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Showing NP-Card for Propyl propionate (NP0045524)

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Record Information
Version2.0
Created at2022-03-17 19:21:25 UTC
Updated at2022-03-17 19:21:25 UTC
NP-MRD IDNP0045524
Secondary Accession NumbersNone
Natural Product Identification
Common NamePropyl propionate
DescriptionPropyl propionate, also known as fema 2958, belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group). Propyl propionate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Propyl propionate is a sweet, bitter, and chemical tasting compound. Outside of the human body, Propyl propionate has been detected, but not quantified in, a few different foods, such as apples, black elderberries, and sweet cherries. This could make propyl propionate a potential biomarker for the consumption of these foods. Propyl propionate, with regard to humans, has been found to be associated with several diseases such as ulcerative colitis, nonalcoholic fatty liver disease, and crohn's disease; propyl propionate has also been linked to the inborn metabolic disorder celiac disease. Propyl propionate is found in Fragaria ananassa and Tagetes minuta. Propyl propionate was first documented in 2005 (PMID: 15691743). A propanoate ester resulting from the formal condensation of the hydroxy group of propanol with the carboxy group of propanoic acid (PMID: 19746921) (PMID: 28332665) (PMID: 23870484) (PMID: 19555224) (PMID: 23991713) (PMID: 25307263).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0045524 (Propyl propionate)


  Mrv0541 05061304592D          

  8  7  0  0  0  0            999 V2000
   -1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3349    1.1270    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
    1.6204    0.7145    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
    0.9059    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914    0.7145    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  4  1  0  0  0  0
  7  6  2  0  0  0  0
  8  5  1  0  0  0  0
  8  6  1  0  0  0  0
M  END
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3D MOL for NP0045524 (Propyl propionate)

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3D SDF for NP0045524 (Propyl propionate)

  Mrv0541 05061304592D          

  8  7  0  0  0  0            999 V2000
   -1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3349    1.1270    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
    1.6204    0.7145    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
    0.9059    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914    0.7145    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  4  1  0  0  0  0
  7  6  2  0  0  0  0
  8  5  1  0  0  0  0
  8  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045524

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCOC(=O)CC

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O2/c1-3-5-8-6(7)4-2/h3-5H2,1-2H3

> <INCHI_KEY>
MCSINKKTEDDPNK-UHFFFAOYSA-N

> <FORMULA>
C6H12O2

> <MOLECULAR_WEIGHT>
116.1583

> <EXACT_MASS>
116.083729628

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
13.369726029077096

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
propyl propanoate

> <ALOGPS_LOGP>
1.81

> <JCHEM_LOGP>
1.5024145383333334

> <ALOGPS_LOGS>
-1.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.0296563317377805

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
31.3123

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.09e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
propyl propanoate

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0045524 (Propyl propionate)
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PDB for NP0045524 (Propyl propionate)
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      -3.644   2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.358   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.310   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.025   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.976   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.691   2.104   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.691   3.644   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.357   1.334   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    8                                                       
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    5    6                                                       
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END

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3D PDB for NP0045524 (Propyl propionate)
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SMILES for NP0045524 (Propyl propionate)
CCCOC(=O)CC
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INCHI for NP0045524 (Propyl propionate)
InChI=1S/C6H12O2/c1-3-5-8-6(7)4-2/h3-5H2,1-2H3
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View in JSmol
Synonyms
ValueSource
N-Propyl N-propionateChEBI
N-Propyl propanoateChEBI
N-Propyl propionateChEBI
Propanoic acid, propyl esterChEBI
Propionic acid N-propyl esterChEBI
Propionic acid, propyl esterChEBI
Propyl ester OF propanoic acidChEBI
Propyl propanoateChEBI
N-Propyl N-propionic acidGenerator
N-Propyl propanoic acidGenerator
N-Propyl propionic acidGenerator
Propanoate, propyl esterGenerator
Propionate N-propyl esterGenerator
Propionate, propyl esterGenerator
Propyl ester OF propanoateGenerator
Propyl propanoic acidGenerator
Propyl propionic acidGenerator
FEMA 2958HMDB
Propyl-propanoateHMDB
Propylester kyseliny propionoveHMDB
Chemical FormulaC6H12O2
Average Mass116.1583 Da
Monoisotopic Mass116.08373 Da
IUPAC Namepropyl propanoate
Traditional Namepropyl propanoate
CAS Registry Number106-36-5
SMILES
CCCOC(=O)CC
InChI Identifier
InChI=1S/C6H12O2/c1-3-5-8-6(7)4-2/h3-5H2,1-2H3
InChI KeyMCSINKKTEDDPNK-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Fragaria x ananassaLOTUS Database
Prunus aviumFooDB
    • J. P. Mattheis, D. A. Buchanan, and J. K. Fellman Volatile Constituents of Bing Sweet Cherry Frui...
Sambucus nigraFooDB
Tagetes minutaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassCarboxylic acid derivatives  
Direct ParentCarboxylic acid esters  
Alternative Parents
Substituents
  • Carboxylic acid ester
    • 

  • Monocarboxylic acid or derivatives
    • 

  • 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
logP1.81ALOGPS
logP1.5ChemAxon
logS-1ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.31 m³·mol⁻¹ChemAxon
Polarizability13.37 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0030059  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001367  
KNApSAcK IDNot Available
Chemspider ID7515  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPropyl_propanoate  
METLIN IDNot Available
PubChem Compound7803  
PDB IDNot Available
ChEBI ID89828  
Good Scents IDNot Available
References
General References
  1. Cometto PM, Daele V, Idir M, Lane SI, Mellouki A: Reaction rate coefficients of OH radicals and Cl atoms with ethyl propanoate, n-propyl propanoate, methyl 2-methylpropanoate, and ethyl n-butanoate. J Phys Chem A. 2009 Oct 8;113(40):10745-52. doi: 10.1021/jp9061708. [PubMed:19746921  ] 
  2. Neurock M, Tao Z, Chemburkar A, Hibbitts DD, Iglesia E: Theoretical insights into the sites and mechanisms for base catalyzed esterification and aldol condensation reactions over Cu. Faraday Discuss. 2017 Apr 28;197:59-86. doi: 10.1039/c6fd00226a. [PubMed:28332665  ] 
  3. Mochalski P, Sponring A, King J, Unterkofler K, Troppmair J, Amann A: Release and uptake of volatile organic compounds by human hepatocellular carcinoma cells (HepG2) in vitro. Cancer Cell Int. 2013 Jul 17;13(1):72. doi: 10.1186/1475-2867-13-72. [PubMed:23870484  ] 
  4. Buzzini P, Romano S, Turchetti B, Vaughan A, Pagnoni UM, Davoli P: Production of volatile organic sulfur compounds (VOSCs) by basidiomycetous yeasts. FEMS Yeast Res. 2005 Feb;5(4-5):379-85. doi: 10.1016/j.femsyr.2004.10.011. [PubMed:15691743  ] 
  5. Wise PM, Toczydlowski SE, Zhao K, Wysocki CJ: Temporal integration in nasal lateralization of homologous propionates. Inhal Toxicol. 2009 Aug;21(10):819-27. doi: 10.1080/08958370802555880. [PubMed:19555224  ] 
  6. Povarov VG, Keresten AA: Propyl propionate methanolysis kinetics: experiment and modeling. J Phys Chem A. 2013 Sep 26;117(38):9115-9. doi: 10.1021/jp403967b. Epub 2013 Sep  17. [PubMed:23991713  ] 
  7. Mochalski P, Al-Zoairy R, Niederwanger A, Unterkofler K, Amann A: Quantitative analysis of volatile organic compounds released and consumed by rat L6 skeletal muscle cells in vitro. J Breath Res. 2014 Oct 13;8(4):046003. doi: 10.1088/1752-7155/8/4/046003. [PubMed:25307263  ] 
  8. Rosier E, Loix S, Develter W, Van de Voorde W, Tytgat J, Cuypers E: The Search for a Volatile Human Specific Marker in the Decomposition Process. PLoS One. 2015 Sep 16;10(9):e0137341. doi: 10.1371/journal.pone.0137341. eCollection 2015. [PubMed:26375029  ] 
  9. Rosier E, Loix S, Develter W, Van de Voorde W, Cuypers E, Tytgat J: Differentiation between decomposed remains of human origin and bigger mammals. J Forensic Leg Med. 2017 Aug;50:28-35. doi: 10.1016/j.jflm.2017.06.003. Epub 2017 Jun 19. [PubMed:28686981  ]