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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 03:42:49 UTC

Update Date

2021-09-24 03:42:49 UTC

HMDB ID

HMDB0303669

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Gluconapoleiferin

Description

Gluconapoleiferin is a member of the class of compounds known as alkylglucosinolates. Alkylglucosinolates are organic compounds containing a glucosinolate moiety that carries an alkyl chain. Gluconapoleiferin is soluble (in water) and an extremely strong acidic compound (based on its pKa). Gluconapoleiferin can be found in a number of food items such as swede, broccoli, chinese cabbage, and turnip, which makes gluconapoleiferin a potential biomarker for the consumption of these food products.

Structure

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

HMDB0303669
     RDKit          3D
Gluconapoleiferin
 46 46  0  0  0  0  0  0  0  0999 V2000
    4.5719   -3.2019   -1.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6361   -2.3983   -0.7724 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5068   -0.9656   -1.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7083   -0.0921    0.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5883    1.2281   -0.4309 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7891   -0.3896    1.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3657   -0.2449    0.9028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6885    0.6145    1.5987 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3288    1.3698    2.5597 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3009    3.0658    2.3096 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.5296    3.3244    0.8289 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3832    3.7578    3.0439 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2170    3.6835    2.6843 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5022   -1.1853   -0.3140 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2424   -0.8046   -0.4048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5123    0.4770   -0.8461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8371    0.7986   -0.7090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3214    1.7410   -1.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6164    2.9394   -1.8085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7720   -0.3795   -0.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0771    0.1419   -0.6538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4682   -1.2671    0.4495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7011   -2.5904    0.0386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9985   -1.1093    0.8656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8887   -0.0742    1.7878 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465   -4.2224   -0.9904 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2176   -2.7496   -2.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9799   -2.8034   -0.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5560   -0.7697   -1.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3701   -0.7612   -1.9001 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7453   -0.2519    0.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3733    1.5367   -0.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0268   -1.4458    1.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1066    0.2215    2.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3266    4.5135    2.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6843   -1.4923   -1.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9775    1.3200    0.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3852    1.9511   -1.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2512    1.2066   -2.7809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0547    3.0529   -1.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7344   -0.9324   -1.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5382   -0.2094    0.1462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1373   -1.1082    1.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8129   -2.9767   -0.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6933   -2.0839    1.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6740   -0.4343    2.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  2  0
 10 13  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
 24 15  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
 13 35  1  0
 15 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 20 41  1  0
 21 42  1  0
 22 43  1  0
 23 44  1  0
 24 45  1  0
 25 46  1  0
M  END


  Mrv0541 02241216392D          

 25 25  0  0  0  0            999 V2000
    0.2469    2.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2469    1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9899    1.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0719    0.2885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4121   -0.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3295   -1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0719   -1.4434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7323   -1.1135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8969    0.1232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3295   -1.4434    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0726   -1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0726   -0.2066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8149   -2.2684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8149   -1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4747   -1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2170   -1.4434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2170    0.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4747   -0.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8149    0.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7323    1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4747    1.4434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2170   -1.8559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1448   -2.2684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4747   -1.5261    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8872   -0.7837    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  9  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  8 24  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 12 19  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 18  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 21  1  0  0  0  0
 22 24  2  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303669

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC1OC(S\C(CC(O)CC=C)=N\OS(O)(=O)=O)C(O)C(O)C1O

> <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+

> <INCHI_KEY>
ZEGLQSKFSKZGRO-MDWZMJQESA-N

> <FORMULA>
C12H21NO10S2

> <MOLECULAR_WEIGHT>
403.426

> <EXACT_MASS>
403.060687277

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
37.46273893273931

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(E)-(3-hydroxy-1-{[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>
-3.529833489762063

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3754294915516233

> <JCHEM_POLAR_SURFACE_AREA>
186.33999999999997

> <JCHEM_REFRACTIVITY>
85.41459999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.78e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303669
     RDKit          3D
Gluconapoleiferin
 46 46  0  0  0  0  0  0  0  0999 V2000
    4.5719   -3.2019   -1.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6361   -2.3983   -0.7724 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5068   -0.9656   -1.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7083   -0.0921    0.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5883    1.2281   -0.4309 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7891   -0.3896    1.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3657   -0.2449    0.9028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6885    0.6145    1.5987 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3288    1.3698    2.5597 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3009    3.0658    2.3096 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.5296    3.3244    0.8289 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3832    3.7578    3.0439 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2170    3.6835    2.6843 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5022   -1.1853   -0.3140 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2424   -0.8046   -0.4048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5123    0.4770   -0.8461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8371    0.7986   -0.7090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3214    1.7410   -1.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6164    2.9394   -1.8085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7720   -0.3795   -0.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0771    0.1419   -0.6538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4682   -1.2671    0.4495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7011   -2.5904    0.0386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9985   -1.1093    0.8656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8887   -0.0742    1.7878 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465   -4.2224   -0.9904 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2176   -2.7496   -2.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9799   -2.8034   -0.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5560   -0.7697   -1.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3701   -0.7612   -1.9001 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7453   -0.2519    0.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3733    1.5367   -0.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0268   -1.4458    1.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1066    0.2215    2.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3266    4.5135    2.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6843   -1.4923   -1.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9775    1.3200    0.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3852    1.9511   -1.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2512    1.2066   -2.7809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0547    3.0529   -1.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7344   -0.9324   -1.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5382   -0.2094    0.1462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1373   -1.1082    1.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8129   -2.9767   -0.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6933   -2.0839    1.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6740   -0.4343    2.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  2  0
 10 13  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
 24 15  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
 13 35  1  0
 15 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 20 41  1  0
 21 42  1  0
 22 43  1  0
 23 44  1  0
 24 45  1  0
 25 46  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       0.461   4.234   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.461   2.694   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.848   2.079   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.001   0.539   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.769  -0.386   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.615  -1.924   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.001  -2.694   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0       3.234  -2.079   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       3.541   0.230   0.000  0.00  0.00           O+0
HETATM   10  S   UNK     0      -0.615  -2.694   0.000  0.00  0.00           S+0
HETATM   11  C   UNK     0      -2.002  -1.924   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.002  -0.386   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -3.388  -4.234   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.388  -2.694   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.619  -1.924   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -6.005  -2.694   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -6.005   0.384   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.619  -0.386   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.388   0.384   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.234   1.924   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.619   2.694   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.005  -3.464   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.004  -4.234   0.000  0.00  0.00           O+0
HETATM   24  S   UNK     0       4.619  -2.849   0.000  0.00  0.00           S+0
HETATM   25  O   UNK     0       5.389  -1.463   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7   24                                                       
CONECT    9    4                                                            
CONECT   10    6   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   19                                                       
CONECT   13   14                                                            
CONECT   14   11   13   15                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15                                                            
CONECT   17   18                                                            
CONECT   18   15   17   19                                                  
CONECT   19   12   18   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   24                                                            
CONECT   23   24                                                            
CONECT   24    8   22   23   25                                             
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

COMPND    HMDB0303669
HETATM    1  C1  UNL     1       4.572  -3.202  -1.308  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.636  -2.398  -0.772  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.507  -0.966  -1.196  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.708  -0.092   0.011  1.00  0.00           C  
HETATM    5  O1  UNL     1       3.588   1.228  -0.431  1.00  0.00           O  
HETATM    6  C5  UNL     1       2.789  -0.390   1.156  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.366  -0.245   0.903  1.00  0.00           C  
HETATM    8  N1  UNL     1       0.689   0.615   1.599  1.00  0.00           N  
HETATM    9  O2  UNL     1       1.329   1.370   2.560  1.00  0.00           O  
HETATM   10  S1  UNL     1       1.301   3.066   2.310  1.00  0.00           S  
HETATM   11  O3  UNL     1       1.530   3.324   0.829  1.00  0.00           O  
HETATM   12  O4  UNL     1       2.383   3.758   3.044  1.00  0.00           O  
HETATM   13  O5  UNL     1      -0.217   3.684   2.684  1.00  0.00           O  
HETATM   14  S2  UNL     1       0.502  -1.185  -0.314  1.00  0.00           S  
HETATM   15  C7  UNL     1      -1.242  -0.805  -0.405  1.00  0.00           C  
HETATM   16  O6  UNL     1      -1.512   0.477  -0.846  1.00  0.00           O  
HETATM   17  C8  UNL     1      -2.837   0.799  -0.709  1.00  0.00           C  
HETATM   18  C9  UNL     1      -3.321   1.741  -1.807  1.00  0.00           C  
HETATM   19  O7  UNL     1      -2.616   2.939  -1.808  1.00  0.00           O  
HETATM   20  C10 UNL     1      -3.772  -0.380  -0.711  1.00  0.00           C  
HETATM   21  O8  UNL     1      -5.077   0.142  -0.654  1.00  0.00           O  
HETATM   22  C11 UNL     1      -3.468  -1.267   0.449  1.00  0.00           C  
HETATM   23  O9  UNL     1      -3.701  -2.590   0.039  1.00  0.00           O  
HETATM   24  C12 UNL     1      -1.999  -1.109   0.866  1.00  0.00           C  
HETATM   25  O10 UNL     1      -1.889  -0.074   1.788  1.00  0.00           O  
HETATM   26  H1  UNL     1       4.647  -4.222  -0.990  1.00  0.00           H  
HETATM   27  H2  UNL     1       5.218  -2.750  -2.056  1.00  0.00           H  
HETATM   28  H3  UNL     1       2.980  -2.803  -0.030  1.00  0.00           H  
HETATM   29  H4  UNL     1       2.556  -0.770  -1.734  1.00  0.00           H  
HETATM   30  H5  UNL     1       4.370  -0.761  -1.900  1.00  0.00           H  
HETATM   31  H6  UNL     1       4.745  -0.252   0.368  1.00  0.00           H  
HETATM   32  H7  UNL     1       4.373   1.537  -0.919  1.00  0.00           H  
HETATM   33  H8  UNL     1       3.027  -1.446   1.482  1.00  0.00           H  
HETATM   34  H9  UNL     1       3.107   0.221   2.044  1.00  0.00           H  
HETATM   35  H10 UNL     1      -0.327   4.514   2.123  1.00  0.00           H  
HETATM   36  H11 UNL     1      -1.684  -1.492  -1.185  1.00  0.00           H  
HETATM   37  H12 UNL     1      -2.977   1.320   0.261  1.00  0.00           H  
HETATM   38  H13 UNL     1      -4.385   1.951  -1.599  1.00  0.00           H  
HETATM   39  H14 UNL     1      -3.251   1.207  -2.781  1.00  0.00           H  
HETATM   40  H15 UNL     1      -2.055   3.053  -1.002  1.00  0.00           H  
HETATM   41  H16 UNL     1      -3.734  -0.932  -1.695  1.00  0.00           H  
HETATM   42  H17 UNL     1      -5.538  -0.209   0.146  1.00  0.00           H  
HETATM   43  H18 UNL     1      -4.137  -1.108   1.328  1.00  0.00           H  
HETATM   44  H19 UNL     1      -2.813  -2.977  -0.166  1.00  0.00           H  
HETATM   45  H20 UNL     1      -1.693  -2.084   1.272  1.00  0.00           H  
HETATM   46  H21 UNL     1      -1.674  -0.434   2.673  1.00  0.00           H  
CONECT    1    2    2   26   27
CONECT    2    3   28
CONECT    3    4   29   30
CONECT    4    5    6   31
CONECT    5   32
CONECT    6    7   33   34
CONECT    7    8    8   14
CONECT    8    9
CONECT    9   10
CONECT   10   11   11   12   12
CONECT   10   13
CONECT   13   35
CONECT   14   15
CONECT   15   16   24   36
CONECT   16   17
CONECT   17   18   20   37
CONECT   18   19   38   39
CONECT   19   40
CONECT   20   21   22   41
CONECT   21   42
CONECT   22   23   24   43
CONECT   23   44
CONECT   24   25   45
CONECT   25   46
END

HMDB0303669
     RDKit          3D
Gluconapoleiferin
 46 46  0  0  0  0  0  0  0  0999 V2000
    4.5719   -3.2019   -1.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6361   -2.3983   -0.7724 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5068   -0.9656   -1.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7083   -0.0921    0.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5883    1.2281   -0.4309 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7891   -0.3896    1.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3657   -0.2449    0.9028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6885    0.6145    1.5987 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3288    1.3698    2.5597 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3009    3.0658    2.3096 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.5296    3.3244    0.8289 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3832    3.7578    3.0439 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2170    3.6835    2.6843 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5022   -1.1853   -0.3140 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2424   -0.8046   -0.4048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5123    0.4770   -0.8461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8371    0.7986   -0.7090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3214    1.7410   -1.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6164    2.9394   -1.8085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7720   -0.3795   -0.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0771    0.1419   -0.6538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4682   -1.2671    0.4495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7011   -2.5904    0.0386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9985   -1.1093    0.8656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8887   -0.0742    1.7878 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465   -4.2224   -0.9904 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2176   -2.7496   -2.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9799   -2.8034   -0.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5560   -0.7697   -1.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3701   -0.7612   -1.9001 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7453   -0.2519    0.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3733    1.5367   -0.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0268   -1.4458    1.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1066    0.2215    2.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3266    4.5135    2.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6843   -1.4923   -1.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9775    1.3200    0.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3852    1.9511   -1.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2512    1.2066   -2.7809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0547    3.0529   -1.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7344   -0.9324   -1.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5382   -0.2094    0.1462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1373   -1.1082    1.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8129   -2.9767   -0.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6933   -2.0839    1.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6740   -0.4343    2.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  2  0
 10 13  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
 24 15  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
 13 35  1  0
 15 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 20 41  1  0
 21 42  1  0
 22 43  1  0
 23 44  1  0
 24 45  1  0
 25 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
{[(e)-(3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}hex-5-en-1-ylidene)amino]oxy}sulfonate	Generator
{[(e)-(3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}hex-5-en-1-ylidene)amino]oxy}sulphonate	Generator
{[(e)-(3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}hex-5-en-1-ylidene)amino]oxy}sulphonic acid	Generator

Chemical Formula

C₁₂H₂₁NO₁₀S₂

Average Molecular Weight

403.426

Monoisotopic Molecular Weight

403.060687277

IUPAC Name

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

CAS Registry Number

Not Available

SMILES

OCC1OC(S\C(CC(O)CC=C)=N\OS(O)(=O)=O)C(O)C(O)C1O

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+

InChI Key

ZEGLQSKFSKZGRO-MDWZMJQESA-N

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
Polyol
Oxacycle
Organoheterocyclic compound
Sulfenyl compound
Alcohol
Hydrocarbon derivative
Organosulfur compound
Organonitrogen compound
Organic oxide
Primary alcohol
Organic nitrogen compound
Organopnictogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0303669)

Swede (FooDB: FOOD00028)

Leaf vegetable

Rocket salad (ssp.) (FooDB: FOOD00077)
Rocket salad (FooDB: FOOD00244)

Herb and spice

Spice

Horseradish (FooDB: FOOD00018)
Capers (FooDB: FOOD00039)

Herb

Turnip (FooDB: FOOD00036)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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
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	37.46 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	187.566	32859911
AllCCS	[M+H-H2O]+	185.266	32859911
AllCCS	[M+Na]+	190.281	32859911
AllCCS	[M+NH4]+	189.678	32859911
AllCCS	[M-H]-	179.957	32859911
AllCCS	[M+Na-2H]-	180.447	32859911
AllCCS	[M+HCOO]-	181.116	32859911
DeepCCS	[M+H]+	182.995	30932474
DeepCCS	[M-H]-	180.604	30932474
DeepCCS	[M-2H]-	215.025	30932474
DeepCCS	[M+Na]+	191.316	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	11.4034 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	8.32 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1341.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	226.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	71.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	177.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	63.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	328.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	373.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	288.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	685.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	187.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1238.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	207.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	224.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	533.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	295.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	255.3 seconds	40023050

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Gluconapoleiferin,6TMS,isomer #1	C=CCC(C/C(=N\OS(=O)(=O)O[Si](C)(C)C)SC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C)O[Si](C)(C)C	2953.2	Semi standard non polar	33892256
Gluconapoleiferin,6TMS,isomer #1	C=CCC(C/C(=N\OS(=O)(=O)O[Si](C)(C)C)SC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C)O[Si](C)(C)C	3498.9	Standard non polar	33892256
Gluconapoleiferin,6TMS,isomer #1	C=CCC(C/C(=N\OS(=O)(=O)O[Si](C)(C)C)SC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C)O[Si](C)(C)C	3761.7	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gluconapoleiferin 10V, Positive-QTOF	splash10-0f7a-1659300000-32f7504d85d2acd752a1	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gluconapoleiferin 20V, Positive-QTOF	splash10-00dl-2491000000-578d3ec1c38aa2900583	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gluconapoleiferin 40V, Positive-QTOF	splash10-052f-9020000000-881059a2a2d027c9fdf0	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gluconapoleiferin 10V, Negative-QTOF	splash10-0fdo-3290000000-c984934e4c8b2a62db76	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gluconapoleiferin 20V, Negative-QTOF	splash10-0ab9-4950000000-ebf4976776d118822d88	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gluconapoleiferin 40V, Negative-QTOF	splash10-0c0r-6930000000-a847deffc5c5ac80eecd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gluconapoleiferin 10V, Positive-QTOF	splash10-0udr-0006900000-13562915cf4715005f38	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gluconapoleiferin 20V, Positive-QTOF	splash10-0uy0-2329400000-1f57330eff7234b864e5	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gluconapoleiferin 40V, Positive-QTOF	splash10-01ox-6931000000-c72a611ad4ed1f75ed7e	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gluconapoleiferin 10V, Negative-QTOF	splash10-0udi-0300900000-9f340285b71b66a6c340	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gluconapoleiferin 20V, Negative-QTOF	splash10-0udl-2952100000-e9541972e31fc7477902	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gluconapoleiferin 40V, Negative-QTOF	splash10-014i-2900000000-a06ce305cec7f919f069	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB017770

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

Not Available

PubChem Compound

14390045

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

Not Available

Showing metabocard for Gluconapoleiferin (HMDB0303669)

MOL for HMDB0303669 (Gluconapoleiferin)

3D MOL for HMDB0303669 (Gluconapoleiferin)

3D SDF for HMDB0303669 (Gluconapoleiferin)

3D-SDF for HMDB0303669 (Gluconapoleiferin)

PDB for HMDB0303669 (Gluconapoleiferin)

3D PDB for HMDB0303669 (Gluconapoleiferin)

SMILES for HMDB0303669 (Gluconapoleiferin)

INCHI for HMDB0303669 (Gluconapoleiferin)

Structure for HMDB0303669 (Gluconapoleiferin)

3D Structure for HMDB0303669 (Gluconapoleiferin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra