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Showing NP-Card for 7-Epi-12-hydroxyjasmonic acid glucoside (NP0049706)

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Record Information
Version1.0
Created at2022-03-17 21:16:47 UTC
Updated at2022-03-17 21:16:47 UTC
NP-MRD IDNP0049706
Secondary Accession NumbersNone
Natural Product Identification
Common Name7-Epi-12-hydroxyjasmonic acid glucoside
Description7-Epi-12-hydroxyjasmonic acid glucoside 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. 7-Epi-12-hydroxyjasmonic acid glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 7-Epi-12-hydroxyjasmonic acid glucoside has been detected, but not quantified in, alcoholic beverages and potato. It was first documented in 2000 (PMID: 11413487). This could make 7-epi-12-hydroxyjasmonic acid glucoside a potential biomarker for the consumption of these foods (PMID: 16902246) (PMID: 17374880) (PMID: 20044567).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0049706 (7-Epi-12-hydroxyjasmonic acid glucoside)


  Mrv0541 05061312042D          

 27 28  0  0  0  0            999 V2000
   -3.7617    6.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3748    5.4654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9332    6.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2032    4.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3387    3.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0837    4.4035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3201    7.3764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6486    2.9514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6962    8.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1637    3.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4186    4.4035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512    4.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4808    9.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3130    2.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6523    9.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4370   10.0944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0501    9.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8785    8.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0831    9.3296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512    5.7134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4926    2.1115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7980    1.5303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0393   10.3915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6085   10.9014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8347    9.7973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4916    8.1834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0939    8.4805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  0  0  0  0
  7  3  1  0  0  0  0
 10  5  1  0  0  0  0
 10  8  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  9  1  0  0  0  0
 14  8  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  9  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  7  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
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3D MOL for NP0049706 (7-Epi-12-hydroxyjasmonic acid glucoside)

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3D SDF for NP0049706 (7-Epi-12-hydroxyjasmonic acid glucoside)

  Mrv0541 05061312042D          

 27 28  0  0  0  0            999 V2000
   -3.7617    6.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3748    5.4654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9332    6.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2032    4.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3387    3.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0837    4.4035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3201    7.3764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6486    2.9514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6962    8.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1637    3.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4186    4.4035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512    4.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4808    9.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3130    2.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6523    9.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4370   10.0944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0501    9.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8785    8.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0831    9.3296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512    5.7134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4926    2.1115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7980    1.5303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0393   10.3915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6085   10.9014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8347    9.7973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4916    8.1834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0939    8.4805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  0  0  0  0
  7  3  1  0  0  0  0
 10  5  1  0  0  0  0
 10  8  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  9  1  0  0  0  0
 14  8  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  9  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  7  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>
NP0049706

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OCC\C=C\CC2C(CC(O)=O)CCC2=O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C18H28O9/c19-9-13-15(23)16(24)17(25)18(27-13)26-7-3-1-2-4-11-10(8-14(21)22)5-6-12(11)20/h1-2,10-11,13,15-19,23-25H,3-9H2,(H,21,22)/b2-1+

> <INCHI_KEY>
JFDNMLUPLXZXGV-OWOJBTEDSA-N

> <FORMULA>
C18H28O9

> <MOLECULAR_WEIGHT>
388.4095

> <EXACT_MASS>
388.173332494

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
39.832338490237774

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.28

> <JCHEM_LOGP>
-0.7932033846666664

> <ALOGPS_LOGS>
-2.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.210972766837358

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.4626287129632365

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083411872574

> <JCHEM_POLAR_SURFACE_AREA>
153.74999999999997

> <JCHEM_REFRACTIVITY>
92.89849999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.79e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0049706 (7-Epi-12-hydroxyjasmonic acid glucoside)
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PDB for NP0049706 (7-Epi-12-hydroxyjasmonic acid glucoside)
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      -7.022  11.232   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.166  10.202   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.342  12.739   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.846   8.696   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.366   6.755   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.890   8.220   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.198  13.769   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.811   5.509   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.300  16.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.906   6.755   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.381   8.220   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.136   9.125   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.764  16.861   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.184   4.102   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.084  18.367   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.549  18.843   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.694  17.812   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.373  16.306   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.155  17.415   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -5.136  10.665   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -4.653   3.941   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -7.090   2.857   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -1.940  19.397   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -4.869  20.349   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -7.158  18.288   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -6.518  15.276   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -3.909  15.830   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    7                                                       
CONECT    4    2   11                                                       
CONECT    5    6   10                                                       
CONECT    6    5   12                                                       
CONECT    7    3   26                                                       
CONECT    8   10   14                                                       
CONECT    9   13   19                                                       
CONECT   10    5    8   11                                                  
CONECT   11    4   10   12                                                  
CONECT   12    6   11   20                                                  
CONECT   13    9   15   27                                                  
CONECT   14    8   21   22                                                  
CONECT   15   13   16   23                                                  
CONECT   16   15   17   24                                                  
CONECT   17   16   18   25                                                  
CONECT   18   17   26   27                                                  
CONECT   19    9                                                            
CONECT   20   12                                                            
CONECT   21   14                                                            
CONECT   22   14                                                            
CONECT   23   15                                                            
CONECT   24   16                                                            
CONECT   25   17                                                            
CONECT   26    7   18                                                       
CONECT   27   13   18                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

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3D PDB for NP0049706 (7-Epi-12-hydroxyjasmonic acid glucoside)
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SMILES for NP0049706 (7-Epi-12-hydroxyjasmonic acid glucoside)
OCC1OC(OCC\C=C\CC2C(CC(O)=O)CCC2=O)C(O)C(O)C1O
Download
INCHI for NP0049706 (7-Epi-12-hydroxyjasmonic acid glucoside)
InChI=1S/C18H28O9/c19-9-13-15(23)16(24)17(25)18(27-13)26-7-3-1-2-4-11-10(8-14(21)22)5-6-12(11)20/h1-2,10-11,13,15-19,23-25H,3-9H2,(H,21,22)/b2-1+
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View in JSmol
Synonyms
ValueSource
7-Epi-12-hydroxyjasmonate glucosideGenerator
2-{3-oxo-2-[(2E)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl}acetateGenerator
Chemical FormulaC18H28O9
Average Mass388.4095 Da
Monoisotopic Mass388.17333 Da
IUPAC Name2-{3-oxo-2-[(2E)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl}acetic acid
Traditional Name{3-oxo-2-[(2E)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl}acetic acid
CAS Registry Number124649-25-8
SMILES
OCC1OC(OCC\C=C\CC2C(CC(O)=O)CCC2=O)C(O)C(O)C1O
InChI Identifier
InChI=1S/C18H28O9/c19-9-13-15(23)16(24)17(25)18(27-13)26-7-3-1-2-4-11-10(8-14(21)22)5-6-12(11)20/h1-2,10-11,13,15-19,23-25H,3-9H2,(H,21,22)/b2-1+
InChI KeyJFDNMLUPLXZXGV-OWOJBTEDSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Solanum tuberosumFooDB
    • 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.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acyl glycosides  
Direct ParentFatty 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 FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.28ALOGPS
logP-0.79ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)4.46ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area153.75 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity92.9 m³·mol⁻¹ChemAxon
Polarizability39.83 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0040706  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB020509  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6123144  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487  ] 
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246  ] 
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880  ] 
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567  ]