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Showing metabocard for Isopentyl acetate (HMDB0031528)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:43:52 UTC
Update Date2023-02-21 17:20:45 UTC
HMDB IDHMDB0031528
Secondary Accession Numbers
  • HMDB31528
Metabolite Identification
Common NameIsopentyl 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
Data?1677000045
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031528 (Isopentyl acetate)

  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 HMDB0031528 (Isopentyl acetate)

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 HMDB0031528 (Isopentyl acetate)

  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>
HMDB0031528

> <DATABASE_NAME>
hmdb

> <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 HMDB0031528 (Isopentyl acetate)

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 HMDB0031528 (Isopentyl acetate)

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 HMDB0031528 (Isopentyl acetate)

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 HMDB0031528 (Isopentyl acetate)

CC(C)CCOC(C)=O
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INCHI for HMDB0031528 (Isopentyl acetate)

InChI=1S/C7H14O2/c1-6(2)4-5-9-7(3)8/h6H,4-5H2,1-3H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC7H14O2
Average Molecular Weight130.1849
Monoisotopic Molecular Weight130.099379692
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
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
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Environmental roleIndustrial applicationBiological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-78.5 °CNot Available
Boiling Point142.00 to 143.00 °C. @ 756.00 mm HgThe Good Scents Company Information System
Water Solubility2 mg/mL at 25 °CNot Available
LogP2.25Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothUlcerative colitis details
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Crohn's disease
  1. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Ulcerative colitis
  1. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008132
KNApSAcK IDC00035116
Chemspider ID29016
KEGG Compound IDC12296
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIsoamyl acetate
METLIN IDNot Available
PubChem Compound31276
PDB IDNot Available
ChEBI ID31725
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1006711
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .