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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-05-30 20:56:03 UTC

HMDB ID

HMDB0000943

Secondary Accession Numbers

HMDB0062620
HMDB00943
HMDB62620

Metabolite Identification

Common Name

Threonic acid

Description

Threonic acid, also known as threonate, 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. Threonic acid is a sugar acid derived from threose. The L-isomer is a metabolite of ascorbic acid (vitamin C). One study suggested that because L-threonate inhibits DKK1 expression in vitro, it may have potential in the treatment of androgenic alopecia (PMID:21034532 ). Threonic acid is probably derived from glycated proteins or from degradation of ascorbic acid. It is a normal component in aqueous humour and blood (PMID:10420182 ). Threonic acid is a substrate of L-threonate 3-dehydrogenase (EC 1.1.1.129) in the ascorbate and aldarate metabolism pathway (KEGG). It has been found to be a microbial metabolite (PMID:20615997 ).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
L-Threonate	Kegg
(2R,3S)-2,3,4-Trihydroxybutanoic acid	Kegg
L-Threonic acid	Generator
(2R,3S)-2,3,4-Trihydroxybutanoate	Generator
Threonate	Generator
Threonic acid, (R-(r,s))-isomer	HMDB
2,3,4-Trihydroxy-(threo)-butanoic acid	HMDB
Threonic acid, (r,r)-isomer	HMDB
2,3,4-Trihydroxybutanoic acid	HMDB
2,3,4-Trihydroxybutyric acid	HMDB
Threonic acid	MeSH, HMDB

Chemical Formula

C₄H₈O₅

Average Molecular Weight

136.1033

Monoisotopic Molecular Weight

136.037173366

IUPAC Name

(2R,3S)-2,3,4-trihydroxybutanoic acid

Traditional Name

threonate

CAS Registry Number

7306-96-9

SMILES

OC[C@H](O)[C@@H](O)C(O)=O

InChI Identifier

InChI=1S/C4H8O5/c5-1-2(6)3(7)4(8)9/h2-3,5-7H,1H2,(H,8,9)/t2-,3+/m0/s1

InChI Key

JPIJQSOTBSSVTP-STHAYSLISA-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Sugar acids and derivatives

Alternative Parents

Substituents

Beta-hydroxy acid
Short-chain hydroxy acid
Sugar acid
Alpha-hydroxy acid
Hydroxy acid
Monosaccharide
Fatty acid
Secondary alcohol
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Alcohol
Carbonyl group
Primary alcohol
Hydrocarbon derivative
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

threonic acid (CHEBI:15908 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 25105552)
Saliva (PMID: 22308371)

Organ

Placenta (HMDB: HMDB0000943)

Excreta

Biofluid or Excreta

Urine (PMID: 8087979)
Feces (PMID: 20669995)
Sweat (PMID: 26755145)

Cellular substructure

Cytoplasm (HMDB: HMDB0000943)

Source

Exogenous

Exogenous (HMDB: HMDB0000943)

Food

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Endogenous

Endogenous (HMDB: HMDB0000943)

Microbe

Microbe (HMDB: HMDB0000943)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Eosinophilic esophagitis (MarkerDB: MDB00000287)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	53 mg/mL	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	122.2	30932474
[M-H]-	Not Available	122.2	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001837

Predicted Molecular Properties

Property	Value	Source
Water Solubility	488 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-2.1	ChemAxon
logS	0.55	ALOGPS
pKa (Strongest Acidic)	3.4	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	26.35 m³·mol⁻¹	ChemAxon
Polarizability	11.61 Å³	ChemAxon
Number of Rings	0	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]+	127.37	31661259
DarkChem	[M-H]-	123.351	31661259
AllCCS	[M+H]+	132.748	32859911
AllCCS	[M-H]-	122.433	32859911
DeepCCS	[M+H]+	126.124	30932474
DeepCCS	[M-H]-	122.26	30932474
DeepCCS	[M-2H]-	159.678	30932474
DeepCCS	[M+Na]+	135.175	30932474
AllCCS	[M+H]+	132.7	32859911
AllCCS	[M+H-H2O]+	128.7	32859911
AllCCS	[M+NH4]+	136.6	32859911
AllCCS	[M+Na]+	137.7	32859911
AllCCS	[M-H]-	122.4	32859911
AllCCS	[M+Na-2H]-	125.1	32859911
AllCCS	[M+HCOO]-	128.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Threonic acid	OC[C@H](O)[C@@H](O)C(O)=O	2597.8	Standard polar	33892256
Threonic acid	OC[C@H](O)[C@@H](O)C(O)=O	1311.5	Standard non polar	33892256
Threonic acid	OC[C@H](O)[C@@H](O)C(O)=O	1333.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Threonic acid,1TMS,isomer #1	C[Si](C)(C)OC[C@H](O)[C@@H](O)C(=O)O	1354.5	Semi standard non polar	33892256
Threonic acid,1TMS,isomer #2	C[Si](C)(C)O[C@@H](CO)[C@@H](O)C(=O)O	1356.6	Semi standard non polar	33892256
Threonic acid,1TMS,isomer #3	C[Si](C)(C)O[C@@H](C(=O)O)[C@@H](O)CO	1359.9	Semi standard non polar	33892256
Threonic acid,1TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](O)[C@@H](O)CO	1318.3	Semi standard non polar	33892256
Threonic acid,2TMS,isomer #1	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@@H](O)C(=O)O	1449.8	Semi standard non polar	33892256
Threonic acid,2TMS,isomer #2	C[Si](C)(C)OC[C@H](O)[C@@H](O[Si](C)(C)C)C(=O)O	1454.3	Semi standard non polar	33892256
Threonic acid,2TMS,isomer #3	C[Si](C)(C)OC[C@H](O)[C@@H](O)C(=O)O[Si](C)(C)C	1437.0	Semi standard non polar	33892256
Threonic acid,2TMS,isomer #4	C[Si](C)(C)O[C@@H](CO)[C@@H](O[Si](C)(C)C)C(=O)O	1439.3	Semi standard non polar	33892256
Threonic acid,2TMS,isomer #5	C[Si](C)(C)OC(=O)[C@H](O)[C@H](CO)O[Si](C)(C)C	1416.2	Semi standard non polar	33892256
Threonic acid,2TMS,isomer #6	C[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C)[C@@H](O)CO	1404.9	Semi standard non polar	33892256
Threonic acid,3TMS,isomer #1	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O	1521.6	Semi standard non polar	33892256
Threonic acid,3TMS,isomer #2	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C	1516.2	Semi standard non polar	33892256
Threonic acid,3TMS,isomer #3	C[Si](C)(C)OC[C@H](O)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1516.3	Semi standard non polar	33892256
Threonic acid,3TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C)[C@H](CO)O[Si](C)(C)C	1506.0	Semi standard non polar	33892256
Threonic acid,4TMS,isomer #1	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1591.3	Semi standard non polar	33892256
Threonic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](O)[C@@H](O)C(=O)O	1633.2	Semi standard non polar	33892256
Threonic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H](CO)[C@@H](O)C(=O)O	1624.4	Semi standard non polar	33892256
Threonic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H](C(=O)O)[C@@H](O)CO	1638.1	Semi standard non polar	33892256
Threonic acid,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)[C@@H](O)CO	1576.5	Semi standard non polar	33892256
Threonic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O	1889.2	Semi standard non polar	33892256
Threonic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	1924.1	Semi standard non polar	33892256
Threonic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H](O)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C	1873.3	Semi standard non polar	33892256
Threonic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	1908.6	Semi standard non polar	33892256
Threonic acid,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)[C@H](CO)O[Si](C)(C)C(C)(C)C	1870.2	Semi standard non polar	33892256
Threonic acid,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CO	1860.3	Semi standard non polar	33892256
Threonic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	2194.4	Semi standard non polar	33892256
Threonic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C	2164.7	Semi standard non polar	33892256
Threonic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2173.9	Semi standard non polar	33892256
Threonic acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)O[Si](C)(C)C(C)(C)C	2172.6	Semi standard non polar	33892256
Threonic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](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)C	2390.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Threonic acid GC-MS (4 TMS)	splash10-0gc3-1980000000-1134cc7dbfebc81101f0	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Threonic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-08i0-9000000000-8d139618fe1977b7f75c	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Threonic acid GC-MS (4 TMS) - 70eV, Positive	splash10-05i9-9135200000-540f14ba652277646ad0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Threonic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Threonic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Threonic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Threonic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Threonic acid GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Threonic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Threonic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Threonic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Threonic acid GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Threonic acid GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Threonic acid GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Threonic acid GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Threonic acid GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Threonic acid GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Threonic acid GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Threonic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Threonic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Threonic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Threonic acid GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Threonic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Threonic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Threonic acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Threonic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-00kp-9400000000-65ee9acbf3bfc5e1217d	2020-02-03	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Threonic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-00l2-9100000000-530757fa85c48c04e4f7	2020-02-03	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Threonic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-014j-9100000000-0598e87e111f68c2e5ad	2020-02-03	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Threonic acid 10V, Positive-QTOF	splash10-014r-3900000000-2b3d3fb29e0133c070fa	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Threonic acid 20V, Positive-QTOF	splash10-03di-9300000000-9c5553554eff5afd7d2c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Threonic acid 40V, Positive-QTOF	splash10-0r6v-9100000000-b760f5ab8de654f72611	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Threonic acid 10V, Negative-QTOF	splash10-009l-9300000000-cea0b9791733d92b7dac	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Threonic acid 20V, Negative-QTOF	splash10-0abl-9100000000-5893bc2f3c3758ba4459	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Threonic acid 40V, Negative-QTOF	splash10-0ab9-9000000000-b86ae9d1fd6d44595e98	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Threonic acid 10V, Negative-QTOF	splash10-0079-9600000000-6a27bf7d90c481d7453b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Threonic acid 20V, Negative-QTOF	splash10-0a6r-9000000000-42cf915c3e1d04404a86	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Threonic acid 40V, Negative-QTOF	splash10-052f-9000000000-07a84de0d3017aafde8a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Threonic acid 10V, Positive-QTOF	splash10-0uxr-4900000000-f56da89e34354eb5ec58	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Threonic acid 20V, Positive-QTOF	splash10-0w93-9400000000-85332419870fbb4b3f79	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Threonic acid 40V, Positive-QTOF	splash10-0007-9000000000-0708461d5ccadb4dda2e	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2020-02-03	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Feces
Saliva
Sweat
Urine

Tissue Locations

Placenta

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	24740205	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24801555	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	22411374	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24029555	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	20669995	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Sweat	Detected but not Quantified	Not Quantified	Adult	Both	Normal	26755145	details
Urine	Detected and Quantified	14.8 (8.6-36.1) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21389975	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	63.0 +/- 21.0 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	88.928 +/- 40.543 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	10.0 +/- 7.0 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	20.8 (10.2 - 39.3) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	14.2 (4.2-36.1) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	8087979	details
Urine	Detected and Quantified	13.4 (5.1-46.0) umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	8087979	details
Urine	Detected and Quantified	4.5 (2.1-13.6) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	3.1(1.7-13.7) umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	89.49 (69.00-103.31) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25105552	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	gastric cancer	21443661	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	superficial gastric cancer	21443661	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Sweat	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	screen-positive CF	Adriana Nori...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details
Urine	Detected and Quantified	114.997 +/- 87.963 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25105552	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] 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 ]
Stomach cancer
Yu L, Aa J, Xu J, Sun M, Qian S, Cheng L, Yang S, Shi R: Metabolomic phenotype of gastric cancer and precancerous stages based on gas chromatography time-of-flight mass spectrometry. J Gastroenterol Hepatol. 2011 Aug;26(8):1290-7. doi: 10.1111/j.1440-1746.2011.06724.x. [PubMed:21443661 ]
Cystic fibrosis
Adriana Nori de Macedo. Robust capillary electrophoresis methods for biomarker discovery and routine measurements in clinical and epidemiological applications. March 2017 [Link]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

114500 (Colorectal cancer)
137215 (Stomach cancer)
219700 (Cystic fibrosis)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

DB11192

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

Threonic_acid

METLIN ID

Not Available

PubChem Compound

5460407

PDB ID

Not Available

ChEBI ID

15908

Food Biomarker Ontology

Not Available

VMH ID

THRNT

MarkerDB ID

MDB00000287

Good Scents ID

Not Available

References

Synthesis Reference

Song J Z; Huang D P; Tian S J; Sun Z P Determination of L-threonate in calcium L-threonate preparations by capillary electrophoresis with indirect UV detection. Electrophoresis (1999), 20(9), 1850-5.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
Chalmers RA, Lawson AM, Hauschildt S, Watts RW: The urinary excretion of glycollic acid and threonic acid by xylitol-infused patients and their relationship to the possible role of 'active glycoladehyde' in the transketolase reaction in vivo. Biochem Soc Trans. 1975;3(4):518-21. [PubMed:1183712 ]
Harding JJ, Hassett PC, Rixon KC, Bron AJ, Harvey DJ: Sugars including erythronic and threonic acids in human aqueous humour. Curr Eye Res. 1999 Aug;19(2):131-6. [PubMed:10420182 ]
Leveque N, Mac-Mary S, Muret P, Makki S, Aubin F, Kantelip JP, Heusele C, S S, Humbert P: Evaluation of a sunscreen photoprotective effect by ascorbic acid assessment in human dermis using microdialysis and gas chromatography mass spectrometry. Exp Dermatol. 2005 Mar;14(3):176-81. [PubMed:15740589 ]
Watts RW, Hauschildt S, Chalmers RA, Lawson AM: Metabolic investigations during xylitol infusion. Int Z Vitam Ernahrungsforsch Beih. 1976;15:216-25. [PubMed:821885 ]
van Duynhoven J, Vaughan EE, Jacobs DM, Kemperman RA, van Velzen EJ, Gross G, Roger LC, Possemiers S, Smilde AK, Dore J, Westerhuis JA, Van de Wiele T: Metabolic fate of polyphenols in the human superorganism. Proc Natl Acad Sci U S A. 2011 Mar 15;108 Suppl 1:4531-8. doi: 10.1073/pnas.1000098107. Epub 2010 Jun 25. [PubMed:20615997 ]
Kwack MH, Ahn JS, Kim MK, Kim JC, Sung YK: Preventable effect of L-threonate, an ascorbate metabolite, on androgen-driven balding via repression of dihydrotestosterone-induced dickkopf-1 expression in human hair dermal papilla cells. BMB Rep. 2010 Oct;43(10):688-92. doi: 10.5483/BMBRep.2010.43.10.688. [PubMed:21034532 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Threonic acid (HMDB0000943)

MOL for HMDB0000943 (Threonic acid)

3D MOL for HMDB0000943 (Threonic acid)

3D SDF for HMDB0000943 (Threonic acid)

3D-SDF for HMDB0000943 (Threonic acid)

PDB for HMDB0000943 (Threonic acid)

3D PDB for HMDB0000943 (Threonic acid)

SMILES for HMDB0000943 (Threonic acid)

INCHI for HMDB0000943 (Threonic acid)

Structure for HMDB0000943 (Threonic acid)

3D Structure for HMDB0000943 (Threonic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra