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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-22 15:12:01 UTC
Update Date2022-03-07 02:49:16 UTC
HMDB IDHMDB0002649
Secondary Accession Numbers
  • HMDB02649
Metabolite Identification
Common NameErythrose
DescriptionErythrose is a tetrose saccharide with the chemical formula C4H8O4. It has one aldehyde group, and is thus part of the aldose family. The natural isomer is D-erythrose. It 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). 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.
Structure
Data?1582752253
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
[H][C@@]1(O)COC([H])(O)[C@]1([H])O
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
Description 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
Disposition

Biological location

Source

Physical Properties
StateLiquid
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 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
Polarizability10.73 ųChemAxon
Number of Rings1ChemAxon
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]+124.13731661259
DarkChem[M-H]-119.92131661259
DeepCCS[M+H]+127.71130932474
DeepCCS[M-H]-125.82530932474
DeepCCS[M-2H]-160.70530932474
DeepCCS[M+Na]+134.18230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Erythrose[H][C@@]1(O)COC([H])(O)[C@]1([H])O2499.3Standard polar33892256
Erythrose[H][C@@]1(O)COC([H])(O)[C@]1([H])O1169.8Standard non polar33892256
Erythrose[H][C@@]1(O)COC([H])(O)[C@]1([H])O1161.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Erythrose,1TMS,isomer #1C[Si](C)(C)O[C@@H]1COC(O)[C@@H]1O1261.6Semi standard non polar33892256
Erythrose,1TMS,isomer #2C[Si](C)(C)OC1OC[C@@H](O)[C@H]1O1275.9Semi standard non polar33892256
Erythrose,1TMS,isomer #3C[Si](C)(C)O[C@H]1C(O)OC[C@H]1O1264.5Semi standard non polar33892256
Erythrose,2TMS,isomer #1C[Si](C)(C)OC1OC[C@@H](O[Si](C)(C)C)[C@H]1O1357.7Semi standard non polar33892256
Erythrose,2TMS,isomer #2C[Si](C)(C)O[C@@H]1COC(O)[C@@H]1O[Si](C)(C)C1348.0Semi standard non polar33892256
Erythrose,2TMS,isomer #3C[Si](C)(C)OC1OC[C@@H](O)[C@H]1O[Si](C)(C)C1346.5Semi standard non polar33892256
Erythrose,3TMS,isomer #1C[Si](C)(C)OC1OC[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C1412.6Semi standard non polar33892256
Erythrose,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1COC(O)[C@@H]1O1487.0Semi standard non polar33892256
Erythrose,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1OC[C@@H](O)[C@H]1O1499.1Semi standard non polar33892256
Erythrose,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@H]1C(O)OC[C@H]1O1486.7Semi standard non polar33892256
Erythrose,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O1794.0Semi standard non polar33892256
Erythrose,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H]1COC(O)[C@@H]1O[Si](C)(C)C(C)(C)C1790.2Semi standard non polar33892256
Erythrose,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1OC[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C1797.5Semi standard non polar33892256
Erythrose,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C2074.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Erythrose GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-446a7809c52925c9cccf2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Erythrose GC-MS (3 TMS) - 70eV, Positivesplash10-0079-9261000000-19140e354324df2a78072017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Erythrose 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 - Erythrose Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-00dl-6900000000-67190e070c91e864cf812012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Erythrose Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-002f-9000000000-29833cdb41877882bc602012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Erythrose Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0ufr-9000000000-9fb5c86d87b3809c81962012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Erythrose LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-0006-9100000000-15d26b9d7a9da6a71e332012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Erythrose LC-ESI-QTOF , positive-QTOFsplash10-0006-9100000000-15d26b9d7a9da6a71e332017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erythrose 10V, Positive-QTOFsplash10-0fk9-1900000000-474cbe56a3684e7601a42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erythrose 20V, Positive-QTOFsplash10-0uk9-2900000000-361280ff6d6e52d3c4dd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erythrose 40V, Positive-QTOFsplash10-0a4r-9000000000-eb0666b2d7a4245a80572017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erythrose 10V, Negative-QTOFsplash10-014i-0900000000-fef7e3c0dd5f8b112b132017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erythrose 20V, Negative-QTOFsplash10-0uxr-1900000000-8e6b0d5d085203ace9f72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erythrose 40V, Negative-QTOFsplash10-0kfx-9100000000-e33833b098899221c99b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erythrose 10V, Negative-QTOFsplash10-059i-9200000000-044dc2e77678dcbb96412021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erythrose 20V, Negative-QTOFsplash10-0a4l-9000000000-bbb949d2057a9d5e93e22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erythrose 40V, Negative-QTOFsplash10-052f-9000000000-e7284f21f4112eb3ddea2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erythrose 10V, Positive-QTOFsplash10-0udj-9700000000-0d38e10775e45e5137ce2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erythrose 20V, Positive-QTOFsplash10-0006-9000000000-390349bf60b415ba32012021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erythrose 40V, Positive-QTOFsplash10-0007-9000000000-a206c8b4add95411dcb62021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • Cartilage
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>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
FooDB IDFDB023039
KNApSAcK IDC00035355
Chemspider ID388659
KEGG Compound IDC01796
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkErythrose
METLIN ID289
PubChem Compound439574
PDB IDNot Available
ChEBI ID23956
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]