMed:35112855 ]
Wang L, Jiang H, Liang X, Zhou W, Qiu Y, Xue C, Sun J, Mao X: Preparation of Sulforaphene from Radish Seed Extracts with Recombinant Food-Grade Yarrowia lipolytica Harboring High Myrosinase Activity. J Agric Food Chem. 2021 May 12;69(18):5363-5371. doi: 10.1021/acs.jafc.1c01400. Epub 2021 Apr 30. [PubMed:33929187 ]
Kim SY, Seo HY, Ha JH: A colorimetric sensor array for the discrimination of glucosinolates. Food Chem. 2020 Oct 30;328:127149. doi: 10.1016/j.foodchem.2020.127149. Epub 2020 May 26. [PubMed:32480264 ]
Zhang J, Feng C, Tan X, Hagedoorn PL, Gu C, Xu H, Zhou X: Effect of aliphatic diamine spacer length on enzymatic performance of myrosinase immobilized on chitosan microsphere and its application for sulforaphene production. J Biotechnol. 2019 Jun 20;299:79-85. doi: 10.1016/j.jbiotec.2019.04.023. Epub 2019 Apr 28. [PubMed:31042585 ]
Blazevic I, Dulovic A, Cikes Culic V, Burcul F, Ljubenkov I, Ruscic M, Generalic Mekinic I: Bunias erucago L.: Glucosinolate Profile and In Vitro Biological Potential. Molecules. 2019 Feb 19;24(4):741. doi: 10.3390/molecules24040741. [PubMed:30791395 ]
Kntayya SB, Ibrahim MD, Mohd Ain N, Iori R, Ioannides C, Abdull Razis AF: Induction of Apoptosis and Cytotoxicity by Isothiocyanate Sulforaphene in Human Hepatocarcinoma HepG2 Cells. Nutrients. 2018 Jun 4;10(6):718. doi: 10.3390/nu10060718. [PubMed:29866995 ]
LOTUS database [Link]

Showing NP-Card for (2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-{[(1z)-5-methanesulfinyl-1-(sulfoimino)pent-4-en-1-yl]sulfanyl}oxane-3,4,5-triol (NP0295007)

MOL for NP0295007 ((2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-{[(1z)-5-methanesulfinyl-1-(sulfoimino)pent-4-en-1-yl]sulfanyl}oxane-3,4,5-triol)

3D MOL for NP0295007 ((2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-{[(1z)-5-methanesulfinyl-1-(sulfoimino)pent-4-en-1-yl]sulfanyl}oxane-3,4,5-triol)

3D SDF for NP0295007 ((2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-{[(1z)-5-methanesulfinyl-1-(sulfoimino)pent-4-en-1-yl]sulfanyl}oxane-3,4,5-triol)

3D-SDF for NP0295007 ((2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-{[(1z)-5-methanesulfinyl-1-(sulfoimino)pent-4-en-1-yl]sulfanyl}oxane-3,4,5-triol)

PDB for NP0295007 ((2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-{[(1z)-5-methanesulfinyl-1-(sulfoimino)pent-4-en-1-yl]sulfanyl}oxane-3,4,5-triol)

3D PDB for NP0295007 ((2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-{[(1z)-5-methanesulfinyl-1-(sulfoimino)pent-4-en-1-yl]sulfanyl}oxane-3,4,5-triol)

SMILES for NP0295007 ((2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-{[(1z)-5-methanesulfinyl-1-(sulfoimino)pent-4-en-1-yl]sulfanyl}oxane-3,4,5-triol)

INCHI for NP0295007 ((2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-{[(1z)-5-methanesulfinyl-1-(sulfoimino)pent-4-en-1-yl]sulfanyl}oxane-3,4,5-triol)

Structure for NP0295007 ((2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-{[(1z)-5-methanesulfinyl-1-(sulfoimino)pent-4-en-1-yl]sulfanyl}oxane-3,4,5-triol)

3D Structure for NP0295007 ((2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-{[(1z)-5-methanesulfinyl-1-(sulfoimino)pent-4-en-1-yl]sulfanyl}oxane-3,4,5-triol)