NP-MRD: Showing NP-Card for 2-Hydroxypentyl glucosinolate (NP0049105)

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Record Information

Version

2.0

Created at

2022-03-17 21:07:12 UTC

Updated at

2022-03-17 21:07:12 UTC

NP-MRD ID

NP0049105

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Hydroxypentyl glucosinolate

Description

2-Hydroxypentyl glucosinolate belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain. 2-Hydroxypentyl glucosinolate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2-Hydroxypentyl glucosinolate has been detected, but not quantified in, brassicas and horseradish. This could make 2-hydroxypentyl 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    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
    2.8579    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
    2.8579    5.7750    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
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  6  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  4  1  0  0  0  0
  9  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13  8  2  0  0  0  0
 14  5  1  0  0  0  0
 15  6  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
 22  7  1  0  0  0  0
 22 12  1  0  0  0  0
 23 13  1  0  0  0  0
 24  8  1  0  0  0  0
 24 12  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>
NP0049105

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H23NO10S2/c1-2-3-6(15)4-8(13-23-25(19,20)21)24-12-11(18)10(17)9(16)7(5-14)22-12/h6-7,9-12,14-18H,2-5H2,1H3,(H,19,20,21)/b13-8+

> <INCHI_KEY>
XTEJYKQXWYEDHX-MDWZMJQESA-N

> <FORMULA>
C12H23NO10S2

> <MOLECULAR_WEIGHT>
405.442

> <EXACT_MASS>
405.076337341

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
38.49171676398481

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.56

> <JCHEM_LOGP>
-3.1974809882038113

> <ALOGPS_LOGS>
-1.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.446454585366247

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.5030813797235014

> <JCHEM_PKA_STRONGEST_BASIC>
-0.34313558811990463

> <JCHEM_POLAR_SURFACE_AREA>
186.33999999999997

> <JCHEM_REFRACTIVITY>
85.37049999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.82e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(E)-(3-hydroxy-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   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.671   8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.337   9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.337  10.780   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.003  11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669  10.780   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669   9.240   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       8.002  10.780   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0      16.004   9.240   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       5.335  10.780   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    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    6                                                       
CONECT    4    6    8                                                       
CONECT    5    7   14                                                       
CONECT    6    3    4   15                                                  
CONECT    7    5    9   22                                                  
CONECT    8    4   13   24                                                  
CONECT    9    7   10   16                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12   18                                                  
CONECT   12   11   22   24                                                  
CONECT   13    8   23                                                       
CONECT   14    5                                                            
CONECT   15    6                                                            
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   25                                                            
CONECT   20   25                                                            
CONECT   21   25                                                            
CONECT   22    7   12                                                       
CONECT   23   13   25                                                       
CONECT   24    8   12                                                       
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
2-Hydroxypentyl glucosinolic acid	Generator
1-Thio-b-D-glucopyranose 1-[3-hydroxy-N-(sulfooxy)hexanimidate], 9ci	HMDB
{[(e)-(3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}hexylidene)amino]oxy}sulfonate	Generator
{[(e)-(3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}hexylidene)amino]oxy}sulphonate	Generator
{[(e)-(3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}hexylidene)amino]oxy}sulphonic acid	Generator

Chemical Formula

C₁₂H₂₃NO₁₀S₂

Average Mass

405.4420 Da

Monoisotopic Mass

405.07634 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

76265-23-1

SMILES

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

InChI Identifier

InChI=1S/C12H23NO10S2/c1-2-3-6(15)4-8(13-23-25(19,20)21)24-12-11(18)10(17)9(16)7(5-14)22-12/h6-7,9-12,14-18H,2-5H2,1H3,(H,19,20,21)/b13-8+

InChI Key

XTEJYKQXWYEDHX-MDWZMJQESA-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
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	-1.6	ALOGPS
logP	-3.2	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	-3.5	ChemAxon
pKa (Strongest Basic)	-0.34	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	186.34 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	85.37 m³·mol⁻¹	ChemAxon
Polarizability	38.49 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0038413

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017771

KNApSAcK ID

C00007815

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

131752361

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2-Hydroxypentyl glucosinolate (NP0049105)

MOL for NP0049105 (2-Hydroxypentyl glucosinolate)

3D MOL for NP0049105 (2-Hydroxypentyl glucosinolate)

3D SDF for NP0049105 (2-Hydroxypentyl glucosinolate)

3D-SDF for NP0049105 (2-Hydroxypentyl glucosinolate)

PDB for NP0049105 (2-Hydroxypentyl glucosinolate)

3D PDB for NP0049105 (2-Hydroxypentyl glucosinolate)

SMILES for NP0049105 (2-Hydroxypentyl glucosinolate)

INCHI for NP0049105 (2-Hydroxypentyl glucosinolate)

Structure for NP0049105 (2-Hydroxypentyl glucosinolate)

3D Structure for NP0049105 (2-Hydroxypentyl glucosinolate)