NP-MRD: Showing NP-Card for 4-Methylpentyl glucosinolate (NP0049112)

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Record Information

Version

2.0

Created at

2022-03-17 21:07:19 UTC

Updated at

2022-03-17 21:07:19 UTC

NP-MRD ID

NP0049112

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-Methylpentyl glucosinolate

Description

4-Methylpentyl 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-Methylpentyl glucosinolate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 4-Methylpentyl glucosinolate has been detected, but not quantified in, brassicas and radish. This could make 4-methylpentyl glucosinolate a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310262D          

 25 25  0  0  0  0            999 V2000
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    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
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    4.9500    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
    7.1447    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7474    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.0125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  7  4  1  0  0  0  0
  8  6  1  0  0  0  0
  9  5  1  0  0  0  0
 10  8  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14  9  2  0  0  0  0
 15  6  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 22  8  1  0  0  0  0
 22 13  1  0  0  0  0
 23 14  1  0  0  0  0
 24  9  1  0  0  0  0
 24 13  1  0  0  0  0
 25 19  1  0  0  0  0
 25 20  2  0  0  0  0
 25 21  2  0  0  0  0
 25 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049112

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CCC\C(SC1OC(CO)C(O)C(O)C1O)=N/OS(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H25NO9S2/c1-7(2)4-3-5-9(14-23-25(19,20)21)24-13-12(18)11(17)10(16)8(6-15)22-13/h7-8,10-13,15-18H,3-6H2,1-2H3,(H,19,20,21)/b14-9+

> <INCHI_KEY>
PVFJQLBPPQHTLU-NTEUORMPSA-N

> <FORMULA>
C13H25NO9S2

> <MOLECULAR_WEIGHT>
403.469

> <EXACT_MASS>
403.097072783

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
39.162668830882836

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.14

> <JCHEM_LOGP>
-1.6074667818360384

> <ALOGPS_LOGS>
-1.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.44767579660656

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.4037884716543756

> <JCHEM_PKA_STRONGEST_BASIC>
-0.16384129741584286

> <JCHEM_POLAR_SURFACE_AREA>
166.10999999999999

> <JCHEM_REFRACTIVITY>
88.40359999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.58e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(E)-(5-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}hexylidene)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       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  10.780   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       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.671   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.337   9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.337  10.780   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.003  11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669  10.780   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669   9.240   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       8.002  10.780   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0      16.004   9.240   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      14.671  11.550   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      12.003  13.090   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.336  11.550   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       8.208  13.090   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.128  13.090   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.668  14.630   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      12.003   8.470   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.668  11.550   0.000  0.00  0.00           O+0
HETATM   24  S   UNK     0       9.336   8.470   0.000  0.00  0.00           S+0
HETATM   25  S   UNK     0       6.668  13.090   0.000  0.00  0.00           S+0
CONECT    1    7                                                            
CONECT    2    7                                                            
CONECT    3    4    5                                                       
CONECT    4    3    7                                                       
CONECT    5    3    9                                                       
CONECT    6    8   15                                                       
CONECT    7    1    2    4                                                  
CONECT    8    6   10   22                                                  
CONECT    9    5   14   24                                                  
CONECT   10    8   11   16                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11   13   18                                                  
CONECT   13   12   22   24                                                  
CONECT   14    9   23                                                       
CONECT   15    6                                                            
CONECT   16   10                                                            
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19   25                                                            
CONECT   20   25                                                            
CONECT   21   25                                                            
CONECT   22    8   13                                                       
CONECT   23   14   25                                                       
CONECT   24    9   13                                                       
CONECT   25   19   20   21   23                                             
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

View in JSmol

Synonyms

Value	Source
4-Methylpentyl glucosinolic acid	Generator
{[(e)-(5-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}hexylidene)amino]oxy}sulfonate	Generator
{[(e)-(5-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}hexylidene)amino]oxy}sulphonate	Generator
{[(e)-(5-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}hexylidene)amino]oxy}sulphonic acid	Generator

Chemical Formula

C₁₃H₂₅NO₉S₂

Average Mass

403.4690 Da

Monoisotopic Mass

403.09707 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(C)CCC\C(SC1OC(CO)C(O)C(O)C1O)=N/OS(O)(=O)=O

InChI Identifier

InChI=1S/C13H25NO9S2/c1-7(2)4-3-5-9(14-23-25(19,20)21)24-13-12(18)11(17)10(16)8(6-15)22-13/h7-8,10-13,15-18H,3-6H2,1-2H3,(H,19,20,21)/b14-9+

InChI Key

PVFJQLBPPQHTLU-NTEUORMPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Raphanus sativus	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
Oxane
Monothioacetal
Organic sulfuric acid or derivatives
Secondary alcohol
Polyol
Oxacycle
Organoheterocyclic compound
Sulfenyl compound
Alcohol
Hydrocarbon derivative
Organosulfur compound
Organonitrogen compound
Organic oxide
Primary alcohol
Organic nitrogen compound
Organopnictogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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	-1.1	ALOGPS
logP	-1.6	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	-3.4	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	88.4 m³·mol⁻¹	ChemAxon
Polarizability	39.16 Å³	ChemAxon
Number of Rings	1	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

HMDB0038420

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017778

KNApSAcK ID

C00007828

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

131752366

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4-Methylpentyl glucosinolate (NP0049112)

MOL for NP0049112 (4-Methylpentyl glucosinolate)

3D MOL for NP0049112 (4-Methylpentyl glucosinolate)

3D SDF for NP0049112 (4-Methylpentyl glucosinolate)

3D-SDF for NP0049112 (4-Methylpentyl glucosinolate)

PDB for NP0049112 (4-Methylpentyl glucosinolate)

3D PDB for NP0049112 (4-Methylpentyl glucosinolate)

SMILES for NP0049112 (4-Methylpentyl glucosinolate)

INCHI for NP0049112 (4-Methylpentyl glucosinolate)

Structure for NP0049112 (4-Methylpentyl glucosinolate)

3D Structure for NP0049112 (4-Methylpentyl glucosinolate)