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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-05-22 15:12:01 UTC
Update Date2018-05-20 02:41:15 UTC
HMDB IDHMDB0002649
Secondary Accession Numbers
  • HMDB02649
Metabolite Identification
Common NameErythrose
DescriptionErythrose, also known as L-threose, is a member of the class of compounds known as pentoses. Pentoses are monosaccharides in which the carbohydrate moiety contains five carbon atoms. Erythrose is very soluble (in water) and a very weakly acidic compound (based on its pKa). Erythrose can be found in blood, as well as in human cartilage tissue. Within the cell, erythrose is primarily located in the cytoplasm (predicted from logP). Erythrose exists in all living organisms, ranging from bacteria to humans. Erythrose is found to be associated with schizophrenia. Erythrose was first isolated in 1849 from rhubarb by the French pharmacist Louis Feux Joseph Garot (1798-1869) and was named as such because of its red hue in the presence of alkali metals (ἐρυθρός, "red") (Wikipedia). D-Erythrose is a tetrose carbohydrate with chemical formula C4H8O4. It has one aldehyde group, and therefore is part of the aldose family. It is a syrupy liquid at room temperature.
Structure
Thumb
Synonyms
ValueSource
(R*,r*)-2,3,4-trihydroxybutanalHMDB
D-erythro-TetroseHMDB
D-ErythroseHMDB
L-threo-AldoseHMDB
L-ThreoseHMDB
LTrHMDB
ThreoseHMDB
Chemical FormulaC4H8O4
Average Molecular Weight120.1039
Monoisotopic Molecular Weight120.042258744
IUPAC Name(3R,4R)-oxolane-2,3,4-triol
Traditional NameD-erythro-tetrose
CAS Registry Number1758-51-6
SMILES
O[C@@H]1COC(O)[C@@H]1O
InChI Identifier
InChI=1S/C4H8O4/c5-2-1-8-4(7)3(2)6/h2-7H,1H2/t2-,3-,4?/m1/s1
InChI KeyFMAORJIQYMIRHF-HERZVMAMSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentoses
Alternative Parents
Substituents
  • Pentose monosaccharide
  • Tetrahydrofuran
  • Secondary alcohol
  • Hemiacetal
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1430 g/LALOGPS
logP-2.3ALOGPS
logP-1.7ChemAxon
logS1.08ALOGPS
pKa (Strongest Acidic)11.32ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.92 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity24 m³·mol⁻¹ChemAxon
Polarizability10.71 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-446a7809c52925c9cccfView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0079-9261000000-19140e354324df2a7807View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00dl-6900000000-67190e070c91e864cf81View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-002f-9000000000-29833cdb41877882bc60View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0ufr-9000000000-9fb5c86d87b3809c8196View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0006-9100000000-15d26b9d7a9da6a71e33View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-9100000000-15d26b9d7a9da6a71e33View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-1900000000-474cbe56a3684e7601a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-2900000000-361280ff6d6e52d3c4ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9000000000-eb0666b2d7a4245a8057View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-fef7e3c0dd5f8b112b13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uxr-1900000000-8e6b0d5d085203ace9f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kfx-9100000000-e33833b098899221c99bView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
Tissue Locations
  • Cartilage
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)BothSchizophrenia details
Associated Disorders and Diseases
Disease References
Schizophrenia
  1. Xuan J, Pan G, Qiu Y, Yang L, Su M, Liu Y, Chen J, Feng G, Fang Y, Jia W, Xing Q, He L: Metabolomic profiling to identify potential serum biomarkers for schizophrenia and risperidone action. J Proteome Res. 2011 Dec 2;10(12):5433-43. doi: 10.1021/pr2006796. Epub 2011 Nov 8. [PubMed:22007635 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023039
KNApSAcK IDNot Available
Chemspider ID388659
KEGG Compound IDC01796
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkErythrose
METLIN ID289
PubChem Compound439574
PDB IDNot Available
ChEBI ID23956
References
Synthesis ReferenceCovimilla, Bernard M.; Ajiri, Masafumi; Arai, Kunio. Preparation of erythrose. Jpn. Kokai Tokkyo Koho (1998), 5 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Verzijl N, DeGroot J, Ben ZC, Brau-Benjamin O, Maroudas A, Bank RA, Mizrahi J, Schalkwijk CG, Thorpe SR, Baynes JW, Bijlsma JW, Lafeber FP, TeKoppele JM: Crosslinking by advanced glycation end products increases the stiffness of the collagen network in human articular cartilage: a possible mechanism through which age is a risk factor for osteoarthritis. Arthritis Rheum. 2002 Jan;46(1):114-23. [PubMed:11822407 ]
  2. DeGroot J, Verzijl N, Jacobs KM, Budde M, Bank RA, Bijlsma JW, TeKoppele JM, Lafeber FP: Accumulation of advanced glycation endproducts reduces chondrocyte-mediated extracellular matrix turnover in human articular cartilage. Osteoarthritis Cartilage. 2001 Nov;9(8):720-6. [PubMed:11795991 ]
  3. Jansen G, Muskiet FA, Schierbeek H, Berger R, van der Slik W: Capillary gas chromatographic profiling of urinary, plasma and erythrocyte sugars and polyols as their trimethylsilyl derivatives, preceded by a simple and rapid prepurification method. Clin Chim Acta. 1986 Jun 30;157(3):277-93. [PubMed:3731489 ]