NP-MRD: Showing NP-Card for Glucocheirolin (NP0049099)

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Record Information

Version

2.0

Created at

2022-03-17 21:07:07 UTC

Updated at

2022-03-17 21:07:07 UTC

NP-MRD ID

NP0049099

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glucocheirolin

Description

Glucocheirolin belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain. Glucocheirolin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Glucocheirolin has been detected, but not quantified in, several different foods, such as brassicas, cauliflowers, horseradish, swedes, and turnips. Glucocheirolin is found in Aethionema armenum, Arabis laevigata, Brassica napus var. napobrassica , Calepina irregularis, Erysimum allionii, Erysimum asperum, Erysimum capitatum, Cheiranthus cheiri , Erysimum cuspidatum, Erysimum diffusum , Erysimum hieracifolium, Erysimum linifolium, Erysimum ochrolecum, Erysimum perofskianum, Erysimum rupestre, Erysimum sisymbrioides, Goldbachia laevigata, Iberis crenata, Iberis linifolia, Iberis simplex, Lepidium draba , Lesquerella douglasii, Malcolmia africana, Malcomia littorea, Malcomia maritima, Matthiola bicornis, Neslia paniculata, Rapistrum rugosum and Sinapis arvensis . This could make glucocheirolin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310262D          

 26 26  0  0  0  0            999 V2000
   -2.1434   -4.5375    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
    0.0000   -2.4750    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
    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
   -1.0164   -4.8395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -3.4105    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   -1.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    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
  4  2  1  0  0  0  0
  6  5  1  0  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
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 22  6  1  0  0  0  0
 22 11  1  0  0  0  0
 23 12  1  0  0  0  0
 24  7  1  0  0  0  0
 24 11  1  0  0  0  0
 25  1  1  0  0  0  0
 25  4  1  0  0  0  0
 25 17  2  0  0  0  0
 25 18  2  0  0  0  0
 26 19  1  0  0  0  0
 26 20  2  0  0  0  0
 26 21  2  0  0  0  0
 26 23  1  0  0  0  0
M  END


  Mrv0541 05061310262D          

 26 26  0  0  0  0            999 V2000
   -2.1434   -4.5375    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
    0.0000   -2.4750    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
    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
   -1.0164   -4.8395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -3.4105    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   -1.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    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
  4  2  1  0  0  0  0
  6  5  1  0  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
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 22  6  1  0  0  0  0
 22 11  1  0  0  0  0
 23 12  1  0  0  0  0
 24  7  1  0  0  0  0
 24 11  1  0  0  0  0
 25  1  1  0  0  0  0
 25  4  1  0  0  0  0
 25 17  2  0  0  0  0
 25 18  2  0  0  0  0
 26 19  1  0  0  0  0
 26 20  2  0  0  0  0
 26 21  2  0  0  0  0
 26 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049099

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H21NO11S3/c1-25(17,18)4-2-3-7(12-23-26(19,20)21)24-11-10(16)9(15)8(14)6(5-13)22-11/h6,8-11,13-16H,2-5H2,1H3,(H,19,20,21)/b12-7+

> <INCHI_KEY>
OFKKQTQFWWIRBD-KPKJPENVSA-N

> <FORMULA>
C11H21NO11S3

> <MOLECULAR_WEIGHT>
439.48

> <EXACT_MASS>
439.027672589

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
39.60230077580437

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.80

> <JCHEM_LOGP>
-5.053849371567402

> <ALOGPS_LOGS>
-1.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.447671415298185

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.7190978039113043

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5647050686739864

> <JCHEM_POLAR_SURFACE_AREA>
200.24999999999997

> <JCHEM_REFRACTIVITY>
88.77039999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.46e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(E)-(4-methanesulfonyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}butylidene)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      -4.001  -8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   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  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.897  -9.034   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -3.437  -6.366   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -3.231  -0.976   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -4.771  -3.644   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   24  S   UNK     0       1.334  -2.310   0.000  0.00  0.00           S+0
HETATM   25  S   UNK     0      -2.667  -7.700   0.000  0.00  0.00           S+0
HETATM   26  S   UNK     0      -4.001  -2.310   0.000  0.00  0.00           S+0
CONECT    1   25                                                            
CONECT    2    3    4                                                       
CONECT    3    2    7                                                       
CONECT    4    2   25                                                       
CONECT    5    6   13                                                       
CONECT    6    5    8   22                                                  
CONECT    7    3   12   24                                                  
CONECT    8    6    9   14                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10   22   24                                                  
CONECT   12    7   23                                                       
CONECT   13    5                                                            
CONECT   14    8                                                            
CONECT   15    9                                                            
CONECT   16   10                                                            
CONECT   17   25                                                            
CONECT   18   25                                                            
CONECT   19   26                                                            
CONECT   20   26                                                            
CONECT   21   26                                                            
CONECT   22    6   11                                                       
CONECT   23   12   26                                                       
CONECT   24    7   11                                                       
CONECT   25    1    4   17   18                                             
CONECT   26   19   20   21   23                                             
MASTER        0    0    0    0    0    0    0    0   26    0   52    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₁₁H₂₁NO₁₁S₃

Average Mass

439.4800 Da

Monoisotopic Mass

439.02767 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

554-86-9

SMILES

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

InChI Identifier

InChI=1S/C11H21NO11S3/c1-25(17,18)4-2-3-7(12-23-26(19,20)21)24-11-10(16)9(15)8(14)6(5-13)22-11/h6,8-11,13-16H,2-5H2,1H3,(H,19,20,21)/b12-7+

InChI Key

OFKKQTQFWWIRBD-KPKJPENVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aethionema armenum	Plant	KNApSAcK
Arabis laevigata	Plant	KNApSAcK
Armoracia rusticana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Brassica napus	FooDB	KNAPSACK
Brassica napus var.napobrassica	Plant	KNApSAcK
Brassica oleracea var. botrytis	FooDB	KNAPSACK
Brassica rapa var. rapa	FooDB	KNAPSACK
Calepina irregularis	Plant	KNApSAcK
Erysimum allionii	Plant	KNApSAcK
Erysimum asperum	Plant	KNApSAcK
Erysimum capitatum	Plant	KNApSAcK
Erysimum cheiri	Plant	KNApSAcK
Erysimum cuspidatum	Plant	KNApSAcK
Erysimum diffusum	Plant	KNApSAcK
Erysimum hieracifolium	Plant	KNApSAcK
Erysimum linifolium	Plant	KNApSAcK
Erysimum ochrolecum	Plant	KNApSAcK
Erysimum perofskianum	Plant	KNApSAcK
Erysimum rupestre	Plant	KNApSAcK
Erysimum sisymbrioides	Plant	KNApSAcK
Goldbachia laevigata	Plant	KNApSAcK
Iberis amara	Plant	KNApSAcK
Iberis linifolia	Plant	KNApSAcK
Iberis simplex	Plant	KNApSAcK
Lepidium draba	Plant	KNApSAcK
Lesquerella douglasii	Plant	KNApSAcK
Malcolmia africana	Plant	KNApSAcK
Malcomia littorea	-	KNApSAcK
Malcomia maritima	-	KNApSAcK
Matthiola bicornis	Plant	KNApSAcK
Neslia paniculata	Plant	KNApSAcK
Rapistrum rugosum	Plant	KNApSAcK
Sinapis arvensis	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
Glycosyl compound
S-glycosyl compound
Oxane
Monothioacetal
Organic sulfuric acid or derivatives
Sulfone
Sulfonyl
Secondary alcohol
Polyol
Sulfenyl compound
Organoheterocyclic compound
Oxacycle
Organic oxide
Alcohol
Organic nitrogen compound
Primary alcohol
Organopnictogen compound
Organosulfur compound
Organonitrogen compound
Hydrocarbon derivative
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	-1.8	ALOGPS
logP	-5.1	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	-3.7	ChemAxon
pKa (Strongest Basic)	-0.56	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	9	ChemAxon
Refractivity	88.77 m³·mol⁻¹	ChemAxon
Polarizability	39.6 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

HMDB0038407

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017761

KNApSAcK ID

C00001466

Chemspider ID

7848404

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9573943

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Glucocheirolin (NP0049099)

MOL for NP0049099 (Glucocheirolin)

3D MOL for NP0049099 (Glucocheirolin)

3D SDF for NP0049099 (Glucocheirolin)

3D-SDF for NP0049099 (Glucocheirolin)

PDB for NP0049099 (Glucocheirolin)

3D PDB for NP0049099 (Glucocheirolin)

SMILES for NP0049099 (Glucocheirolin)

INCHI for NP0049099 (Glucocheirolin)

Structure for NP0049099 (Glucocheirolin)

3D Structure for NP0049099 (Glucocheirolin)