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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:32 UTC

Update Date

2021-09-14 15:19:34 UTC

HMDB ID

HMDB0002025

Secondary Accession Numbers

HMDB02025

Metabolite Identification

Common Name

2,3-Dimethyl-3-hydroxyglutaric acid

Description

2,3-Dimethyl-3-hydroxyglutaric 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 significant number of articles have been published on 2,3-Dimethyl-3-hydroxyglutaric acid.

Structure

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

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 2-Keto-6-aminocaproic acid.mol                    
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       2.207   0.564   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.873  -0.206   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.461   0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.231  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.771  -0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.207   2.104   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.541  -0.206   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -3.541  -2.104   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -3.541   0.564   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.794   1.334   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.309   1.897   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.873  -1.746   0.000  0.00  0.00           C+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3   12                                                  
CONECT    3    2    4   10   11                                             
CONECT    4    3    5                                                       
CONECT    5    4    8    9                                                  
CONECT    6    1                                                            
CONECT    7    1                                                            
CONECT    8    5                                                            
CONECT    9    5                                                            
CONECT   10    3                                                            
CONECT   11    3                                                            
CONECT   12    2                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,3-Dimethyl-3-hydroxyglutarate	Generator
2,3-Dimethyl-3-hydroxy-glutarate	Generator, HMDB

Chemical Formula

C₇H₁₂O₅

Average Molecular Weight

176.1672

Monoisotopic Molecular Weight

176.068473494

IUPAC Name

3-hydroxy-2,3-dimethylpentanedioic acid

Traditional Name

3-hydroxy-2,3-dimethylpentanedioic acid

CAS Registry Number

87764-48-5

SMILES

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

InChI Identifier

InChI=1S/C7H12O5/c1-4(6(10)11)7(2,12)3-5(8)9/h4,12H,3H2,1-2H3,(H,8,9)(H,10,11)

InChI Key

CCFYMOIEFAALDH-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

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Dicarboxylic acids (LMFA01170081 )

Ontology

Not Available

Urine (HMDB: HMDB0002025)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002025)

Source

Endogenous

Endogenous (HMDB: HMDB0002025)

Animal

Animal (HMDB: HMDB0002025)

Exogenous

Food

Food (HMDB: HMDB0002025)

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

Chemical reaction

Lipid peroxidation (HMDB: HMDB0002025)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0002025)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0002025)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0002025)

Nutrient

Nutrient (HMDB: HMDB0002025)

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	221 g/L	ALOGPS
logP	-0.23	ALOGPS
logP	-0.21	ChemAxon
logS	0.1	ALOGPS
pKa (Strongest Acidic)	3.79	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	38.71 m³·mol⁻¹	ChemAxon
Polarizability	16.45 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]+	138.583	31661259
DarkChem	[M-H]-	134.487	31661259
DeepCCS	[M+H]+	133.144	30932474
DeepCCS	[M-H]-	129.315	30932474
DeepCCS	[M-2H]-	166.789	30932474
DeepCCS	[M+Na]+	142.328	30932474
AllCCS	[M+H]+	139.4	32859911
AllCCS	[M+H-H2O]+	135.6	32859911
AllCCS	[M+NH4]+	142.9	32859911
AllCCS	[M+Na]+	144.0	32859911
AllCCS	[M-H]-	135.6	32859911
AllCCS	[M+Na-2H]-	137.2	32859911
AllCCS	[M+HCOO]-	139.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,3-Dimethyl-3-hydroxyglutaric acid	CC(C(O)=O)C(C)(O)CC(O)=O	2666.9	Standard polar	33892256
2,3-Dimethyl-3-hydroxyglutaric acid	CC(C(O)=O)C(C)(O)CC(O)=O	1261.0	Standard non polar	33892256
2,3-Dimethyl-3-hydroxyglutaric acid	CC(C(O)=O)C(C)(O)CC(O)=O	1463.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,3-Dimethyl-3-hydroxyglutaric acid,1TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)C(C)(O)CC(=O)O	1520.7	Semi standard non polar	33892256
2,3-Dimethyl-3-hydroxyglutaric acid,1TMS,isomer #2	CC(C(=O)O)C(C)(CC(=O)O)O[Si](C)(C)C	1537.5	Semi standard non polar	33892256
2,3-Dimethyl-3-hydroxyglutaric acid,1TMS,isomer #3	CC(C(=O)O)C(C)(O)CC(=O)O[Si](C)(C)C	1525.9	Semi standard non polar	33892256
2,3-Dimethyl-3-hydroxyglutaric acid,2TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)C(C)(CC(=O)O)O[Si](C)(C)C	1593.2	Semi standard non polar	33892256
2,3-Dimethyl-3-hydroxyglutaric acid,2TMS,isomer #2	CC(C(=O)O[Si](C)(C)C)C(C)(O)CC(=O)O[Si](C)(C)C	1570.2	Semi standard non polar	33892256
2,3-Dimethyl-3-hydroxyglutaric acid,2TMS,isomer #3	CC(C(=O)O)C(C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1596.4	Semi standard non polar	33892256
2,3-Dimethyl-3-hydroxyglutaric acid,3TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)C(C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1649.7	Semi standard non polar	33892256
2,3-Dimethyl-3-hydroxyglutaric acid,1TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)C(C)(O)CC(=O)O	1786.0	Semi standard non polar	33892256
2,3-Dimethyl-3-hydroxyglutaric acid,1TBDMS,isomer #2	CC(C(=O)O)C(C)(CC(=O)O)O[Si](C)(C)C(C)(C)C	1775.6	Semi standard non polar	33892256
2,3-Dimethyl-3-hydroxyglutaric acid,1TBDMS,isomer #3	CC(C(=O)O)C(C)(O)CC(=O)O[Si](C)(C)C(C)(C)C	1784.8	Semi standard non polar	33892256
2,3-Dimethyl-3-hydroxyglutaric acid,2TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)C(C)(CC(=O)O)O[Si](C)(C)C(C)(C)C	2042.5	Semi standard non polar	33892256
2,3-Dimethyl-3-hydroxyglutaric acid,2TBDMS,isomer #2	CC(C(=O)O[Si](C)(C)C(C)(C)C)C(C)(O)CC(=O)O[Si](C)(C)C(C)(C)C	2034.4	Semi standard non polar	33892256
2,3-Dimethyl-3-hydroxyglutaric acid,2TBDMS,isomer #3	CC(C(=O)O)C(C)(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2051.1	Semi standard non polar	33892256
2,3-Dimethyl-3-hydroxyglutaric acid,3TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)C(C)(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2289.1	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 - 2,3-Dimethyl-3-hydroxyglutaric acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uxr-4900000000-f64a8e34525009a0ad8b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dimethyl-3-hydroxyglutaric acid GC-MS (3 TMS) - 70eV, Positive	splash10-009b-7096000000-a8823c05ccb1cebf1a79	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dimethyl-3-hydroxyglutaric 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-Dimethyl-3-hydroxyglutaric acid 10V, Positive-QTOF	splash10-0a4l-0900000000-ce03a402197a2c4e23cd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethyl-3-hydroxyglutaric acid 20V, Positive-QTOF	splash10-0btc-2900000000-22a41184bcad0f67ed23	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethyl-3-hydroxyglutaric acid 40V, Positive-QTOF	splash10-03ka-9500000000-d612de6858f746f40844	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethyl-3-hydroxyglutaric acid 10V, Negative-QTOF	splash10-01si-0900000000-9dfa24e67c02ee9ffbda	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethyl-3-hydroxyglutaric acid 20V, Negative-QTOF	splash10-0bu0-4900000000-aeeb8b194520d4463a3e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethyl-3-hydroxyglutaric acid 40V, Negative-QTOF	splash10-0a4r-9200000000-1749d2408be7f42a33f9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethyl-3-hydroxyglutaric acid 10V, Positive-QTOF	splash10-07i2-5900000000-9ce71d7328bea8810e7a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethyl-3-hydroxyglutaric acid 20V, Positive-QTOF	splash10-06ya-9100000000-a771a86507ee00d3262d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethyl-3-hydroxyglutaric acid 40V, Positive-QTOF	splash10-0a4j-9000000000-4a56664fcd9af036bd50	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethyl-3-hydroxyglutaric acid 10V, Negative-QTOF	splash10-06z9-3900000000-31a0aa5f436a6f384c23	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethyl-3-hydroxyglutaric acid 20V, Negative-QTOF	splash10-03dr-5900000000-23c64cd6d43a6946ccbc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethyl-3-hydroxyglutaric acid 40V, Negative-QTOF	splash10-0abc-9100000000-1a4e93d8b77666c36848	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)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart 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

FDB022803

KNApSAcK ID

Not Available

Chemspider ID

13628288

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6446

PubChem Compound

21252268

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

Pollitt RJ: The occurrence of substituted 3-methyl-3-hydroxyglutaric acids in urine in propionic acidaemia and in beta-ketothiolase deficiency. Biomed Mass Spectrom. 1983 Apr;10(4):253-7. [PubMed:6133567 ]

Showing metabocard for 2,3-Dimethyl-3-hydroxyglutaric acid (HMDB0002025)

MOL for HMDB0002025 (2,3-Dimethyl-3-hydroxyglutaric acid)

3D MOL for HMDB0002025 (2,3-Dimethyl-3-hydroxyglutaric acid)

3D SDF for HMDB0002025 (2,3-Dimethyl-3-hydroxyglutaric acid)

3D-SDF for HMDB0002025 (2,3-Dimethyl-3-hydroxyglutaric acid)

PDB for HMDB0002025 (2,3-Dimethyl-3-hydroxyglutaric acid)

3D PDB for HMDB0002025 (2,3-Dimethyl-3-hydroxyglutaric acid)

SMILES for HMDB0002025 (2,3-Dimethyl-3-hydroxyglutaric acid)

INCHI for HMDB0002025 (2,3-Dimethyl-3-hydroxyglutaric acid)

Structure for HMDB0002025 (2,3-Dimethyl-3-hydroxyglutaric acid)

3D Structure for HMDB0002025 (2,3-Dimethyl-3-hydroxyglutaric acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra