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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-08 14:58:39 UTC

Update Date

2022-03-07 03:17:33 UTC

HMDB ID

HMDB0029169

Secondary Accession Numbers

HMDB29169

Metabolite Identification

Common Name

3-Hydroxy-2-methylglutaric acid

Description

3-Hydroxy-2-methylglutaric acid (CAS: 54665-33-7), also known as 2,4-dideoxy-2-methylpentaric 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. 3-Hydroxy-2-methylglutaric acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Hydroxy-2-methylglutarate	Generator
(2S,3R)-3-Hydroxy-2-methylpentanedioate	HMDB
2,4-Dideoxy-2-methylpentarate	HMDB
2,4-Dideoxy-2-methylpentaric acid	HMDB
3R-Hydroxy-2S-methylglutarate	HMDB
3R-Hydroxy-2S-methylglutaric acid	HMDB
3-Hydroxy-2-methylglutaric acid	HMDB

Chemical Formula

C₆H₁₀O₅

Average Molecular Weight

162.141

Monoisotopic Molecular Weight

162.052823422

IUPAC Name

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

Traditional Name

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

CAS Registry Number

1189155-79-0

SMILES

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

InChI Identifier

InChI=1S/C6H10O5/c1-3(6(10)11)4(7)2-5(8)9/h3-4,7H,2H2,1H3,(H,8,9)(H,10,11)/t3-,4+/m0/s1

InChI Key

JJSWRLIXMHKPEW-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

Methyl-branched fatty acid
Short-chain hydroxy acid
Hydroxy fatty acid
Branched fatty acid
Beta-hydroxy acid
Hydroxy acid
Dicarboxylic acid or derivatives
Secondary 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

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0029169)

Process

Not Available

Role

Not Available

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	77.7 g/L	ALOGPS
logP	-0.45	ALOGPS
logP	-0.49	ChemAxon
logS	-0.2	ALOGPS
pKa (Strongest Acidic)	3.66	ChemAxon
pKa (Strongest Basic)	-3	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	34.07 m³·mol⁻¹	ChemAxon
Polarizability	14.76 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
DeepCCS	[M+H]+	134.08	30932474
DeepCCS	[M-H]-	131.684	30932474
DeepCCS	[M-2H]-	166.852	30932474
DeepCCS	[M+Na]+	141.594	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxy-2-methylglutaric acid	C[C@@H]([C@H](O)CC(O)=O)C(O)=O	2562.4	Standard polar	33892256
3-Hydroxy-2-methylglutaric acid	C[C@@H]([C@H](O)CC(O)=O)C(O)=O	1303.3	Standard non polar	33892256
3-Hydroxy-2-methylglutaric acid	C[C@@H]([C@H](O)CC(O)=O)C(O)=O	1472.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxy-2-methylglutaric acid,1TMS,isomer #1	C[C@H](C(=O)O)[C@@H](CC(=O)O)O[Si](C)(C)C	1450.0	Semi standard non polar	33892256
3-Hydroxy-2-methylglutaric acid,1TMS,isomer #2	C[C@H](C(=O)O)[C@H](O)CC(=O)O[Si](C)(C)C	1471.9	Semi standard non polar	33892256
3-Hydroxy-2-methylglutaric acid,1TMS,isomer #3	C[C@H](C(=O)O[Si](C)(C)C)[C@H](O)CC(=O)O	1442.6	Semi standard non polar	33892256
3-Hydroxy-2-methylglutaric acid,2TMS,isomer #1	C[C@H](C(=O)O[Si](C)(C)C)[C@@H](CC(=O)O)O[Si](C)(C)C	1510.3	Semi standard non polar	33892256
3-Hydroxy-2-methylglutaric acid,2TMS,isomer #2	C[C@H](C(=O)O)[C@@H](CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1539.1	Semi standard non polar	33892256
3-Hydroxy-2-methylglutaric acid,2TMS,isomer #3	C[C@H](C(=O)O[Si](C)(C)C)[C@H](O)CC(=O)O[Si](C)(C)C	1541.3	Semi standard non polar	33892256
3-Hydroxy-2-methylglutaric acid,3TMS,isomer #1	C[C@H](C(=O)O[Si](C)(C)C)[C@@H](CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1627.4	Semi standard non polar	33892256
3-Hydroxy-2-methylglutaric acid,1TBDMS,isomer #1	C[C@H](C(=O)O)[C@@H](CC(=O)O)O[Si](C)(C)C(C)(C)C	1685.6	Semi standard non polar	33892256
3-Hydroxy-2-methylglutaric acid,1TBDMS,isomer #2	C[C@H](C(=O)O)[C@H](O)CC(=O)O[Si](C)(C)C(C)(C)C	1724.0	Semi standard non polar	33892256
3-Hydroxy-2-methylglutaric acid,1TBDMS,isomer #3	C[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@H](O)CC(=O)O	1698.8	Semi standard non polar	33892256
3-Hydroxy-2-methylglutaric acid,2TBDMS,isomer #1	C[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](CC(=O)O)O[Si](C)(C)C(C)(C)C	1958.2	Semi standard non polar	33892256
3-Hydroxy-2-methylglutaric acid,2TBDMS,isomer #2	C[C@H](C(=O)O)[C@@H](CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1990.8	Semi standard non polar	33892256
3-Hydroxy-2-methylglutaric acid,2TBDMS,isomer #3	C[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@H](O)CC(=O)O[Si](C)(C)C(C)(C)C	1979.0	Semi standard non polar	33892256
3-Hydroxy-2-methylglutaric acid,3TBDMS,isomer #1	C[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2250.1	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 - 3-Hydroxy-2-methylglutaric acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-2-methylglutaric 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 - 3-Hydroxy-2-methylglutaric acid 10V, Negative-QTOF	splash10-014i-9800000000-c1bbe3d18ff535394854	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-methylglutaric acid 20V, Negative-QTOF	splash10-006w-9100000000-95ea3daaa2789d86c7a8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-methylglutaric acid 40V, Negative-QTOF	splash10-0a4i-9000000000-9dbc43a918d8c1b16f72	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-methylglutaric acid 10V, Positive-QTOF	splash10-00os-2900000000-452b35bc037014ea9620	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-methylglutaric acid 20V, Positive-QTOF	splash10-05i0-9100000000-867a2c2584aff00c18a7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-methylglutaric acid 40V, Positive-QTOF	splash10-0abc-9000000000-8bda03e6e8075af32f1c	2021-09-23	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

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

156908029

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

Not Available

Showing metabocard for 3-Hydroxy-2-methylglutaric acid (HMDB0029169)

MOL for HMDB0029169 (3-Hydroxy-2-methylglutaric acid)

3D MOL for HMDB0029169 (3-Hydroxy-2-methylglutaric acid)

3D SDF for HMDB0029169 (3-Hydroxy-2-methylglutaric acid)

3D-SDF for HMDB0029169 (3-Hydroxy-2-methylglutaric acid)

PDB for HMDB0029169 (3-Hydroxy-2-methylglutaric acid)

3D PDB for HMDB0029169 (3-Hydroxy-2-methylglutaric acid)

SMILES for HMDB0029169 (3-Hydroxy-2-methylglutaric acid)

INCHI for HMDB0029169 (3-Hydroxy-2-methylglutaric acid)

Structure for HMDB0029169 (3-Hydroxy-2-methylglutaric acid)

3D Structure for HMDB0029169 (3-Hydroxy-2-methylglutaric acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra