Showing NP-Card for Pear ester (NP0048550)

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Record Information
Version2.0
Created at2022-03-17 20:58:14 UTC
Updated at2022-03-17 20:58:14 UTC
NP-MRD IDNP0048550
Secondary Accession NumbersNone
Natural Product Identification
Common NamePear ester
DescriptionEthyl 2Z,4E-decadienoic acid, also known as ethyl (2E,4Z)-decadienoate or ethyl 2-trans-4-cis-decadienoate, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Ethyl 2Z,4E-decadienoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Ethyl 2Z,4E-decadienoic acid is a sweet, apple, and creamy tasting compound. Outside of the human body, Ethyl 2Z,4E-decadienoic acid has been detected, but not quantified in, several different foods, such as asian pears, fruits, pears, and pomes. This could make ethyl 2Z,4E-decadienoic acid a potential biomarker for the consumption of these foods. A fatty acid ethyl ester resulting from the formal condensation of the carboxy group of (2E,4E)-deca-2,4-dienoic acid with the hydroxy group of ethanol. Pear ester is found in Strychnos madagascariensis , Thrixspermum arachnites and Vitis spp. . Pear ester was first documented in 2007 (PMID: 17992562). Ethyl 2Z,4E-decadienoic acid is a potentially toxic compound (PMID: 18189264) (PMID: 18284724) (PMID: 21882697) (PMID: 22507015).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048550 (Pear ester)

  Mrv0541 05061309132D          

 14 13  0  0  0  0            999 V2000
   -0.1914   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    2.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    2.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243    1.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    1.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  0  0  0  0
 10  9  1  0  0  0  0
 11 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13 12  2  0  0  0  0
 14  4  1  0  0  0  0
 14 12  1  0  0  0  0
M  END
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3D MOL for NP0048550 (Pear ester)

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3D SDF for NP0048550 (Pear ester)
  Mrv0541 05061309132D          

 14 13  0  0  0  0            999 V2000
   -0.1914   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    2.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    2.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243    1.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    1.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  0  0  0  0
 10  9  1  0  0  0  0
 11 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13 12  2  0  0  0  0
 14  4  1  0  0  0  0
 14 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048550

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC\C=C/C=C/C(=O)OCC

> <INCHI_IDENTIFIER>
InChI=1S/C12H20O2/c1-3-5-6-7-8-9-10-11-12(13)14-4-2/h8-11H,3-7H2,1-2H3/b9-8-,11-10+

> <INCHI_KEY>
OPCRGEVPIBLWAY-QNRZBPGKSA-N

> <FORMULA>
C12H20O2

> <MOLECULAR_WEIGHT>
196.286

> <EXACT_MASS>
196.146329884

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
23.263920253490813

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl (2E,4Z)-deca-2,4-dienoate

> <ALOGPS_LOGP>
4.53

> <JCHEM_LOGP>
3.961107964666666

> <ALOGPS_LOGS>
-4.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.805476530816901

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
61.205200000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl (2E,4Z)-2,4-decadienoate

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0048550 (Pear ester)
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PDB for NP0048550 (Pear ester)
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      -0.357  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.978   5.596   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.976  -2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.645   4.826   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.644  -2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.977  -1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.311  -2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.645  -1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.645   0.206   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.978   0.976   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.978   2.516   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.312   3.286   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       7.645   3.286   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2   14                                                       
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14    4   12                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

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3D PDB for NP0048550 (Pear ester)
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SMILES for NP0048550 (Pear ester)
CCCCC\C=C/C=C/C(=O)OCC
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INCHI for NP0048550 (Pear ester)
InChI=1S/C12H20O2/c1-3-5-6-7-8-9-10-11-12(13)14-4-2/h8-11H,3-7H2,1-2H3/b9-8-,11-10+
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View in JSmol
Synonyms
Chemical FormulaC12H20O2
Average Mass196.2860 Da
Monoisotopic Mass196.14633 Da
IUPAC Nameethyl (2E,4Z)-deca-2,4-dienoate
Traditional Nameethyl (2E,4Z)-2,4-decadienoate
CAS Registry Number3025-30-7
SMILES
CCCCC\C=C/C=C/C(=O)OCC
InChI Identifier
InChI=1S/C12H20O2/c1-3-5-6-7-8-9-10-11-12(13)14-4-2/h8-11H,3-7H2,1-2H3/b9-8-,11-10+
InChI KeyOPCRGEVPIBLWAY-QNRZBPGKSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Pyrus communisFooDB
    • Christian Chervin, Jim Speirs, Brian Loveys, Brian D Patterson. Influence of low oxygen storage o...
Pyrus pyrifoliaFooDB
    • Gary R. Takeoka, Ron G. Buttery, and Robert A. Flath. Volatile Constituents of Asian Pear (Pyrus ...
Strychnos madagascariensisPlant
Thrixspermum arachnitesPlant
Vitis spp.Plant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acid esters  
Direct ParentFatty acid esters  
Alternative Parents
Substituents
  • Fatty acid ester
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Carboxylic acid ester
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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
logP4.53ALOGPS
logP3.96ChemAxon
logS-4.2ALOGPS
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity61.21 m³·mol⁻¹ChemAxon
Polarizability23.26 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0036599  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB015513  
KNApSAcK IDC00001309  
Chemspider ID4444602  
KEGG Compound IDC08486  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthyl_decadienoate  
METLIN IDNot Available
PubChem Compound5281162  
PDB IDNot Available
ChEBI ID4896  
Good Scents IDNot Available
References
General References
  1. Landolt PJ, Suckling DM, Judd GJ: Positive interaction of a feeding attractant and a host kairomone for trapping the codling moth, Cydia pomonella (L.). J Chem Ecol. 2007 Dec;33(12):2236-44. doi: 10.1007/s10886-007-9391-1. Epub 2007 Nov 9. [PubMed:17992562  ] 
  2. Mitchell VJ, Manning LA, Cole L, Suckling DM, El-Sayed AM: Efficacy of the pear ester as a monitoring tool for codling moth Cydia pomonella (Lepidoptera: Tortricidae) in New Zealand apple orchards. Pest Manag Sci. 2008 Mar;64(3):209-14. doi: 10.1002/ps.1479. [PubMed:18189264  ] 
  3. Schmidt S, Anfora G, Ioriatti C, Germinara GS, Rotundo G, De Cristofaro A: Biological activity of ethyl (e,z)-2,4-decadienoate on different tortricid species: electrophysiological responses and field tests. Environ Entomol. 2007 Oct;36(5):1025-31. doi: 10.1603/0046-225x(2007)36[1025:baoeeo]2.0.co;2. [PubMed:18284724  ] 
  4. Light DM, Knight AL: Microencapsulated pear ester enhances insecticide efficacy in walnuts for codling moth (Lepidoptera: Tortricidae) and navel orangeworm (Lepidoptera: Pyralidae). J Econ Entomol. 2011 Aug;104(4):1309-15. doi: 10.1603/ec11058. [PubMed:21882697  ] 
  5. Knight A, Light D, Chebny V: Evaluating dispensers loaded with codlemone and pear ester for disruption of codling moth (Lepidoptera: Tortricidae). Environ Entomol. 2012 Apr;41(2):399-406. doi: 10.1603/EN11309. [PubMed:22507015  ]