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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:31:14 UTC

Update Date

2022-09-22 18:34:23 UTC

HMDB ID

HMDB0029576

Secondary Accession Numbers

HMDB29576

Metabolite Identification

Common Name

2,3-Dihydroxy-2-methylbutanoic acid

Description

2,3-Dihydroxy-2-methylbutanoic acid, also known as 2,3-dimethylglyceric 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 a small amount of articles have been published on 2,3-Dihydroxy-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
2,3-Dihydroxy-2-methylbutanoate	Generator
2,3-Dimethylglyceric acid	HMDB

Chemical Formula

C₅H₁₀O₄

Average Molecular Weight

134.1305

Monoisotopic Molecular Weight

134.057908808

IUPAC Name

2,3-dihydroxy-2-methylbutanoic acid

Traditional Name

2,3-dihydroxy-2-methylbutanoic acid

CAS Registry Number

14868-24-7

SMILES

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

InChI Identifier

InChI=1S/C5H10O4/c1-3(6)5(2,9)4(7)8/h3,6,9H,1-2H3,(H,7,8)

InChI Key

AOWPAWLEXIYETE-UHFFFAOYSA-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
Alpha-hydroxy acid
Hydroxy acid
Tertiary alcohol
Secondary alcohol
1,2-diol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

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	441 g/L	ALOGPS
logP	-0.89	ALOGPS
logP	-0.67	ChemAxon
logS	0.52	ALOGPS
pKa (Strongest Acidic)	3.76	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	29.52 m³·mol⁻¹	ChemAxon
Polarizability	12.51 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]+	128.581	31661259
DarkChem	[M-H]-	123.519	31661259
DeepCCS	[M+H]+	123.708	30932474
DeepCCS	[M-H]-	120.531	30932474
DeepCCS	[M-2H]-	157.379	30932474
DeepCCS	[M+Na]+	132.32	30932474
AllCCS	[M+H]+	132.3	32859911
AllCCS	[M+H-H2O]+	128.2	32859911
AllCCS	[M+NH4]+	136.1	32859911
AllCCS	[M+Na]+	137.2	32859911
AllCCS	[M-H]-	125.5	32859911
AllCCS	[M+Na-2H]-	128.3	32859911
AllCCS	[M+HCOO]-	131.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,3-Dihydroxy-2-methylbutanoic acid	CC(O)C(C)(O)C(O)=O	2519.1	Standard polar	33892256
2,3-Dihydroxy-2-methylbutanoic acid	CC(O)C(C)(O)C(O)=O	1094.1	Standard non polar	33892256
2,3-Dihydroxy-2-methylbutanoic acid	CC(O)C(C)(O)C(O)=O	1134.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,3-Dihydroxy-2-methylbutanoic acid,1TMS,isomer #1	CC(O[Si](C)(C)C)C(C)(O)C(=O)O	1233.7	Semi standard non polar	33892256
2,3-Dihydroxy-2-methylbutanoic acid,1TMS,isomer #2	CC(O)C(C)(O[Si](C)(C)C)C(=O)O	1259.3	Semi standard non polar	33892256
2,3-Dihydroxy-2-methylbutanoic acid,1TMS,isomer #3	CC(O)C(C)(O)C(=O)O[Si](C)(C)C	1147.2	Semi standard non polar	33892256
2,3-Dihydroxy-2-methylbutanoic acid,2TMS,isomer #1	CC(O[Si](C)(C)C)C(C)(O[Si](C)(C)C)C(=O)O	1330.6	Semi standard non polar	33892256
2,3-Dihydroxy-2-methylbutanoic acid,2TMS,isomer #2	CC(O[Si](C)(C)C)C(C)(O)C(=O)O[Si](C)(C)C	1261.9	Semi standard non polar	33892256
2,3-Dihydroxy-2-methylbutanoic acid,2TMS,isomer #3	CC(O)C(C)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1255.8	Semi standard non polar	33892256
2,3-Dihydroxy-2-methylbutanoic acid,3TMS,isomer #1	CC(O[Si](C)(C)C)C(C)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1364.1	Semi standard non polar	33892256
2,3-Dihydroxy-2-methylbutanoic acid,1TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)C(C)(O)C(=O)O	1487.2	Semi standard non polar	33892256
2,3-Dihydroxy-2-methylbutanoic acid,1TBDMS,isomer #2	CC(O)C(C)(O[Si](C)(C)C(C)(C)C)C(=O)O	1501.3	Semi standard non polar	33892256
2,3-Dihydroxy-2-methylbutanoic acid,1TBDMS,isomer #3	CC(O)C(C)(O)C(=O)O[Si](C)(C)C(C)(C)C	1385.8	Semi standard non polar	33892256
2,3-Dihydroxy-2-methylbutanoic acid,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)C(C)(O[Si](C)(C)C(C)(C)C)C(=O)O	1761.4	Semi standard non polar	33892256
2,3-Dihydroxy-2-methylbutanoic acid,2TBDMS,isomer #2	CC(O[Si](C)(C)C(C)(C)C)C(C)(O)C(=O)O[Si](C)(C)C(C)(C)C	1717.6	Semi standard non polar	33892256
2,3-Dihydroxy-2-methylbutanoic acid,2TBDMS,isomer #3	CC(O)C(C)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1717.8	Semi standard non polar	33892256
2,3-Dihydroxy-2-methylbutanoic acid,3TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)C(C)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1993.6	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 - 2,3-Dihydroxy-2-methylbutanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-000l-9000000000-8060c77c70d1401c6296	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dihydroxy-2-methylbutanoic acid GC-MS (3 TMS) - 70eV, Positive	splash10-0159-5693000000-e6114a40a3e178e75a6f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dihydroxy-2-methylbutanoic acid 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 - 2,3-Dihydroxy-2-methylbutanoic acid 10V, Positive-QTOF	splash10-000i-5900000000-23e969df406e88f97161	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxy-2-methylbutanoic acid 20V, Positive-QTOF	splash10-00rj-9500000000-98a61ebd4254fd477f61	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxy-2-methylbutanoic acid 40V, Positive-QTOF	splash10-00di-9000000000-14933eec5b98adfb43f9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxy-2-methylbutanoic acid 10V, Negative-QTOF	splash10-0019-9600000000-5973372858938417b6f2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxy-2-methylbutanoic acid 20V, Negative-QTOF	splash10-000i-9000000000-f760aedb6486baf6aecf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxy-2-methylbutanoic acid 40V, Negative-QTOF	splash10-00di-9000000000-9e34d48afdfc64e229e1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxy-2-methylbutanoic acid 10V, Negative-QTOF	splash10-0019-9500000000-7bb83293cba61b428e56	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxy-2-methylbutanoic acid 20V, Negative-QTOF	splash10-00du-9100000000-21f6885e812b3d4e8ced	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxy-2-methylbutanoic acid 40V, Negative-QTOF	splash10-0006-9000000000-80c26ba46da018f73c4f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxy-2-methylbutanoic acid 10V, Positive-QTOF	splash10-006t-9100000000-ff8bec7e4f1070dbff42	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxy-2-methylbutanoic acid 20V, Positive-QTOF	splash10-0002-9000000000-5569a336b1ae620ba37a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxy-2-methylbutanoic acid 40V, Positive-QTOF	splash10-0002-9000000000-192d9f73cc356b2b25c2	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

FDB000732

KNApSAcK ID

C00012985

Chemspider ID

266858

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

301941

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

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 2,3-Dihydroxy-2-methylbutanoic acid (HMDB0029576)

MOL for HMDB0029576 (2,3-Dihydroxy-2-methylbutanoic acid)

3D MOL for HMDB0029576 (2,3-Dihydroxy-2-methylbutanoic acid)

3D SDF for HMDB0029576 (2,3-Dihydroxy-2-methylbutanoic acid)

3D-SDF for HMDB0029576 (2,3-Dihydroxy-2-methylbutanoic acid)

PDB for HMDB0029576 (2,3-Dihydroxy-2-methylbutanoic acid)

3D PDB for HMDB0029576 (2,3-Dihydroxy-2-methylbutanoic acid)

SMILES for HMDB0029576 (2,3-Dihydroxy-2-methylbutanoic acid)

INCHI for HMDB0029576 (2,3-Dihydroxy-2-methylbutanoic acid)

Structure for HMDB0029576 (2,3-Dihydroxy-2-methylbutanoic acid)

3D Structure for HMDB0029576 (2,3-Dihydroxy-2-methylbutanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra