NP-MRD: Showing NP-Card for Glucobrassicanapin (NP0049109)

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Record Information

Version

2.0

Created at

2022-03-17 21:07:16 UTC

Updated at

2022-03-17 21:07:16 UTC

NP-MRD ID

NP0049109

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glucobrassicanapin

Description

Glucobrassicanapin belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain. Glucobrassicanapin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Glucobrassicanapin has been detected, but not quantified in, several different foods, such as swedes, cauliflowers, cabbages, white mustards, and broccoli. Glucobrassicanapin is found in Alyssum alyssoides, Aurinia saxatilis, Berteroa incana, Brassica cretica, Brassica napus var. napobrassica , Brassica oleracea , Brassica sp., Cakile edentula, Cakile lanceolata, Cakile maritima , Capsella bursa-pastoris , Cardamine hirsuta, Cardamine impatiens, Carrichtera annua, Descurainia pinnata, Descurainia richardsonii, Diplotaxis siifolia, Hirschfeldia incana , Leavenworthia torulosa, Lepidium draba , Lepidium meyenii, Lepidium subulatum, Lobularia maritima, Schouwia purpurea, Thelypodium crispum, Thelypodium eucosmum, Thelypodium howellii, Thelypodium laciniatum, Thelypodium laxiflorum and Thelypodium paniculatum. This could make glucobrassicanapin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310262D          

 24 24  0  0  0  0            999 V2000
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    5.7750    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
    5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7474    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.0125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  7  6  1  0  0  0  0
  8  5  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  8  1  0  0  0  0
 23 12  1  0  0  0  0
 24 18  1  0  0  0  0
 24 19  2  0  0  0  0
 24 20  2  0  0  0  0
 24 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049109

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H21NO9S2/c1-2-3-4-5-8(13-22-24(18,19)20)23-12-11(17)10(16)9(15)7(6-14)21-12/h2,7,9-12,14-17H,1,3-6H2,(H,18,19,20)/b13-8+

> <INCHI_KEY>
XMJFVIGTHMOGNZ-MDWZMJQESA-N

> <FORMULA>
C12H21NO9S2

> <MOLECULAR_WEIGHT>
387.426

> <EXACT_MASS>
387.065772655

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
36.85260084601283

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.47

> <JCHEM_LOGP>
-2.2448939529622707

> <ALOGPS_LOGS>
-1.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.44767466549575

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.4887843090415975

> <JCHEM_PKA_STRONGEST_BASIC>
-0.25913838036888504

> <JCHEM_POLAR_SURFACE_AREA>
166.10999999999999

> <JCHEM_REFRACTIVITY>
83.89909999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.95e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(E)-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}hex-5-en-1-ylidene)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       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.671   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.337   9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.337  10.780   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.003  11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669  10.780   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669   9.240   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       8.002  10.780   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0      16.004   9.240   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      14.671  11.550   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      12.003  13.090   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       9.336  11.550   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.208  13.090   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.128  13.090   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.668  14.630   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      12.003   8.470   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.668  11.550   0.000  0.00  0.00           O+0
HETATM   23  S   UNK     0       9.336   8.470   0.000  0.00  0.00           S+0
HETATM   24  S   UNK     0       6.668  13.090   0.000  0.00  0.00           S+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    8                                                       
CONECT    6    7   14                                                       
CONECT    7    6    9   21                                                  
CONECT    8    5   13   23                                                  
CONECT    9    7   10   15                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11   21   23                                                  
CONECT   13    8   22                                                       
CONECT   14    6                                                            
CONECT   15    9                                                            
CONECT   16   10                                                            
CONECT   17   11                                                            
CONECT   18   24                                                            
CONECT   19   24                                                            
CONECT   20   24                                                            
CONECT   21    7   12                                                       
CONECT   22   13   24                                                       
CONECT   23    8   12                                                       
CONECT   24   18   19   20   22                                             
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

View in JSmol

Synonyms

Value	Source
1-Thio-b-D-glucopyranose 1-[N-(sulfooxy)-5-hexenimidate], 9ci	HMDB
{[(e)-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}hex-5-en-1-ylidene)amino]oxy}sulfonate	Generator
{[(e)-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}hex-5-en-1-ylidene)amino]oxy}sulphonate	Generator
{[(e)-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}hex-5-en-1-ylidene)amino]oxy}sulphonic acid	Generator

Chemical Formula

C₁₂H₂₁NO₉S₂

Average Mass

387.4260 Da

Monoisotopic Mass

387.06577 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

19041-10-2

SMILES

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

InChI Identifier

InChI=1S/C12H21NO9S2/c1-2-3-4-5-8(13-22-24(18,19)20)23-12-11(17)10(16)9(15)7(6-14)21-12/h2,7,9-12,14-17H,1,3-6H2,(H,18,19,20)/b13-8+

InChI Key

XMJFVIGTHMOGNZ-MDWZMJQESA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alyssum alyssoides	Plant	KNApSAcK
Armoracia rusticana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Aurinia saxatilis	Plant	KNApSAcK
Berteroa incana	Plant	KNApSAcK
Brassica cretica	LOTUS Database	35616633
Brassica juncea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Brassica napus	FooDB	KNAPSACK
Brassica napus var.napobrassica	Plant	KNApSAcK
Brassica oleracea	Plant	KNApSAcK
Brassica oleracea var. botrytis	FooDB	Karen Sones, Robert K. Heaney, G. Roger Fenwick. Glucosinolates in Brassica vegetables. Analysis ...
Brassica oleracea var. capitata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Brassica oleracea var. italica	FooDB	12720387
Brassica rapa	FooDB	KNAPSACK
Brassica rapa var. rapa	FooDB	KNAPSACK
Brassica sp.	Plant	KNApSAcK
Cakile edentula	Plant	KNApSAcK
Cakile lanceolata	Plant	KNApSAcK
Cakile maritima	Plant	KNApSAcK
Capparis spinosa	FooDB	PHYTOHUB
Capsella bursa-pastoris	Plant	KNApSAcK
Cardamine hirsuta	Plant	KNApSAcK
Cardamine impatiens	Plant	KNApSAcK
Carrichtera annua	Plant	KNApSAcK
Descurainia pinnata	Plant	KNApSAcK
Descurainia richardsonii	Plant	KNApSAcK
Diplotaxis siifolia	Plant	KNApSAcK
Eutrema japonicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Hirschfeldia incana	Plant	KNApSAcK
Leavenworthia torulosa	Plant	KNApSAcK
Lepidium draba	Plant	KNApSAcK
Lepidium meyenii	LOTUS Database	35616633
Lepidium subulatum	Plant	KNApSAcK
Lobularia maritima	Plant	KNApSAcK
Schouwia purpurea	Plant	KNApSAcK
Sinapis alba	FooDB	KNAPSACK
Thelypodium crispum	Plant	KNApSAcK
Thelypodium eucosmum	Plant	KNApSAcK
Thelypodium howellii	Plant	KNApSAcK
Thelypodium laciniatum	Plant	KNApSAcK
Thelypodium laxiflorum	Plant	KNApSAcK
Thelypodium paniculatum	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
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

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	-1.5	ALOGPS
logP	-2.2	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	-3.5	ChemAxon
pKa (Strongest Basic)	-0.26	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	9	ChemAxon
Refractivity	83.9 m³·mol⁻¹	ChemAxon
Polarizability	36.85 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