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Showing NP-Card for 1,4-Dimethoxyglucobrassicin (NP0335237)

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Record Information
Version2.0
Created at2024-09-11 00:41:03 UTC
Updated at2024-09-11 00:41:03 UTC
NP-MRD IDNP0335237
Secondary Accession NumbersNone
Natural Product Identification
Common Name1,4-Dimethoxyglucobrassicin
Description 1,4-Dimethoxyglucobrassicin was first documented in 2001 (PMID: 11312886). Based on a literature review very few articles have been published on 1,4-Dimethoxyglucobrassicin (PMID: 12657300).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0335237 (1,4-Dimethoxyglucobrassicin)


  Mrv2104 05262303132D          

 33 35  0  0  0  0            999 V2000
    3.9934   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0769    2.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0572   -4.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3121   -4.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179   -1.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1191   -3.8350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3740   -3.0504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8220   -2.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0150   -2.6088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1659   -0.5980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6092   -5.4042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711   -4.4481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1810   -2.8788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0769   -1.6527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6832    1.4128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4819    1.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7443    0.2477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7601   -3.3934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4208    0.1866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4630   -1.9957    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1312    0.7997    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  2  0  0  0  0
 12  8  1  0  0  0  0
 13  6  1  0  0  0  0
 14  9  1  0  0  0  0
 14 10  2  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 13  2  0  0  0  0
 20  7  1  0  0  0  0
 20 10  1  0  0  0  0
 21  8  1  0  0  0  0
 22 15  1  0  0  0  0
 23 16  1  0  0  0  0
 24 17  1  0  0  0  0
 28  1  1  0  0  0  0
 28 11  1  0  0  0  0
 29  2  1  0  0  0  0
 29 20  1  0  0  0  0
 30 12  1  0  0  0  0
 30 18  1  0  0  0  0
 31 19  1  0  0  0  0
 32 13  1  0  0  0  0
 32 18  1  0  0  0  0
 33 25  1  0  0  0  0
 33 26  2  0  0  0  0
 33 27  2  0  0  0  0
 33 31  1  0  0  0  0
M  END
Download

3D MOL for NP0335237 (1,4-Dimethoxyglucobrassicin)

Download
3D SDF for NP0335237 (1,4-Dimethoxyglucobrassicin)

  Mrv2104 05262303132D          

 33 35  0  0  0  0            999 V2000
    3.9934   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0769    2.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0572   -4.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3121   -4.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179   -1.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1191   -3.8350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3740   -3.0504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8220   -2.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0150   -2.6088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1659   -0.5980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6092   -5.4042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711   -4.4481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1810   -2.8788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0769   -1.6527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6832    1.4128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4819    1.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7443    0.2477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7601   -3.3934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4208    0.1866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4630   -1.9957    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1312    0.7997    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  2  0  0  0  0
 12  8  1  0  0  0  0
 13  6  1  0  0  0  0
 14  9  1  0  0  0  0
 14 10  2  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 13  2  0  0  0  0
 20  7  1  0  0  0  0
 20 10  1  0  0  0  0
 21  8  1  0  0  0  0
 22 15  1  0  0  0  0
 23 16  1  0  0  0  0
 24 17  1  0  0  0  0
 28  1  1  0  0  0  0
 28 11  1  0  0  0  0
 29  2  1  0  0  0  0
 29 20  1  0  0  0  0
 30 12  1  0  0  0  0
 30 18  1  0  0  0  0
 31 19  1  0  0  0  0
 32 13  1  0  0  0  0
 32 18  1  0  0  0  0
 33 25  1  0  0  0  0
 33 26  2  0  0  0  0
 33 27  2  0  0  0  0
 33 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335237

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CON1C=C(C\C(SC2OC(CO)C(O)C(O)C2O)=N/OS(O)(=O)=O)C2=C1C=CC=C2OC

> <INCHI_IDENTIFIER>
InChI=1/C18H24N2O11S2/c1-28-11-5-3-4-10-14(11)9(7-20(10)29-2)6-13(19-31-33(25,26)27)32-18-17(24)16(23)15(22)12(8-21)30-18/h3-5,7,12,15-18,21-24H,6,8H2,1-2H3,(H,25,26,27)/b19-13+

> <INCHI_KEY>
OTCXWQPXFQXGTP-CPNJWEJPNA-N

> <FORMULA>
C18H24N2O11S2

> <MOLECULAR_WEIGHT>
508.51

> <EXACT_MASS>
508.082151949

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
48.247079489516956

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-2.5950132465167592

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.44713856275477

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.6215092170206544

> <JCHEM_PKA_STRONGEST_BASIC>
-0.42158558027057963

> <JCHEM_POLAR_SURFACE_AREA>
189.49999999999997

> <JCHEM_REFRACTIVITY>
115.35429999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0335237 (1,4-Dimethoxyglucobrassicin)
Download
PDB for NP0335237 (1,4-Dimethoxyglucobrassicin)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0       7.454  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.877   4.625   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.846  -1.941   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.973  -8.943   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.449  -7.479   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.340  -2.261   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.956  -7.159   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.431  -5.694   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.401  -4.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.895  -4.870   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       0.310  -1.116   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       3.322   2.016   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       3.004 -10.088   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.986  -8.303   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.938  -5.374   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.877  -3.085   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.275   2.637   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.900   2.523   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -1.389   0.462   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.846   3.481   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       1.419  -6.334   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.785   0.348   0.000  0.00  0.00           O+0
HETATM   32  S   UNK     0       0.864  -3.725   0.000  0.00  0.00           S+0
HETATM   33  S   UNK     0      -0.245   1.493   0.000  0.00  0.00           S+0
CONECT    1   28                                                            
CONECT    2   29                                                            
CONECT    3    4    5                                                       
CONECT    4    3   10                                                       
CONECT    5    3   11                                                       
CONECT    6    9   13                                                       
CONECT    7    9   20                                                       
CONECT    8   12   21                                                       
CONECT    9    6    7   14                                                  
CONECT   10    4   14   20                                                  
CONECT   11    5   14   28                                                  
CONECT   12    8   15   30                                                  
CONECT   13    6   19   32                                                  
CONECT   14    9   10   11                                                  
CONECT   15   12   16   22                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   18   24                                                  
CONECT   18   17   30   32                                                  
CONECT   19   13   31                                                       
CONECT   20    7   10   29                                                  
CONECT   21    8                                                            
CONECT   22   15                                                            
CONECT   23   16                                                            
CONECT   24   17                                                            
CONECT   25   33                                                            
CONECT   26   33                                                            
CONECT   27   33                                                            
CONECT   28    1   11                                                       
CONECT   29    2   20                                                       
CONECT   30   12   18                                                       
CONECT   31   19   33                                                       
CONECT   32   13   18                                                       
CONECT   33   25   26   27   31                                             
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

Download
3D PDB for NP0335237 (1,4-Dimethoxyglucobrassicin)
Download
SMILES for NP0335237 (1,4-Dimethoxyglucobrassicin)
CON1C=C(C\C(SC2OC(CO)C(O)C(O)C2O)=N/OS(O)(=O)=O)C2=C1C=CC=C2OC
Download
INCHI for NP0335237 (1,4-Dimethoxyglucobrassicin)
InChI=1/C18H24N2O11S2/c1-28-11-5-3-4-10-14(11)9(7-20(10)29-2)6-13(19-31-33(25,26)27)32-18-17(24)16(23)15(22)12(8-21)30-18/h3-5,7,12,15-18,21-24H,6,8H2,1-2H3,(H,25,26,27)/b19-13+
Download
View in JSmol
SynonymsNot Available
Chemical FormulaC18H24N2O11S2
Average Mass508.5100 Da
Monoisotopic Mass508.08215 Da
IUPAC Name{[(E)-[2-(1,4-dimethoxy-1H-indol-3-yl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}ethylidene]amino]oxy}sulfonic acid
Traditional Name[(E)-[2-(1,4-dimethoxyindol-3-yl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}ethylidene]amino]oxysulfonic acid
CAS Registry NumberNot Available
SMILES
CON1C=C(C\C(SC2OC(CO)C(O)C(O)C2O)=N/OS(O)(=O)=O)C2=C1C=CC=C2OC
InChI Identifier
InChI=1/C18H24N2O11S2/c1-28-11-5-3-4-10-14(11)9(7-20(10)29-2)6-13(19-31-33(25,26)27)32-18-17(24)16(23)15(22)12(8-21)30-18/h3-5,7,12,15-18,21-24H,6,8H2,1-2H3,(H,25,26,27)/b19-13+
InChI KeyOTCXWQPXFQXGTP-CPNJWEJPNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
ClassificationNot classified
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.6ChemAxon
pKa (Strongest Acidic)-3.6ChemAxon
pKa (Strongest Basic)-0.42ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area189.5 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity115.35 m³·mol⁻¹ChemAxon
Polarizability48.25 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Agerbirk N, Orgaard M, Nielsen JK: Glucosinolates, flea beetle resistance, and leaf pubescence as taxonomic characters in the genus Barbarea (Brassicaceae). Phytochemistry. 2003 May;63(1):69-80. doi: 10.1016/s0031-9422(02)00750-1. [PubMed:12657300  ] 
  2. Agerbirk N, Petersen BL, Olsen CE, Halkier BA, Nielsen JK: 1,4-Dimethoxyglucobrassicin in Barbarea and 4-hydroxyglucobrassicin in Arabidopsis and Brassica. J Agric Food Chem. 2001 Mar;49(3):1502-7. doi: 10.1021/jf001256r. [PubMed:11312886  ]