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Showing NP-Card for Hexyl butyrate (NP0044873)

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Record Information
Version2.0
Created at2022-03-10 18:36:59 UTC
Updated at2022-03-10 22:21:12 UTC
NP-MRD IDNP0044873
Secondary Accession NumbersNone
Natural Product Identification
Common NameHexyl butyrate
DescriptionButanoic acid-hexyl ester or hexyl butyrate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid consisting of 6 or more carbons. Hexyl butyrate is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It is a clear, colorless liquid obtained by the formal condensation of hexanol with butyric acid. Hexyl butyrate has a sweet, slightly waxy, fruity, apple, and apple peel aroma, with a similar green/soapy taste. Hexyl butyrate occurs naturally in many fruits and has been detected, but not quantified in apples, yellow passion fruit, roman camomiles, pears, sweet cherries, and other fruits. This could make hexyl butyrate a potential biomarker for the consumption of these foods. Hexyl butyrate is one of the main volatile chemicals released by the Tarnished plant bugs, Lygus hesperus and Lygus lineolaris when they are attacked or disturbed ( PMID: 12775153 ). Hexyl butyrate has also been found in Cannabis sativa (PMID: 6991645 , 26657499 ).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0044873 (Hexyl butyrate)


  Mrv1652303202019022D          

 12 11  0  0  0  0            999 V2000
   -1.4271   -0.6194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7136   -1.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7136   -1.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4271   -0.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7136   -1.8553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1411   -1.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8560   -0.6209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5701   -1.0341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2850   -0.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9990   -1.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7139   -0.6238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  6  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
Download

3D MOL for NP0044873 (Hexyl butyrate)

     RDKit          3D

 32 31  0  0  0  0  0  0  0  0999 V2000
   -4.5915    0.9547    0.9951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7699    0.0789    0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5373   -0.3574    0.8014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6454   -1.2326   -0.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1619   -0.5427   -1.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3720    0.7039   -0.9856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7624    0.4650   -0.2156 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8202   -0.3282   -0.5392 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8216   -0.9308   -1.6405 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0023   -0.5373    0.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0819    0.4149   -0.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3484    0.3153    0.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6176    1.1340    0.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6050    0.4578    1.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1239    1.9498    1.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3726   -0.8316   -0.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5346    0.6302   -0.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0400    0.5338    1.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8584   -0.9678    1.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2524   -2.1035   -0.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8068   -1.6221    0.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9929   -0.3541   -1.9944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4757   -1.2464   -1.8045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9739    1.4795   -0.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1282    1.1606   -1.9905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7290   -0.3236    1.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3583   -1.5875    0.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1895    0.2663   -1.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6555    1.4450   -0.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2596    0.9003    1.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1534    0.8047    0.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6779   -0.7292    0.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 12 32  1  0
M  END
Download

3D SDF for NP0044873 (Hexyl butyrate)


  Mrv1652303202019022D          

 12 11  0  0  0  0            999 V2000
   -1.4271   -0.6194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7136   -1.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7136   -1.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4271   -0.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7136   -1.8553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1411   -1.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8560   -0.6209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5701   -1.0341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2850   -0.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9990   -1.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7139   -0.6238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  6  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044873

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCOC(=O)CCC

> <INCHI_IDENTIFIER>
InChI=1S/C10H20O2/c1-3-5-6-7-9-12-10(11)8-4-2/h3-9H2,1-2H3

> <INCHI_KEY>
XAPCMTMQBXLDBB-UHFFFAOYSA-N

> <FORMULA>
C10H20O2

> <MOLECULAR_WEIGHT>
172.2646

> <EXACT_MASS>
172.146329884

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
21.52007400307047

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
hexyl butanoate

> <ALOGPS_LOGP>
3.83

> <JCHEM_LOGP>
3.2806891983333326

> <ALOGPS_LOGS>
-3.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.032619683221385

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
49.7163

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butanoic acid, hexyl ester

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0044873 (Hexyl butyrate)

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PDB for NP0044873 (Hexyl butyrate)
HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  O   UNK     0      -2.664  -1.156   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.332  -1.923   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -1.156   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.332  -1.923   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.664  -1.156   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.332  -3.463   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -3.997  -1.928   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.331  -1.159   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.664  -1.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.999  -1.162   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -9.331  -1.933   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -10.666  -1.164   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    2                                                            
CONECT    7    1    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

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3D PDB for NP0044873 (Hexyl butyrate)
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SMILES for NP0044873 (Hexyl butyrate)
CCCCCCOC(=O)CCC
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INCHI for NP0044873 (Hexyl butyrate)
InChI=1S/C10H20O2/c1-3-5-6-7-9-12-10(11)8-4-2/h3-9H2,1-2H3
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View in JSmol
Synonyms
ValueSource
Hexyl butyric acidGenerator
1-Hexyl butyrateHMDB
Butanoic acid, hexyl esterHMDB
Butyric acid, hexyl esterHMDB
Hexyl butanoateHMDB
N-Hexyl butanoateHMDB
N-Hexyl butyrateHMDB
N-Hexyl N-butanoateHMDB
N-Hexyl N-butyrateHMDB
Chemical FormulaC10H20O2
Average Mass172.2646 Da
Monoisotopic Mass172.14633 Da
IUPAC Namehexyl butanoate
Traditional Namebutanoic acid, hexyl ester
CAS Registry Number2639-63-6
SMILES
CCCCCCOC(=O)CCC
InChI Identifier
InChI=1S/C10H20O2/c1-3-5-6-7-9-12-10(11)8-4-2/h3-9H2,1-2H3
InChI KeyXAPCMTMQBXLDBB-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
Cannabis sativaNULL
      Not Available
Chamaemelum nobileFooDB
Citrus iyoLOTUS Database
Cleistopholis patensLOTUS Database
Feijoa sellowianaPlant
Heracleum antasiaticumLOTUS Database
Heracleum persicumLOTUS Database
Lavandula angustifoliaPlant
Lavandula latifoliaLOTUS Database
Malpighia emarginataLOTUS Database
Malus pumilaFooDB
Mandragora autumnalisPlant
Mandragora officinarumLOTUS Database
Musa paradisiacaLOTUS Database
Passiflora edulisFooDB
Pelargonium quercifoliumLOTUS Database
Prunus armeniacaLOTUS Database
Prunus aviumFooDB
    • J. P. Mattheis, D. A. Buchanan, and J. K. Fellman Volatile Constituents of Bing Sweet Cherry Frui...
Pternistria bispinaLOTUS Database
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 ...
Spondias mombinLOTUS Database
Vanilla planifolia Jacks.LOTUS Database
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
    • 

  • 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
logP3.83ALOGPS
logP3.28ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity49.72 m³·mol⁻¹ChemAxon
Polarizability21.52 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033620  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011708  
KNApSAcK IDC00035702  
Chemspider ID16570  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound17525  
PDB IDNot Available
ChEBI ID87559  
Good Scents IDNot Available
References
General References
  1. Wardle AR, Borden JH, Pierce HD Jr, Gries R: Volatile compounds released by disturbed and calm adults of the tarnished plant bug, Lygus lineolaris. J Chem Ecol. 2003 Apr;29(4):931-44. doi: 10.1023/a:1022987901330. [PubMed:12775153  ] 
  2. Fountain M, Jastad G, Hall D, Douglas P, Farman D, Cross J: Further studies on sex pheromones of female Lygus and related bugs: development of effective lures and investigation of species-specificity. J Chem Ecol. 2014 Jan;40(1):71-83. doi: 10.1007/s10886-013-0375-z. Epub 2014 Jan  4. [PubMed:24390623  ] 
  3. Yang CY, Kim SJ, Kim J, Kang TJ, Ahn SJ: Sex pheromones and reproductive isolation in five mirid species. PLoS One. 2015 May 14;10(5):e0127051. doi: 10.1371/journal.pone.0127051. eCollection 2015. [PubMed:25973902  ]