MiMeDB: Showing metabocard for Isoamyl isobutyrate (MMDBc0047709)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 15:39:03 UTC

Update Date

2024-04-30 20:28:57 UTC

Metabolite ID

MMDBc0047709

Metabolite Identification

Common Name

Isoamyl isobutyrate

Description

Isoamyl isobutyrate, or 3-methylbutyl 2-methylpropanoate is a flavouring ingredient. 3-Methylbutyl 2-methylpropanoate belongs to the family of Carboxylic Acid Esters. These are carboxylic acid derivatives in which the carbo atom from the carbonyl group is atached to an alkyl or oaryl moiety through an oxygen atom (forming an ester group).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0036234
     RDKit          3D
3-Methylbutyl 2-methylpropanoate
 29 28  0  0  0  0  0  0  0  0999 V2000
   -3.2881    1.0456   -1.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7506    0.3202    0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4964   -0.9684    0.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2689    0.1025   -0.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6370   -0.6129    0.9473 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7181   -0.8297    0.7825 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830    0.1508    0.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2611    1.3324    0.6551 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1296   -0.1784    0.4574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3198   -1.0137   -0.7795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9277    1.0836    0.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4859    1.2223   -1.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6977    2.0372   -0.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0746    0.4508   -1.7397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9119    0.9458    0.9095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2799   -1.4436    1.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5875   -0.7157    0.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3398   -1.6466   -0.6726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1601   -0.5121   -1.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8234    1.1022   -0.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9053   -0.0682    1.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1056   -1.6330    1.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4821   -0.7937    1.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3307   -1.4185   -0.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9984   -0.4217   -1.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6028   -1.8788   -0.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4486    1.7948    1.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9374    1.5969   -0.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9733    0.9499    0.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
M  END

HMDB0036234
     RDKit          3D
3-Methylbutyl 2-methylpropanoate
 29 28  0  0  0  0  0  0  0  0999 V2000
   -3.2881    1.0456   -1.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7506    0.3202    0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4964   -0.9684    0.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2689    0.1025   -0.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6370   -0.6129    0.9473 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7181   -0.8297    0.7825 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830    0.1508    0.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2611    1.3324    0.6551 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1296   -0.1784    0.4574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3198   -1.0137   -0.7795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9277    1.0836    0.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4859    1.2223   -1.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6977    2.0372   -0.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0746    0.4508   -1.7397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9119    0.9458    0.9095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2799   -1.4436    1.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5875   -0.7157    0.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3398   -1.6466   -0.6726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1601   -0.5121   -1.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8234    1.1022   -0.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9053   -0.0682    1.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1056   -1.6330    1.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4821   -0.7937    1.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3307   -1.4185   -0.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9984   -0.4217   -1.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6028   -1.8788   -0.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4486    1.7948    1.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9374    1.5969   -0.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9733    0.9499    0.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
M  END

COMPND    HMDB0036234
HETATM    1  C1  UNL     1      -3.288   1.046  -1.204  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.751   0.320   0.006  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.496  -0.968   0.197  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.269   0.103  -0.202  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.637  -0.613   0.947  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.718  -0.830   0.783  1.00  0.00           O  
HETATM    7  C6  UNL     1       1.683   0.151   0.633  1.00  0.00           C  
HETATM    8  O2  UNL     1       1.261   1.332   0.655  1.00  0.00           O  
HETATM    9  C7  UNL     1       3.130  -0.178   0.457  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.320  -1.014  -0.780  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.928   1.084   0.441  1.00  0.00           C  
HETATM   12  H1  UNL     1      -2.486   1.222  -1.971  1.00  0.00           H  
HETATM   13  H2  UNL     1      -3.698   2.037  -0.963  1.00  0.00           H  
HETATM   14  H3  UNL     1      -4.075   0.451  -1.740  1.00  0.00           H  
HETATM   15  H4  UNL     1      -2.912   0.946   0.910  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.280  -1.444   1.167  1.00  0.00           H  
HETATM   17  H6  UNL     1      -4.587  -0.716   0.174  1.00  0.00           H  
HETATM   18  H7  UNL     1      -3.340  -1.647  -0.673  1.00  0.00           H  
HETATM   19  H8  UNL     1      -1.160  -0.512  -1.133  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.823   1.102  -0.298  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.905  -0.068   1.884  1.00  0.00           H  
HETATM   22  H11 UNL     1      -1.106  -1.633   1.102  1.00  0.00           H  
HETATM   23  H12 UNL     1       3.482  -0.794   1.325  1.00  0.00           H  
HETATM   24  H13 UNL     1       4.331  -1.419  -0.843  1.00  0.00           H  
HETATM   25  H14 UNL     1       2.998  -0.422  -1.648  1.00  0.00           H  
HETATM   26  H15 UNL     1       2.603  -1.879  -0.693  1.00  0.00           H  
HETATM   27  H16 UNL     1       3.449   1.795   1.173  1.00  0.00           H  
HETATM   28  H17 UNL     1       3.937   1.597  -0.540  1.00  0.00           H  
HETATM   29  H18 UNL     1       4.973   0.950   0.835  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4   15
CONECT    3   16   17   18
CONECT    4    5   19   20
CONECT    5    6   21   22
CONECT    6    7
CONECT    7    8    8    9
CONECT    9   10   11   23
CONECT   10   24   25   26
CONECT   11   27   28   29
END

HMDB0036234
     RDKit          3D
3-Methylbutyl 2-methylpropanoate
 29 28  0  0  0  0  0  0  0  0999 V2000
   -3.2881    1.0456   -1.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7506    0.3202    0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4964   -0.9684    0.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2689    0.1025   -0.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6370   -0.6129    0.9473 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7181   -0.8297    0.7825 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830    0.1508    0.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2611    1.3324    0.6551 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1296   -0.1784    0.4574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3198   -1.0137   -0.7795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9277    1.0836    0.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4859    1.2223   -1.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6977    2.0372   -0.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0746    0.4508   -1.7397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9119    0.9458    0.9095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2799   -1.4436    1.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5875   -0.7157    0.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3398   -1.6466   -0.6726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1601   -0.5121   -1.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8234    1.1022   -0.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9053   -0.0682    1.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1056   -1.6330    1.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4821   -0.7937    1.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3307   -1.4185   -0.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9984   -0.4217   -1.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6028   -1.8788   -0.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4486    1.7948    1.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9374    1.5969   -0.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9733    0.9499    0.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
M  END

Synonyms

Value	Source
Isoamyl 2-methylpropanoate	ChEBI
Isopentyl 2-methylpropanoate	ChEBI
Isopentyl isobutyrate	ChEBI
Isoamyl 2-methylpropanoic acid	Generator
Isopentyl 2-methylpropanoic acid	Generator
Isopentyl isobutyric acid	Generator
3-Methylbutyl 2-methylpropanoic acid	Generator
3-Methylbutyl isobutyrate	HMDB
FEMA 3507	HMDB
Isoamyl isobutanoate	HMDB
Isoamyl isobutyrate	HMDB
Isobutyric acid, isopentyl ester	HMDB
Isopentyl isobutanoate	HMDB
Propanoic acid, 2-methyl-, 3-methylbutyl ester	HMDB
3-Methylbutyl 2-methylpropionic acid	Generator

Molecular Formula

C₉H₁₈O₂

Average Mass

158.238

Monoisotopic Mass

158.13067982

IUPAC Name

3-methylbutyl 2-methylpropanoate

Traditional Name

3-methylbutyl 2-methylpropanoate

CAS Registry Number

Not Available

SMILES

CC(C)CCOC(=O)C(C)C

InChI Identifier

InChI=1S/C9H18O2/c1-7(2)5-6-11-9(10)8(3)4/h7-8H,5-6H2,1-4H3

InChI Key

VFTGLSWXJMRZNB-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).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Carboxylic 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 Framework

Aliphatic acyclic compounds

External Descriptors

fatty acid ester (CHEBI:87537 )
Wax monoesters (LMFA07010572 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.89 g/L	ALOGPS
logP	2.89	ALOGPS
logP	2.78	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	45.04 m³·mol⁻¹	ChemAxon
Polarizability	19.2 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-006x-9000000000-f52f38a23e150d10c7c8	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-006x-9000000000-f52f38a23e150d10c7c8	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9000000000-60dc1a049045a8956a9c	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ab9-6900000000-a0b48a6cbf5a213c2299	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9100000000-353411580b7954eee1a5	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05fr-9000000000-8cfa01dae8eb02b9a943	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-5900000000-f9f75abc153b20f90c8e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9200000000-10959c6781b619c61245	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kr-9000000000-32023c69989fb151960d	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9000000000-426f1b6001084d873f5c	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000000000-90c84c09ac984fce7519	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-6d0188dd32d0a2360f58	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9300000000-c0bdfe03b851672dec5f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9100000000-4535bd6e237068590577	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-9000000000-a1bc130a2defab57a5c2	2021-09-22	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Plant		Musa acuminata	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0036234

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB015092

KNApSAcK ID

C00055662

Chemspider ID

453397

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

519786

PDB ID

Not Available

ChEBI ID

87537

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Robinson AL, Ebeler SE, Heymann H, Boss PK, Solomon PS, Trengove RD: Interactions between wine volatile compounds and grape and wine matrix components influence aroma compound headspace partitioning. J Agric Food Chem. 2009 Nov 11;57(21):10313-22. doi: 10.1021/jf902586n. [PubMed:19845354 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for Isoamyl isobutyrate (MMDBc0047709)

MOL for #<Metabolite:0x00007f47056da210>

3D MOL for #<Metabolite:0x00007f47056da210>

3D SDF for #<Metabolite:0x00007f47056da210>

3D-SDF for #<Metabolite:0x00007f47056da210>

PDB for #<Metabolite:0x00007f47056da210>

3D PDB for #<Metabolite:0x00007f47056da210>

SMILES for #<Metabolite:0x00007f47056da210>

INCHI for #<Metabolite:0x00007f47056da210>

Structure for #<Metabolite:0x00007f47056da210>

3D Structure for #<Metabolite:0x00007f47056da210>