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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:24:51 UTC

Update Date

2021-09-26 22:53:45 UTC

HMDB ID

HMDB0245333

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2,2-Dimethylbutyric acid

Description

2,2-dimethylbutyric acid, also known as DMB or a,a-dimethylbutanoate, belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. Based on a literature review a small amount of articles have been published on 2,2-dimethylbutyric acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2,2-dimethylbutyric acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2,2-Dimethylbutyric acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
alpha,alpha-Dimethylbutanoic acid	ChEBI
alpha,alpha-Dimethylbutyric acid	ChEBI
DMB	ChEBI
a,a-Dimethylbutanoate	Generator
a,a-Dimethylbutanoic acid	Generator
alpha,alpha-Dimethylbutanoate	Generator
Α,α-dimethylbutanoate	Generator
Α,α-dimethylbutanoic acid	Generator
a,a-Dimethylbutyrate	Generator
a,a-Dimethylbutyric acid	Generator
alpha,alpha-Dimethylbutyrate	Generator
Α,α-dimethylbutyrate	Generator
Α,α-dimethylbutyric acid	Generator
2,2-Dimethylbutyrate	Generator
2,2-Dimethylbutanoate	Generator
Sodium 2,2-dimethylbutyrate	MeSH
2,2-Dimethylbutyric acid	MeSH
ST-20 Compound	MeSH
2,2-DMB	MeSH
2,2-Dimethylbutanoic acid	MeSH
SDMB	MeSH

Chemical Formula

C₆H₁₂O₂

Average Molecular Weight

116.16

Monoisotopic Molecular Weight

116.083729626

IUPAC Name

2,2-dimethylbutanoic acid

Traditional Name

2,2-dimethyl butyric acid

CAS Registry Number

Not Available

SMILES

CCC(C)(C)C(O)=O

InChI Identifier

InChI=1S/C6H12O2/c1-4-6(2,3)5(7)8/h4H2,1-3H3,(H,7,8)

InChI Key

VUAXHMVRKOTJKP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Methyl-branched fatty acids

Alternative Parents

Substituents

Methyl-branched fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dimethylbutyric acid (CHEBI:38649 )
Branched fatty acids (LMFA01020078 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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	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
logP	1.84	ALOGPS
logP	2.02	ChemAxon
logS	-0.78	ALOGPS
pKa (Strongest Acidic)	5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	30.95 m³·mol⁻¹	ChemAxon
Polarizability	12.84 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	129.976	30932474
DeepCCS	[M-H]-	127.214	30932474
DeepCCS	[M-2H]-	163.697	30932474
DeepCCS	[M+Na]+	138.449	30932474
AllCCS	[M+H]+	127.7	32859911
AllCCS	[M+H-H2O]+	123.6	32859911
AllCCS	[M+NH4]+	131.6	32859911
AllCCS	[M+Na]+	132.8	32859911
AllCCS	[M-H]-	127.2	32859911
AllCCS	[M+Na-2H]-	130.6	32859911
AllCCS	[M+HCOO]-	134.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,2-Dimethylbutyric acid	CCC(C)(C)C(O)=O	1592.5	Standard polar	33892256
2,2-Dimethylbutyric acid	CCC(C)(C)C(O)=O	866.4	Standard non polar	33892256
2,2-Dimethylbutyric acid	CCC(C)(C)C(O)=O	904.8	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 - 2,2-Dimethylbutyric acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00bc-9100000000-322b8ae9e48656cf43b7	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,2-Dimethylbutyric acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,2-Dimethylbutyric acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,2-Dimethylbutyric acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	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 - 2,2-Dimethylbutyric acid 10V, Positive-QTOF	splash10-014i-8900000000-6414401c45360d4b4d3f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2-Dimethylbutyric acid 20V, Positive-QTOF	splash10-00xr-9100000000-457ce6605eef7df7761a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2-Dimethylbutyric acid 40V, Positive-QTOF	splash10-0ab9-9000000000-a4a0d65d76c617b30bc2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2-Dimethylbutyric acid 10V, Negative-QTOF	splash10-014i-1900000000-dbeed058312961eeb960	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2-Dimethylbutyric acid 20V, Negative-QTOF	splash10-00xr-9600000000-b3949ee905d2924dc674	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2-Dimethylbutyric acid 40V, Negative-QTOF	splash10-060c-9000000000-b54bffb1b6686f609c1f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2-Dimethylbutyric acid 10V, Positive-QTOF	splash10-00di-9100000000-4dbb11d9b5fe6d97cc9f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2-Dimethylbutyric acid 20V, Positive-QTOF	splash10-05fu-9000000000-ccf2e72c042db4d4433f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2-Dimethylbutyric acid 40V, Positive-QTOF	splash10-00kf-9000000000-4e1b57522a4141d30963	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2-Dimethylbutyric acid 10V, Negative-QTOF	splash10-014i-0900000000-f02a8c6af96b787bcd37	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2-Dimethylbutyric acid 20V, Negative-QTOF	splash10-014i-0900000000-0e94be25ed9046c8caf8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2-Dimethylbutyric acid 40V, Negative-QTOF	splash10-0006-9000000000-d948d5d95ae14e701f57	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

11193

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

38649

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 2,2-Dimethylbutyric acid (HMDB0245333)

MOL for HMDB0245333 (2,2-Dimethylbutyric acid)

3D MOL for HMDB0245333 (2,2-Dimethylbutyric acid)

3D SDF for HMDB0245333 (2,2-Dimethylbutyric acid)

3D-SDF for HMDB0245333 (2,2-Dimethylbutyric acid)

PDB for HMDB0245333 (2,2-Dimethylbutyric acid)

3D PDB for HMDB0245333 (2,2-Dimethylbutyric acid)

SMILES for HMDB0245333 (2,2-Dimethylbutyric acid)

INCHI for HMDB0245333 (2,2-Dimethylbutyric acid)

Structure for HMDB0245333 (2,2-Dimethylbutyric acid)

3D Structure for HMDB0245333 (2,2-Dimethylbutyric acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra