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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:35 UTC
Update Date2023-02-21 17:16:07 UTC
HMDB IDHMDB0002074
Secondary Accession Numbers
  • HMDB02074
Metabolite Identification
Common Name2,2-Dimethylsuccinic acid
Description2,2-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
Data?1676999767
Synonyms
ValueSource
2,2-DimethylsuccinateGenerator
2,2,-DimethylsuccinateHMDB
2,2-Dimethyl succinateHMDB
2,2-Dimethyl succinic acidHMDB
2,2-DimethylbutanedioateHMDB
2,2-Dimethylbutanedioic acidHMDB
alpha,alpha-Dimethyl-succinateHMDB
alpha,alpha-Dimethyl-succinic acidHMDB
2,2-Dimethyl-succinateGenerator, HMDB
2,2-Dimethylsuccinic acidMeSH
Chemical FormulaC6H10O4
Average Molecular Weight146.1412
Monoisotopic Molecular Weight146.057908808
IUPAC Name2,2-dimethylbutanedioic acid
Traditional Name2,2-dimethylsuccinic acid
CAS Registry Number597-43-3
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 KeyGOHPTLYPQCTZSE-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMethyl-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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point140.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility70 mg/mL at 14 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility91.5 g/LALOGPS
logP0.41ALOGPS
logP0.7ChemAxon
logS-0.2ALOGPS
pKa (Strongest Acidic)4.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity32.61 m³·mol⁻¹ChemAxon
Polarizability13.75 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+132.1831661259
DarkChem[M-H]-125.84131661259
DeepCCS[M+H]+127.67530932474
DeepCCS[M-H]-124.09630932474
DeepCCS[M-2H]-161.44830932474
DeepCCS[M+Na]+136.51330932474
AllCCS[M+H]+133.032859911
AllCCS[M+H-H2O]+129.032859911
AllCCS[M+NH4]+136.732859911
AllCCS[M+Na]+137.732859911
AllCCS[M-H]-128.932859911
AllCCS[M+Na-2H]-131.332859911
AllCCS[M+HCOO]-133.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2,2-Dimethylsuccinic acidCC(C)(CC(O)=O)C(O)=O2072.7Standard polar33892256
2,2-Dimethylsuccinic acidCC(C)(CC(O)=O)C(O)=O1000.8Standard non polar33892256
2,2-Dimethylsuccinic acidCC(C)(CC(O)=O)C(O)=O1234.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2,2-Dimethylsuccinic acid,1TMS,isomer #1CC(C)(CC(=O)O[Si](C)(C)C)C(=O)O1275.7Semi standard non polar33892256
2,2-Dimethylsuccinic acid,1TMS,isomer #2CC(C)(CC(=O)O)C(=O)O[Si](C)(C)C1241.4Semi standard non polar33892256
2,2-Dimethylsuccinic acid,2TMS,isomer #1CC(C)(CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1316.8Semi standard non polar33892256
2,2-Dimethylsuccinic acid,1TBDMS,isomer #1CC(C)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O1529.0Semi standard non polar33892256
2,2-Dimethylsuccinic acid,1TBDMS,isomer #2CC(C)(CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C1523.9Semi standard non polar33892256
2,2-Dimethylsuccinic acid,2TBDMS,isomer #1CC(C)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1782.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2,2-Dimethylsuccinic acid GC-MS (2 TMS)splash10-001i-4980000000-5105aaf553beeefe377c2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,2-Dimethylsuccinic acid GC-MS (Non-derivatized)splash10-001i-4980000000-5105aaf553beeefe377c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,2-Dimethylsuccinic acid GC-EI-TOF (Non-derivatized)splash10-0002-0920000000-05a94b287119beca19c22017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,2-Dimethylsuccinic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udu-9400000000-9947c90d53531626cd252017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,2-Dimethylsuccinic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00g0-9430000000-d26f2eeb172ada9e80f52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,2-Dimethylsuccinic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,2-Dimethylsuccinic acid Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-0ufr-3900000000-3d10946770dc9c44ef682012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,2-Dimethylsuccinic acid Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-0a4i-9000000000-de0369a8d850fa2d7c432012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,2-Dimethylsuccinic acid Quattro_QQQ 40V, N/A-QTOF (Annotated)splash10-0a4i-9000000000-52887714518980e7756c2012-07-25HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,2-Dimethylsuccinic acid 10V, Positive-QTOFsplash10-004i-1900000000-ca087f657b35822e66872017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,2-Dimethylsuccinic acid 20V, Positive-QTOFsplash10-0zi0-9800000000-e380a944ee329c094e662017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,2-Dimethylsuccinic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-2d0359b1151cf61d19862017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,2-Dimethylsuccinic acid 10V, Negative-QTOFsplash10-0f6t-0900000000-eb6fca2883e8360d7a742017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,2-Dimethylsuccinic acid 20V, Negative-QTOFsplash10-0udj-2900000000-9af1c58c0fa97f927dc02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,2-Dimethylsuccinic acid 40V, Negative-QTOFsplash10-0a5l-9100000000-e3d91c1a0034e4d592842017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,2-Dimethylsuccinic acid 10V, Positive-QTOFsplash10-0fbi-4900000000-029b21f02c1a014351862021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,2-Dimethylsuccinic acid 20V, Positive-QTOFsplash10-0006-9000000000-71e0f1ced39229b44c412021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,2-Dimethylsuccinic acid 40V, Positive-QTOFsplash10-0006-9000000000-c106f41a0abe167cbfb12021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,2-Dimethylsuccinic acid 10V, Negative-QTOFsplash10-0f6t-2900000000-334522a3848b5e3c358b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,2-Dimethylsuccinic acid 20V, Negative-QTOFsplash10-0f79-9300000000-4575bd45c2d6c701c61f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,2-Dimethylsuccinic acid 40V, Negative-QTOFsplash10-0006-9000000000-b0de2ded65eb4df48dbc2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022833
KNApSAcK IDNot Available
Chemspider ID11209
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6473
PubChem Compound11701
PDB IDNot Available
ChEBI ID86537
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Kelley RI: Octenylsuccinic aciduria in children fed protein-hydrolysate formulas containing modified cornstarch. Pediatr Res. 1991 Dec;30(6):564-9. [PubMed:1805153 ]
  2. 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 ]