NP-MRD: Showing NP-Card for 4-Methoxyglucobrassicin (NP0049102)

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Record Information

Version

2.0

Created at

2022-03-17 21:07:09 UTC

Updated at

2022-03-17 21:07:09 UTC

NP-MRD ID

NP0049102

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-Methoxyglucobrassicin

Description

4-Methoxyglucobrassicin is found in Apis cerana, Arabidopsis thaliana, Barbarea vulgaris, Brassica napus var. purple top , Brassica napus var. napobrassica , Brassica oleracea, Brassica oleracea var. gongylodes , Brassica sp., Brassicaceae, Dimorphocarpa wislizeni, Diplotaxis erucoides , Isatis djurdjura, Isatis tinctoria , Lepidium meyenii, Moricandia arvensis , Raphanus sativus and Tovaria pendula.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241217072D          

 31 33  0  0  0  0            999 V2000
    2.2994   -0.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7926   -0.9853    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0818   -0.5746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6568    0.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3955   -0.2459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4782   -1.0671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7918   -0.1640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0531    0.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9706    1.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6274    1.5603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3669    1.2315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1493    1.3959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4925    0.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2470    1.2315    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.9857    0.7390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9031   -0.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5599   -0.5746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5599   -1.3959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2994   -1.6421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5456   -2.4634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8888   -3.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0674   -2.7922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9031   -1.9710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0826   -1.8066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3281   -2.5453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7244    1.1497    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8069    1.9710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3669    2.6278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9562    1.5603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5456    2.2998    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2175    3.0384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 17  2  0  0  0  0
  2 19  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 13  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 26  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 23  2  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 27  1  0  0  0  0
 27 30  1  0  0  0  0
 28 30  2  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
M  END


  Mrv0541 02241217072D          

 31 33  0  0  0  0            999 V2000
    2.2994   -0.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7926   -0.9853    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0818   -0.5746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6568    0.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3955   -0.2459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4782   -1.0671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7918   -0.1640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0531    0.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9706    1.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6274    1.5603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3669    1.2315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1493    1.3959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4925    0.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2470    1.2315    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.9857    0.7390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9031   -0.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5599   -0.5746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5599   -1.3959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2994   -1.6421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5456   -2.4634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8888   -3.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0674   -2.7922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9031   -1.9710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0826   -1.8066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3281   -2.5453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7244    1.1497    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8069    1.9710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3669    2.6278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9562    1.5603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5456    2.2998    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2175    3.0384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 17  2  0  0  0  0
  2 19  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 13  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 26  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 23  2  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 27  1  0  0  0  0
 27 30  1  0  0  0  0
 28 30  2  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049102

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C(C\C(SC3OC(CO)C(O)C(O)C3O)=N\OS(O)(=O)=O)=CNC2=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H22N2O10S2/c1-27-10-4-2-3-9-13(10)8(6-18-9)5-12(19-29-31(24,25)26)30-17-16(23)15(22)14(21)11(7-20)28-17/h2-4,6,11,14-18,20-23H,5,7H2,1H3,(H,24,25,26)/b19-12-

> <INCHI_KEY>
IIAGSABLXRZUSE-UNOMPAQXSA-N

> <FORMULA>
C17H22N2O10S2

> <MOLECULAR_WEIGHT>
478.494

> <EXACT_MASS>
478.071586314

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
44.759278955913445

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(Z)-[2-(4-methoxy-1H-indol-3-yl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}ethylidene]amino]oxy}sulfonic acid

> <ALOGPS_LOGP>
-0.95

> <JCHEM_LOGP>
-2.2536511100401904

> <ALOGPS_LOGS>
-2.53

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.446550790312209

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.562480327532678

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3666320891423397

> <JCHEM_POLAR_SURFACE_AREA>
191.13

> <JCHEM_REFRACTIVITY>
107.69669999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.41e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(Z)-[2-(4-methoxy-1H-indol-3-yl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}ethylidene]amino]oxysulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       4.292  -0.612   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       5.213  -1.839   0.000  0.00  0.00           N+0
HETATM    3  O   UNK     0      -0.153  -1.073   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.226   0.153   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.605  -0.459   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.759  -1.992   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -5.211  -0.306   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.832   0.460   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.678   1.993   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.904   2.913   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -6.285   2.299   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -2.145   2.606   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.919   1.687   0.000  0.00  0.00           C+0
HETATM   14  S   UNK     0       0.461   2.299   0.000  0.00  0.00           S+0
HETATM   15  C   UNK     0       1.840   1.379   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.686  -0.152   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.912  -1.073   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.912  -2.606   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.292  -3.065   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.752  -4.598   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.526  -5.672   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.992  -5.212   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.686  -3.679   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.154  -3.372   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.612  -4.751   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       3.219   2.146   0.000  0.00  0.00           N+0
HETATM   27  O   UNK     0       3.373   3.679   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       6.285   4.905   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       5.518   2.913   0.000  0.00  0.00           O+0
HETATM   30  S   UNK     0       4.752   4.293   0.000  0.00  0.00           S+0
HETATM   31  O   UNK     0       4.139   5.672   0.000  0.00  0.00           O+0
CONECT    1    2   17                                                       
CONECT    2    1   19                                                       
CONECT    3    4                                                            
CONECT    4    3    5   13                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5                                                            
CONECT    7    8                                                            
CONECT    8    5    7    9                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13    4   12   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   26                                                  
CONECT   16   15   17                                                       
CONECT   17    1   16   18                                                  
CONECT   18   17   19   23                                                  
CONECT   19    2   18   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   18   22   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   15   27                                                       
CONECT   27   26   30                                                       
CONECT   28   30                                                            
CONECT   29   30                                                            
CONECT   30   27   28   29   31                                             
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Value	Source
Methoxyglucobrassicin	MeSH

Chemical Formula

C₁₇H₂₂N₂O₁₀S₂

Average Mass

478.4940 Da

Monoisotopic Mass

478.07159 Da

IUPAC Name

{[(Z)-[2-(4-methoxy-1H-indol-3-yl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}ethylidene]amino]oxy}sulfonic acid

Traditional Name

[(Z)-[2-(4-methoxy-1H-indol-3-yl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}ethylidene]amino]oxysulfonic acid

CAS Registry Number

83327-21-3

SMILES

COC1=C2C(C\C(SC3OC(CO)C(O)C(O)C3O)=N\OS(O)(=O)=O)=CNC2=CC=C1

InChI Identifier

InChI=1S/C17H22N2O10S2/c1-27-10-4-2-3-9-13(10)8(6-18-9)5-12(19-29-31(24,25)26)30-17-16(23)15(22)14(21)11(7-20)28-17/h2-4,6,11,14-18,20-23H,5,7H2,1H3,(H,24,25,26)/b19-12-

InChI Key

IIAGSABLXRZUSE-UNOMPAQXSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633
Arabidopsis thaliana	Plant	KNApSAcK
Barbarea vulgaris	LOTUS Database	35616633
Brassica juncea	FooDB	KNAPSACK
Brassica napus	FooDB	KNAPSACK
Brassica napus var. purple top	Plant	KNApSAcK
Brassica napus var.napobrassica	Plant	KNApSAcK
Brassica oleracea	LOTUS Database	35616633
Brassica oleracea var. botrytis	FooDB	15963940
Brassica oleracea var. gemmifera	FooDB	15963940
Brassica oleracea var. gongylodes	Plant	KNApSAcK
Brassica oleracea var. italica	FooDB	12720387
Brassica rapa	FooDB	KNAPSACK
Brassica rapa var. rapa	FooDB	PHYTOHUB
Brassica sp.	Plant	KNApSAcK
Brassicaceae	-	KNApSAcK
Capparis spinosa	FooDB	KNAPSACK
Dimorphocarpa wislizenii	LOTUS Database	35616633
Diplotaxis erucoides	Plant	KNApSAcK
Isatis djurdjura	Plant	KNApSAcK
Isatis tinctoria	Plant	KNApSAcK
Lepidium meyenii	LOTUS Database	35616633
Moricandia arvensis	Plant	KNApSAcK
Raphanus sativus	Plant	KNApSAcK
Ribes uva-crispa	FooDB	PHYTOHUB
Tovaria pendula	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
3-alkylindole
Indole
Indole or derivatives
Anisole
Alkyl aryl ether
Oxane
Substituted pyrrole
Benzenoid
Heteroaromatic compound
Monothioacetal
Organic sulfuric acid or derivatives
Pyrrole
Secondary alcohol
Polyol
Oxacycle
Ether
Azacycle
Organoheterocyclic compound
Sulfenyl compound
Primary alcohol
Organosulfur compound
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	-0.95	ALOGPS
logP	-2.3	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	-3.6	ChemAxon
pKa (Strongest Basic)	-0.37	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	191.13 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	107.7 m³·mol⁻¹	ChemAxon
Polarizability	44.76 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017767

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

6122984

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4-Methoxyglucobrassicin (NP0049102)

MOL for NP0049102 (4-Methoxyglucobrassicin)

3D MOL for NP0049102 (4-Methoxyglucobrassicin)

3D SDF for NP0049102 (4-Methoxyglucobrassicin)

3D-SDF for NP0049102 (4-Methoxyglucobrassicin)

PDB for NP0049102 (4-Methoxyglucobrassicin)

3D PDB for NP0049102 (4-Methoxyglucobrassicin)

SMILES for NP0049102 (4-Methoxyglucobrassicin)

INCHI for NP0049102 (4-Methoxyglucobrassicin)

Structure for NP0049102 (4-Methoxyglucobrassicin)

3D Structure for NP0049102 (4-Methoxyglucobrassicin)