NP-MRD: Showing NP-Card for 2-(Methylthio)ethyl glucosinolate (NP0049100)

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Record Information

Version

2.0

Created at

2022-03-17 21:07:08 UTC

Updated at

2022-03-17 21:07:08 UTC

NP-MRD ID

NP0049100

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(Methylthio)ethyl glucosinolate

Description

2-(Methylthio)ethyl glucosinolate, also known as glucoviorylin, belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain. 2-(Methylthio)ethyl glucosinolate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2-(Methylthio)ethyl glucosinolate has been detected, but not quantified in, brassicas and horseradish. This could make 2-(methylthio)ethyl glucosinolate a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310262D          

 23 23  0  0  0  0            999 V2000
   -1.4289   -4.1250    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
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  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
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309   -0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559   -1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   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
    0.7145   -1.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  2  1  0  0  0  0
  7  5  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  6  2  0  0  0  0
 12  4  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 19  5  1  0  0  0  0
 19 10  1  0  0  0  0
 20 11  1  0  0  0  0
 21  1  1  0  0  0  0
 21  3  1  0  0  0  0
 22  6  1  0  0  0  0
 22 10  1  0  0  0  0
 23 16  1  0  0  0  0
 23 17  2  0  0  0  0
 23 18  2  0  0  0  0
 23 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049100

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CSCC\C(SC1OC(CO)C(O)C(O)C1O)=N/OS(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H19NO9S3/c1-21-3-2-6(11-20-23(16,17)18)22-10-9(15)8(14)7(13)5(4-12)19-10/h5,7-10,12-15H,2-4H2,1H3,(H,16,17,18)/b11-6+

> <INCHI_KEY>
ZQKUEDRZCDZXIY-IZZDOVSWSA-N

> <FORMULA>
C10H19NO9S3

> <MOLECULAR_WEIGHT>
393.454

> <EXACT_MASS>
393.022193281

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
36.81765761457619

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.61

> <JCHEM_LOGP>
-2.965704507903433

> <ALOGPS_LOGS>
-1.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.447586836364504

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.561605852526199

> <JCHEM_PKA_STRONGEST_BASIC>
-0.36328818182255607

> <JCHEM_POLAR_SURFACE_AREA>
166.10999999999999

> <JCHEM_REFRACTIVITY>
82.50629999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -3.231  -0.976   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -4.771  -3.644   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   21  S   UNK     0      -1.334  -6.930   0.000  0.00  0.00           S+0
HETATM   22  S   UNK     0       1.334  -2.310   0.000  0.00  0.00           S+0
HETATM   23  S   UNK     0      -4.001  -2.310   0.000  0.00  0.00           S+0
CONECT    1   21                                                            
CONECT    2    3    6                                                       
CONECT    3    2   21                                                       
CONECT    4    5   12                                                       
CONECT    5    4    7   19                                                  
CONECT    6    2   11   22                                                  
CONECT    7    5    8   13                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9   19   22                                                  
CONECT   11    6   20                                                       
CONECT   12    4                                                            
CONECT   13    7                                                            
CONECT   14    8                                                            
CONECT   15    9                                                            
CONECT   16   23                                                            
CONECT   17   23                                                            
CONECT   18   23                                                            
CONECT   19    5   10                                                       
CONECT   20   11   23                                                       
CONECT   21    1    3                                                       
CONECT   22    6   10                                                       
CONECT   23   16   17   18   20                                             
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

View in JSmol

Synonyms

Value	Source
2-(Methylthio)ethyl glucosinolic acid	Generator
1-Thio-b-D-glucopyranose 1-[3-(methylthio)-N-(sulfooxy)propanimidate], 9ci	HMDB
Glucoviorylin	HMDB
{[(e)-[3-(methylsulfanyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}propylidene]amino]oxy}sulfonate	Generator
{[(e)-[3-(methylsulphanyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}propylidene]amino]oxy}sulphonate	Generator
{[(e)-[3-(methylsulphanyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}propylidene]amino]oxy}sulphonic acid	Generator

Chemical Formula

C₁₀H₁₉NO₉S₃

Average Mass

393.4540 Da

Monoisotopic Mass

393.02219 Da

IUPAC Name

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

Traditional Name

[(E)-[3-(methylsulfanyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}propylidene]amino]oxysulfonic acid

CAS Registry Number

27303-30-6

SMILES

CSCC\C(SC1OC(CO)C(O)C(O)C1O)=N/OS(O)(=O)=O

InChI Identifier

InChI=1S/C10H19NO9S3/c1-21-3-2-6(11-20-23(16,17)18)22-10-9(15)8(14)7(13)5(4-12)19-10/h5,7-10,12-15H,2-4H2,1H3,(H,16,17,18)/b11-6+

InChI Key

ZQKUEDRZCDZXIY-IZZDOVSWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Armoracia rusticana	FooDB	KNAPSACK

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
Thioether
Organoheterocyclic compound
Sulfenyl compound
Dialkylthioether
Alcohol
Hydrocarbon derivative
Organosulfur compound
Primary alcohol
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Organonitrogen 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	-1.6	ALOGPS
logP	-3	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	-3.6	ChemAxon
pKa (Strongest Basic)	-0.36	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	166.11 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	82.51 m³·mol⁻¹	ChemAxon
Polarizability	36.82 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

HMDB0038408

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017762

KNApSAcK ID

C00007843

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

131752358

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2-(Methylthio)ethyl glucosinolate (NP0049100)

MOL for NP0049100 (2-(Methylthio)ethyl glucosinolate)

3D MOL for NP0049100 (2-(Methylthio)ethyl glucosinolate)

3D SDF for NP0049100 (2-(Methylthio)ethyl glucosinolate)

3D-SDF for NP0049100 (2-(Methylthio)ethyl glucosinolate)

PDB for NP0049100 (2-(Methylthio)ethyl glucosinolate)

3D PDB for NP0049100 (2-(Methylthio)ethyl glucosinolate)

SMILES for NP0049100 (2-(Methylthio)ethyl glucosinolate)

INCHI for NP0049100 (2-(Methylthio)ethyl glucosinolate)

Structure for NP0049100 (2-(Methylthio)ethyl glucosinolate)

3D Structure for NP0049100 (2-(Methylthio)ethyl glucosinolate)