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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-04-06 16:19:54 UTC
Update Date2021-09-14 15:45:46 UTC
HMDB IDHMDB0012141
Secondary Accession Numbers
  • HMDB12141
Metabolite Identification
Common Name(R)-2,3-Dihydroxy-isovalerate
Description(R) 2,3-Dihydroxy-isovalerate is an intermediate in valine, leucine and isoleucine biosynthesis. The pathway of valine biosynthesis is a four-step pathway that shares all of its steps with the parallel pathway of isoleucine biosynthesis. These entwined pathways are part of the superpathway of leucine, valine, and isoleucine biosynthesis , that generates not only isoleucine and valine, but also leucine. (R) 2,3-Dihydroxy-isovalerate is generated from 3-Hydroxy-3-methyl-2-oxobutanoic acid via the enzyme ketol-acid reductoisomerase (EC 1.1.1.86) then it is converted to 2-Oxoisovalerate via the dihydroxy-acid dehydratase (EC:4.2.1.9).
Structure
Data?1600461080
Synonyms
ValueSource
(R)-2,3-Dihydroxy-isovaleric acidChEBI
(2R)-2,3-Dihydroxy-3-methylbutanoateKegg
(2R)-2,3-Dihydroxy-3-methylbutanoic acidGenerator
(R)-2,3-Dihydroxy-3-methylbutanoateHMDB
(R)-2,3-Dihydroxy-3-methylbutanoic acidHMDB
(R)-(-)-alpha,beta-Dihydroxyisovaleric acidHMDB
(R)-(-)-α,β-Dihydroxyisovaleric acidHMDB
(R)-2,3-Dihydroxy-isovalerateHMDB
Chemical FormulaC5H10O4
Average Molecular Weight134.1305
Monoisotopic Molecular Weight134.057908808
IUPAC Name(2R)-2,3-dihydroxy-3-methylbutanoic acid
Traditional Name(R)-2,3-dihydroxy-isovalerate
CAS Registry Number19451-56-0
SMILES
CC(C)(O)[C@@H](O)C(O)=O
InChI Identifier
InChI=1S/C5H10O4/c1-5(2,9)3(6)4(7)8/h3,6,9H,1-2H3,(H,7,8)/t3-/m0/s1
InChI KeyJTEYKUFKXGDTEU-VKHMYHEASA-N
Chemical Taxonomy
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
  • Hydroxy acid
  • Monosaccharide
  • Tertiary alcohol
  • 1,2-diol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility529 g/LALOGPS
logP-0.83ALOGPS
logP-0.82ChemAxon
logS0.6ALOGPS
pKa (Strongest Acidic)3.8ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity29.44 m³·mol⁻¹ChemAxon
Polarizability12.48 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]+128.8631661259
DarkChem[M-H]-124.23231661259
DeepCCS[M+H]+126.72630932474
DeepCCS[M-H]-122.89730932474
DeepCCS[M-2H]-160.16430932474
DeepCCS[M+Na]+135.630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(R)-2,3-Dihydroxy-isovalerateCC(C)(O)[C@@H](O)C(O)=O2348.5Standard polar33892256
(R)-2,3-Dihydroxy-isovalerateCC(C)(O)[C@@H](O)C(O)=O1070.2Standard non polar33892256
(R)-2,3-Dihydroxy-isovalerateCC(C)(O)[C@@H](O)C(O)=O1122.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(R)-2,3-Dihydroxy-isovalerate,1TMS,isomer #1CC(C)(O[Si](C)(C)C)[C@@H](O)C(=O)O1245.9Semi standard non polar33892256
(R)-2,3-Dihydroxy-isovalerate,1TMS,isomer #2CC(C)(O)[C@@H](O[Si](C)(C)C)C(=O)O1252.4Semi standard non polar33892256
(R)-2,3-Dihydroxy-isovalerate,1TMS,isomer #3CC(C)(O)[C@@H](O)C(=O)O[Si](C)(C)C1140.0Semi standard non polar33892256
(R)-2,3-Dihydroxy-isovalerate,2TMS,isomer #1CC(C)(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O1328.4Semi standard non polar33892256
(R)-2,3-Dihydroxy-isovalerate,2TMS,isomer #2CC(C)(O[Si](C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C1290.0Semi standard non polar33892256
(R)-2,3-Dihydroxy-isovalerate,2TMS,isomer #3CC(C)(O)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C1250.7Semi standard non polar33892256
(R)-2,3-Dihydroxy-isovalerate,3TMS,isomer #1CC(C)(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C1372.0Semi standard non polar33892256
(R)-2,3-Dihydroxy-isovalerate,1TBDMS,isomer #1CC(C)(O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O1517.1Semi standard non polar33892256
(R)-2,3-Dihydroxy-isovalerate,1TBDMS,isomer #2CC(C)(O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O1487.9Semi standard non polar33892256
(R)-2,3-Dihydroxy-isovalerate,1TBDMS,isomer #3CC(C)(O)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C1368.5Semi standard non polar33892256
(R)-2,3-Dihydroxy-isovalerate,2TBDMS,isomer #1CC(C)(O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O1778.3Semi standard non polar33892256
(R)-2,3-Dihydroxy-isovalerate,2TBDMS,isomer #2CC(C)(O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C1738.7Semi standard non polar33892256
(R)-2,3-Dihydroxy-isovalerate,2TBDMS,isomer #3CC(C)(O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1714.2Semi standard non polar33892256
(R)-2,3-Dihydroxy-isovalerate,3TBDMS,isomer #1CC(C)(O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2011.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (R)-2,3-Dihydroxy-isovalerate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9000000000-59e6990530d9502275202016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-2,3-Dihydroxy-isovalerate GC-MS (3 TMS) - 70eV, Positivesplash10-00s9-9473000000-9708bfc20ee5ae0436782017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-2,3-Dihydroxy-isovalerate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-isovalerate 10V, Positive-QTOFsplash10-00kr-4900000000-196ffbbf313a33f24f272015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-isovalerate 20V, Positive-QTOFsplash10-00ri-9300000000-aebebbbe2c7c11465a672015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-isovalerate 40V, Positive-QTOFsplash10-0006-9000000000-92af6a04d8cb7601ab352015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-isovalerate 10V, Negative-QTOFsplash10-0019-9500000000-2837622949a6bd6880942015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-isovalerate 20V, Negative-QTOFsplash10-00s9-9400000000-0fc7aa81197fc5feb4442015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-isovalerate 40V, Negative-QTOFsplash10-00dr-9000000000-45f3b95b2f30ea8445c12015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-isovalerate 10V, Negative-QTOFsplash10-001i-2900000000-fab4ee9aeca7067a92072021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-isovalerate 20V, Negative-QTOFsplash10-056r-9100000000-b3da44872fd12f996ec62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-isovalerate 40V, Negative-QTOFsplash10-05fr-9000000000-571b504e001a1456ab102021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-isovalerate 10V, Positive-QTOFsplash10-00kr-9600000000-e4a123bb359dea0126e32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-isovalerate 20V, Positive-QTOFsplash10-05g0-9000000000-30fdda4eee690af3ee502021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-isovalerate 40V, Positive-QTOFsplash10-0006-9000000000-285f7931bf8163b701da2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified<25 umol/mmol creatinineNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Metastatic melanoma
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleAttachment loss  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleMissing teeth details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MalePeriodontal Probing Depth details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
UrineDetected and Quantified782-2500 umol/mmol creatinineInfant (0-1 year old)Both
Short-chain enoyl-CoA hydratase deficiency
details
UrineDetected and Quantified27-406 umol/mmol creatinineNot SpecifiedNot Specified
Methylmalonyl-CoA mutase deficiency
details
UrineDetected and Quantified82-187 umol/mmol creatinineNot SpecifiedNot Specified
Propionic acidemia
details
UrineDetected and Quantified566-704 umol/mmol creatinineChildren (1-13 years old)Female3-Hydroxyisobutyryl-coa hydrolase deficiency details
UrineDetected and Quantified638 umol/mmol creatinineNot SpecifiedNot SpecifiedCobalamin A disease details
UrineDetected and Quantified33 umol/mmol creatinineNot SpecifiedNot SpecifiedCobalamin C disease details
Associated Disorders and Diseases
Disease References
Metastatic melanoma
  1. Frankel AE, Coughlin LA, Kim J, Froehlich TW, Xie Y, Frenkel EP, Koh AY: Metagenomic Shotgun Sequencing and Unbiased Metabolomic Profiling Identify Specific Human Gut Microbiota and Metabolites Associated with Immune Checkpoint Therapy Efficacy in Melanoma Patients. Neoplasia. 2017 Oct;19(10):848-855. doi: 10.1016/j.neo.2017.08.004. Epub 2017 Sep 15. [PubMed:28923537 ]
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Attachment loss
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Missing teeth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Methylmalonyl-CoA mutase deficiency
  1. Peters H, Ferdinandusse S, Ruiter JP, Wanders RJ, Boneh A, Pitt J: Metabolite studies in HIBCH and ECHS1 defects: Implications for screening. Mol Genet Metab. 2015 Aug;115(4):168-73. doi: 10.1016/j.ymgme.2015.06.008. Epub 2015 Jun 24. [PubMed:26163321 ]
3-Hydroxyisobutyryl-coa hydrolase deficiency
  1. Peters H, Ferdinandusse S, Ruiter JP, Wanders RJ, Boneh A, Pitt J: Metabolite studies in HIBCH and ECHS1 defects: Implications for screening. Mol Genet Metab. 2015 Aug;115(4):168-73. doi: 10.1016/j.ymgme.2015.06.008. Epub 2015 Jun 24. [PubMed:26163321 ]
Cobalamin A disease
  1. Peters H, Ferdinandusse S, Ruiter JP, Wanders RJ, Boneh A, Pitt J: Metabolite studies in HIBCH and ECHS1 defects: Implications for screening. Mol Genet Metab. 2015 Aug;115(4):168-73. doi: 10.1016/j.ymgme.2015.06.008. Epub 2015 Jun 24. [PubMed:26163321 ]
Methylmalonic aciduria and homocystinuria, cblC type
  1. Peters H, Ferdinandusse S, Ruiter JP, Wanders RJ, Boneh A, Pitt J: Metabolite studies in HIBCH and ECHS1 defects: Implications for screening. Mol Genet Metab. 2015 Aug;115(4):168-73. doi: 10.1016/j.ymgme.2015.06.008. Epub 2015 Jun 24. [PubMed:26163321 ]
Associated OMIM IDs
  • 114500 (Colorectal cancer)
  • 250620 (3-Hydroxyisobutyryl-coa hydrolase deficiency)
  • 277400 (Methylmalonic aciduria and homocystinuria, cblC type)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028799
KNApSAcK IDNot Available
Chemspider ID389255
KEGG Compound IDC04272
BioCyc IDCPD-13357
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440279
PDB IDNot Available
ChEBI ID15684
Food Biomarker OntologyNot Available
VMH ID23DHMB
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.