NP-MRD: Showing NP-Card for Gluconapin (NP0049118)

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Record Information

Version

2.0

Created at

2022-03-17 21:07:24 UTC

Updated at

2022-03-17 21:07:24 UTC

NP-MRD ID

NP0049118

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gluconapin

Description

Gluconapin belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain. Gluconapin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Gluconapin has been detected, but not quantified in, several different foods, such as cauliflowers, chinese mustards, cabbages, horseradish, and brassicas. Gluconapin is found in Alyssoides utriculata, Alyssum alyssoides, Alyssum perennial, Arabidopsis thaliana, Aurinia saxatilis, Boreava aptera, Boreava orientalis, Brassica napus L. , Brassica nigra , Brassica oleracea , Brassica spp., Brassica sprouts, Cakile artica, Cakile constricta, Cakile edentula, Cakile geniculata, Cakile lanceolata, Cakile maritima , Capparis flexuosa, Capparis inermis , Cardamine flexuosa, Cardamine hirsuta, Cardamine impatiens, Carrichtera annua, Chorispora purpurascens, Coincya longirostra, Coincya monensis , Coincya rupestris, Conringia orientalis, Conringia planisiliqua, Crambe filiformis, Crambe juncea, Crambe koktebelica, Crambe maritima , Crambe orientalis , Crucihimalaya wallichii, Descurainia appendiculata, Descurainia pinnata, Descurainia richardsonii, Descurainia sophia , Diplotaxis catholica , Diplotaxis erucoides , Diplotaxis siifolia, Diplotaxis virgata, Draba nemorosa, Eremobium aegyptiacum, Eruca longirostris, Eruca vesicaria, Erucastrum gallicum, Erucastrum laevigatum, Farsetia clypeata, Farsetia jacquemontii , Farsetia ramosissima, Fibigia macrocarpa, Hesperis matronalis , Hirschfeldia incana , Iberis amara , Isatis aleppica, Isatis cappadocica, Isatis costata, Isatis djurdjura, Isatis glauca, Isatis iberica, Isatis tinctoria , Lepidium draba , Lepidium subulatum, Alyssum maritimum, Moricandia arvensis , Notoceras bicorne, Peltaria alliaceae, Peltaria angustifolia, Pringlea antiscorbutica, Raphanus sativus, Rapistrum rugosum , Reboudia pinnata, Rhynchosinapis hispida, Rorippa hilariana, Rorippa islandica, Schimpera arabica, Schouwia purpurea, Sinapis arvensis , Sisymbrella aspera, Sisymbrium altissimum, Sisymbrium orientale, Sisymbrium pinnata, Stanleya pinnata, Sterigmostemum incanum, Streptanthus arizonicus, Thelypodium brachycarpum, Thelypodium crispum, Thelypodium eucosmum, Thelypodium howellii, Thelypodium laciniatum, Thelypodium laxiflorum, Thelypodium paniculatum, Thelypodium rollinsii, Thelypodium texanum and Thelypodium wrightii. This could make gluconapin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310272D          

 23 23  0  0  0  0            999 V2000
   -1.4289   -4.1250    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309   -0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559   -1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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
    0.7145   -1.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  4  1  0  0  0  0
  8  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12  7  2  0  0  0  0
 13  5  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 20  6  1  0  0  0  0
 20 11  1  0  0  0  0
 21 12  1  0  0  0  0
 22  7  1  0  0  0  0
 22 11  1  0  0  0  0
 23 17  1  0  0  0  0
 23 18  2  0  0  0  0
 23 19  2  0  0  0  0
 23 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049118

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(S\C(CCC=C)=N\OS(O)(=O)=O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C11H19NO9S2/c1-2-3-4-7(12-21-23(17,18)19)22-11-10(16)9(15)8(14)6(5-13)20-11/h2,6,8-11,13-16H,1,3-5H2,(H,17,18,19)/b12-7+

> <INCHI_KEY>
PLYQBXHVYUJNQB-KPKJPENVSA-N

> <FORMULA>
C11H19NO9S2

> <MOLECULAR_WEIGHT>
373.4

> <EXACT_MASS>
373.050122591

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
34.28310242009375

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.64

> <JCHEM_LOGP>
-2.726548335233849

> <ALOGPS_LOGS>
-1.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.44764244534068

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.5510889028244446

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3338563851087629

> <JCHEM_POLAR_SURFACE_AREA>
166.10999999999999

> <JCHEM_REFRACTIVITY>
79.29809999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.49e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(E)-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene)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      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -3.231  -0.976   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -4.771  -3.644   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667   0.000   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  S   UNK     0       1.334  -2.310   0.000  0.00  0.00           S+0
HETATM   23  S   UNK     0      -4.001  -2.310   0.000  0.00  0.00           S+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    7                                                       
CONECT    5    6   13                                                       
CONECT    6    5    8   20                                                  
CONECT    7    4   12   22                                                  
CONECT    8    6    9   14                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10   20   22                                                  
CONECT   12    7   21                                                       
CONECT   13    5                                                            
CONECT   14    8                                                            
CONECT   15    9                                                            
CONECT   16   10                                                            
CONECT   17   23                                                            
CONECT   18   23                                                            
CONECT   19   23                                                            
CONECT   20    6   11                                                       
CONECT   21   12   23                                                       
CONECT   22    7   11                                                       
CONECT   23   17   18   19   21                                             
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

View in JSmol

Synonyms

Value	Source
1-Thio-b-D-glucopyranose 1-[N-(sulfooxy)-4-pentenimidate], 9ci	HMDB
3-Butenylglucosinolate	HMDB
{[(e)-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene)amino]oxy}sulfonate	Generator
{[(e)-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}pent-4-en-1-ylidene)amino]oxy}sulphonate	Generator
{[(e)-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}pent-4-en-1-ylidene)amino]oxy}sulphonic acid	Generator
3-Butenyl glucosinolate	MeSH
Gluconapin	MeSH

Chemical Formula

C₁₁H₁₉NO₉S₂

Average Mass

373.4000 Da

Monoisotopic Mass

373.05012 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

19041-09-9

SMILES

OCC1OC(S\C(CCC=C)=N\OS(O)(=O)=O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C11H19NO9S2/c1-2-3-4-7(12-21-23(17,18)19)22-11-10(16)9(15)8(14)6(5-13)20-11/h2,6,8-11,13-16H,1,3-5H2,(H,17,18,19)/b12-7+

InChI Key

PLYQBXHVYUJNQB-KPKJPENVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alyssoides utriculata	Plant	KNApSAcK
Alyssum alyssoides	Plant	KNApSAcK
Alyssum perennial	Plant	KNApSAcK
Arabidopsis thaliana	Plant	KNApSAcK
Armoracia rusticana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Aurinia saxatilis	Plant	KNApSAcK
Boreava aptera	Plant	KNApSAcK
Boreava orientalis	Plant	KNApSAcK
Brassica juncea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Brassica napus	FooDB	KNAPSACK
Brassica napus L.	Plant	KNApSAcK
Brassica nigra	Plant	KNApSAcK
Brassica oleracea	Plant	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	12720387
Brassica rapa	FooDB	KNAPSACK
Brassica rapa var. rapa	FooDB	PHYTOHUB
Brassica spp.	Plant	KNApSAcK
Brassica sprouts	Plant	KNApSAcK
Cakile artica	Plant	KNApSAcK
Cakile constricta	Plant	KNApSAcK
Cakile edentula	Plant	KNApSAcK
Cakile geniculata	Plant	KNApSAcK
Cakile lanceolata	Plant	KNApSAcK
Cakile maritima	Plant	KNApSAcK
Capparis flexuosa	Plant	KNApSAcK
Capparis inermis	Plant	KNApSAcK
Capparis spinosa	FooDB	PHYTOHUB
Cardamine flexuosa	Plant	KNApSAcK
Cardamine hirsuta	Plant	KNApSAcK
Cardamine impatiens	Plant	KNApSAcK
Carrichtera annua	Plant	KNApSAcK
Chorispora purpurascens	Plant	KNApSAcK
Coincya longirostra	Plant	KNApSAcK
Coincya monensis	Plant	KNApSAcK
Coincya rupestris	Plant	KNApSAcK
Conringia orientalis	Plant	KNApSAcK
Conringia planisiliqua	Plant	KNApSAcK
Crambe filiformis	Plant	KNApSAcK
Crambe juncea	Plant	KNApSAcK
Crambe koktebelica	Plant	KNApSAcK
Crambe maritima	Plant	KNApSAcK
Crambe orientalis	Plant	KNApSAcK
Crucihimalaya wallichii	Plant	KNApSAcK
Descurainia appendiculata	Plant	KNApSAcK
Descurainia pinnata	Plant	KNApSAcK
Descurainia richardsonii	Plant	KNApSAcK
Descurainia Sophia	Plant	KNApSAcK
Diplotaxis catholica	Plant	KNApSAcK
Diplotaxis erucoides	Plant	KNApSAcK
Diplotaxis siifolia	Plant	KNApSAcK
Diplotaxis virgata	Plant	KNApSAcK
Draba nemorosa	Plant	KNApSAcK
Eremobium aegyptiacum	LOTUS Database	35616633
Eruca longirostris	Plant	KNApSAcK
Eruca vesicaria	LOTUS Database	35616633
Erucastrum gallicum	Plant	KNApSAcK
Erucastrum laevigatum	Plant	KNApSAcK
Eutrema japonicum	FooDB	KNAPSACK
Farsetia clypeata	Plant	KNApSAcK
Farsetia jacquemontii	Plant	KNApSAcK
Farsetia ramosissima	Plant	KNApSAcK
Fibigia macrocarpa	Plant	KNApSAcK
Hesperis matronalis	Plant	KNApSAcK
Hirschfeldia incana	Plant	KNApSAcK
Iberis amara	Plant	KNApSAcK
Isatis aleppica	Plant	KNApSAcK
Isatis cappadocica	Plant	KNApSAcK
Isatis costata	Plant	KNApSAcK
Isatis djurdjura	Plant	KNApSAcK
Isatis glauca	Plant	KNApSAcK
Isatis iberica	Plant	KNApSAcK
Isatis tinctoria	Plant	KNApSAcK
Lepidium draba	Plant	KNApSAcK
Lepidium subulatum	Plant	KNApSAcK
Lobularia maritima	Plant	KNApSAcK
Moricandia arvensis	Plant	KNApSAcK
Notoceras bicorne	Plant	KNApSAcK
Peltaria alliaceae	Plant	KNApSAcK
Peltaria angustifolia	Plant	KNApSAcK
Pringlea antiscorbutica	Plant	KNApSAcK
Raphanus sativus	LOTUS Database	35616633
Rapistrum rugosum	Plant	KNApSAcK
Reboudia pinnata	Plant	KNApSAcK
Rhynchosinapis hispida	-	KNApSAcK
Rorippa hilariana	Plant	KNApSAcK
Rorippa islandica	Plant	KNApSAcK
Schimpera arabica	Plant	KNApSAcK
Schouwia purpurea	Plant	KNApSAcK
Sinapis alba	FooDB	KNAPSACK
Sinapis arvensis	Plant	KNApSAcK
Sisymbrella aspera	Plant	KNApSAcK
Sisymbrium altissimum	Plant	KNApSAcK
Sisymbrium orientale	Plant	KNApSAcK
Sisymbrium pinnata	Plant	KNApSAcK
Stanleya pinnata	LOTUS Database	35616633
Sterigmostemum incanum	Plant	KNApSAcK
Streptanthus arizonicus	Plant	KNApSAcK
Thelypodium brachycarpum	Plant	KNApSAcK
Thelypodium crispum	Plant	KNApSAcK
Thelypodium eucosmum	Plant	KNApSAcK
Thelypodium howellii	Plant	KNApSAcK
Thelypodium laciniatum	Plant	KNApSAcK
Thelypodium laxiflorum	Plant	KNApSAcK
Thelypodium paniculatum	Plant	KNApSAcK
Thelypodium rollinsii	Plant	KNApSAcK
Thelypodium texanum	Plant	KNApSAcK
Thelypodium wrightii	Plant	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	-2.7	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	-3.6	ChemAxon
pKa (Strongest Basic)	-0.33	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	8	ChemAxon
Refractivity	79.3 m³·mol⁻¹	ChemAxon
Polarizability	34.28 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

HMDB0038427

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017785

KNApSAcK ID

C00007586

Chemspider ID

Not Available

KEGG Compound ID

C08415

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14390048

PDB ID

Not Available

ChEBI ID

5411

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Gluconapin (NP0049118)

MOL for NP0049118 (Gluconapin)

3D MOL for NP0049118 (Gluconapin)

3D SDF for NP0049118 (Gluconapin)

3D-SDF for NP0049118 (Gluconapin)

PDB for NP0049118 (Gluconapin)

3D PDB for NP0049118 (Gluconapin)

SMILES for NP0049118 (Gluconapin)

INCHI for NP0049118 (Gluconapin)

Structure for NP0049118 (Gluconapin)

3D Structure for NP0049118 (Gluconapin)