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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:14:45 UTC

HMDB ID

HMDB0000351

Secondary Accession Numbers

HMDB00351

Metabolite Identification

Common Name

(2S,3R)-3-Hydroxy-2-methylbutanoic acid

Description

(2S,3R)-3-Hydroxy-2-methylbutanoic acid, also known as 3-hydroxy-2-methyl-[R-(r*,s*)]-butanoate or (2S,3R)-nilic acid, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. Based on a literature review very few articles have been published on (2S,3R)-3-Hydroxy-2-methylbutanoic acid.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2S,3R)-3-Hydroxy-2-methylbutanoate	Generator
3-Hydroxy-2-methyl-[R-(r,s)]-butanoate	HMDB
3-Hydroxy-2-methyl-[R-(r,s)]-butanoic acid	HMDB
3-Hydroxy-2-methyl-[R-(R,S)]-butanoate	HMDB
(2S,3R)-3-Hydroxy-2-methylbutyric acid	HMDB
(2S,3R)-Nilic acid	HMDB
3-Hydroxy-2-methyl-[R-(R,S)]-butanoic acid	HMDB
HMBA	HMDB
(2S,3R)-3-Hydroxy-2-methylbutanoic acid	HMDB

Chemical Formula

C₅H₁₀O₃

Average Molecular Weight

118.1311

Monoisotopic Molecular Weight

118.062994186

IUPAC Name

(2S,3R)-3-hydroxy-2-methylbutanoic acid

Traditional Name

(2S,3R)-3-hydroxy-2-methylbutanoic acid

CAS Registry Number

71526-30-2

SMILES

C[C@@H](O)[C@H](C)C(O)=O

InChI Identifier

InChI=1S/C5H10O3/c1-3(4(2)6)5(7)8/h3-4,6H,1-2H3,(H,7,8)/t3-,4+/m0/s1

InChI Key

VEXDRERIMPLZLU-IUYQGCFVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Hydroxy fatty acids

Alternative Parents

Substituents

Beta-hydroxy acid
Branched fatty acid
Hydroxy fatty acid
Short-chain hydroxy acid
Methyl-branched fatty acid
Hydroxy acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0000351)
Cell membrane (HMDB: HMDB0000351)

Organelle

Adiposome (HMDB: HMDB0000351)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0000351)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000351)

Source

Endogenous

Endogenous (HMDB: HMDB0000351)

Animal

Animal (HMDB: HMDB0000351)

Exogenous

Food

Food (HMDB: HMDB0000351)

Animal origin

Poultry

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000351)

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000351)

Biochemical process

Lipid transport (HMDB: HMDB0000351)

Role

Biological role

Energy storage (HMDB: HMDB0000351)

Physical Properties

State

Solid

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	336 g/L	ALOGPS
logP	-0.13	ALOGPS
logP	0.16	ChemAxon
logS	0.45	ALOGPS
pKa (Strongest Acidic)	4.51	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	28.04 m³·mol⁻¹	ChemAxon
Polarizability	11.76 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]+	127.319	31661259
DarkChem	[M+H]+	127.319	31661259
DarkChem	[M-H]-	122.085	31661259
DarkChem	[M-H]-	122.085	31661259
DarkChem	[M+H]+	127.319	31661259
DarkChem	[M+H]+	127.319	31661259
DarkChem	[M-H]-	122.085	31661259
DarkChem	[M-H]-	122.085	31661259
AllCCS	[M+H]+	129.865	32859911
AllCCS	[M-H]-	125.833	32859911
DeepCCS	[M+H]+	126.428	30932474
DeepCCS	[M-H]-	122.856	30932474
DeepCCS	[M-2H]-	160.075	30932474
DeepCCS	[M+Na]+	135.552	30932474
AllCCS	[M+H]+	129.9	32859911
AllCCS	[M+H-H2O]+	125.7	32859911
AllCCS	[M+NH4]+	133.7	32859911
AllCCS	[M+Na]+	134.9	32859911
AllCCS	[M-H]-	125.8	32859911
AllCCS	[M+Na-2H]-	129.2	32859911
AllCCS	[M+HCOO]-	132.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(2S,3R)-3-Hydroxy-2-methylbutanoic acid	C[C@@H](O)[C@H](C)C(O)=O	2083.5	Standard polar	33892256
(2S,3R)-3-Hydroxy-2-methylbutanoic acid	C[C@@H](O)[C@H](C)C(O)=O	1019.9	Standard non polar	33892256
(2S,3R)-3-Hydroxy-2-methylbutanoic acid	C[C@@H](O)[C@H](C)C(O)=O	1040.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(2S,3R)-3-Hydroxy-2-methylbutanoic acid,1TMS,isomer #1	C[C@H](C(=O)O)[C@@H](C)O[Si](C)(C)C	1128.6	Semi standard non polar	33892256
(2S,3R)-3-Hydroxy-2-methylbutanoic acid,1TMS,isomer #2	C[C@H](C(=O)O[Si](C)(C)C)[C@@H](C)O	1061.3	Semi standard non polar	33892256
(2S,3R)-3-Hydroxy-2-methylbutanoic acid,2TMS,isomer #1	C[C@H](C(=O)O[Si](C)(C)C)[C@@H](C)O[Si](C)(C)C	1206.7	Semi standard non polar	33892256
(2S,3R)-3-Hydroxy-2-methylbutanoic acid,1TBDMS,isomer #1	C[C@H](C(=O)O)[C@@H](C)O[Si](C)(C)C(C)(C)C	1367.1	Semi standard non polar	33892256
(2S,3R)-3-Hydroxy-2-methylbutanoic acid,1TBDMS,isomer #2	C[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](C)O	1283.7	Semi standard non polar	33892256
(2S,3R)-3-Hydroxy-2-methylbutanoic acid,2TBDMS,isomer #1	C[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](C)O[Si](C)(C)C(C)(C)C	1646.1	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 - (2S,3R)-3-Hydroxy-2-methylbutanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0097-9100000000-4296c67313a78a015074	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00y1-9820000000-7256ed8afed29ebf4daa	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0r0r-9200000000-a7d6bf6e90c8c752f69c	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0a4j-9000000000-fe9a2716010ffb94cff8	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0a4l-9000000000-715b545170085466a6b2	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid 10V, Positive-QTOF	splash10-0uxr-3900000000-d8f24d02712f429591a7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid 20V, Positive-QTOF	splash10-0zgi-9800000000-0821ba5748054e7de369	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid 40V, Positive-QTOF	splash10-0a4i-9000000000-e5b2f743cb4dd5e99ec5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid 10V, Negative-QTOF	splash10-014i-5900000000-587bb9b1fdf10856b3a1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid 20V, Negative-QTOF	splash10-05fr-9100000000-a33491d8a46967cdd2d3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid 40V, Negative-QTOF	splash10-0a4i-9000000000-1ec2b5bb3af9f3c925ca	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid 10V, Negative-QTOF	splash10-01b9-8900000000-6e362f577b3d827a8387	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid 20V, Negative-QTOF	splash10-05fr-9100000000-6950ab2628a11bf6839a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid 40V, Negative-QTOF	splash10-052f-9000000000-5278bf25a974c9f30369	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid 10V, Positive-QTOF	splash10-0zgi-9400000000-aee3a280a6df1ae985b6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid 20V, Positive-QTOF	splash10-0002-9000000000-45e4e2c8c6ea7216859f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoic acid 40V, Positive-QTOF	splash10-052b-9000000000-845222220a578798d8ce	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)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Acylcarnitine (2S,3R)-3-Hydroxy-2-methylbutanoylcarnitine		Not Available

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

FDB021974

KNApSAcK ID

Not Available

Chemspider ID

13628066

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5340

PubChem Compound

12313370

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Neri, Claudia; Williams, Jonathan M. J. Racemic auxiliaries: applications to asymmetric synthesis. Tetrahedron Letters (2002), 43(23), 4257-4260.

Material Safety Data Sheet (MSDS)

Not Available

General References

Heil M, Podebrad F, Prado E, Beck T, Mosand A, Sewell AC, Bohles H, Lehnert W: Enantioselective analysis of ketone bodies in patients with beta-ketothiolase deficiency, medium-chain acyl coenzyme A dehydrogenase deficiency and ketonemic vomiting. J Chromatogr B Biomed Sci Appl. 2000 Mar 10;739(2):313-24. [PubMed:10755375 ]

Showing metabocard for (2S,3R)-3-Hydroxy-2-methylbutanoic acid (HMDB0000351)

MOL for HMDB0000351 ((2S,3R)-3-Hydroxy-2-methylbutanoic acid)

3D MOL for HMDB0000351 ((2S,3R)-3-Hydroxy-2-methylbutanoic acid)

3D SDF for HMDB0000351 ((2S,3R)-3-Hydroxy-2-methylbutanoic acid)

3D-SDF for HMDB0000351 ((2S,3R)-3-Hydroxy-2-methylbutanoic acid)

PDB for HMDB0000351 ((2S,3R)-3-Hydroxy-2-methylbutanoic acid)

3D PDB for HMDB0000351 ((2S,3R)-3-Hydroxy-2-methylbutanoic acid)

SMILES for HMDB0000351 ((2S,3R)-3-Hydroxy-2-methylbutanoic acid)

INCHI for HMDB0000351 ((2S,3R)-3-Hydroxy-2-methylbutanoic acid)

Structure for HMDB0000351 ((2S,3R)-3-Hydroxy-2-methylbutanoic acid)

3D Structure for HMDB0000351 ((2S,3R)-3-Hydroxy-2-methylbutanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra