NP-MRD: Showing NP-Card for Methyl jasmonate (NP0002788)

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Record Information

Version

1.0

Created at

2020-11-23 19:40:27 UTC

Updated at

2021-08-12 19:52:09 UTC

NP-MRD ID

NP0002788

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Methyl jasmonate

Provided By

BMRB

Description

Methyl 2-[(1R,2R)-3-oxo-2-[(2E)-pent-2-en-1-yl]cyclopentyl]acetate 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 jasmonate is found in Arabidopsis thaliana, Artemisia absinthium , Artemisia tridentata, Camellia japonica , Camellia sasanqua , Camellia sinensis , Chlorella sp., Citrus limon , Eschscholzia californica , Ficus superba, Jasminum grandiflorum , Malva sylvestris and Rauvolfia canescens. It was first documented in 2008 (PMID: 17984079). Based on a literature review very few articles have been published on methyl 2-[(1R,2R)-3-oxo-2-[(2E)-pent-2-en-1-yl]cyclopentyl]acetate (PMID: 34378779) (PMID: 34371628) (PMID: 34366598) (PMID: 34363225).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


     RDKit          2D

 36 36  0  0  0  0  0  0  0  0999 V2000
    5.6340   -1.6930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5598   -0.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4856    0.4009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0418   -0.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9676    1.0410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067    2.0879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9397    3.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4202    4.7425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3835    2.9285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4427    1.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0356    0.9102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6993   -0.4350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3630   -1.7802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5300   -3.0275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8598   -1.8779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5236   -3.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5871   -2.7672    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6809   -0.6187    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7082   -2.7399    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6067    0.4282    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5128   -1.7202    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8551    1.8547    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6722   -1.4597    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0145    2.1152    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4849    0.4066    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0468    3.0468    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8803    2.8307    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6372    4.4069    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9867    0.0318    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9272    1.6452    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4184    0.4056    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1153    0.0598    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3541   -1.0987    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8687   -2.5593    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1784   -3.8868    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1873   -4.5682    0.0000 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  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 11  6  1  0
  1 17  1  1
  1 18  1  0
  1 19  1  0
  2 20  1  6
  2 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  1
  5 25  1  0
  6 26  1  1
  9 27  1  1
  9 28  1  0
 10 29  1  6
 10 30  1  0
 11 31  1  6
 12 32  1  6
 12 33  1  0
 16 34  1  1
 16 35  1  0
 16 36  1  0
M  END

NP0002788
     RDKit          3D

 36 36  0  0  0  0  0  0  0  0999 V2000
    4.9052    1.8508    0.4895 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8440    1.5576   -0.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5703    1.1438    0.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0874   -0.0613   -0.1401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8330   -0.4878    0.5213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2660   -0.8001   -0.5052 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3034   -1.9017   -1.3359 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0676   -1.8876   -2.2777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2867   -3.1360   -0.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6738   -2.6858   -0.4411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4667   -1.3029    0.1501 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7383   -0.5767    0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8170    0.7855    0.4911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9039    1.4552    1.0158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0235    1.4531    0.3609 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2546    2.7610    0.7642 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7376    1.1255    0.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2869    2.8986    0.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4572    1.7573    1.4993 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1943    0.7919   -1.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6055    2.4979   -1.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0918    1.8252    0.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -0.7003   -0.8224 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042    0.1800    1.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0590   -1.4903    0.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3559    0.0800   -1.1430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2415   -3.3464    0.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2539   -3.9977   -1.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2077   -2.5465   -1.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2242   -3.3519    0.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2457   -1.4829    1.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5260   -1.1788    0.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0871   -0.5927   -1.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1169    3.1971    0.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5843    2.7510    1.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3540    3.4158    0.6716 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  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 11  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
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  1
 12 32  1  0
 12 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
M  END


     RDKit          2D

 36 36  0  0  0  0  0  0  0  0999 V2000
    5.6340   -1.6930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5598   -0.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4856    0.4009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0418   -0.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9676    1.0410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067    2.0879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9397    3.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4202    4.7425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3835    2.9285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4427    1.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0356    0.9102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6993   -0.4350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3630   -1.7802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5300   -3.0275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8598   -1.8779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5236   -3.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5871   -2.7672    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6809   -0.6187    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7082   -2.7399    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6067    0.4282    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5128   -1.7202    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8551    1.8547    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6722   -1.4597    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0145    2.1152    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4849    0.4066    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0468    3.0468    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8803    2.8307    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6372    4.4069    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9867    0.0318    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9272    1.6452    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4184    0.4056    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1153    0.0598    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3541   -1.0987    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8687   -2.5593    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1784   -3.8868    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1873   -4.5682    0.0000 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  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 11  6  1  0
  1 17  1  1
  1 18  1  0
  1 19  1  0
  2 20  1  6
  2 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  1
  5 25  1  0
  6 26  1  1
  9 27  1  1
  9 28  1  0
 10 29  1  6
 10 30  1  0
 11 31  1  6
 12 32  1  6
 12 33  1  0
 16 34  1  1
 16 35  1  0
 16 36  1  0
M  END
> <DATABASE_ID>
NP0002788

> <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-XKFHPXPTSA-N

> <FORMULA>
C13H20O3

> <MOLECULAR_WEIGHT>
224.3

> <EXACT_MASS>
224.141244504

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
25.322381768594205

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
2.560204933666667

> <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>
63.32560000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl [(1R,2R)-3-oxo-2-[(2E)-pent-2-en-1-yl]cyclopentyl]acetate

> <JCHEM_VEBER_RULE>
0

$$$$

NP0002788
     RDKit          3D

 36 36  0  0  0  0  0  0  0  0999 V2000
    4.9052    1.8508    0.4895 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8440    1.5576   -0.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5703    1.1438    0.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0874   -0.0613   -0.1401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8330   -0.4878    0.5213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2660   -0.8001   -0.5052 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3034   -1.9017   -1.3359 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0676   -1.8876   -2.2777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2867   -3.1360   -0.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6738   -2.6858   -0.4411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4667   -1.3029    0.1501 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7383   -0.5767    0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8170    0.7855    0.4911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9039    1.4552    1.0158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0235    1.4531    0.3609 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2546    2.7610    0.7642 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7376    1.1255    0.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2869    2.8986    0.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4572    1.7573    1.4993 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1943    0.7919   -1.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6055    2.4979   -1.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0918    1.8252    0.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -0.7003   -0.8224 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042    0.1800    1.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0590   -1.4903    0.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3559    0.0800   -1.1430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2415   -3.3464    0.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2539   -3.9977   -1.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2077   -2.5465   -1.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2242   -3.3519    0.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2457   -1.4829    1.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5260   -1.1788    0.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0871   -0.5927   -1.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1169    3.1971    0.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5843    2.7510    1.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3540    3.4158    0.6716 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  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 11  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
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  1
 12 32  1  0
 12 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
M  END

HEADER    PROTEIN                                 23-NOV-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-NOV-20         0                                  
HETATM    1  C   UNK     0      -0.002   6.724   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.268  -5.595   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.147   5.694   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.826   4.187   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.971   3.157   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.651   1.651   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.011  -2.943   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.543  -3.104   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -0.894  -4.188   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   16                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5   11                                                       
CONECT    7    8   10                                                       
CONECT    8    7   12                                                       
CONECT    9   10   13                                                       
CONECT   10    7    9   11                                                  
CONECT   11    6   10   12                                                  
CONECT   12    8   11   14                                                  
CONECT   13    9   15   16                                                  
CONECT   14   12                                                            
CONECT   15   13                                                            
CONECT   16    2   13                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    NP0002788
HETATM    1  C1  UNL     1       4.905   1.851   0.489  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.844   1.558  -0.546  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.570   1.144   0.135  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.087  -0.061  -0.140  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.833  -0.488   0.521  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.266  -0.800  -0.505  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.303  -1.902  -1.336  1.00  0.00           C  
HETATM    8  O1  UNL     1       1.068  -1.888  -2.278  1.00  0.00           O  
HETATM    9  C8  UNL     1      -0.287  -3.136  -0.751  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.674  -2.686  -0.441  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.467  -1.303   0.150  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.738  -0.577   0.021  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.817   0.786   0.491  1.00  0.00           C  
HETATM   14  O2  UNL     1      -1.904   1.455   1.016  1.00  0.00           O  
HETATM   15  O3  UNL     1      -4.024   1.453   0.361  1.00  0.00           O  
HETATM   16  C13 UNL     1      -4.255   2.761   0.764  1.00  0.00           C  
HETATM   17  H1  UNL     1       5.738   1.125   0.384  1.00  0.00           H  
HETATM   18  H2  UNL     1       5.287   2.899   0.352  1.00  0.00           H  
HETATM   19  H3  UNL     1       4.457   1.757   1.499  1.00  0.00           H  
HETATM   20  H4  UNL     1       4.194   0.792  -1.241  1.00  0.00           H  
HETATM   21  H5  UNL     1       3.606   2.498  -1.123  1.00  0.00           H  
HETATM   22  H6  UNL     1       2.092   1.825   0.817  1.00  0.00           H  
HETATM   23  H7  UNL     1       2.597  -0.700  -0.822  1.00  0.00           H  
HETATM   24  H8  UNL     1       0.504   0.180   1.316  1.00  0.00           H  
HETATM   25  H9  UNL     1       1.059  -1.490   0.991  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.356   0.080  -1.143  1.00  0.00           H  
HETATM   27  H11 UNL     1       0.241  -3.346   0.202  1.00  0.00           H  
HETATM   28  H12 UNL     1      -0.254  -3.998  -1.445  1.00  0.00           H  
HETATM   29  H13 UNL     1      -2.208  -2.546  -1.413  1.00  0.00           H  
HETATM   30  H14 UNL     1      -2.224  -3.352   0.246  1.00  0.00           H  
HETATM   31  H15 UNL     1      -1.246  -1.483   1.242  1.00  0.00           H  
HETATM   32  H16 UNL     1      -3.526  -1.179   0.557  1.00  0.00           H  
HETATM   33  H17 UNL     1      -3.087  -0.593  -1.055  1.00  0.00           H  
HETATM   34  H18 UNL     1      -5.117   3.197   0.189  1.00  0.00           H  
HETATM   35  H19 UNL     1      -4.584   2.751   1.824  1.00  0.00           H  
HETATM   36  H20 UNL     1      -3.354   3.416   0.672  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4    4   22
CONECT    4    5   23
CONECT    5    6   24   25
CONECT    6    7   11   26
CONECT    7    8    8    9
CONECT    9   10   27   28
CONECT   10   11   29   30
CONECT   11   12   31
CONECT   12   13   32   33
CONECT   13   14   14   15
CONECT   15   16
CONECT   16   34   35   36
END

NP0002788
     RDKit          3D

36 36  0  0  0  0  0  0  0  0999 V2000
    4.9052    1.8508    0.4895 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8440    1.5576   -0.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5703    1.1438    0.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0874   -0.0613   -0.1401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8330   -0.4878    0.5213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2660   -0.8001   -0.5052 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3034   -1.9017   -1.3359 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0676   -1.8876   -2.2777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2867   -3.1360   -0.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6738   -2.6858   -0.4411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4667   -1.3029    0.1501 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7383   -0.5767    0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8170    0.7855    0.4911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9039    1.4552    1.0158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0235    1.4531    0.3609 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2546    2.7610    0.7642 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7376    1.1255    0.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2869    2.8986    0.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4572    1.7573    1.4993 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1943    0.7919   -1.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6055    2.4979   -1.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0918    1.8252    0.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -0.7003   -0.8224 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042    0.1800    1.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0590   -1.4903    0.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3559    0.0800   -1.1430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2415   -3.3464    0.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2539   -3.9977   -1.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2077   -2.5465   -1.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2242   -3.3519    0.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2457   -1.4829    1.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5260   -1.1788    0.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0871   -0.5927   -1.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1169    3.1971    0.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5843    2.7510    1.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3540    3.4158    0.6716 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  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 11  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
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  1
 12 32  1  0
 12 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
M  END

View in JSmol

Synonyms

Value	Source
Methyl 2-[(1R,2R)-3-oxo-2-[(2E)-pent-2-en-1-yl]cyclopentyl]acetic acid	Generator
Methyl jasmonic acid	Generator
Jasmonic acid methyl ester	MeSH
3-oxo-2-(2-Pentenyl)cyclopentaneacetic acid methyl ester	MeSH
Methyl epijasmonate	MeSH

Chemical Formula

C₁₃H₂₀O₃

Average Mass

224.3000 Da

Monoisotopic Mass

224.14124 Da

IUPAC Name

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

Traditional Name

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

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-XKFHPXPTSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Arabidopsis thaliana	Plant	KNApSAcK
Artemisia absinthium	Plant	KNApSAcK
Artemisia tridentata	Plant	KNApSAcK
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Camellia japonica	Plant	KNApSAcK
Camellia sasanqua	Plant	KNApSAcK
Camellia sinensis	Plant	KNApSAcK
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Chlorella sp.	Plant	KNApSAcK
Citrus limon	Plant	KNApSAcK
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Eschscholzia californica	Plant	KNApSAcK
Ficus superba	Plant	KNApSAcK
Gallus gallus	FooDB	FooDB
Jasminum grandiflorum	Plant	KNApSAcK
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Malva sylvestris	Plant	KNApSAcK
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mentha x piperita	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Rauvolfia canescens	Plant	KNApSAcK
Salvia rosmarinus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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

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	2.56	ChemAxon
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	25.32 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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4937273

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6432008

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
Agnello AM, Combs DB, Filgueiras CC, Willett DS, Mafra-Neto A: Reduced Infestation by Xylosandrus germanus (Coleoptera: Curculionidae: Scolytinae) in Apple Trees Treated with Host Plant Defense Compounds. J Econ Entomol. 2021 Aug 11. pii: 6347851. doi: 10.1093/jee/toab153. [PubMed:34378779 ]
Repkina N, Ignatenko A, Holoptseva E, MiszalskI Z, Kaszycki P, Talanova V: Exogenous Methyl Jasmonate Improves Cold Tolerance with Parallel Induction of Two Cold-Regulated (COR) Genes Expression in Triticum aestivum L. Plants (Basel). 2021 Jul 12;10(7). pii: plants10071421. doi: 10.3390/plants10071421. [PubMed:34371628 ]
Saral A, Kanekar S, Koul KK, Bhagyawant SS: Plant growth promoting bacteria induce anti-quorum-sensing substances in chickpea legume seedling bioassay. Physiol Mol Biol Plants. 2021 Jul;27(7):1577-1595. doi: 10.1007/s12298-021-01034-x. Epub 2021 Jul 17. [PubMed:34366598 ]
Manzoor MA, Guohui L, Muhammad A, Han W, Wenlong H, Yang Z, Xinya W, Yu Z, Xiaofeng F, Qing J, Shafique MS, Yongping C: Genome-wide investigation and comparative analysis of MATE gene family in Rosaceae species and their regulatory role in abiotic stress responses in Chinese pear (Pyrus bretschneideri). Physiol Plant. 2021 Aug 6. doi: 10.1111/ppl.13511. [PubMed:34363225 ]

Showing NP-Card for Methyl jasmonate (NP0002788)

MOL for NP0002788 (Methyl jasmonate)

3D MOL for NP0002788 (Methyl jasmonate)

3D SDF for NP0002788 (Methyl jasmonate)

3D-SDF for NP0002788 (Methyl jasmonate)

PDB for NP0002788 (Methyl jasmonate)

3D PDB for NP0002788 (Methyl jasmonate)

SMILES for NP0002788 (Methyl jasmonate)

INCHI for NP0002788 (Methyl jasmonate)

Structure for NP0002788 (Methyl jasmonate)

3D Structure for NP0002788 (Methyl jasmonate)