Showing NP-Card for Butyl 2-methylbutanoate (NP0049345)

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Record Information
Version2.0
Created at2022-03-17 21:11:00 UTC
Updated at2022-03-17 21:11:00 UTC
NP-MRD IDNP0049345
Secondary Accession NumbersNone
Natural Product Identification
Common NameButyl 2-methylbutanoate
DescriptionButyl 2-methylbutanoate, also known as fema 3393, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Butyl 2-methylbutanoate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Butyl 2-methylbutanoate is a chocolate, cocoa, and fruity tasting compound. Outside of the human body, Butyl 2-methylbutanoate has been detected, but not quantified in, apples and sweet cherries. This could make butyl 2-methylbutanoate a potential biomarker for the consumption of these foods. Butyl 2-methylbutanoate is found in Prunus armeniaca. Butyl 2-methylbutanoate, with regard to humans, has been found to be associated with several diseases such as diarrhoea predominant irritable bowel syndrome and nonalcoholic fatty liver disease; butyl 2-methylbutanoate has also been linked to the inborn metabolic disorder celiac disease.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049345 (Butyl 2-methylbutanoate)

  Mrv0541 05061310562D          

 11 10  0  0  0  0            999 V2000
   -2.3645   -1.0164    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
    1.9224   -0.1914    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
    2.6368   -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
   -0.2211   -1.4289    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
    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
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  6  1  0  0  0  0
  8  3  1  0  0  0  0
  8  5  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11  7  1  0  0  0  0
 11  9  1  0  0  0  0
M  END
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3D MOL for NP0049345 (Butyl 2-methylbutanoate)

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3D SDF for NP0049345 (Butyl 2-methylbutanoate)
  Mrv0541 05061310562D          

 11 10  0  0  0  0            999 V2000
   -2.3645   -1.0164    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
    1.9224   -0.1914    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
    2.6368   -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
   -0.2211   -1.4289    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
    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
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  6  1  0  0  0  0
  8  3  1  0  0  0  0
  8  5  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11  7  1  0  0  0  0
 11  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049345

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCOC(=O)C(C)CC

> <INCHI_IDENTIFIER>
InChI=1S/C9H18O2/c1-4-6-7-11-9(10)8(3)5-2/h8H,4-7H2,1-3H3

> <INCHI_KEY>
OTKQNSSMCDLVQV-UHFFFAOYSA-N

> <FORMULA>
C9H18O2

> <MOLECULAR_WEIGHT>
158.238

> <EXACT_MASS>
158.13067982

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
19.22604354900944

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
butyl 2-methylbutanoate

> <ALOGPS_LOGP>
3.40

> <JCHEM_LOGP>
2.9345381466666662

> <ALOGPS_LOGS>
-2.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.068456610255728

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
45.088800000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butyl 2-methylbutanoate

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0049345 (Butyl 2-methylbutanoate)
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PDB for NP0049345 (Butyl 2-methylbutanoate)
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      -4.414  -1.897   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       3.588  -0.357   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.080  -2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.922  -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      -0.413  -2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.588  -1.897   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    4                                                            
CONECT    2    5                                                            
CONECT    3    8                                                            
CONECT    4    1    6                                                       
CONECT    5    2    8                                                       
CONECT    6    4    7                                                       
CONECT    7    6   11                                                       
CONECT    8    3    5    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    7    9                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for NP0049345 (Butyl 2-methylbutanoate)
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SMILES for NP0049345 (Butyl 2-methylbutanoate)
CCCCOC(=O)C(C)CC
Download
INCHI for NP0049345 (Butyl 2-methylbutanoate)
InChI=1S/C9H18O2/c1-4-6-7-11-9(10)8(3)5-2/h8H,4-7H2,1-3H3
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View in JSmol
Synonyms
ValueSource
Butyl 2-methylbutanoic acidGenerator
alpha-Butyl 2-methylbutylateHMDB
Butanoic acid, 2-methyl-, butyl esterHMDB
Butyl 2-methylbutyrateHMDB
BUTYL-2-methylbutyrATEHMDB
Butyric acid, 2-methyl-, butyl esterHMDB
FEMA 3393HMDB
N-Butyl 2-methyl butyrateHMDB
N-Butyl 2-methylbutyrateHMDB
N-Butyl-2-methylbutyrateHMDB
Butyl 2-methyl-butanoic acidGenerator
Chemical FormulaC9H18O2
Average Mass158.2380 Da
Monoisotopic Mass158.13068 Da
IUPAC Namebutyl 2-methylbutanoate
Traditional Namebutyl 2-methylbutanoate
CAS Registry Number15706-73-7
SMILES
CCCCOC(=O)C(C)CC
InChI Identifier
InChI=1S/C9H18O2/c1-4-6-7-11-9(10)8(3)5-2/h8H,4-7H2,1-3H3
InChI KeyOTKQNSSMCDLVQV-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Malus pumilaFooDB
Prunus armeniacaLOTUS Database
Prunus aviumFooDB
    • J. P. Mattheis, D. A. Buchanan, and J. K. Fellman Volatile Constituents of Bing Sweet Cherry Frui...
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
logP3.4ALOGPS
logP2.93ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity45.09 m³·mol⁻¹ChemAxon
Polarizability19.23 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0039216  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB018748  
KNApSAcK IDNot Available
Chemspider ID55692  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound61812  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References