Showing NP-Card for Pentyl butanoate (NP0047879)

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Record Information
Version2.0
Created at2022-03-17 20:47:27 UTC
Updated at2022-03-17 20:47:27 UTC
NP-MRD IDNP0047879
Secondary Accession NumbersNone
Natural Product Identification
Common NamePentyl butanoate
DescriptionPentyl butanoate, also known as amyl butyrate or amyl butyric acid, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Pentyl butanoate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Pentyl butanoate is a sweet, banana, and cherry tasting compound. Outside of the human body, Pentyl butanoate has been detected, but not quantified in, several different foods, such as milk (cow), apples, sweet cherries, pomes, and cocoa beans. This could make pentyl butanoate a potential biomarker for the consumption of these foods. Pentyl butanoate is found in Annona reticulata and Prunus armeniaca. Pentyl butanoate was first documented in 2011 (PMID: 21887525). The butyrate ester of pentan-1-ol.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047879 (Pentyl butanoate)

  Mrv1652307171819252D          

 11 10  0  0  0  0            999 V2000
   -3.0789   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3513   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6368   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9224   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4934   -1.0164    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  4  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  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 NP0047879 (Pentyl butanoate)

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3D SDF for NP0047879 (Pentyl butanoate)
  Mrv1652307171819252D          

 11 10  0  0  0  0            999 V2000
   -3.0789   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3513   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6368   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9224   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4934   -1.0164    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  4  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  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>
NP0047879

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCOC(=O)CCC

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

> <INCHI_KEY>
CFNJLPHOBMVMNS-UHFFFAOYSA-N

> <FORMULA>
C9H18O2

> <MOLECULAR_WEIGHT>
158.238

> <EXACT_MASS>
158.13067982

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
19.430660589435366

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
pentyl butanoate

> <ALOGPS_LOGP>
3.32

> <JCHEM_LOGP>
2.836120533333333

> <ALOGPS_LOGS>
-2.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.032619680887206

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
45.115300000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pentyl butyrate

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0047879 (Pentyl butanoate)
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PDB for NP0047879 (Pentyl butanoate)
HEADER    PROTEIN                                 17-JUL-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUL-18         0                                  
HETATM    1  C   UNK     0      -5.747  -2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.256  -1.897   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.414  -1.897   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.922  -2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.080  -2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.746  -1.897   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.588  -1.897   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.413  -2.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.255  -2.667   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.255  -4.207   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.921  -1.897   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2    7                                                       
CONECT    5    3    6                                                       
CONECT    6    5    8                                                       
CONECT    7    4    9                                                       
CONECT    8    6   11                                                       
CONECT    9    7   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 NP0047879 (Pentyl butanoate)
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SMILES for NP0047879 (Pentyl butanoate)
CCCCCOC(=O)CCC
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INCHI for NP0047879 (Pentyl butanoate)
InChI=1S/C9H18O2/c1-3-5-6-8-11-9(10)7-4-2/h3-8H2,1-2H3
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View in JSmol
Synonyms
Chemical FormulaC9H18O2
Average Mass158.2380 Da
Monoisotopic Mass158.13068 Da
IUPAC Namepentyl butanoate
Traditional Namepentyl butyrate
CAS Registry Number540-18-1
SMILES
CCCCCOC(=O)CCC
InChI Identifier
InChI=1S/C9H18O2/c1-3-5-6-8-11-9(10)7-4-2/h3-8H2,1-2H3
InChI KeyCFNJLPHOBMVMNS-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
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
logP3.32ALOGPS
logP2.84ChemAxon
logS-2.6ALOGPS
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
Polarizability19.43 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0034162  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012448  
KNApSAcK IDNot Available
Chemspider ID10428  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPentyl butyrate  
METLIN IDNot Available
PubChem Compound10890  
PDB IDNot Available
ChEBI ID87684  
Good Scents IDNot Available
References
General References
  1. Cha DH, Powell TH, Feder JL, Linn CE Jr: Identification of fruit volatiles from green hawthorn (Crataegus viridis) and blueberry hawthorn (Crataegus brachyacantha) host plants attractive to different phenotypes of Rhagoletis pomonella flies in the southern United States. J Chem Ecol. 2011 Sep;37(9):974-83. doi: 10.1007/s10886-011-0014-5. Epub 2011 Sep 2. [PubMed:21887525  ]