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Record Information
Version3.6
Creation Date2006-05-22 14:17:35 UTC
Update Date2016-02-11 01:05:16 UTC
HMDB IDHMDB02074
Secondary Accession NumbersNone
Metabolite Identification
Common Name2,2-Dimethylsuccinic acid
Description2,2-Dimethylsuccinic acid has been identified in urine samples from children investigated for a possible inherited metabolic disease (PMID 2134344 ), and in children fed elemental or protein-hydrolysate formulas that use Octanylsuccinic acid-modified cornstarch as an emulsifying agent (PMID 1805153 ).
Structure
Thumb
Synonyms
ValueSource
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
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 KeyInChIKey=GOHPTLYPQCTZSE-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point140.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility70 mg/mL at 14 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility91.5 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity32.61 m3·mol-1ChemAxon
Polarizability13.75 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-4980000000-5105aaf553beeefe377cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0ufr-3900000000-3d10946770dc9c44ef68View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0a4i-9000000000-de0369a8d850fa2d7c43View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0a4i-9000000000-52887714518980e7756cView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022833
KNApSAcK IDNot Available
Chemspider ID11209
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02074
Metagene LinkHMDB02074
METLIN ID6473
PubChem Compound11701
PDB IDNot Available
ChEBI 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. [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. [2134344 ]