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Showing Compound 2-Hydroxy-2-methylbutanedioic acid (FDB001372)

Record Information
Version1.0
Creation date2010-04-08 22:04:56 UTC
Update date2019-11-26 02:56:24 UTC
Primary IDFDB001372
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-Hydroxy-2-methylbutanedioic acid
DescriptionCitramalic acid, also known as citramalate or 2-methylmalate, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. Based on a literature review a significant number of articles have been published on Citramalic acid.
CAS Number597-44-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility297 g/LALOGPS
logP-0.91ALOGPS
logP-0.68ChemAxon
logS0.3ALOGPS
pKa (Strongest Acidic)3.35ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity29.59 m³·mol⁻¹ChemAxon
Polarizability12.69 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H8O5
IUPAC name2-hydroxy-2-methylbutanedioic acid
InChI IdentifierInChI=1S/C5H8O5/c1-5(10,4(8)9)2-3(6)7/h10H,2H2,1H3,(H,6,7)(H,8,9)
InChI KeyXFTRTWQBIOMVPK-UHFFFAOYSA-N
Isomeric SMILESCC(O)(CC(O)=O)C(O)=O
Average Molecular Weight148.114
Monoisotopic Molecular Weight148.037173366
Classification
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Short-chain hydroxy acid
  • Hydroxy fatty acid
  • Alpha-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Tertiary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2-Hydroxy-2-methylbutanedioic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000l-9200000000-d88cf81bb63b8badd74dSpectrum
Predicted GC-MS2-Hydroxy-2-methylbutanedioic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00gs-8492000000-d1c8fb9235f1de536d15Spectrum
Predicted GC-MS2-Hydroxy-2-methylbutanedioic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Hydroxy-2-methylbutanedioic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Hydroxy-2-methylbutanedioic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Hydroxy-2-methylbutanedioic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Hydroxy-2-methylbutanedioic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Hydroxy-2-methylbutanedioic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Hydroxy-2-methylbutanedioic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Hydroxy-2-methylbutanedioic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Hydroxy-2-methylbutanedioic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Hydroxy-2-methylbutanedioic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Hydroxy-2-methylbutanedioic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Hydroxy-2-methylbutanedioic acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Hydroxy-2-methylbutanedioic acid, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Hydroxy-2-methylbutanedioic acid, TBDMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000j-7900000000-efbe2adf2c82decc64a62012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-052u-9000000000-3754186783f820cbff7c2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-052o-9000000000-0656e8e194378442727f2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-2900000000-be1cc6b0ea685f5d7ac22017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-002r-8900000000-7dd192ed79cd2d306ea52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-000i-9500000000-c96a62314140c10f12452017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Negativesplash10-0002-2900000000-716fb4163867531131372021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-20ae5f1dfa6847e56e0d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-4bc688d98054e464cf072021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0a4r-9000000000-61294657ce4e2d5d6d052021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-9400000000-d027e4da9369388ea3c22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-e7930822f64c0c43d7c02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-9500000000-2e922f07663d3c3992402021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-9400000000-b372db83cd99e22fb0ac2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-093483f4bf2d387fa4052021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001a-5900000000-437d36fe16a8d6f79c682016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9200000000-6aed3a8e654948bbd5e82016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-31c6a41b79f5b68fa4312016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uds-4900000000-0d782e5134753ac75aeb2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zg0-9800000000-79154974b5c30f915ea52016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-16648250719da0016f962016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f79-7900000000-7ad97a16a3c93f065dc02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pbi-9200000000-5a2fa29950e165d19eee2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-6e51c64fc7bc0e0253732021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-7900000000-8d007c21807d42c8e41b2021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 400 MHz, H2O, experimental)Spectrum
ChemSpider ID1051
ChEMBL IDNot Available
KEGG Compound IDC00815
Pubchem Compound ID1081
Pubchem Substance IDNot Available
ChEBI ID15584
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00426
CRC / DFC (Dictionary of Food Compounds) IDBZT91-U:BZT91-U
EAFUS IDNot Available
Dr. Duke ID2-METHYL-MALIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).