NP-MRD: Showing NP-Card for Methyl 7-epi-12-hydroxyjasmonate glucoside (NP0047325)

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Record Information

Version

2.0

Created at

2022-03-17 20:38:19 UTC

Updated at

2022-03-17 20:38:19 UTC

NP-MRD ID

NP0047325

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Methyl 7-epi-12-hydroxyjasmonate glucoside

Description

Methyl 7-epi-12-hydroxyjasmonate 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. Methyl 7-epi-12-hydroxyjasmonate glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Methyl 7-epi-12-hydroxyjasmonate glucoside has been detected, but not quantified in, potato and root vegetables. This could make methyl 7-epi-12-hydroxyjasmonate glucoside a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061306072D          

 28 29  0  0  0  0            999 V2000
   -0.7112    3.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8498    6.6515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0652    6.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4629    6.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4521    6.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    5.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6674    6.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2475    6.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8974    5.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3313    9.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    5.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674    6.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    7.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1598    8.4782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5619    4.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7729    7.9262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6014    7.1192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8167    6.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2036    7.4163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1159    9.5401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    8.0036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2586    4.4017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5575    8.1811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2145    6.5672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6452    6.0573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0468    3.8205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4190    7.1614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3752    8.2233    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
  5  3  1  0  0  0  0
  7  6  1  0  0  0  0
  8  4  1  0  0  0  0
 11  6  1  0  0  0  0
 11  9  1  0  0  0  0
 12  5  1  0  0  0  0
 12 11  1  0  0  0  0
 13  7  1  0  0  0  0
 13 12  1  0  0  0  0
 14 10  1  0  0  0  0
 15  9  1  0  0  0  0
 16 14  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 10  1  0  0  0  0
 21 13  2  0  0  0  0
 22 15  2  0  0  0  0
 23 16  1  0  0  0  0
 24 17  1  0  0  0  0
 25 18  1  0  0  0  0
 26  1  1  0  0  0  0
 26 15  1  0  0  0  0
 27  8  1  0  0  0  0
 27 19  1  0  0  0  0
 28 14  1  0  0  0  0
 28 19  1  0  0  0  0
M  END


  Mrv0541 05061306072D          

 28 29  0  0  0  0            999 V2000
   -0.7112    3.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8498    6.6515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0652    6.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4629    6.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4521    6.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    5.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6674    6.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2475    6.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8974    5.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3313    9.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    5.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674    6.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    7.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1598    8.4782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5619    4.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7729    7.9262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6014    7.1192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8167    6.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2036    7.4163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1159    9.5401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    8.0036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2586    4.4017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5575    8.1811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2145    6.5672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6452    6.0573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0468    3.8205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4190    7.1614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3752    8.2233    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
  5  3  1  0  0  0  0
  7  6  1  0  0  0  0
  8  4  1  0  0  0  0
 11  6  1  0  0  0  0
 11  9  1  0  0  0  0
 12  5  1  0  0  0  0
 12 11  1  0  0  0  0
 13  7  1  0  0  0  0
 13 12  1  0  0  0  0
 14 10  1  0  0  0  0
 15  9  1  0  0  0  0
 16 14  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 10  1  0  0  0  0
 21 13  2  0  0  0  0
 22 15  2  0  0  0  0
 23 16  1  0  0  0  0
 24 17  1  0  0  0  0
 25 18  1  0  0  0  0
 26  1  1  0  0  0  0
 26 15  1  0  0  0  0
 27  8  1  0  0  0  0
 27 19  1  0  0  0  0
 28 14  1  0  0  0  0
 28 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047325

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC1CCC(=O)C1C\C=C\CCOC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C19H30O9/c1-26-15(22)9-11-6-7-13(21)12(11)5-3-2-4-8-27-19-18(25)17(24)16(23)14(10-20)28-19/h2-3,11-12,14,16-20,23-25H,4-10H2,1H3/b3-2+

> <INCHI_KEY>
AJWIFVNLXHFTFD-NSCUHMNNSA-N

> <FORMULA>
C19H30O9

> <MOLECULAR_WEIGHT>
402.4361

> <EXACT_MASS>
402.188982558

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
41.854607368300535

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.16

> <JCHEM_LOGP>
-0.6473093286666664

> <ALOGPS_LOGS>
-2.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.200250946661985

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.210972759890888

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083411872574

> <JCHEM_POLAR_SURFACE_AREA>
142.75

> <JCHEM_REFRACTIVITY>
97.66759999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.76e+00 g/l

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

> <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      -1.328   5.725   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.320  12.416   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.855  11.940   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.464  11.386   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.711  12.971   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.770  11.030   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.246  12.495   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.929  11.862   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.675   9.784   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -11.818  17.332   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.770  11.030   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.246  12.495   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  13.400   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -11.498  15.826   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.049   8.377   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -12.643  14.796   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -12.323  13.289   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -10.858  12.813   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -9.713  13.844   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0     -13.283  17.808   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000  14.940   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.483   8.217   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0     -14.107  15.271   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0     -13.467  12.259   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0     -10.538  11.307   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -1.954   7.132   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -8.249  13.368   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0     -10.034  15.350   0.000  0.00  0.00           O+0
CONECT    1   26                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3   12                                                       
CONECT    6    7   11                                                       
CONECT    7    6   13                                                       
CONECT    8    4   27                                                       
CONECT    9   11   15                                                       
CONECT   10   14   20                                                       
CONECT   11    6    9   12                                                  
CONECT   12    5   11   13                                                  
CONECT   13    7   12   21                                                  
CONECT   14   10   16   28                                                  
CONECT   15    9   22   26                                                  
CONECT   16   14   17   23                                                  
CONECT   17   16   18   24                                                  
CONECT   18   17   19   25                                                  
CONECT   19   18   27   28                                                  
CONECT   20   10                                                            
CONECT   21   13                                                            
CONECT   22   15                                                            
CONECT   23   16                                                            
CONECT   24   17                                                            
CONECT   25   18                                                            
CONECT   26    1   15                                                       
CONECT   27    8   19                                                       
CONECT   28   14   19                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

View in JSmol

Synonyms

Value	Source
Methyl 7-epi-12-hydroxyjasmonic acid glucoside	Generator
Methyl 2-{3-oxo-2-[(2E)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl}acetic acid	Generator

Chemical Formula

C₁₉H₃₀O₉

Average Mass

402.4361 Da

Monoisotopic Mass

402.18898 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

142465-56-3

SMILES

COC(=O)CC1CCC(=O)C1C\C=C\CCOC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C19H30O9/c1-26-15(22)9-11-6-7-13(21)12(11)5-3-2-4-8-27-19-18(25)17(24)16(23)14(10-20)28-19/h2-3,11-12,14,16-20,23-25H,4-10H2,1H3/b3-2+

InChI Key

AJWIFVNLXHFTFD-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
Methyl ester
Carboxylic acid ester
Ketone
Cyclic ketone
Secondary alcohol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Acetal
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	0.16	ALOGPS
logP	-0.65	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	142.75 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	97.67 m³·mol⁻¹	ChemAxon
Polarizability	41.85 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

HMDB0031763

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008436

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

131751189

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Methyl 7-epi-12-hydroxyjasmonate glucoside (NP0047325)

MOL for NP0047325 (Methyl 7-epi-12-hydroxyjasmonate glucoside)

3D MOL for NP0047325 (Methyl 7-epi-12-hydroxyjasmonate glucoside)

3D SDF for NP0047325 (Methyl 7-epi-12-hydroxyjasmonate glucoside)

3D-SDF for NP0047325 (Methyl 7-epi-12-hydroxyjasmonate glucoside)

PDB for NP0047325 (Methyl 7-epi-12-hydroxyjasmonate glucoside)

3D PDB for NP0047325 (Methyl 7-epi-12-hydroxyjasmonate glucoside)

SMILES for NP0047325 (Methyl 7-epi-12-hydroxyjasmonate glucoside)

INCHI for NP0047325 (Methyl 7-epi-12-hydroxyjasmonate glucoside)

Structure for NP0047325 (Methyl 7-epi-12-hydroxyjasmonate glucoside)

3D Structure for NP0047325 (Methyl 7-epi-12-hydroxyjasmonate glucoside)