NP-MRD: Showing NP-Card for 3-Phenylpropyl glucosinolate (NP0049114)

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Record Information

Version

2.0

Created at

2022-03-17 21:07:21 UTC

Updated at

2022-03-17 21:07:21 UTC

NP-MRD ID

NP0049114

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-Phenylpropyl glucosinolate

Description

3-Phenylpropyl glucosinolate belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain. 3-Phenylpropyl glucosinolate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3-Phenylpropyl glucosinolate has been detected, but not quantified in, brassicas and horseradish. This could make 3-phenylpropyl glucosinolate a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310262D          

 28 29  0  0  0  0            999 V2000
    3.5724    4.5375    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
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    8.2500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   12.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    7.7270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    6.2980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   10.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    9.4875    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    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  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  4  1  0  0  0  0
  8  4  1  0  0  0  0
 10  5  2  0  0  0  0
 10  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 12  2  0  0  0  0
 18  9  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  1  0  0  0  0
 25 11  1  0  0  0  0
 25 16  1  0  0  0  0
 26 17  1  0  0  0  0
 27 12  1  0  0  0  0
 27 16  1  0  0  0  0
 28 22  1  0  0  0  0
 28 23  2  0  0  0  0
 28 24  2  0  0  0  0
 28 26  1  0  0  0  0
M  END


  Mrv0541 05061310262D          

 28 29  0  0  0  0            999 V2000
    3.5724    4.5375    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
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    8.2500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   12.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    7.7270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    6.2980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   10.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    9.4875    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    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  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  4  1  0  0  0  0
  8  4  1  0  0  0  0
 10  5  2  0  0  0  0
 10  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 12  2  0  0  0  0
 18  9  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  1  0  0  0  0
 25 11  1  0  0  0  0
 25 16  1  0  0  0  0
 26 17  1  0  0  0  0
 27 12  1  0  0  0  0
 27 16  1  0  0  0  0
 28 22  1  0  0  0  0
 28 23  2  0  0  0  0
 28 24  2  0  0  0  0
 28 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049114

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(S\C(CCCC2=CC=CC=C2)=N\OS(O)(=O)=O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H23NO9S2/c18-9-11-13(19)14(20)15(21)16(25-11)27-12(17-26-28(22,23)24)8-4-7-10-5-2-1-3-6-10/h1-3,5-6,11,13-16,18-21H,4,7-9H2,(H,22,23,24)/b17-12+

> <INCHI_KEY>
AAVHHGNQWFTUKS-SFQUDFHCSA-N

> <FORMULA>
C16H23NO9S2

> <MOLECULAR_WEIGHT>
437.485

> <EXACT_MASS>
437.081422719

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
42.04079803508762

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.91

> <JCHEM_LOGP>
-1.2284789340278646

> <ALOGPS_LOGS>
-2.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.447674629350495

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.4862749123260093

> <JCHEM_PKA_STRONGEST_BASIC>
-0.15682832150486126

> <JCHEM_POLAR_SURFACE_AREA>
166.10999999999999

> <JCHEM_REFRACTIVITY>
99.34899999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.11e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(E)-(4-phenyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}butylidene)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       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  13.860   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002  10.780   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  13.090   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  15.400   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  22.330   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  20.790   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  16.170   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  20.020   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  18.480   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  17.710   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  18.480   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       2.667  15.400   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       0.000  23.100   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.334  20.790   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.334  17.710   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.334  16.170   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.564  14.424   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.104  11.756   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.000  12.320   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       2.667  20.020   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.667  13.860   0.000  0.00  0.00           O+0
HETATM   27  S   UNK     0       4.001  17.710   0.000  0.00  0.00           S+0
HETATM   28  S   UNK     0       1.334  13.090   0.000  0.00  0.00           S+0
CONECT    1    2    3                                                       
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    7    8                                                       
CONECT    5    2   10                                                       
CONECT    6    3   10                                                       
CONECT    7    4   10                                                       
CONECT    8    4   12                                                       
CONECT    9   11   18                                                       
CONECT   10    5    6    7                                                  
CONECT   11    9   13   25                                                  
CONECT   12    8   17   27                                                  
CONECT   13   11   14   19                                                  
CONECT   14   13   15   20                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15   25   27                                                  
CONECT   17   12   26                                                       
CONECT   18    9                                                            
CONECT   19   13                                                            
CONECT   20   14                                                            
CONECT   21   15                                                            
CONECT   22   28                                                            
CONECT   23   28                                                            
CONECT   24   28                                                            
CONECT   25   11   16                                                       
CONECT   26   17   28                                                       
CONECT   27   12   16                                                       
CONECT   28   22   23   24   26                                             
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₁₆H₂₃NO₉S₂

Average Mass

437.4850 Da

Monoisotopic Mass

437.08142 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

76265-25-3

SMILES

OCC1OC(S\C(CCCC2=CC=CC=C2)=N\OS(O)(=O)=O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C16H23NO9S2/c18-9-11-13(19)14(20)15(21)16(25-11)27-12(17-26-28(22,23)24)8-4-7-10-5-2-1-3-6-10/h1-3,5-6,11,13-16,18-21H,4,7-9H2,(H,22,23,24)/b17-12+

InChI Key

AAVHHGNQWFTUKS-SFQUDFHCSA-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	-0.91	ALOGPS
logP	-1.2	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	-3.5	ChemAxon
pKa (Strongest Basic)	-0.16	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	99.35 m³·mol⁻¹	ChemAxon
Polarizability	42.04 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

HMDB0038422

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017780

KNApSAcK ID

C00007856

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

131752368

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3-Phenylpropyl glucosinolate (NP0049114)

MOL for NP0049114 (3-Phenylpropyl glucosinolate)

3D MOL for NP0049114 (3-Phenylpropyl glucosinolate)

3D SDF for NP0049114 (3-Phenylpropyl glucosinolate)

3D-SDF for NP0049114 (3-Phenylpropyl glucosinolate)

PDB for NP0049114 (3-Phenylpropyl glucosinolate)

3D PDB for NP0049114 (3-Phenylpropyl glucosinolate)

SMILES for NP0049114 (3-Phenylpropyl glucosinolate)

INCHI for NP0049114 (3-Phenylpropyl glucosinolate)

Structure for NP0049114 (3-Phenylpropyl glucosinolate)

3D Structure for NP0049114 (3-Phenylpropyl glucosinolate)