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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:17:48 UTC

Update Date

2023-02-21 17:28:51 UTC

HMDB ID

HMDB0041603

Secondary Accession Numbers

HMDB41603

Metabolite Identification

Common Name

Methyl 3-hydroxybutyrate

Description

Methyl 3-hydroxybutyrate belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. Methyl 3-hydroxybutyrate is found, on average, in the highest concentration within pineapples (Ananas comosus). This could make methyl 3-hydroxybutyrate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Methyl 3-hydroxybutyrate.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Methyl 3-hydroxybutyric acid	Generator
Methyl-b-hydroxybutyrate	Generator
Methyl-b-hydroxybutyric acid	Generator
Methyl-beta-hydroxybutyric acid	Generator
Methyl-β-hydroxybutyrate	Generator
Methyl-β-hydroxybutyric acid	Generator

Chemical Formula

C₅H₁₀O₃

Average Molecular Weight

118.132

Monoisotopic Molecular Weight

118.062994182

IUPAC Name

methyl 3-hydroxybutanoate

Traditional Name

methyl 3-hydroxybutyrate

CAS Registry Number

1487-49-6

SMILES

COC(=O)CC(C)O

InChI Identifier

InChI=1S/C5H10O3/c1-4(6)3-5(7)8-2/h4,6H,3H2,1-2H3

InChI Key

LDLDJEAVRNAEBW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents

Substituents

Beta-hydroxy acid
Fatty acid ester
Fatty acid methyl ester
Fatty acyl
Methyl ester
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Wax monoesters (LMFA07010513 )

Ontology

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0041603)

Endogenous

Endogenous (HMDB: HMDB0041603)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	158.00 to 160.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	472800 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-0.412 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	500 g/L	ALOGPS
logP	-0.08	ALOGPS
logP	-0.24	ChemAxon
logS	0.63	ALOGPS
pKa (Strongest Acidic)	15.41	ChemAxon
pKa (Strongest Basic)	-2.6	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	3	ChemAxon
Refractivity	28.23 m³·mol⁻¹	ChemAxon
Polarizability	12.07 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	126.747	31661259
DarkChem	[M-H]-	120.407	31661259
DeepCCS	[M+H]+	128.282	30932474
DeepCCS	[M-H]-	126.049	30932474
DeepCCS	[M-2H]-	162.108	30932474
DeepCCS	[M+Na]+	136.919	30932474
AllCCS	[M+H]+	129.9	32859911
AllCCS	[M+H-H2O]+	125.7	32859911
AllCCS	[M+NH4]+	133.8	32859911
AllCCS	[M+Na]+	134.9	32859911
AllCCS	[M-H]-	127.0	32859911
AllCCS	[M+Na-2H]-	130.3	32859911
AllCCS	[M+HCOO]-	134.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl 3-hydroxybutyrate	COC(=O)CC(C)O	1449.4	Standard polar	33892256
Methyl 3-hydroxybutyrate	COC(=O)CC(C)O	866.5	Standard non polar	33892256
Methyl 3-hydroxybutyrate	COC(=O)CC(C)O	941.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methyl 3-hydroxybutyrate,1TMS,isomer #1	COC(=O)CC(C)O[Si](C)(C)C	1031.1	Semi standard non polar	33892256
Methyl 3-hydroxybutyrate,1TBDMS,isomer #1	COC(=O)CC(C)O[Si](C)(C)C(C)(C)C	1242.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl 3-hydroxybutyrate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4m-9100000000-2f53e310d610a36eff16	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl 3-hydroxybutyrate GC-MS (1 TMS) - 70eV, Positive	splash10-01dr-9700000000-e543ec98a0ab1fa58984	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl 3-hydroxybutyrate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl 3-hydroxybutyrate 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 - Methyl 3-hydroxybutyrate 10V, Positive-QTOF	splash10-0uxr-6900000000-df35618c412788fdc69d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-hydroxybutyrate 20V, Positive-QTOF	splash10-0uxr-9800000000-86c03303a8df11e0a271	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-hydroxybutyrate 40V, Positive-QTOF	splash10-0006-9000000000-356911e4438c7dd9e4c4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-hydroxybutyrate 10V, Negative-QTOF	splash10-014i-8900000000-8a402c7e64d202f2270f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-hydroxybutyrate 20V, Negative-QTOF	splash10-014r-9300000000-baf775ea49882d9b2d92	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-hydroxybutyrate 40V, Negative-QTOF	splash10-0aou-9000000000-873dae99ae32c366c200	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-hydroxybutyrate 10V, Negative-QTOF	splash10-01bc-9700000000-2c841182fb5aaaca7a2c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-hydroxybutyrate 20V, Negative-QTOF	splash10-0006-9000000000-ab3ea65814aa8c7caef9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-hydroxybutyrate 40V, Negative-QTOF	splash10-014l-9000000000-a5d5f906b7f123185fdb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-hydroxybutyrate 10V, Positive-QTOF	splash10-0v4j-9300000000-86207f8d43d38a3db0d7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-hydroxybutyrate 20V, Positive-QTOF	splash10-0002-9000000000-fdcff6401d1c8167512b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-hydroxybutyrate 40V, Positive-QTOF	splash10-0002-9000000000-541d7073aa951b0b2d42	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹³C 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

Cytoplasm
Extracellular
Membrane

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

FDB003804

KNApSAcK ID

Not Available

Chemspider ID

14417

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15146

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1415671

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Methyl 3-hydroxybutyrate (HMDB0041603)

MOL for HMDB0041603 (Methyl 3-hydroxybutyrate)

3D MOL for HMDB0041603 (Methyl 3-hydroxybutyrate)

3D SDF for HMDB0041603 (Methyl 3-hydroxybutyrate)

3D-SDF for HMDB0041603 (Methyl 3-hydroxybutyrate)

PDB for HMDB0041603 (Methyl 3-hydroxybutyrate)

3D PDB for HMDB0041603 (Methyl 3-hydroxybutyrate)

SMILES for HMDB0041603 (Methyl 3-hydroxybutyrate)

INCHI for HMDB0041603 (Methyl 3-hydroxybutyrate)

Structure for HMDB0041603 (Methyl 3-hydroxybutyrate)

3D Structure for HMDB0041603 (Methyl 3-hydroxybutyrate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra