Showing NP-Card for Hexyl propionate (NP0048021)

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Record Information
Version2.0
Created at2022-03-17 20:49:48 UTC
Updated at2022-03-17 20:49:49 UTC
NP-MRD IDNP0048021
Secondary Accession NumbersNone
Natural Product Identification
Common NameHexyl propionate
DescriptionHexyl propionate, also known as fema 2576, 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). Hexyl propionate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Hexyl propionate is a fruity, green, and melon tasting compound. Outside of the human body, Hexyl propionate has been detected, but not quantified in, a few different foods, such as apples, asian pears, and sweet cherries. This could make hexyl propionate a potential biomarker for the consumption of these foods. Hexyl propionate was first documented in 1982 (PMID: 24414891). A propanoate ester of hexan-1-ol (PMID: 21892724).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0048021 (Hexyl propionate)

  Mrv0541 05061307572D          

 11 10  0  0  0  0            999 V2000
   -3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5263    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8118    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0461    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3316    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0974    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0974    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3829    1.4289    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  4  1  0  0  0  0
 10  9  2  0  0  0  0
 11  8  1  0  0  0  0
 11  9  1  0  0  0  0
M  END
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3D MOL for NP0048021 (Hexyl propionate)

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3D SDF for NP0048021 (Hexyl propionate)
  Mrv0541 05061307572D          

 11 10  0  0  0  0            999 V2000
   -3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5263    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8118    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0461    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3316    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0974    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0974    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3829    1.4289    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  4  1  0  0  0  0
 10  9  2  0  0  0  0
 11  8  1  0  0  0  0
 11  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048021

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCOC(=O)CC

> <INCHI_IDENTIFIER>
InChI=1S/C9H18O2/c1-3-5-6-7-8-11-9(10)4-2/h3-8H2,1-2H3

> <INCHI_KEY>
GOKKOFHHJFGZHW-UHFFFAOYSA-N

> <FORMULA>
C9H18O2

> <MOLECULAR_WEIGHT>
158.238

> <EXACT_MASS>
158.13067982

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
19.603082943923354

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
hexyl propanoate

> <ALOGPS_LOGP>
3.42

> <JCHEM_LOGP>
2.836120533333333

> <ALOGPS_LOGS>
-2.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.029676529101351

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
45.115300000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
propanoic acid, hexyl ester

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0048021 (Hexyl propionate)
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PDB for NP0048021 (Hexyl 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      -7.287   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.716   3.437   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.954   3.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.382   2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.620   2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.286   3.437   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.953   2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.619   3.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.048   3.437   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.048   4.977   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.715   2.667   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2    9                                                       
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7   11                                                       
CONECT    9    4   10   11                                                  
CONECT   10    9                                                            
CONECT   11    8    9                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for NP0048021 (Hexyl propionate)
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SMILES for NP0048021 (Hexyl propionate)
CCCCCCOC(=O)CC
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INCHI for NP0048021 (Hexyl propionate)
InChI=1S/C9H18O2/c1-3-5-6-7-8-11-9(10)4-2/h3-8H2,1-2H3
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Synonyms
ValueSource
Hexyl propionic acidGenerator
1-Hexyl propanoateHMDB
1-Hexyl propionateHMDB
FEMA 2576HMDB
Hexyl propanoateHMDB
N-Hexyl N-propionateHMDB
N-Hexyl propionateHMDB
Propanoic acid, hexyl esterHMDB
Propionic acid, hexyl esterHMDB
Chemical FormulaC9H18O2
Average Mass158.2380 Da
Monoisotopic Mass158.13068 Da
IUPAC Namehexyl propanoate
Traditional Namepropanoic acid, hexyl ester
CAS Registry Number2445-76-3
SMILES
CCCCCCOC(=O)CC
InChI Identifier
InChI=1S/C9H18O2/c1-3-5-6-7-8-11-9(10)4-2/h3-8H2,1-2H3
InChI KeyGOKKOFHHJFGZHW-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Prunus aviumFooDB
    • J. P. Mattheis, D. A. Buchanan, and J. K. Fellman Volatile Constituents of Bing Sweet Cherry Frui...
Pyrus pyrifoliaFooDB
    • Gary R. Takeoka, Ron G. Buttery, and Robert A. Flath. Volatile Constituents of Asian Pear (Pyrus ...
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
logP3.42ALOGPS
logP2.84ChemAxon
logS-2.8ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity45.12 m³·mol⁻¹ChemAxon
Polarizability19.6 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0034606  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013123  
KNApSAcK IDNot Available
Chemspider ID79806  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound88454  
PDB IDNot Available
ChEBI ID87549  
Good Scents IDNot Available
References
General References
  1. Cha DH, Powell TH, Feder JL, Linn CE Jr: Identification of host fruit volatiles from three mayhaw species (Crataegus series Aestivales) attractive to mayhaw-origin Rhagoletis pomonella flies in the southern United States. J Chem Ecol. 2011 Sep;37(9):961-73. doi: 10.1007/s10886-011-0013-6. Epub 2011 Sep 3. [PubMed:21892724  ] 
  2. Fein BL, Reissig WH, Roelofs WL: Identification of apple volatiles attractive to the apple maggot,Rhagoletis pomonella. J Chem Ecol. 1982 Dec;8(12):1473-87. doi: 10.1007/BF00989104. [PubMed:24414891  ]