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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2013-05-09 21:01:49 UTC
Update Date2022-03-07 03:17:40 UTC
HMDB IDHMDB0060180
Secondary Accession Numbers
  • HMDB60180
Metabolite Identification
Common NameD-Glycerate 3-phosphate
Description(2R)-2-Hydroxy-3-(phosphonatooxy)propanoate, also known as 3-phospho-(R)-glycerate or D-glycerate 3-phosphate, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group (2R)-2-Hydroxy-3-(phosphonatooxy)propanoate is a drug (2R)-2-hydroxy-3-(phosphonatooxy)propanoate has been detected, but not quantified, in several different foods, such as poppies, small-leaf lindens, lupines, pomegranates, and kombus. These are compounds containing a saccharide unit which bears a carboxylic acid group.
Structure
Data?1563866024
Synonyms
ValueSource
3-Phospho-(R)-glycerateChEBI
3-Phospho-D-glycerateChEBI
3-PhosphoglycerateChEBI
3-Phospho-(R)-glyceric acidGenerator
3-Phospho-D-glyceric acidGenerator
3-Phosphoglyceric acidGenerator
D-Glyceric acid 3-phosphoric acidGenerator
(2R)-2-Hydroxy-3-(phosphonatooxy)propanoic acidHMDB
(2R)-2-Hydroxy-3-(phosphonooxy)propanoic acidHMDB
2-Hydroxy-3-(phosphonatooxy)propanoateHMDB
D-(-)-3-Phosphoglyceric acidHMDB
D-3-Phosphoglyceric acidHMDB
D-Glyceric acid 3-phosphateHMDB
Glycerate 3-phosphateMeSH
3-Phosphoglycerate, trisodium saltMeSH
3-Phosphoglycerate, monosodium saltMeSH
3-Phosphoglycerate, (R)-isomerMeSH
D-Glycerate 3-phosphateChEBI
Chemical FormulaC3H7O7P
Average Molecular Weight186.0572
Monoisotopic Molecular Weight185.99293909
IUPAC Name(2R)-2-hydroxy-3-(phosphonooxy)propanoic acid
Traditional NameD-glycerate 3-phosphate
CAS Registry Number3443-58-1
SMILES
O[C@H](COP(O)(O)=O)C(O)=O
InChI Identifier
InChI=1S/C3H7O7P/c4-2(3(5)6)1-10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)/t2-/m1/s1
InChI KeyOSJPPGNTCRNQQC-UWTATZPHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar acids and derivatives
Alternative Parents
Substituents
  • Glyceric_acid
  • Monoalkyl phosphate
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateNot Available
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 Solubility21 g/LALOGPS
logP-2.3ALOGPS
logP-1.6ChemAxon
logS-0.95ALOGPS
pKa (Strongest Acidic)1.3ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area124.29 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.26 m³·mol⁻¹ChemAxon
Polarizability13.54 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]+140.07331661259
DarkChem[M-H]-135.63131661259
DeepCCS[M+H]+125.91130932474
DeepCCS[M-H]-122.09930932474
DeepCCS[M-2H]-159.66930932474
DeepCCS[M+Na]+135.14830932474
AllCCS[M+H]+140.732859911
AllCCS[M+H-H2O]+136.932859911
AllCCS[M+NH4]+144.232859911
AllCCS[M+Na]+145.232859911
AllCCS[M-H]-130.332859911
AllCCS[M+Na-2H]-132.232859911
AllCCS[M+HCOO]-134.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
D-Glycerate 3-phosphateO[C@H](COP(O)(O)=O)C(O)=O2685.6Standard polar33892256
D-Glycerate 3-phosphateO[C@H](COP(O)(O)=O)C(O)=O1423.5Standard non polar33892256
D-Glycerate 3-phosphateO[C@H](COP(O)(O)=O)C(O)=O1684.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
D-Glycerate 3-phosphate,1TMS,isomer #1C[Si](C)(C)O[C@H](COP(=O)(O)O)C(=O)O1678.8Semi standard non polar33892256
D-Glycerate 3-phosphate,1TMS,isomer #2C[Si](C)(C)OC(=O)[C@H](O)COP(=O)(O)O1642.5Semi standard non polar33892256
D-Glycerate 3-phosphate,1TMS,isomer #3C[Si](C)(C)OP(=O)(O)OC[C@@H](O)C(=O)O1704.6Semi standard non polar33892256
D-Glycerate 3-phosphate,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O)O[Si](C)(C)C1680.6Semi standard non polar33892256
D-Glycerate 3-phosphate,2TMS,isomer #2C[Si](C)(C)O[C@H](COP(=O)(O)O[Si](C)(C)C)C(=O)O1742.6Semi standard non polar33892256
D-Glycerate 3-phosphate,2TMS,isomer #3C[Si](C)(C)OC(=O)[C@H](O)COP(=O)(O)O[Si](C)(C)C1695.0Semi standard non polar33892256
D-Glycerate 3-phosphate,2TMS,isomer #4C[Si](C)(C)OP(=O)(OC[C@@H](O)C(=O)O)O[Si](C)(C)C1755.2Semi standard non polar33892256
D-Glycerate 3-phosphate,3TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C1754.5Semi standard non polar33892256
D-Glycerate 3-phosphate,3TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C1751.2Standard non polar33892256
D-Glycerate 3-phosphate,3TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C2147.0Standard polar33892256
D-Glycerate 3-phosphate,3TMS,isomer #2C[Si](C)(C)O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O1794.7Semi standard non polar33892256
D-Glycerate 3-phosphate,3TMS,isomer #2C[Si](C)(C)O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O1765.0Standard non polar33892256
D-Glycerate 3-phosphate,3TMS,isomer #2C[Si](C)(C)O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O1996.4Standard polar33892256
D-Glycerate 3-phosphate,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C1751.4Semi standard non polar33892256
D-Glycerate 3-phosphate,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C1742.6Standard non polar33892256
D-Glycerate 3-phosphate,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C1949.6Standard polar33892256
D-Glycerate 3-phosphate,4TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C1824.5Semi standard non polar33892256
D-Glycerate 3-phosphate,4TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C1817.9Standard non polar33892256
D-Glycerate 3-phosphate,4TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C1906.3Standard polar33892256
D-Glycerate 3-phosphate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O)O)C(=O)O1911.5Semi standard non polar33892256
D-Glycerate 3-phosphate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)COP(=O)(O)O1894.6Semi standard non polar33892256
D-Glycerate 3-phosphate,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@@H](O)C(=O)O1950.5Semi standard non polar33892256
D-Glycerate 3-phosphate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O)O[Si](C)(C)C(C)(C)C2100.7Semi standard non polar33892256
D-Glycerate 3-phosphate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)O2144.3Semi standard non polar33892256
D-Glycerate 3-phosphate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)COP(=O)(O)O[Si](C)(C)C(C)(C)C2115.5Semi standard non polar33892256
D-Glycerate 3-phosphate,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OP(=O)(OC[C@@H](O)C(=O)O)O[Si](C)(C)C(C)(C)C2175.8Semi standard non polar33892256
D-Glycerate 3-phosphate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2358.8Semi standard non polar33892256
D-Glycerate 3-phosphate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2390.3Standard non polar33892256
D-Glycerate 3-phosphate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2448.6Standard polar33892256
D-Glycerate 3-phosphate,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O2387.1Semi standard non polar33892256
D-Glycerate 3-phosphate,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O2330.9Standard non polar33892256
D-Glycerate 3-phosphate,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O2333.0Standard polar33892256
D-Glycerate 3-phosphate,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2365.0Semi standard non polar33892256
D-Glycerate 3-phosphate,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2357.4Standard non polar33892256
D-Glycerate 3-phosphate,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2301.3Standard polar33892256
D-Glycerate 3-phosphate,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2603.4Semi standard non polar33892256
D-Glycerate 3-phosphate,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2515.6Standard non polar33892256
D-Glycerate 3-phosphate,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2342.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - D-Glycerate 3-phosphate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9200000000-2d6f0050126bbc72d7712016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Glycerate 3-phosphate GC-MS (2 TMS) - 70eV, Positivesplash10-03dj-9150000000-ebe296689ddfcee96d612017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Glycerate 3-phosphate 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 - D-Glycerate 3-phosphate LC-ESI-ITFT , negative-QTOFsplash10-00kb-9500000000-3a504199c8820dbd44a12017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glycerate 3-phosphate 10V, Positive-QTOFsplash10-00kr-2900000000-97a3da464b710b2684a92015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glycerate 3-phosphate 20V, Positive-QTOFsplash10-00kv-8900000000-f897e638356fb29020cb2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glycerate 3-phosphate 40V, Positive-QTOFsplash10-0006-9100000000-655876160dc523273c422015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glycerate 3-phosphate 10V, Negative-QTOFsplash10-003r-5900000000-b5d234c9dd7df39204892015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glycerate 3-phosphate 20V, Negative-QTOFsplash10-004i-9100000000-6b06c4977ed320e922a22015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glycerate 3-phosphate 40V, Negative-QTOFsplash10-004i-9000000000-69afa1a98654e3a171ea2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glycerate 3-phosphate 10V, Positive-QTOFsplash10-0002-9000000000-e64736ac1f9d1f7dd9ef2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glycerate 3-phosphate 20V, Positive-QTOFsplash10-0002-9000000000-b24e251f42140de98ced2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glycerate 3-phosphate 40V, Positive-QTOFsplash10-001i-9000000000-7c1557a43a172be0e63d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glycerate 3-phosphate 10V, Negative-QTOFsplash10-004j-9000000000-0b41dc890757740bbb512021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glycerate 3-phosphate 20V, Negative-QTOFsplash10-004i-9000000000-a5e502a2627af2048a1f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glycerate 3-phosphate 40V, Negative-QTOFsplash10-004i-9000000000-a5e502a2627af2048a1f2021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified1.26 +/- 1.21 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified1.54 +/- 1.04 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified1.66 +/- 2.97 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified1.69 +/- 0.706 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04510
Phenol Explorer Compound IDNot Available
FooDB IDFDB030460
KNApSAcK IDC00019551
Chemspider ID388326
KEGG Compound IDC00197
BioCyc IDG3P
BiGG IDNot Available
Wikipedia Link3-Phosphoglyceric_acid
METLIN IDNot Available
PubChem Compound439183
PDB IDNot Available
ChEBI ID17794
Food Biomarker OntologyNot Available
VMH ID3PG
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]