NP-MRD: Showing NP-Card for Sinigrin (NP0047840)

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Record Information

Version

2.0

Created at

2022-03-17 20:46:49 UTC

Updated at

2024-09-03 04:17:09 UTC

NP-MRD ID

NP0047840

Natural Product DOI

https://doi.org/10.57994/0935

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sinigrin

Description

Sinigrin, also known as myronate or myronic acid, belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain. Sinigrin is an extremely weak basic (essentially neutral) compound (based on its pKa). Sinigrin is a bitter tasting compound. Outside of the human body, Sinigrin has been detected, but not quantified in, several different foods, such as white cabbages, garden cress, cauliflowers, broccoli, and brassicas. This could make sinigrin a potential biomarker for the consumption of these foods. Sinigrin stereochemical configuration on the CN double bond was for a time uncertain, and has been resolved by X-ray crystallography in 1963 to be the Z (or syn) isomer. Seeds of white mustard, Sinapis alba, will give a much less pungent mustard because this species contains a different glucosinolate, sinalbin. Singrin is also known to be allelopathic. Whenever sinigrin-containing plant tissue is crushed or otherwise damaged, the enzyme myrosinase degrades sinigrin to a mustard oil (allyl isothiocyanate), which is responsible for the pungent taste of mustard and horseradish. Sinigrin is found in Brassica carinata, Brassica insularis, Brassica napus, Brassica nigra, Pringlea antiscorbutica and Thlaspi arvense. The chemical name of sinigrin is allylglucosinolate or 2-propenylglucosinolate.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241215142D          

 22 22  0  0  1  0            999 V2000
   -1.3415   -1.2457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6270   -0.8332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0875   -1.2457    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8019   -0.8332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5164   -1.2457    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2309   -0.8332    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.3743   -1.2457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0888   -0.8332    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.8032   -0.4207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5013   -1.5477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6763   -0.1187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5164   -2.0707    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2309   -2.4832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8019   -2.4832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8019   -3.3082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0875   -2.0707    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6270   -2.4832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9454   -1.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9454   -2.0707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6598   -2.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6598   -3.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6598   -0.8332    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  8 11  2  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  3 16  1  0  0  0  0
 16 17  1  6  0  0  0
  6 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 18 22  2  0  0  0  0
 22  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047840

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](S\C(=N\OS(O)(=O)=O)CC=C)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H17NO9S2/c1-2-3-6(11-20-22(16,17)18)21-10-9(15)8(14)7(13)5(4-12)19-10/h2,5,7-10,12-15H,1,3-4H2,(H,16,17,18)/b11-6+/t5-,7-,8+,9-,10+/m1/s1

> <INCHI_KEY>
PHZOWSSBXJXFOR-PTGZALFTSA-N

> <FORMULA>
C10H17NO9S2

> <MOLECULAR_WEIGHT>
359.373

> <EXACT_MASS>
359.034472527

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
32.48707473812115

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(E)-(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}but-3-en-1-ylidene)amino]oxy}sulfonic acid

> <ALOGPS_LOGP>
-1.73

> <JCHEM_LOGP>
-3.2342296417139957

> <ALOGPS_LOGS>
-1.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.447214216566284

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.6183476179623524

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4916051886020759

> <JCHEM_POLAR_SURFACE_AREA>
166.11

> <JCHEM_REFRACTIVITY>
74.69709999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.26e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(E)-(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}but-3-en-1-ylidene)amino]oxysulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -2.504  -2.325   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.170  -1.555   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.163  -2.325   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.497  -1.555   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.831  -2.325   0.000  0.00  0.00           C+0
HETATM    6  S   UNK     0       4.164  -1.555   0.000  0.00  0.00           S+0
HETATM    7  O   UNK     0       8.165  -2.325   0.000  0.00  0.00           O+0
HETATM    8  S   UNK     0       9.499  -1.555   0.000  0.00  0.00           S+0
HETATM    9  O   UNK     0      10.833  -0.785   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      10.269  -2.889   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       8.729  -0.222   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.831  -3.865   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.164  -4.635   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.497  -4.635   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.497  -6.175   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.163  -3.865   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.170  -4.635   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.498  -2.325   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.498  -3.865   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.832  -4.635   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.832  -6.175   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       6.832  -1.555   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5   18                                                       
CONECT    7    8   22                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12    5   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    3   17                                                  
CONECT   17   16                                                            
CONECT   18    6   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   18    7                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Value	Source
1-Thio-b-D-glucopyranose 1-[N-(sulfooxy)-3-butenimidate], 9ci	HMDB
2-Phenylethyl glucosinolate	HMDB
Allyl glucosinolate	HMDB
Myronate	HMDB
Myronic acid	HMDB
Sinigrin, monopotassium salt	HMDB
{[(e)-(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}but-3-en-1-ylidene)amino]oxy}sulfonate	Generator
{[(e)-(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}but-3-en-1-ylidene)amino]oxy}sulphonate	Generator
{[(e)-(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}but-3-en-1-ylidene)amino]oxy}sulphonic acid	Generator
Sinigrin	MeSH

Chemical Formula

C₁₀H₁₇NO₉S₂

Average Mass

359.3730 Da

Monoisotopic Mass

359.03447 Da

IUPAC Name

{[(E)-(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}but-3-en-1-ylidene)amino]oxy}sulfonic acid

Traditional Name

[(E)-(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}but-3-en-1-ylidene)amino]oxysulfonic acid

CAS Registry Number

534-69-0

SMILES

OC[C@H]1O[C@@H](S\C(=N\OS(O)(=O)=O)CC=C)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C10H17NO9S2/c1-2-3-6(11-20-22(16,17)18)21-10-9(15)8(14)7(13)5(4-12)19-10/h2,5,7-10,12-15H,1,3-4H2,(H,16,17,18)/b11-6+/t5-,7-,8+,9-,10+/m1/s1

InChI Key

PHZOWSSBXJXFOR-PTGZALFTSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
MLEV NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-09-19	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-09-19	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-09-19	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-09-19	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-09-19	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Armoracia rusticana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Brassica carinata	LOTUS Database	35616633
Brassica insularis	LOTUS Database	35616633
Brassica juncea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Brassica napus	LOTUS Database	35616633
Brassica nigra	LOTUS Database	35616633
Brassica oleracea	FooDB	KNAPSACK
Brassica oleracea var. botrytis	FooDB	15963940
Brassica oleracea var. capitata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Brassica oleracea var. gemmifera	FooDB	15963940
Brassica oleracea var. italica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Brassica oleracea var. sabauda	FooDB	PHYTOHUB
Capparis spinosa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Eutrema japonicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lepidium sativum	FooDB	KNAPSACK
Pringlea antiscorbutica	LOTUS Database	35616633
Raphanus sativus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sinapis alba	FooDB	KNAPSACK
Thlaspi arvense	LOTUS Database	35616633

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	-1.7	ALOGPS
logP	-3.2	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	-3.6	ChemAxon
pKa (Strongest Basic)	-0.49	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	166.11 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	74.7 m³·mol⁻¹	ChemAxon
Polarizability	32.49 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