NP-MRD: Showing NP-Card for Glucoerucin (NP0049094)

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Record Information

Version

2.0

Created at

2022-03-17 21:07:02 UTC

Updated at

2022-03-17 21:07:02 UTC

NP-MRD ID

NP0049094

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glucoerucin

Description

Glucoerucin belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain. Glucoerucin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Glucoerucin has been detected, but not quantified in, several different foods, such as cabbages, chinese cabbages, white cabbages, brassicas, and common cabbages. Glucoerucin is found in Alyssoides utriculata, Alyssum argenteum, Alyssum chondrogynum, Alyssum tortuosum, Arabidopsis thaliana, Aurinia saxatilis, Brassica oleracea var. napobrassica , Brassica sprouts, Cakile constricta, Cakile edentula, Cakile geniculata, Cakile lanceolata, Cakile maritima , Camelina sativa , Capsella bursa-pastoris , Cardaria chalapensis, Carrichtera annua, Chorispora tenella, Diplotaxis erucoides , Diplotaxis griffithii, Diplotaxis tenuifolia , Diplotaxis viminea, Draba aizoides, Eruca longirostris, Eruca vesicaria, Erysimum allionii, Erysimum cheiranthoides, Cheiranthus cheiri , Erysimum hieracifolium, Erysimum perofskianum, Erysimum repandum, Farsetia clypeata, Farsetia jacquemontii , Farsetia ramosissima, Hesperis matronalis , Iberis amara , Iberis sempervirens, Lepidium draba , Lepidium iberis, Lepidium perfoliatum, Lesquerella engelmannii, Lesquerella globosa, Matthiola bicornis, Matthiola fruticulosa, Physaria angustifolia, Pringlea antiscorbutica, Thelypodium crispum, Thelypodium eucosmum and Thelypodium laciniatum. This could make glucoerucin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310252D          

 25 25  0  0  0  0            999 V2000
    2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    7.0125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5408    8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8908    8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    5.7750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    8.2500    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
  5  3  1  0  0  0  0
  7  6  1  0  0  0  0
  8  4  1  0  0  0  0
  9  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13  8  2  0  0  0  0
 14  6  1  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 21  7  1  0  0  0  0
 21 12  1  0  0  0  0
 22 13  1  0  0  0  0
 23  1  1  0  0  0  0
 23  5  1  0  0  0  0
 24  8  1  0  0  0  0
 24 12  1  0  0  0  0
 25 18  1  0  0  0  0
 25 19  2  0  0  0  0
 25 20  2  0  0  0  0
 25 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049094

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H23NO9S3/c1-23-5-3-2-4-8(13-22-25(18,19)20)24-12-11(17)10(16)9(15)7(6-14)21-12/h7,9-12,14-17H,2-6H2,1H3,(H,18,19,20)/b13-8+

> <INCHI_KEY>
GKUMMDFLKGFCKH-MDWZMJQESA-N

> <FORMULA>
C12H23NO9S3

> <MOLECULAR_WEIGHT>
421.507

> <EXACT_MASS>
421.053493409

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
40.609862934398706

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.28

> <JCHEM_LOGP>
-2.190347807717175

> <ALOGPS_LOGS>
-2.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.44767576429426

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.544322143918646

> <JCHEM_PKA_STRONGEST_BASIC>
-0.21811535657922254

> <JCHEM_POLAR_SURFACE_AREA>
166.10999999999999

> <JCHEM_REFRACTIVITY>
91.86229999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(E)-[5-(methylsulfanyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pentylidene]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  11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  11.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002  10.780   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669  10.780   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.672  10.780   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.338  11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.003  11.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.338  13.090   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.004  13.860   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.671  13.090   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.671  11.550   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      12.003  13.090   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0      20.005  11.550   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      18.672  13.860   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      16.004  15.400   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      13.337  13.860   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      12.209  15.400   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.129  15.400   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      10.669  16.940   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      16.004  10.780   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      10.669  13.860   0.000  0.00  0.00           O+0
HETATM   23  S   UNK     0       5.335  10.780   0.000  0.00  0.00           S+0
HETATM   24  S   UNK     0      13.337  10.780   0.000  0.00  0.00           S+0
HETATM   25  S   UNK     0      10.669  15.400   0.000  0.00  0.00           S+0
CONECT    1   23                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3   23                                                       
CONECT    6    7   14                                                       
CONECT    7    6    9   21                                                  
CONECT    8    4   13   24                                                  
CONECT    9    7   10   15                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11   21   24                                                  
CONECT   13    8   22                                                       
CONECT   14    6                                                            
CONECT   15    9                                                            
CONECT   16   10                                                            
CONECT   17   11                                                            
CONECT   18   25                                                            
CONECT   19   25                                                            
CONECT   20   25                                                            
CONECT   21    7   12                                                       
CONECT   22   13   25                                                       
CONECT   23    1    5                                                       
CONECT   24    8   12                                                       
CONECT   25   18   19   20   22                                             
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

View in JSmol

Synonyms

Value	Source
1-Thio-b-D-glucopyranose 1-[5-(methylthio)-N-(sulfooxy)pentanimidate], 9ci	HMDB
4-Methylthiobutyl glucosinolate	HMDB
{[(e)-[5-(methylsulfanyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pentylidene]amino]oxy}sulfonate	Generator
{[(e)-[5-(methylsulphanyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}pentylidene]amino]oxy}sulphonate	Generator
{[(e)-[5-(methylsulphanyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}pentylidene]amino]oxy}sulphonic acid	Generator
Glucoerucin	MeSH

Chemical Formula

C₁₂H₂₃NO₉S₃

Average Mass

421.5070 Da

Monoisotopic Mass

421.05349 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

21973-56-8

SMILES

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

InChI Identifier

InChI=1S/C12H23NO9S3/c1-23-5-3-2-4-8(13-22-25(18,19)20)24-12-11(17)10(16)9(15)7(6-14)21-12/h7,9-12,14-17H,2-6H2,1H3,(H,18,19,20)/b13-8+

InChI Key

GKUMMDFLKGFCKH-MDWZMJQESA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alyssoides utriculata	Plant	KNApSAcK
Alyssum argenteum	Plant	KNApSAcK
Alyssum chondrogynum	Plant	KNApSAcK
Alyssum tortuosum	Plant	KNApSAcK
Arabidopsis thaliana	Plant	KNApSAcK
Armoracia rusticana	FooDB	KNAPSACK
Aurinia saxatilis	Plant	KNApSAcK
Brassica napus	FooDB	PHYTOHUB
Brassica oleracea	FooDB	KNAPSACK
Brassica oleracea var. botrytis	FooDB	15963940
Brassica oleracea var. capitata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Brassica oleracea var. gemmifera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Brassica oleracea var. italica	FooDB	16713696
Brassica oleracea var. napobrassica	Plant	KNApSAcK
Brassica rapa	FooDB	KNAPSACK
Brassica rapa var. rapa	FooDB	KNAPSACK
Brassica sprouts	Plant	KNApSAcK
Cakile constricta	Plant	KNApSAcK
Cakile edentula	Plant	KNApSAcK
Cakile geniculata	Plant	KNApSAcK
Cakile lanceolata	Plant	KNApSAcK
Cakile maritima	Plant	KNApSAcK
Camelina sativa	Plant	KNApSAcK
Capsella bursa-pastoris	Plant	KNApSAcK
Cardaria chalapensis	Plant	KNApSAcK
Carrichtera annua	Plant	KNApSAcK
Chorispora tenella	Plant	KNApSAcK
Diplotaxis erucoides	Plant	KNApSAcK
Diplotaxis griffithii	Plant	KNApSAcK
Diplotaxis tenuifolia	Plant	KNApSAcK
Diplotaxis viminea	Plant	KNApSAcK
Draba aizoides	Plant	KNApSAcK
Eruca longirostris	Plant	KNApSAcK
Eruca vesicaria	LOTUS Database	35616633
Eruca vesicaria subsp. Sativa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Erysimum allionii	Plant	KNApSAcK
Erysimum cheiranthoides	Plant	KNApSAcK
Erysimum cheiri	Plant	KNApSAcK
Erysimum hieracifolium	Plant	KNApSAcK
Erysimum perofskianum	Plant	KNApSAcK
Erysimum repandum	Plant	KNApSAcK
Farsetia clypeata	Plant	KNApSAcK
Farsetia jacquemontii	Plant	KNApSAcK
Farsetia ramosissima	Plant	KNApSAcK
Hesperis matronalis	Plant	KNApSAcK
Iberis amara	Plant	KNApSAcK
Iberis sempervirens	Plant	KNApSAcK
Lepidium draba	Plant	KNApSAcK
Lepidium iberis	Plant	KNApSAcK
Lepidium perfoliatum	Plant	KNApSAcK
Lesquerella engelmannii	Plant	KNApSAcK
Lesquerella globosa	Plant	KNApSAcK
Matthiola bicornis	Plant	KNApSAcK
Matthiola fruticulosa	Plant	KNApSAcK
Physaria angustifolia	Plant	KNApSAcK
Pringlea antiscorbutica	Plant	KNApSAcK
Raphanus sativus	FooDB	PHYTOHUB
Sinapis alba	FooDB	KNAPSACK
Thelypodium crispum	Plant	KNApSAcK
Thelypodium eucosmum	Plant	KNApSAcK
Thelypodium laciniatum	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
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	-1.3	ALOGPS
logP	-2.2	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	-3.5	ChemAxon
pKa (Strongest Basic)	-0.22	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	10	ChemAxon
Refractivity	91.86 m³·mol⁻¹	ChemAxon
Polarizability	40.61 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

HMDB0038403

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017755

KNApSAcK ID

C00007344

Chemspider ID

Not Available

KEGG Compound ID

C08409

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15560213

PDB ID

Not Available

ChEBI ID

5404

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Glucoerucin (NP0049094)

MOL for NP0049094 (Glucoerucin)

3D MOL for NP0049094 (Glucoerucin)

3D SDF for NP0049094 (Glucoerucin)

3D-SDF for NP0049094 (Glucoerucin)

PDB for NP0049094 (Glucoerucin)

3D PDB for NP0049094 (Glucoerucin)

SMILES for NP0049094 (Glucoerucin)

INCHI for NP0049094 (Glucoerucin)

Structure for NP0049094 (Glucoerucin)

3D Structure for NP0049094 (Glucoerucin)