NP-MRD: Showing NP-Card for 4-(Methylsulfonyl)butyl glucosinolate (NP0050697)

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Record Information

Version

2.0

Created at

2022-04-27 22:02:33 UTC

Updated at

2022-04-27 22:02:33 UTC

NP-MRD ID

NP0050697

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(Methylsulfonyl)butyl glucosinolate

Description

{[(E)-(5-methanesulfonyl-1-{[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pentylidene)amino]oxy}sulfonic acid belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain. 4-(Methylsulfonyl)butyl glucosinolate is found in Brassica napus var. napobrassica , Descurainia richardsonii, Erysimum allionii, Erysimum asperum, Erysimum perofskianum, Lepidium draba , Lesquerella engelmannii and Thelypodium crispum. Based on a literature review very few articles have been published on {[(E)-(5-methanesulfonyl-1-{[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pentylidene)amino]oxy}sulfonic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282200022D          

 27 27  0  0  1  0            999 V2000
    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 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  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
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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 C   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 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 O   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   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.9500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  5 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  2  0  0  0  0
 14 17  1  0  0  0  0
 11 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
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  2  0  0  0  0
 22 25  1  0  0  0  0
  4 26  1  1  0  0  0
  3 27  1  6  0  0  0
M  END


  Mrv1652304282200022D          

 27 27  0  0  1  0            999 V2000
    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 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  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
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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 C   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 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 O   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   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.9500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  5 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  2  0  0  0  0
 14 17  1  0  0  0  0
 11 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
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  2  0  0  0  0
 22 25  1  0  0  0  0
  4 26  1  1  0  0  0
  3 27  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0050697

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CS(=O)(=O)CCCC\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/C12H23NO11S3/c1-26(18,19)5-3-2-4-8(13-24-27(20,21)22)25-12-11(17)10(16)9(15)7(6-14)23-12/h7,9-12,14-17H,2-6H2,1H3,(H,20,21,22)/b13-8+/t7-,9-,10-,11+,12+/m0/s1

> <INCHI_KEY>
WJMGSLJQEIYHOF-VPJITUJYSA-N

> <FORMULA>
C12H23NO11S3

> <MOLECULAR_WEIGHT>
453.49

> <EXACT_MASS>
453.043324087

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
42.082594236093215

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.65

> <JCHEM_LOGP>
-4.598851094853166

> <ALOGPS_LOGS>
-1.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.447675745234136

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.7505369276643075

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5002860223785482

> <JCHEM_POLAR_SURFACE_AREA>
200.24999999999997

> <JCHEM_REFRACTIVITY>
93.37139999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.51e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   10  S   UNK     0       1.334  -2.310   0.000  0.00  0.00           S+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       4.001  -2.310   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   14  S   UNK     0       5.335  -4.620   0.000  0.00  0.00           S+0
HETATM   15  O   UNK     0       3.795  -4.620   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       6.875  -4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.335  -6.160   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   22  S   UNK     0      -0.000  -9.240   0.000  0.00  0.00           S+0
HETATM   23  O   UNK     0      -0.000 -10.780   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -1.540  -9.240   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.540  -9.240   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   27                                                  
CONECT    4    3    5   26                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    5   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14                                                            
CONECT   18   11   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22                                                            
CONECT   26    4                                                            
CONECT   27    3                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   54    0
END

View in JSmol

Synonyms

Value	Source
{[(e)-(5-methanesulfonyl-1-{[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pentylidene)amino]oxy}sulfonate	Generator
{[(e)-(5-methanesulphonyl-1-{[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}pentylidene)amino]oxy}sulphonate	Generator
{[(e)-(5-methanesulphonyl-1-{[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}pentylidene)amino]oxy}sulphonic acid	Generator

Chemical Formula

C₁₂H₂₃NO₁₁S₃

Average Mass

453.4900 Da

Monoisotopic Mass

453.04332 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CS(=O)(=O)CCCC\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/C12H23NO11S3/c1-26(18,19)5-3-2-4-8(13-24-27(20,21)22)25-12-11(17)10(16)9(15)7(6-14)23-12/h7,9-12,14-17H,2-6H2,1H3,(H,20,21,22)/b13-8+/t7-,9-,10-,11+,12+/m0/s1

InChI Key

WJMGSLJQEIYHOF-VPJITUJYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Brassica napus var.napobrassica	Plant	KNApSAcK
Descurainia richardsonii	Plant	KNApSAcK
Erysimum allionii	Plant	KNApSAcK
Erysimum asperum	Plant	KNApSAcK
Erysimum perofskianum	Plant	KNApSAcK
Lepidium draba	Plant	KNApSAcK
Lesquerella engelmannii	Plant	KNApSAcK
Thelypodium crispum	Plant	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
S-glycosyl compound
Glycosyl compound
Oxane
Sulfonyl
Sulfone
Organic sulfuric acid or derivatives
Monothioacetal
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Sulfenyl compound
Polyol
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organosulfur compound
Organonitrogen compound
Alcohol
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	-4.6	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	-3.8	ChemAxon
pKa (Strongest Basic)	-0.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	200.25 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	93.37 m³·mol⁻¹	ChemAxon
Polarizability	42.08 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

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

161522105

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4-(Methylsulfonyl)butyl glucosinolate (NP0050697)

MOL for NP0050697 (4-(Methylsulfonyl)butyl glucosinolate)

3D MOL for NP0050697 (4-(Methylsulfonyl)butyl glucosinolate)

3D SDF for NP0050697 (4-(Methylsulfonyl)butyl glucosinolate)

3D-SDF for NP0050697 (4-(Methylsulfonyl)butyl glucosinolate)

PDB for NP0050697 (4-(Methylsulfonyl)butyl glucosinolate)

3D PDB for NP0050697 (4-(Methylsulfonyl)butyl glucosinolate)

SMILES for NP0050697 (4-(Methylsulfonyl)butyl glucosinolate)

INCHI for NP0050697 (4-(Methylsulfonyl)butyl glucosinolate)

Structure for NP0050697 (4-(Methylsulfonyl)butyl glucosinolate)

3D Structure for NP0050697 (4-(Methylsulfonyl)butyl glucosinolate)