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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-03-07 21:31:32 UTC

Update Date

2023-02-21 17:29:27 UTC

HMDB ID

HMDB0059825

Secondary Accession Numbers

HMDB59825

Metabolite Identification

Common Name

Isoamyl lactate

Description

Isoamyl lactate 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). Isoamyl lactate is an extremely weak basic (essentially neutral) compound (based on its pKa). These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.

Structure

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

COMPND    HMDB0059825
HETATM    1  C1  UNL     1      -3.467   0.827   0.503  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.597  -0.381   0.177  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.739  -0.837  -1.234  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.170   0.021   0.511  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.193  -1.080   0.238  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.100  -0.656   0.567  1.00  0.00           O  
HETATM    7  C6  UNL     1       1.798   0.388   0.010  1.00  0.00           C  
HETATM    8  O2  UNL     1       1.262   1.067  -0.900  1.00  0.00           O  
HETATM    9  C7  UNL     1       3.161   0.678   0.504  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.129   0.592  -0.674  1.00  0.00           C  
HETATM   11  O3  UNL     1       3.492  -0.219   1.498  1.00  0.00           O  
HETATM   12  H1  UNL     1      -3.314   1.560  -0.301  1.00  0.00           H  
HETATM   13  H2  UNL     1      -3.030   1.273   1.433  1.00  0.00           H  
HETATM   14  H3  UNL     1      -4.524   0.543   0.662  1.00  0.00           H  
HETATM   15  H4  UNL     1      -2.938  -1.191   0.848  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.766  -0.697  -1.588  1.00  0.00           H  
HETATM   17  H6  UNL     1      -2.525  -1.927  -1.279  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.086  -0.250  -1.930  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.861   0.919  -0.055  1.00  0.00           H  
HETATM   20  H9  UNL     1      -1.155   0.329   1.587  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.260  -1.352  -0.853  1.00  0.00           H  
HETATM   22  H11 UNL     1      -0.393  -1.996   0.833  1.00  0.00           H  
HETATM   23  H12 UNL     1       3.209   1.736   0.865  1.00  0.00           H  
HETATM   24  H13 UNL     1       3.822  -0.316  -1.243  1.00  0.00           H  
HETATM   25  H14 UNL     1       3.990   1.528  -1.250  1.00  0.00           H  
HETATM   26  H15 UNL     1       5.150   0.484  -0.263  1.00  0.00           H  
HETATM   27  H16 UNL     1       3.903  -1.045   1.148  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
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Isopentyl lactate	ChEBI
Isopentyl lactic acid	Generator
Isoamyl lactic acid	Generator
3-Methylbutyl 2-hydroxypropanoic acid	HMDB
Lactic acid isoamyl ester	HMDB
Isoamyl lactate	ChEBI

Chemical Formula

C₈H₁₆O₃

Average Molecular Weight

160.2108

Monoisotopic Molecular Weight

160.109944378

IUPAC Name

3-methylbutyl 2-hydroxypropanoate

Traditional Name

3-methylbutyl 2-hydroxypropanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C8H16O3/c1-6(2)4-5-11-8(10)7(3)9/h6-7,9H,4-5H2,1-3H3

InChI Key

CRORGGSWAKIXSA-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

Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

carboxylic ester (CHEBI:87534 )

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	17.6 g/L	ALOGPS
logP	1.5	ALOGPS
logP	1.28	ChemAxon
logS	-0.96	ALOGPS
pKa (Strongest Acidic)	13	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	42.03 m³·mol⁻¹	ChemAxon
Polarizability	18.09 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	135.576	31661259
DarkChem	[M-H]-	132.762	31661259
DeepCCS	[M+H]+	141.717	30932474
DeepCCS	[M-H]-	139.057	30932474
DeepCCS	[M-2H]-	175.841	30932474
DeepCCS	[M+Na]+	151.129	30932474
AllCCS	[M+H]+	138.6	32859911
AllCCS	[M+H-H2O]+	134.8	32859911
AllCCS	[M+NH4]+	142.1	32859911
AllCCS	[M+Na]+	143.2	32859911
AllCCS	[M-H]-	138.0	32859911
AllCCS	[M+Na-2H]-	140.2	32859911
AllCCS	[M+HCOO]-	142.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isoamyl lactate	CC(C)CCOC(=O)C(C)O	1594.7	Standard polar	33892256
Isoamyl lactate	CC(C)CCOC(=O)C(C)O	1072.3	Standard non polar	33892256
Isoamyl lactate	CC(C)CCOC(=O)C(C)O	1108.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isoamyl lactate,1TMS,isomer #1	CC(C)CCOC(=O)C(C)O[Si](C)(C)C	1204.4	Semi standard non polar	33892256
Isoamyl lactate,1TBDMS,isomer #1	CC(C)CCOC(=O)C(C)O[Si](C)(C)C(C)(C)C	1414.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Isoamyl lactate EI-B (Non-derivatized)	splash10-0005-9000000000-b5e66780d59559b2e8b9	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isoamyl lactate EI-B (Non-derivatized)	splash10-0005-9000000000-b5e66780d59559b2e8b9	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoamyl lactate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-9000000000-037f5906c7c9da44a0b9	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoamyl lactate GC-MS (1 TMS) - 70eV, Positive	splash10-014i-9800000000-664906ee11856d638035	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoamyl lactate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamyl lactate 10V, Positive-QTOF	splash10-03k9-7900000000-1847d0db9d85dae32285	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamyl lactate 20V, Positive-QTOF	splash10-00di-9100000000-ce512b824366ec1404ef	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamyl lactate 40V, Positive-QTOF	splash10-05fr-9000000000-71f600628fa2c3cfb7b7	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamyl lactate 10V, Negative-QTOF	splash10-0ab9-9600000000-040e1ec47183407b5444	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamyl lactate 20V, Negative-QTOF	splash10-00dr-9100000000-25ba40505cfbdd2c8cd6	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamyl lactate 40V, Negative-QTOF	splash10-00di-9000000000-9c2293ae6acabace03c9	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamyl lactate 10V, Positive-QTOF	splash10-00di-9100000000-8a5bcb8002dbe32f95d4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamyl lactate 20V, Positive-QTOF	splash10-00dj-9000000000-5161c459a09a99dd2f7c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamyl lactate 40V, Positive-QTOF	splash10-0a4l-9000000000-8b5a91b3b5bcb56a54ef	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamyl lactate 10V, Negative-QTOF	splash10-052r-9500000000-9a41217538db514d3785	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamyl lactate 20V, Negative-QTOF	splash10-0079-9100000000-7bfacadaf7c9c03e1d6a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamyl lactate 40V, Negative-QTOF	splash10-0006-9000000000-4b9807ae590ba7262de5	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

86851

PDB ID

Not Available

ChEBI ID

87534

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Isoamyl lactate (HMDB0059825)

MOL for HMDB0059825 (Isoamyl lactate)

3D MOL for HMDB0059825 (Isoamyl lactate)

3D SDF for HMDB0059825 (Isoamyl lactate)

3D-SDF for HMDB0059825 (Isoamyl lactate)

PDB for HMDB0059825 (Isoamyl lactate)

3D PDB for HMDB0059825 (Isoamyl lactate)

SMILES for HMDB0059825 (Isoamyl lactate)

INCHI for HMDB0059825 (Isoamyl lactate)

Structure for HMDB0059825 (Isoamyl lactate)

3D Structure for HMDB0059825 (Isoamyl lactate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra