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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-05-22 15:12:01 UTC

Update Date

2022-09-22 17:44:53 UTC

HMDB ID

HMDB0002649

Secondary Accession Numbers

HMDB02649

Metabolite Identification

Common Name

Erythrose

Description

Erythrose 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(R,r)-2,3,4-trihydroxybutanal	HMDB
D-erythro-Tetrose	HMDB
D-Erythrose	HMDB
L-threo-Aldose	HMDB
L-Threose	HMDB
LTr	HMDB
Threose	HMDB

Chemical Formula

C₄H₈O₄

Average Molecular Weight

120.1039

Monoisotopic Molecular Weight

120.042258744

IUPAC Name

(3R,4R)-oxolane-2,3,4-triol

Traditional Name

D-erythro-tetrose

CAS Registry Number

1758-51-6

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 Key

FMAORJIQYMIRHF-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Pentoses

Alternative Parents

Substituents

Pentose monosaccharide
Tetrahydrofuran
Secondary alcohol
Hemiacetal
1,2-diol
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Aldoses (C01796 )

Ontology

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1430 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-1.7	ChemAxon
logS	1.08	ALOGPS
pKa (Strongest Acidic)	11.32	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.92 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	24 m³·mol⁻¹	ChemAxon
Polarizability	10.73 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	124.137	31661259
DarkChem	[M-H]-	119.921	31661259
DeepCCS	[M+H]+	127.711	30932474
DeepCCS	[M-H]-	125.825	30932474
DeepCCS	[M-2H]-	160.705	30932474
DeepCCS	[M+Na]+	134.182	30932474
AllCCS	[M+H]+	127.6	32859911
AllCCS	[M+H-H2O]+	122.8	32859911
AllCCS	[M+NH4]+	132.1	32859911
AllCCS	[M+Na]+	133.3	32859911
AllCCS	[M-H]-	119.2	32859911
AllCCS	[M+Na-2H]-	121.7	32859911
AllCCS	[M+HCOO]-	124.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Erythrose	[H][C@@]1(O)COC([H])(O)[C@]1([H])O	2499.3	Standard polar	33892256
Erythrose	[H][C@@]1(O)COC([H])(O)[C@]1([H])O	1169.8	Standard non polar	33892256
Erythrose	[H][C@@]1(O)COC([H])(O)[C@]1([H])O	1161.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Erythrose,1TMS,isomer #1	C[Si](C)(C)O[C@@H]1COC(O)[C@@H]1O	1261.6	Semi standard non polar	33892256
Erythrose,1TMS,isomer #2	C[Si](C)(C)OC1OC[C@@H](O)[C@H]1O	1275.9	Semi standard non polar	33892256
Erythrose,1TMS,isomer #3	C[Si](C)(C)O[C@H]1C(O)OC[C@H]1O	1264.5	Semi standard non polar	33892256
Erythrose,2TMS,isomer #1	C[Si](C)(C)OC1OC[C@@H](O[Si](C)(C)C)[C@H]1O	1357.7	Semi standard non polar	33892256
Erythrose,2TMS,isomer #2	C[Si](C)(C)O[C@@H]1COC(O)[C@@H]1O[Si](C)(C)C	1348.0	Semi standard non polar	33892256
Erythrose,2TMS,isomer #3	C[Si](C)(C)OC1OC[C@@H](O)[C@H]1O[Si](C)(C)C	1346.5	Semi standard non polar	33892256
Erythrose,3TMS,isomer #1	C[Si](C)(C)OC1OC[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	1412.6	Semi standard non polar	33892256
Erythrose,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1COC(O)[C@@H]1O	1487.0	Semi standard non polar	33892256
Erythrose,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1OC[C@@H](O)[C@H]1O	1499.1	Semi standard non polar	33892256
Erythrose,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1C(O)OC[C@H]1O	1486.7	Semi standard non polar	33892256
Erythrose,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	1794.0	Semi standard non polar	33892256
Erythrose,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1COC(O)[C@@H]1O[Si](C)(C)C(C)(C)C	1790.2	Semi standard non polar	33892256
Erythrose,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1OC[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	1797.5	Semi standard non polar	33892256
Erythrose,3TBDMS,isomer #1	CC(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)C	2074.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Erythrose GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-446a7809c52925c9cccf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Erythrose GC-MS (3 TMS) - 70eV, Positive	splash10-0079-9261000000-19140e354324df2a7807	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Erythrose GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Erythrose Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-00dl-6900000000-67190e070c91e864cf81	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Erythrose Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-002f-9000000000-29833cdb41877882bc60	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Erythrose Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0ufr-9000000000-9fb5c86d87b3809c8196	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Erythrose LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-0006-9100000000-15d26b9d7a9da6a71e33	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Erythrose LC-ESI-QTOF , positive-QTOF	splash10-0006-9100000000-15d26b9d7a9da6a71e33	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrose 10V, Positive-QTOF	splash10-0fk9-1900000000-474cbe56a3684e7601a4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrose 20V, Positive-QTOF	splash10-0uk9-2900000000-361280ff6d6e52d3c4dd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrose 40V, Positive-QTOF	splash10-0a4r-9000000000-eb0666b2d7a4245a8057	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrose 10V, Negative-QTOF	splash10-014i-0900000000-fef7e3c0dd5f8b112b13	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrose 20V, Negative-QTOF	splash10-0uxr-1900000000-8e6b0d5d085203ace9f7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrose 40V, Negative-QTOF	splash10-0kfx-9100000000-e33833b098899221c99b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrose 10V, Negative-QTOF	splash10-059i-9200000000-044dc2e77678dcbb9641	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrose 20V, Negative-QTOF	splash10-0a4l-9000000000-bbb949d2057a9d5e93e2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrose 40V, Negative-QTOF	splash10-052f-9000000000-e7284f21f4112eb3ddea	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrose 10V, Positive-QTOF	splash10-0udj-9700000000-0d38e10775e45e5137ce	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrose 20V, Positive-QTOF	splash10-0006-9000000000-390349bf60b415ba3201	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrose 40V, Positive-QTOF	splash10-0007-9000000000-a206c8b4add95411dcb6	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Cartilage

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22007635	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Schizophrenia	22007635	details

Associated Disorders and Diseases

Disease References

Schizophrenia
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

181500 (Schizophrenia)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Erythrose

METLIN ID

289

PubChem Compound

439574

PDB ID

Not Available

ChEBI ID

23956

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Covimilla, 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

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 ]
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 ]
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 ]

Showing metabocard for Erythrose (HMDB0002649)

MOL for HMDB0002649 (Erythrose)

3D MOL for HMDB0002649 (Erythrose)

3D SDF for HMDB0002649 (Erythrose)

3D-SDF for HMDB0002649 (Erythrose)

PDB for HMDB0002649 (Erythrose)

3D PDB for HMDB0002649 (Erythrose)

SMILES for HMDB0002649 (Erythrose)

INCHI for HMDB0002649 (Erythrose)

Structure for HMDB0002649 (Erythrose)

3D Structure for HMDB0002649 (Erythrose)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra