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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:35 UTC

Update Date

2023-02-21 17:16:07 UTC

HMDB ID

HMDB0002074

Secondary Accession Numbers

HMDB02074

Metabolite Identification

Common Name

2,2-Dimethylsuccinic acid

Description

2,2-dimethylsuccinic acid is an alpha,omega-dicarboxylic acid that is succinic acid substituted by two methyl groups at positions 2 and 2 respectively. It derives from a succinic acid. 2,2-Dimethylsuccinic acid, also known as 2,2-dimethylbutanedioate, 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. 2,2-Dimethylsuccinic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,2-Dimethylsuccinate	Generator
2,2,-Dimethylsuccinate	HMDB
2,2-Dimethyl succinate	HMDB
2,2-Dimethyl succinic acid	HMDB
2,2-Dimethylbutanedioate	HMDB
2,2-Dimethylbutanedioic acid	HMDB
alpha,alpha-Dimethyl-succinate	HMDB
alpha,alpha-Dimethyl-succinic acid	HMDB
2,2-Dimethyl-succinate	Generator, HMDB
2,2-Dimethylsuccinic acid	MeSH

Chemical Formula

C₆H₁₀O₄

Average Molecular Weight

146.1412

Monoisotopic Molecular Weight

146.057908808

IUPAC Name

2,2-dimethylbutanedioic acid

Traditional Name

2,2-dimethylsuccinic acid

CAS Registry Number

597-43-3

SMILES

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

InChI Identifier

InChI=1S/C6H10O4/c1-6(2,5(9)10)3-4(7)8/h3H2,1-2H3,(H,7,8)(H,9,10)

InChI Key

GOHPTLYPQCTZSE-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
Dicarboxylic 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

alpha,omega-dicarboxylic acid (CHEBI:86537 )
Dicarboxylic acids (LMFA01170080 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0002074)
Cell membrane (HMDB: HMDB0002074)

Organelle

Adiposome (HMDB: HMDB0002074)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0002074)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002074)

Source

Endogenous

Endogenous (HMDB: HMDB0002074)

Animal

Animal (HMDB: HMDB0002074)

Exogenous

Food

Food (HMDB: HMDB0002074)

Animal origin

Poultry

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)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

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)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0002074)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0002074)

Lipid metabolism pathway (HMDB: HMDB0002074)

Biochemical process

Lipid transport (HMDB: HMDB0002074)

Role

Biological role

Energy source (HMDB: HMDB0002074)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	140.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	70 mg/mL at 14 °C	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	91.5 g/L	ALOGPS
logP	0.41	ALOGPS
logP	0.7	ChemAxon
logS	-0.2	ALOGPS
pKa (Strongest Acidic)	4.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	32.61 m³·mol⁻¹	ChemAxon
Polarizability	13.75 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]+	132.18	31661259
DarkChem	[M-H]-	125.841	31661259
DeepCCS	[M+H]+	127.675	30932474
DeepCCS	[M-H]-	124.096	30932474
DeepCCS	[M-2H]-	161.448	30932474
DeepCCS	[M+Na]+	136.513	30932474
AllCCS	[M+H]+	133.0	32859911
AllCCS	[M+H-H2O]+	129.0	32859911
AllCCS	[M+NH4]+	136.7	32859911
AllCCS	[M+Na]+	137.7	32859911
AllCCS	[M-H]-	128.9	32859911
AllCCS	[M+Na-2H]-	131.3	32859911
AllCCS	[M+HCOO]-	133.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,2-Dimethylsuccinic acid	CC(C)(CC(O)=O)C(O)=O	2072.7	Standard polar	33892256
2,2-Dimethylsuccinic acid	CC(C)(CC(O)=O)C(O)=O	1000.8	Standard non polar	33892256
2,2-Dimethylsuccinic acid	CC(C)(CC(O)=O)C(O)=O	1234.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,2-Dimethylsuccinic acid,1TMS,isomer #1	CC(C)(CC(=O)O[Si](C)(C)C)C(=O)O	1275.7	Semi standard non polar	33892256
2,2-Dimethylsuccinic acid,1TMS,isomer #2	CC(C)(CC(=O)O)C(=O)O[Si](C)(C)C	1241.4	Semi standard non polar	33892256
2,2-Dimethylsuccinic acid,2TMS,isomer #1	CC(C)(CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1316.8	Semi standard non polar	33892256
2,2-Dimethylsuccinic acid,1TBDMS,isomer #1	CC(C)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	1529.0	Semi standard non polar	33892256
2,2-Dimethylsuccinic acid,1TBDMS,isomer #2	CC(C)(CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	1523.9	Semi standard non polar	33892256
2,2-Dimethylsuccinic acid,2TBDMS,isomer #1	CC(C)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1782.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2,2-Dimethylsuccinic acid GC-MS (2 TMS)	splash10-001i-4980000000-5105aaf553beeefe377c	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,2-Dimethylsuccinic acid GC-MS (Non-derivatized)	splash10-001i-4980000000-5105aaf553beeefe377c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,2-Dimethylsuccinic acid GC-EI-TOF (Non-derivatized)	splash10-0002-0920000000-05a94b287119beca19c2	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,2-Dimethylsuccinic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udu-9400000000-9947c90d53531626cd25	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,2-Dimethylsuccinic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00g0-9430000000-d26f2eeb172ada9e80f5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,2-Dimethylsuccinic 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,2-Dimethylsuccinic acid Quattro_QQQ 10V, N/A-QTOF (Annotated)	splash10-0ufr-3900000000-3d10946770dc9c44ef68	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,2-Dimethylsuccinic acid Quattro_QQQ 25V, N/A-QTOF (Annotated)	splash10-0a4i-9000000000-de0369a8d850fa2d7c43	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,2-Dimethylsuccinic acid Quattro_QQQ 40V, N/A-QTOF (Annotated)	splash10-0a4i-9000000000-52887714518980e7756c	2012-07-25	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2-Dimethylsuccinic acid 10V, Positive-QTOF	splash10-004i-1900000000-ca087f657b35822e6687	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2-Dimethylsuccinic acid 20V, Positive-QTOF	splash10-0zi0-9800000000-e380a944ee329c094e66	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2-Dimethylsuccinic acid 40V, Positive-QTOF	splash10-0a4i-9000000000-2d0359b1151cf61d1986	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2-Dimethylsuccinic acid 10V, Negative-QTOF	splash10-0f6t-0900000000-eb6fca2883e8360d7a74	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2-Dimethylsuccinic acid 20V, Negative-QTOF	splash10-0udj-2900000000-9af1c58c0fa97f927dc0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2-Dimethylsuccinic acid 40V, Negative-QTOF	splash10-0a5l-9100000000-e3d91c1a0034e4d59284	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2-Dimethylsuccinic acid 10V, Positive-QTOF	splash10-0fbi-4900000000-029b21f02c1a01435186	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2-Dimethylsuccinic acid 20V, Positive-QTOF	splash10-0006-9000000000-71e0f1ced39229b44c41	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2-Dimethylsuccinic acid 40V, Positive-QTOF	splash10-0006-9000000000-c106f41a0abe167cbfb1	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2-Dimethylsuccinic acid 10V, Negative-QTOF	splash10-0f6t-2900000000-334522a3848b5e3c358b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2-Dimethylsuccinic acid 20V, Negative-QTOF	splash10-0f79-9300000000-4575bd45c2d6c701c61f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2-Dimethylsuccinic acid 40V, Negative-QTOF	splash10-0006-9000000000-b0de2ded65eb4df48dbc	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-05	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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	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

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

FDB022833

KNApSAcK ID

Not Available

Chemspider ID

11209

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6473

PubChem Compound

11701

PDB ID

Not Available

ChEBI ID

86537

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)

Download (PDF)

General References

Kelley RI: Octenylsuccinic aciduria in children fed protein-hydrolysate formulas containing modified cornstarch. Pediatr Res. 1991 Dec;30(6):564-9. [PubMed:1805153 ]
Giordano G, McMurray WJ, Previs SF, Welch RD, Rinaldo P: Identification of 2-(2'-octenyl) succinic acid in urine. Rapid Commun Mass Spectrom. 1990 May;4(5):170-2. [PubMed:2134344 ]

Showing metabocard for 2,2-Dimethylsuccinic acid (HMDB0002074)

MOL for HMDB0002074 (2,2-Dimethylsuccinic acid)

3D MOL for HMDB0002074 (2,2-Dimethylsuccinic acid)

3D SDF for HMDB0002074 (2,2-Dimethylsuccinic acid)

3D-SDF for HMDB0002074 (2,2-Dimethylsuccinic acid)

PDB for HMDB0002074 (2,2-Dimethylsuccinic acid)

3D PDB for HMDB0002074 (2,2-Dimethylsuccinic acid)

SMILES for HMDB0002074 (2,2-Dimethylsuccinic acid)

INCHI for HMDB0002074 (2,2-Dimethylsuccinic acid)

Structure for HMDB0002074 (2,2-Dimethylsuccinic acid)

3D Structure for HMDB0002074 (2,2-Dimethylsuccinic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra