NP-MRD: Showing NP-Card for 11-Hydroxyjasmonic acid glucoside (NP0049534)

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Record Information

Version

2.0

Created at

2022-03-17 21:14:02 UTC

Updated at

2022-03-17 21:14:03 UTC

NP-MRD ID

NP0049534

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-Hydroxyjasmonic acid glucoside

Description

Beta-D-Glucopyranosyl-11-hydroxyjasmonic acid belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. Beta-D-Glucopyranosyl-11-hydroxyjasmonic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, beta-D-Glucopyranosyl-11-hydroxyjasmonic acid has been detected, but not quantified in, potato. This could make beta-D-glucopyranosyl-11-hydroxyjasmonic acid a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061311322D          

 27 28  0  0  0  0            999 V2000
   -1.1455    8.1936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8024    6.5797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1893    7.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6309    5.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2337    4.7331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4886    5.5178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0762    4.0657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1354   11.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3608    7.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4087    4.7331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1537    5.5178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212    6.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5223   10.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8967    4.1519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2623   10.9116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8754   10.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7039    9.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0807    9.2977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9639   12.0157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212    6.8277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3816    3.4845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2323    4.9056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4339   11.7186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6600   10.6145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3170    9.0006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2523    8.4907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6938    9.8497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  0  0  0  0
  9  1  1  0  0  0  0
  9  3  1  0  0  0  0
 10  5  1  0  0  0  0
 10  7  1  0  0  0  0
 11  4  1  0  0  0  0
 11 10  1  0  0  0  0
 12  6  1  0  0  0  0
 12 11  1  0  0  0  0
 13  8  1  0  0  0  0
 14  7  1  0  0  0  0
 15 13  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19  8  1  0  0  0  0
 20 12  2  0  0  0  0
 21 14  2  0  0  0  0
 22 14  1  0  0  0  0
 23 15  1  0  0  0  0
 24 16  1  0  0  0  0
 25 17  1  0  0  0  0
 26  9  1  0  0  0  0
 26 18  1  0  0  0  0
 27 13  1  0  0  0  0
 27 18  1  0  0  0  0
M  END


  Mrv0541 05061311322D          

 27 28  0  0  0  0            999 V2000
   -1.1455    8.1936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8024    6.5797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1893    7.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6309    5.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2337    4.7331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4886    5.5178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0762    4.0657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1354   11.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3608    7.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4087    4.7331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1537    5.5178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212    6.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5223   10.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8967    4.1519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2623   10.9116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8754   10.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7039    9.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0807    9.2977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9639   12.0157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212    6.8277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3816    3.4845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2323    4.9056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4339   11.7186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6600   10.6145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3170    9.0006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2523    8.4907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6938    9.8497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  0  0  0  0
  9  1  1  0  0  0  0
  9  3  1  0  0  0  0
 10  5  1  0  0  0  0
 10  7  1  0  0  0  0
 11  4  1  0  0  0  0
 11 10  1  0  0  0  0
 12  6  1  0  0  0  0
 12 11  1  0  0  0  0
 13  8  1  0  0  0  0
 14  7  1  0  0  0  0
 15 13  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19  8  1  0  0  0  0
 20 12  2  0  0  0  0
 21 14  2  0  0  0  0
 22 14  1  0  0  0  0
 23 15  1  0  0  0  0
 24 16  1  0  0  0  0
 25 17  1  0  0  0  0
 26  9  1  0  0  0  0
 26 18  1  0  0  0  0
 27 13  1  0  0  0  0
 27 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049534

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(OC1OC(CO)C(O)C(O)C1O)\C=C\CC1C(CC(O)=O)CCC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H28O9/c1-9(26-18-17(25)16(24)15(23)13(8-19)27-18)3-2-4-11-10(7-14(21)22)5-6-12(11)20/h2-3,9-11,13,15-19,23-25H,4-8H2,1H3,(H,21,22)/b3-2+

> <INCHI_KEY>
LAYQBSCEPAXXNJ-NSCUHMNNSA-N

> <FORMULA>
C18H28O9

> <MOLECULAR_WEIGHT>
388.4095

> <EXACT_MASS>
388.173332494

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
39.555301455060516

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{3-oxo-2-[(2E)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl}acetic acid

> <ALOGPS_LOGP>
-0.69

> <JCHEM_LOGP>
-0.6652895649999999

> <ALOGPS_LOGS>
-1.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.210123389492464

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.391040602667121

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083681947342

> <JCHEM_POLAR_SURFACE_AREA>
153.74999999999997

> <JCHEM_REFRACTIVITY>
92.5623

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.51e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{3-oxo-2-[(2E)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl}acetic 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      -2.138  15.295   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.498  12.282   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.353  13.313   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.178  10.776   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.303   8.835   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.779  10.300   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.142   7.589   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.119  20.923   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.673  14.819   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.763   8.835   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.287  10.300   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.533  11.205   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.975  19.893   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.674   7.750   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.490  20.368   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.634  19.338   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.314  17.832   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.151  17.356   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.799  22.429   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.533  12.745   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.579   6.504   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.300   9.157   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.810  21.875   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -3.099  19.814   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -2.458  16.801   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.471  15.849   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       1.295  18.386   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    3    4                                                       
CONECT    3    2    9                                                       
CONECT    4    2   11                                                       
CONECT    5    6   10                                                       
CONECT    6    5   12                                                       
CONECT    7   10   14                                                       
CONECT    8   13   19                                                       
CONECT    9    1    3   26                                                  
CONECT   10    5    7   11                                                  
CONECT   11    4   10   12                                                  
CONECT   12    6   11   20                                                  
CONECT   13    8   15   27                                                  
CONECT   14    7   21   22                                                  
CONECT   15   13   16   23                                                  
CONECT   16   15   17   24                                                  
CONECT   17   16   18   25                                                  
CONECT   18   17   26   27                                                  
CONECT   19    8                                                            
CONECT   20   12                                                            
CONECT   21   14                                                            
CONECT   22   14                                                            
CONECT   23   15                                                            
CONECT   24   16                                                            
CONECT   25   17                                                            
CONECT   26    9   18                                                       
CONECT   27   13   18                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol

Synonyms

Value	Source
b-D-Glucopyranosyl-11-hydroxyjasmonate	Generator
b-D-Glucopyranosyl-11-hydroxyjasmonic acid	Generator
beta-D-Glucopyranosyl-11-hydroxyjasmonate	Generator
Β-D-glucopyranosyl-11-hydroxyjasmonate	Generator
Β-D-glucopyranosyl-11-hydroxyjasmonic acid	Generator
2-{3-oxo-2-[(2E)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl}acetate	Generator
11-Hydroxyjasmonate glucoside	Generator

Chemical Formula

C₁₈H₂₈O₉

Average Mass

388.4095 Da

Monoisotopic Mass

388.17333 Da

IUPAC Name

2-{3-oxo-2-[(2E)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl}acetic acid

Traditional Name

{3-oxo-2-[(2E)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl}acetic acid

CAS Registry Number

13283-31-3

SMILES

CC(OC1OC(CO)C(O)C(O)C1O)\C=C\CC1C(CC(O)=O)CCC1=O

InChI Identifier

InChI=1S/C18H28O9/c1-9(26-18-17(25)16(24)15(23)13(8-19)27-18)3-2-4-11-10(7-14(21)22)5-6-12(11)20/h2-3,9-11,13,15-19,23-25H,4-8H2,1H3,(H,21,22)/b3-2+

InChI Key

LAYQBSCEPAXXNJ-NSCUHMNNSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Solanum tuberosum	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Jasmonic acid
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Monosaccharide
Oxane
Ketone
Cyclic ketone
Secondary alcohol
Monocarboxylic acid or derivatives
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Primary alcohol
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	-0.69	ALOGPS
logP	-0.67	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	4.39	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.75 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	92.56 m³·mol⁻¹	ChemAxon
Polarizability	39.56 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

HMDB0039964

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB019627

KNApSAcK ID

Not Available

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

131752770

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 11-Hydroxyjasmonic acid glucoside (NP0049534)

MOL for NP0049534 (11-Hydroxyjasmonic acid glucoside)

3D MOL for NP0049534 (11-Hydroxyjasmonic acid glucoside)

3D SDF for NP0049534 (11-Hydroxyjasmonic acid glucoside)

3D-SDF for NP0049534 (11-Hydroxyjasmonic acid glucoside)

PDB for NP0049534 (11-Hydroxyjasmonic acid glucoside)

3D PDB for NP0049534 (11-Hydroxyjasmonic acid glucoside)

SMILES for NP0049534 (11-Hydroxyjasmonic acid glucoside)

INCHI for NP0049534 (11-Hydroxyjasmonic acid glucoside)

Structure for NP0049534 (11-Hydroxyjasmonic acid glucoside)

3D Structure for NP0049534 (11-Hydroxyjasmonic acid glucoside)