AFCDB: L-Threonine (FDB011999)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:56 UTC

Update date

2020-09-17 15:30:55 UTC

Primary ID

FDB011999

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

L-Threonine

Description

Threonine, abbreviated Thr or T, is an essential amino acid in humans. It has a side chain containing a hydroxyl group, making it a polar, uncharged amino acid Threonine is catabolized in mammals largely (70-80%) by threonine dehydrogenase (EC 1.1.1.103) that oxidizes threonine to 2-amino-3-oxobutyrate (which forms glycine and acetyl CoA), and much less by threonine dehydratase (EC 4.2.1.16) that catabolizes threonine into 2-oxobutyrate and ammonia. It is highly concentrated in meat products, cottage cheese and wheat germ. It is abundant in human plasma, particularly in newborns. The threonine content of most infant formulas currently on the market is approximately 20% higher than the threonine concentration in human milk. Premature infants fed these formulas have twice the plasma threonine concentrations of breast-fed infants. Increasing the threonine plasma concentrations leads to accumulation of threonine and glycine in the brain. Such accumulation affects the neurotransmitter balance which may have consequences for the brain development during early postnatal life. Thus, excessive threonine intake during infant feeding should be avoided (PMID 9853925). Threonine is an immunostimulant which promotes the growth of thymus gland and probably promotes cell immune defense function. This amino acid has been useful in the treatment of genetic spasticity disorders and multiple sclerosis at a dose of 1 g per day. Severe deficiency of threonine causes neurological dysfunction and lameness in experimental animals.

CAS Number

72-19-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	477 g/L	ALOGPS
logP	-3	ALOGPS
logP	-3.5	ChemAxon
logS	0.6	ALOGPS
pKa (Strongest Acidic)	2.21	ChemAxon
pKa (Strongest Basic)	9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	83.55 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	26.46 m³·mol⁻¹	ChemAxon
Polarizability	11.08 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

Chemical Formula

C4H9NO3

IUPAC name

(2S,3R)-2-amino-3-hydroxybutanoic acid

InChI Identifier

InChI=1S/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3+/m1/s1

InChI Key

AYFVYJQAPQTCCC-GBXIJSLDSA-N

Isomeric SMILES

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

Average Molecular Weight

119.1192

Monoisotopic Molecular Weight

119.058243159

Classification

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Beta-hydroxy acid
Short-chain hydroxy acid
Hydroxy acid
Fatty acid
Amino acid
Secondary alcohol
Carboxylic acid
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxide
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

aspartate family amino acid (CHEBI:16857 )
proteinogenic amino acid (CHEBI:16857 )
L-alpha-amino acid (CHEBI:16857 )
threonine (CHEBI:16857 )
Common amino acids (C00188 )

Ontology

Heart failure

Cancer:

Leukemia

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Synthetic:

Personal care product

Biological:

Animal

Plant:

Biological location:

Tissue and substructures:

All tissues

Organ and components:

Prostate

Biofluid and excreta:

Subcellular:

Cell and elements:

Extracellular

Role

Industrial application:

Food and nutrition:

Nutritional supplement

Pharmaceutical industry:

Pharmaceutical

Biological role:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 40.33%; H 7.62%; N 11.76%; O 40.29%	DFC
Melting Point	Mp 251-253° dec.	DFC
Boiling Point	Not Available
Experimental Water Solubility	97 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	-2.94	HANSCH,C ET AL. (1995)
Experimental pKa	pKa2 9.62 (NH2)	DFC
Isoelectric point	Not Available
Charge	0
Optical Rotation	[a]26D -33.9 (H2O)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	L-Threonine, 3 TMS, GC-MS Spectrum	splash10-0gb9-0930000000-045341234639d940688b	Spectrum
GC-MS	L-Threonine, non-derivatized, GC-MS Spectrum	splash10-0gb9-0930000000-08f448150a2533471625	Spectrum
GC-MS	L-Threonine, 2 TMS, GC-MS Spectrum	splash10-0159-1910000000-98a39d63665a1a1855dd	Spectrum
GC-MS	L-Threonine, 3 TMS, GC-MS Spectrum	splash10-014i-1960000000-82e1bd8ff2e302e6b51b	Spectrum
GC-MS	L-Threonine, non-derivatized, GC-MS Spectrum	splash10-0159-0910000000-d36a7a07f0444e55e38f	Spectrum
GC-MS	L-Threonine, non-derivatized, GC-MS Spectrum	splash10-014i-0980000000-ebba7965f95f804648ab	Spectrum
GC-MS	L-Threonine, non-derivatized, GC-MS Spectrum	splash10-0gb9-0930000000-045341234639d940688b	Spectrum
GC-MS	L-Threonine, non-derivatized, GC-MS Spectrum	splash10-0gb9-0930000000-08f448150a2533471625	Spectrum
GC-MS	L-Threonine, non-derivatized, GC-MS Spectrum	splash10-0ffa-3921000000-05359581d7eb97866c8f	Spectrum
GC-MS	L-Threonine, non-derivatized, GC-MS Spectrum	splash10-0159-1910000000-98a39d63665a1a1855dd	Spectrum
GC-MS	L-Threonine, non-derivatized, GC-MS Spectrum	splash10-014i-1960000000-82e1bd8ff2e302e6b51b	Spectrum
Predicted GC-MS	L-Threonine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00dl-9000000000-a05d200d324c3242c239	Spectrum
Predicted GC-MS	L-Threonine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fdk-8930000000-c4701f28963821b700b3	Spectrum
Predicted GC-MS	L-Threonine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Threonine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Threonine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Threonine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Threonine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Threonine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Threonine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Threonine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Threonine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Threonine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Threonine, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Threonine, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-9300000000-85dce837b0f965e73c8a	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-9000000000-221510fd551c0b52c362	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4i-9100000000-6ee11649899572cd4867	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-fde7ef1951fddff4b817	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0uk9-8900000000-2d7e5609618437e59272	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-4b43567f4a446aed0828	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-4900000000-45382d9abd25be948e5b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-071b61d3ea723715c1c1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a59-9000000000-c8320d0556dbe72049ca	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0uk9-8900000000-9945ecd06408cb733177	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0ufr-8900000000-c9804e2bfc51ec0e8593	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-02t9-0692200000-f96dba3c74726ede32de	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-00di-9000000000-94eeca12e76e23c1695e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-014i-0930000000-efff9b10ae39f6ce6095	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-014i-0190000000-74ab3cba7b57b1b1b681	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-014i-1900000000-d9348197a5df9756d30c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00di-9100000000-9008bb1dfd2806e9f87d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-00di-9000000000-47fd01696817c86aecc5	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-00di-9000000000-ba9cd5b3e37ded5d3764	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-00di-1900000000-3fa8bd5efd825e5ac3fa	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0kn9-9200000000-063cffd047551fca9ee6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0a4i-9000000000-8b82bffd35f30875a7c0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0a4i-9000000000-1748dd9a759c98e1c5ee	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0a4i-9000000000-e9069de219196460cc61	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uk9-6900000000-d30fcc60bda11aeb88b4	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 400 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16857

Phenol-Explorer ID

Not Available

DrugBank ID

DB00156

HMDB ID

HMDB00167

CRC / DFC (Dictionary of Food Compounds) ID

HCL12-S:HCL15-V

EAFUS ID

3669

Dr. Duke ID

THREONINE|L-(-)-THREONINE

BIGG ID

34186

KNApSAcK ID

C00001394

HET ID

THR

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

L-Threonine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE
anti ulcer	49201	One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.	DUKE
essential			DUKE
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE

Enzymes

Name	Gene Name	UniProt ID
L-serine dehydratase/L-threonine deaminase	SDS	P20132
Serine dehydratase-like	SDSL	Q96GA7
Threonine--tRNA ligase, cytoplasmic	TARS	P26639
Threonine synthase-like 1	THNSL1	Q8IYQ7
Probable threonine--tRNA ligase 2, cytoplasmic	TARSL2	A2RTX5
Threonine--tRNA ligase, mitochondrial	TARS2	Q9BW92

Pathways

Name	SMPDB Link	KEGG Link
Glycine and Serine Metabolism	SMP00004	map00260
Threonine and 2-Oxobutanoate Degradation	SMP00452	Not Available
Transcription/Translation	SMP00019	Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

L-Threonine (FDB011999)

Structure for FDB011999 (L-Threonine)