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Showing NP-Card for 3-butenylglucosinolate (NP0339821)

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Record Information
Version2.0
Created at2024-09-11 23:42:47 UTC
Updated at2024-09-11 23:42:47 UTC
NP-MRD IDNP0339821
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-butenylglucosinolate
Description 3-butenylglucosinolate was first documented in 2006 (PMID: 16719527). Based on a literature review a small amount of articles have been published on 3-butenylglucosinolate (PMID: 33205650) (PMID: 19701726) (PMID: 18712443).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0339821 (3-butenylglucosinolate)


  Mrv2104 05272302152D          

 23 23  0  0  0  0            999 V2000
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    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
    0.0000    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    2.5855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    4.0145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 S   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
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   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 O   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 O   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
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  4  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  2  0  0  0  0
  8 11  1  0  0  0  0
  5 12  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
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 13 22  1  0  0  0  0
M  CHG  1  11  -1
M  END
Download

3D MOL for NP0339821 (3-butenylglucosinolate)

Download
3D SDF for NP0339821 (3-butenylglucosinolate)

  Mrv2104 05272302152D          

 23 23  0  0  0  0            999 V2000
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    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
    0.0000    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    2.5855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    4.0145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 S   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
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   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 O   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 O   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
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  4  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  2  0  0  0  0
  8 11  1  0  0  0  0
  5 12  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
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 13 22  1  0  0  0  0
M  CHG  1  11  -1
M  END
> <DATABASE_ID>
NP0339821

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(SC(CCC=C)=NOS([O-])(=O)=O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1/C11H19NO9S2/c1-2-3-4-7(12-21-23(17,18)19)22-11-10(16)9(15)8(14)6(5-13)20-11/h2,6,8-11,13-16H,1,3-5H2,(H,17,18,19)/p-1

> <INCHI_KEY>
PLYQBXHVYUJNQB-UHFFFAOYNA-M

> <FORMULA>
C11H18NO9S2

> <MOLECULAR_WEIGHT>
372.38

> <EXACT_MASS>
372.042847092

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
33.67797402059413

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene)amino sulfate

> <JCHEM_LOGP>
-2.726548335233849

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.447642445340678

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.5510889028244446

> <JCHEM_PKA_STRONGEST_BASIC>
-0.33385638510876287

> <JCHEM_POLAR_SURFACE_AREA>
168.93999999999997

> <JCHEM_REFRACTIVITY>
78.17640000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene)amino sulfate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0339821 (3-butenylglucosinolate)
Download
PDB for NP0339821 (3-butenylglucosinolate)
HEADER    PROTEIN                                 27-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-23         0                                  
HETATM    1  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       0.000   6.160   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM    8  S   UNK     0       2.667   6.160   0.000  0.00  0.00           S+0
HETATM    9  O   UNK     0       1.897   4.826   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       3.437   7.494   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.001   5.390   0.000  0.00  0.00           O-1
HETATM   12  S   UNK     0       1.334   3.850   0.000  0.00  0.00           S+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12    5   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   13                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

Download
3D PDB for NP0339821 (3-butenylglucosinolate)
Download
SMILES for NP0339821 (3-butenylglucosinolate)
OCC1OC(SC(CCC=C)=NOS([O-])(=O)=O)C(O)C(O)C1O
Download
INCHI for NP0339821 (3-butenylglucosinolate)
InChI=1/C11H19NO9S2/c1-2-3-4-7(12-21-23(17,18)19)22-11-10(16)9(15)8(14)6(5-13)20-11/h2,6,8-11,13-16H,1,3-5H2,(H,17,18,19)/p-1
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View in JSmol
Synonyms
ValueSource
3-Butenylglucosinolic acidGenerator
Chemical FormulaC11H18NO9S2
Average Mass372.3800 Da
Monoisotopic Mass372.04285 Da
IUPAC Name(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene)amino sulfate
Traditional Name(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene)amino sulfate
CAS Registry NumberNot Available
SMILES
OCC1OC(SC(CCC=C)=NOS([O-])(=O)=O)C(O)C(O)C1O
InChI Identifier
InChI=1/C11H19NO9S2/c1-2-3-4-7(12-21-23(17,18)19)22-11-10(16)9(15)8(14)6(5-13)20-11/h2,6,8-11,13-16H,1,3-5H2,(H,17,18,19)/p-1
InChI KeyPLYQBXHVYUJNQB-UHFFFAOYNA-M
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-2.7ChemAxon
pKa (Strongest Acidic)-3.6ChemAxon
pKa (Strongest Basic)-0.33ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area168.94 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity78.18 m³·mol⁻¹ChemAxon
Polarizability33.68 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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. Sun J, Charron CS, Liu Z, Novotny JA, Harrington PB, Ross SA, Seifried HE, Chen P: Study on Human Urinary Metabolic Profiles after Consumption of Kale and Daikon Radish using a High-resolution Mass Spectrometry-Based Non-targeted and Targeted Metabolomic Approach. J Agric Food Chem. 2020 Nov 18. doi: 10.1021/acs.jafc.0c05184. [PubMed:33205650  ] 
  2. Kissen R, Pope TW, Grant M, Pickett JA, Rossiter JT, Powell G: Modifying the alkylglucosinolate profile in Arabidopsis thaliana alters the tritrophic interaction with the herbivore Brevicoryne brassicae and parasitoid Diaeretiella rapae. J Chem Ecol. 2009 Aug;35(8):958-69. doi: 10.1007/s10886-009-9677-6. Epub 2009 Aug  23. [PubMed:19701726  ] 
  3. Pope TW, Kissen R, Grant M, Pickett JA, Rossiter JT, Powell G: Comparative innate responses of the aphid parasitoid Diaeretiella rapae to alkenyl glucosinolate derived isothiocyanates, nitriles, and epithionitriles. J Chem Ecol. 2008 Oct;34(10):1302-10. doi: 10.1007/s10886-008-9531-2. Epub 2008  Aug 19. [PubMed:18712443  ] 
  4. Bennett RN, Rosa EA, Mellon FA, Kroon PA: Ontogenic profiling of glucosinolates, flavonoids, and other secondary metabolites in Eruca sativa (salad rocket), Diplotaxis erucoides (wall rocket), Diplotaxis tenuifolia (wild rocket), and Bunias orientalis (Turkish rocket). J Agric Food Chem. 2006 May 31;54(11):4005-15. doi: 10.1021/jf052756t. [PubMed:16719527  ]