NP-MRD: Showing NP-Card for 4-Phenylbutyl glucosinolate (NP0049107)

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Record Information

Version

2.0

Created at

2022-03-17 21:07:14 UTC

Updated at

2022-03-17 21:07:14 UTC

NP-MRD ID

NP0049107

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-Phenylbutyl glucosinolate

Description

4-Phenylbutyl glucosinolate belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain. 4-Phenylbutyl glucosinolate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 4-Phenylbutyl glucosinolate has been detected, but not quantified in, brassicas and horseradish. This could make 4-phenylbutyl glucosinolate a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310262D          

 29 30  0  0  0  0            999 V2000
    5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    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
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    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    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    1.6500    0.0000 O   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    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  4  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12 10  1  0  0  0  0
 13  9  1  0  0  0  0
 14 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 13  2  0  0  0  0
 19 10  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  1  0  0  0  0
 22 16  1  0  0  0  0
 26 12  1  0  0  0  0
 26 17  1  0  0  0  0
 27 18  1  0  0  0  0
 28 13  1  0  0  0  0
 28 17  1  0  0  0  0
 29 23  1  0  0  0  0
 29 24  2  0  0  0  0
 29 25  2  0  0  0  0
 29 27  1  0  0  0  0
M  END


  Mrv0541 05061310262D          

 29 30  0  0  0  0            999 V2000
    5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    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
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    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    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    1.6500    0.0000 O   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    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  4  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12 10  1  0  0  0  0
 13  9  1  0  0  0  0
 14 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 13  2  0  0  0  0
 19 10  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  1  0  0  0  0
 22 16  1  0  0  0  0
 26 12  1  0  0  0  0
 26 17  1  0  0  0  0
 27 18  1  0  0  0  0
 28 13  1  0  0  0  0
 28 17  1  0  0  0  0
 29 23  1  0  0  0  0
 29 24  2  0  0  0  0
 29 25  2  0  0  0  0
 29 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049107

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(S\C(CCCCC2=CC=CC=C2)=N\OS(O)(=O)=O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C17H25NO9S2/c19-10-12-14(20)15(21)16(22)17(26-12)28-13(18-27-29(23,24)25)9-5-4-8-11-6-2-1-3-7-11/h1-3,6-7,12,14-17,19-22H,4-5,8-10H2,(H,23,24,25)/b18-13+

> <INCHI_KEY>
PJZFULXMEGMUDK-QGOAFFKASA-N

> <FORMULA>
C17H25NO9S2

> <MOLECULAR_WEIGHT>
451.512

> <EXACT_MASS>
451.097072783

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
44.79122478770308

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.53

> <JCHEM_LOGP>
-0.7786699497673747

> <ALOGPS_LOGS>
-2.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.447675794973541

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.5146210121016255

> <JCHEM_PKA_STRONGEST_BASIC>
-0.10550333290777492

> <JCHEM_POLAR_SURFACE_AREA>
166.10999999999999

> <JCHEM_REFRACTIVITY>
103.94999999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.37e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(E)-(5-phenyl-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      10.669   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335   7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001   5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       1.334   5.390   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      -6.668   6.930   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.667   3.080   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.127   3.080   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.207   3.080   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -2.667   7.700   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   28  S   UNK     0       0.000   7.700   0.000  0.00  0.00           S+0
HETATM   29  S   UNK     0       2.667   3.080   0.000  0.00  0.00           S+0
CONECT    1    2    3                                                       
CONECT    2    1    6                                                       
CONECT    3    1    7                                                       
CONECT    4    5    8                                                       
CONECT    5    4    9                                                       
CONECT    6    2   11                                                       
CONECT    7    3   11                                                       
CONECT    8    4   11                                                       
CONECT    9    5   13                                                       
CONECT   10   12   19                                                       
CONECT   11    6    7    8                                                  
CONECT   12   10   14   26                                                  
CONECT   13    9   18   28                                                  
CONECT   14   12   15   20                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   26   28                                                  
CONECT   18   13   27                                                       
CONECT   19   10                                                            
CONECT   20   14                                                            
CONECT   21   15                                                            
CONECT   22   16                                                            
CONECT   23   29                                                            
CONECT   24   29                                                            
CONECT   25   29                                                            
CONECT   26   12   17                                                       
CONECT   27   18   29                                                       
CONECT   28   13   17                                                       
CONECT   29   23   24   25   27                                             
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₁₇H₂₅NO₉S₂

Average Mass

451.5120 Da

Monoisotopic Mass

451.09707 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

76265-26-4

SMILES

OCC1OC(S\C(CCCCC2=CC=CC=C2)=N\OS(O)(=O)=O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C17H25NO9S2/c19-10-12-14(20)15(21)16(22)17(26-12)28-13(18-27-29(23,24)25)9-5-4-8-11-6-2-1-3-7-11/h1-3,6-7,12,14-17,19-22H,4-5,8-10H2,(H,23,24,25)/b18-13+

InChI Key

PJZFULXMEGMUDK-QGOAFFKASA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Armoracia rusticana	FooDB	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
Monocyclic benzene moiety
Oxane
Benzenoid
Monothioacetal
Organic sulfuric acid or derivatives
Secondary alcohol
Sulfenyl compound
Polyol
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Primary alcohol
Organic oxide
Organosulfur compound
Organonitrogen compound
Alcohol
Organopnictogen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	-0.53	ALOGPS
logP	-0.78	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	-3.5	ChemAxon
pKa (Strongest Basic)	-0.11	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	103.95 m³·mol⁻¹	ChemAxon
Polarizability	44.79 Å³	ChemAxon
Number of Rings	2	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

HMDB0038415

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017773

KNApSAcK ID

C00007855

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

131752363

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4-Phenylbutyl glucosinolate (NP0049107)

MOL for NP0049107 (4-Phenylbutyl glucosinolate)

3D MOL for NP0049107 (4-Phenylbutyl glucosinolate)

3D SDF for NP0049107 (4-Phenylbutyl glucosinolate)

3D-SDF for NP0049107 (4-Phenylbutyl glucosinolate)

PDB for NP0049107 (4-Phenylbutyl glucosinolate)

3D PDB for NP0049107 (4-Phenylbutyl glucosinolate)

SMILES for NP0049107 (4-Phenylbutyl glucosinolate)

INCHI for NP0049107 (4-Phenylbutyl glucosinolate)

Structure for NP0049107 (4-Phenylbutyl glucosinolate)

3D Structure for NP0049107 (4-Phenylbutyl glucosinolate)