NP-MRD: Showing NP-Card for methyl 7-epi-jasmonate (NP0251453)

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Record Information

Version

2.0

Created at

2022-09-07 14:39:17 UTC

Updated at

2022-09-07 14:39:17 UTC

NP-MRD ID

NP0251453

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 7-epi-jasmonate

Description

Methyl epijasmonate belongs to the class of organic compounds known as jasmonic acids. These are lipids containing or derived from a jasmonic acid, with a structure characterized by the presence of an alkene chain linked to a 2-(3-oxocyclopentyl)acetic acid moiety. Methyl epijasmonate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 36  0  0  0  0  0  0  0  0999 V2000
   -4.8296    1.6632   -0.7521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8393    0.5246   -0.9070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5731    0.9421   -1.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211    0.8235   -0.8785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2956    0.2547    0.4653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4292   -0.9802    0.5083 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2570   -1.3976    1.9117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9384   -1.1685    2.8932 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9915   -2.2165    1.9479 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6361   -2.0374    0.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9764   -0.7779    0.0529 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6558    0.4075    0.6438 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0496    0.5625    0.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9760   -0.0767    0.7145 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3971    1.3903   -0.8993 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7477    1.5176   -1.3422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4397    2.5931   -1.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0247    1.8885    0.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8151    1.4348   -1.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8292   -0.0621   -0.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3270   -0.1594   -1.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5713    1.3883   -2.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4988    1.1715   -1.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2218    0.1317    1.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7166    1.0265    1.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8620   -1.8057   -0.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6478   -3.2811    2.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6647   -1.9392    2.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3102   -2.9027   -0.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7203   -2.0200    0.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0567   -0.7910   -1.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6286    0.3462    1.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1342    1.3589    0.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3117    0.6358   -0.9231 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2255    2.4399   -0.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7594    1.4168   -2.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 11 10  1  0
 10  9  1  0
  9  7  1  0
  7  8  2  0
  7  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  6
 11 31  1  6
 12 32  1  0
 12 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 10 29  1  0
 10 30  1  0
  9 27  1  0
  9 28  1  0
M  END


  Mrv0541 10111201452D          

 16 16  0  0  1  0            999 V2000
    0.9641   -0.6548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7846   -0.5685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2696   -1.2360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1202    0.1852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6353    0.8526    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8902    1.6372    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2228    2.1222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2228    2.9472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5553    1.6373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8103    0.8526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6748    1.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8463    2.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6309    2.9541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0900   -1.1497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2440    2.4021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0286    2.6570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
  6 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  3 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0251453

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C=C/C[C@H]1[C@@H](CC(=O)OC)CCC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H20O3/c1-3-4-5-6-11-10(7-8-12(11)14)9-13(15)16-2/h4-5,10-11H,3,6-9H2,1-2H3/b5-4-/t10-,11+/m1/s1

> <INCHI_KEY>
GEWDNTWNSAZUDX-KWKBKKAHSA-N

> <FORMULA>
C13H20O3

> <MOLECULAR_WEIGHT>
224.2961

> <EXACT_MASS>
224.141244506

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
25.201511264433073

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-[(1R,2S)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]acetate

> <ALOGPS_LOGP>
2.62

> <JCHEM_LOGP>
2.560204933666667

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.880354377682645

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
63.3256

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.68e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 7-epi-jasmonate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-OCT-12         0                                  
HETATM    1  O   UNK     0       1.800  -1.222   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.331  -1.061   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.237  -2.307   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.958   0.346   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.053   1.592   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.528   3.056   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.283   3.961   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.283   5.501   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.037   3.056   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.513   1.592   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.993   3.532   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.313   5.038   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.778   5.514   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.768  -2.146   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.922   4.484   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.387   4.960   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2   14                                                       
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    5                                                       
CONECT   11    6   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   15                                                       
CONECT   14    3                                                            
CONECT   15   13   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
(+)-7-Isojasmonic acid methyl ester	ChEBI
(1R,2S)-Methyl jasmonate	ChEBI
(3R,7S)-Methyl jasmonate	ChEBI
Methyl 7-epi-jasmonate	ChEBI
(+)-7-Isojasmonate methyl ester	Generator
(1R,2S)-Methyl jasmonic acid	Generator
(3R,7S)-Methyl jasmonic acid	Generator
Methyl 7-epi-jasmonic acid	Generator
Methyl epijasmonic acid	Generator
Jasmonic acid methyl ester	MeSH
Methyl jasmonate	MeSH
3-oxo-2-(2-Pentenyl)cyclopentaneacetic acid methyl ester	MeSH

Chemical Formula

C₁₃H₂₀O₃

Average Mass

224.2961 Da

Monoisotopic Mass

224.14124 Da

IUPAC Name

methyl 2-[(1R,2S)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]acetate

Traditional Name

methyl 7-epi-jasmonate

CAS Registry Number

Not Available

SMILES

CC\C=C/C[C@H]1[C@@H](CC(=O)OC)CCC1=O

InChI Identifier

InChI=1S/C13H20O3/c1-3-4-5-6-11-10(7-8-12(11)14)9-13(15)16-2/h4-5,10-11H,3,6-9H2,1-2H3/b5-4-/t10-,11+/m1/s1

InChI Key

GEWDNTWNSAZUDX-KWKBKKAHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as jasmonic acids. These are lipids containing or derived from a jasmonic acid, with a structure characterized by the presence of an alkene chain linked to a 2-(3-oxocyclopentyl)acetic acid moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Jasmonic acids

Alternative Parents

Substituents

Jasmonic acid
Methyl ester
Cyclic ketone
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

methyl ester (CHEBI:25242 )
jasmonate ester (CHEBI:25242 )
Jasmonic acids (C16318 )
Jasmonic acids (LMFA02020016 )

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	2.62	ALOGPS
logP	2.56	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	63.33 m³·mol⁻¹	ChemAxon
Polarizability	25.2 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001424

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C16318

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6427970

PDB ID

Not Available

ChEBI ID

25242

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 7-epi-jasmonate (NP0251453)

MOL for NP0251453 (methyl 7-epi-jasmonate)

3D MOL for NP0251453 (methyl 7-epi-jasmonate)

3D SDF for NP0251453 (methyl 7-epi-jasmonate)

3D-SDF for NP0251453 (methyl 7-epi-jasmonate)

PDB for NP0251453 (methyl 7-epi-jasmonate)

3D PDB for NP0251453 (methyl 7-epi-jasmonate)

SMILES for NP0251453 (methyl 7-epi-jasmonate)

INCHI for NP0251453 (methyl 7-epi-jasmonate)

Structure for NP0251453 (methyl 7-epi-jasmonate)

3D Structure for NP0251453 (methyl 7-epi-jasmonate)