Showing metabocard for isoamyl acetate (MMDBc0033040)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:32:10 UTC
Update Date2024-04-30 19:59:17 UTC
Metabolite IDMMDBc0033040
Metabolite Identification
Common Nameisoamyl acetate
DescriptionIsopentyl acetate, also known as isoamyl acetate or amylacetic ester, 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). Isopentyl acetate is an ester formed from isoamyl alcohol and acetic acid. It is a colorless liquid that is only slightly soluble in water, but very soluble in most organic solvents. Isopentyl acetate has a sweet, fruity banana odor and similar sweet, fruity banana taste. Isopentyl acetate is used to confer banana flavor in foods. Isopentyl acetate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Outside of the human body, Isopentyl acetate is found, on average, in the highest concentration within a few different foods, such as red wines, white wines, and beers. Isopentyl acetate has also been detected, but not quantified in, several different foods, such as blackberries (Rubus), figs (Ficus carica), red teas, bananas (Musa acuminata), and black elderberries (Sambucus nigra). This could make isopentyl acetate a potential biomarker for the consumption of these foods. Isopentyl acetate occurs naturally in the banana plant and it is also produced synthetically. Based on a literature review a significant number of articles have been published on Isopentyl acetate. Pure isopentyl acetate, or mixtures of isopentyl acetate, amyl acetate, and other flavors may be referred to as banana oil. Because of its intense, pleasant odor and its low toxicity, isopentyl acetate is used to test the effectiveness of respirators or gas masks. Isopentyl acetate is released by a honey bee's sting where it serves as a pheromone beacon to attract other bees and provoke them to sting.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fa4e6ebe3c0>


  Mrv1652303202019002D          

  9  8  0  0  0  0            999 V2000
    4.3974   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  3  1  0  0  0  0
  8  7  2  0  0  0  0
  9  5  1  0  0  0  0
  9  7  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fa4e6ebe3c0>

HMDB0031528
     RDKit          3D
Isopentyl acetate
 23 22  0  0  0  0  0  0  0  0999 V2000
    3.9792   -0.2461    0.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5148   -0.4348    0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9515   -1.2669    1.0405 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7425    0.2575   -0.6164 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3505    0.0970   -0.7687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3539    0.4484    0.5108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8563    0.2932    0.3934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4459    1.1675   -0.6686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1741   -1.1573    0.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2619    0.7073   -0.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5593   -1.1149    0.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1828   -0.0774    1.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2024   -0.9909   -1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0200    0.6509   -1.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1569    1.5108    0.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0493   -0.1529    1.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2748    0.6267    1.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3381    1.7255   -0.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6775    1.9547   -0.9037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7141    0.6233   -1.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0680   -1.5271   -0.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1725   -1.3536    0.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4437   -1.7408    0.8544 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  5 13  1  0
  5 14  1  0
  6 15  1  0
  6 16  1  0
  7 17  1  0
  8 18  1  0
  8 19  1  0
  8 20  1  0
  9 21  1  0
  9 22  1  0
  9 23  1  0
M  END
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3D SDF for #<Metabolite:0x00007fa4e6ebe3c0>


  Mrv1652303202019002D          

  9  8  0  0  0  0            999 V2000
    4.3974   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  3  1  0  0  0  0
  8  7  2  0  0  0  0
  9  5  1  0  0  0  0
  9  7  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033040

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H14O2/c1-6(2)4-5-9-7(3)8/h6H,4-5H2,1-3H3

> <INCHI_KEY>
MLFHJEHSLIIPHL-UHFFFAOYSA-N

> <FORMULA>
C7H14O2

> <MOLECULAR_WEIGHT>
130.1849

> <EXACT_MASS>
130.099379692

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
15.177509520567913

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-methylbutyl acetate

> <ALOGPS_LOGP>
2.36

> <JCHEM_LOGP>
1.533466452666667

> <ALOGPS_LOGS>
-1.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.993831859009882

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
35.83500000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
banana oil

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for #<Metabolite:0x00007fa4e6ebe3c0>

HMDB0031528
     RDKit          3D
Isopentyl acetate
 23 22  0  0  0  0  0  0  0  0999 V2000
    3.9792   -0.2461    0.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5148   -0.4348    0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9515   -1.2669    1.0405 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7425    0.2575   -0.6164 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3505    0.0970   -0.7687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3539    0.4484    0.5108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8563    0.2932    0.3934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4459    1.1675   -0.6686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1741   -1.1573    0.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2619    0.7073   -0.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5593   -1.1149    0.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1828   -0.0774    1.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2024   -0.9909   -1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0200    0.6509   -1.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1569    1.5108    0.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0493   -0.1529    1.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2748    0.6267    1.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3381    1.7255   -0.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6775    1.9547   -0.9037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7141    0.6233   -1.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0680   -1.5271   -0.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1725   -1.3536    0.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4437   -1.7408    0.8544 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  5 13  1  0
  5 14  1  0
  6 15  1  0
  6 16  1  0
  7 17  1  0
  8 18  1  0
  8 19  1  0
  8 20  1  0
  9 21  1  0
  9 22  1  0
  9 23  1  0
M  END
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PDB for #<Metabolite:0x00007fa4e6ebe3c0>

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  C   UNK     0       8.208  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.875   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.206  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.541  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.207   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.875   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.540   1.540   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       2.874  -0.770   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    6                                                            
CONECT    3    7                                                            
CONECT    4    5    6                                                       
CONECT    5    4    9                                                       
CONECT    6    1    2    4                                                  
CONECT    7    3    8    9                                                  
CONECT    8    7                                                            
CONECT    9    5    7                                                       
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for #<Metabolite:0x00007fa4e6ebe3c0>

COMPND    HMDB0031528
HETATM    1  C1  UNL     1       3.979  -0.246   0.436  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.515  -0.435   0.294  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.951  -1.267   1.040  1.00  0.00           O  
HETATM    4  O2  UNL     1       1.743   0.258  -0.616  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.350   0.097  -0.769  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.354   0.448   0.511  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.856   0.293   0.393  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.446   1.167  -0.669  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.174  -1.157   0.235  1.00  0.00           C  
HETATM   10  H1  UNL     1       4.262   0.707  -0.072  1.00  0.00           H  
HETATM   11  H2  UNL     1       4.559  -1.115   0.073  1.00  0.00           H  
HETATM   12  H3  UNL     1       4.183  -0.077   1.525  1.00  0.00           H  
HETATM   13  H4  UNL     1       0.202  -0.991  -1.025  1.00  0.00           H  
HETATM   14  H5  UNL     1      -0.020   0.651  -1.635  1.00  0.00           H  
HETATM   15  H6  UNL     1      -0.157   1.511   0.726  1.00  0.00           H  
HETATM   16  H7  UNL     1      -0.049  -0.153   1.371  1.00  0.00           H  
HETATM   17  H8  UNL     1      -2.275   0.627   1.380  1.00  0.00           H  
HETATM   18  H9  UNL     1      -3.338   1.725  -0.279  1.00  0.00           H  
HETATM   19  H10 UNL     1      -1.677   1.955  -0.904  1.00  0.00           H  
HETATM   20  H11 UNL     1      -2.714   0.623  -1.583  1.00  0.00           H  
HETATM   21  H12 UNL     1      -2.068  -1.527  -0.800  1.00  0.00           H  
HETATM   22  H13 UNL     1      -3.172  -1.354   0.677  1.00  0.00           H  
HETATM   23  H14 UNL     1      -1.444  -1.741   0.854  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   13   14
CONECT    6    7   15   16
CONECT    7    8    9   17
CONECT    8   18   19   20
CONECT    9   21   22   23
END
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SMILES for #<Metabolite:0x00007fa4e6ebe3c0>

CC(C)CCOC(C)=O
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INCHI for #<Metabolite:0x00007fa4e6ebe3c0>

InChI=1S/C7H14O2/c1-6(2)4-5-9-7(3)8/h6H,4-5H2,1-3H3
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Synonyms
ValueSource
3-Methyl-1-butanol acetateChEBI
3-Methyl-1-butyl acetateChEBI
3-Methyl-but-1-yl acetateChEBI
3-Methylbutyl acetateChEBI
3-Methylbutyl ethanoateChEBI
Acetate d'isoamyleChEBI
Acetate d'isopentyleChEBI
Acetate de 3-methylbutyleChEBI
Acetic acid, 3-methylbutyl esterChEBI
Acetic acid, isopentyl esterChEBI
Amylacetic esterChEBI
beta-Methyl butyl acetateChEBI
CH3C(O)O(CH2)2ch(CH3)2ChEBI
I-amyl acetateChEBI
Isoamyl ethanoateChEBI
IsoamylacetatChEBI
IsoamylazetatChEBI
Isopentyl ethanoateChEBI
3-Methyl-1-butanol acetic acidGenerator
3-Methyl-1-butyl acetic acidGenerator
3-Methyl-but-1-yl acetic acidGenerator
3-Methylbutyl acetic acidGenerator
3-Methylbutyl ethanoic acidGenerator
Acetic acid d'isoamyleGenerator
Acetic acid d'isopentyleGenerator
Acetic acid de 3-methylbutyleGenerator
Acetate, 3-methylbutyl esterGenerator
Acetate, isopentyl esterGenerator
b-Methyl butyl acetateGenerator
b-Methyl butyl acetic acidGenerator
beta-Methyl butyl acetic acidGenerator
Β-methyl butyl acetateGenerator
Β-methyl butyl acetic acidGenerator
I-amyl acetic acidGenerator
Isoamyl ethanoic acidGenerator
Isopentyl ethanoic acidGenerator
Isopentyl acetic acidGenerator
IsopentylacetateMeSH
1-Butanol, 3-methyl-, 1-acetateHMDB
1-Butanol, 3-methyl-, acetateHMDB
3-Methyl butyl ester acetic acidHMDB
3-Methyl-1-butanol, acetateHMDB
3-Methyl-1-butanyl acetateHMDB
FEMA 2055HMDB
Isoamyl acetateHMDB
Isopentyl acetateChEBI
Isoamyl acetic acidGenerator
Molecular FormulaC7H14O2
Average Mass130.1849
Monoisotopic Mass130.099379692
IUPAC Name3-methylbutyl acetate
Traditional Namebanana oil
CAS Registry Number123-92-2
SMILES
CC(C)CCOC(C)=O
InChI Identifier
InChI=1S/C7H14O2/c1-6(2)4-5-9-7(3)8/h6H,4-5H2,1-3H3
InChI KeyMLFHJEHSLIIPHL-UHFFFAOYSA-N