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Human Metabolome Database Version 3.5

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Showing metabocard for L-Threonine (HMDB00167)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:01 -0700
HMDB ID HMDB00167
Secondary Accession Numbers None
Metabolite Identification
Common Name L-Threonine
Description Threonine is an essential amino acid in humans. It is abundant in human plasma, particularly in newborns. Severe deficiency of threonine causes neurological dysfunction and lameness in experimental animals. Threonine is an immunostimulant which promotes the growth of thymus gland. It also can probably promote 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 gram daily. It is highly concentrated in meat products, cottage cheese and wheat germ. (http://www.dcnutrition.com/AminoAcids/) The threonine content of most of the infant formulas currently on the market is approximately 20% higher than the threonine concentration in human milk. Due to this high threonine content the plasma threonine concentrations are up to twice as high in premature infants fed these formulas than in infants fed human milk. The whey proteins which are used for infant formulas are sweet whey proteins. Sweet whey results from cheese production. Threonine catabolism in mammals appears to be due primarily (70-80%) to the activity of threonine dehydrogenase (EC 1.1.1.103) that oxidizes threonine to 2-amino-3-oxobutyrate, which forms glycine and acetyl CoA, whereas threonine dehydratase (EC 4.2.1.16) that catabolizes threonine into 2-oxobutyrate and ammonia, is significantly less active. 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 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Threonin
  2. (2S,3R)-(-)-Threonine
  3. (2S,3R)-2-Amino-3-hydroxybutyrate
  4. (2S,3R)-2-Amino-3-hydroxybutyric acid
  5. (R-(R*,S*))-2-Amino-3-hydroxybutanoate
  6. (R-(R*,S*))-2-Amino-3-hydroxybutanoic acid
  7. (S)-Threonine
  8. 2-Amino-3-hydroxybutanoate
  9. 2-Amino-3-hydroxybutanoic acid
  10. 2-Amino-3-hydroxybutyrate
  11. 2-Amino-3-hydroxybutyric acid
  12. L-(-)-Threonine
  13. L-2-Amino-3-hydroxybutyrate
  14. L-2-Amino-3-hydroxybutyric acid
  15. L-alpha-Amino-beta-hydroxybutyrate
  16. L-alpha-Amino-beta-hydroxybutyric acid
  17. Threonine
  18. [R-(R*,S*)]-2-amino-3-hydroxy-Butanoate
  19. [R-(R*,S*)]-2-amino-3-hydroxy-Butanoic acid
  20. [R-(R*,S*)]-2-Amino-3-hydroxybutanoate
  21. [R-(R*,S*)]-2-Amino-3-hydroxybutanoic acid
Chemical Formula C4H9NO3
Average Molecular Weight 119.1192
Monoisotopic Molecular Weight 119.058243159
IUPAC Name (2S,3R)-2-amino-3-hydroxybutanoic acid
Traditional IUPAC Name L-threonine
CAS Registry Number 72-19-5
SMILES C[C@@H](O)[C@H](N)C(O)=O
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
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha Amino Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Common amino acids(KEGG)
  • amino acid zwitterion(ChEBI)
Substituents
  • 1,2 Aminoalcohol
  • Beta Hydroxy Acid
  • Carboxylic Acid
  • Primary Aliphatic Amine (Alkylamine)
  • Secondary Alcohol
Direct Parent Alpha Amino Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Food
  • Plant
  • Drug
Biofunction
  • Component of Aminoacyl-tRNA biosynthesis
  • Component of Glycine, serine and threonine metabolism
  • Essential amino acids
Application Not Available
Cellular locations
  • Cytoplasm
  • Extracellular
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 256 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 97.0 mg/mL Not Available
LogP -2.94 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 477 g/L ALOGPS
LogP -3.01 ALOGPS
LogP -3.5 ChemAxon
LogS 0.60 ALOGPS
pKa (strongest acidic) 2.21 ChemAxon
pKa (strongest basic) 9 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 83.55 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 26.46 ChemAxon
Polarizability 11.25 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
13C NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • All Tissues
  • Prostate
Pathways
Name SMPDB Link KEGG Link
Transcription/Translation SMP00019 Not Available
Glycine and Serine Metabolism SMP00004 map00260 Link_out
Threonine and 2-Oxobutanoate Degradation SMP00452 Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
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127.7 +/- 41 uM Adult (>18 years old) Not Specified Normal Not Available
Blood Detected and Quantified
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102.3 +/- 24.6 uM Adult (>18 years old) Not Specified Normal Not Available
Blood Detected and Quantified
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140.0 (107.0-173.0) uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
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215.0 +/- 60.0 uM Newborn (0-30 days old) Not Specified Normal Not Available
Blood Detected and Quantified
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140.0 +/- 28.0 uM Children (1-13 year old) Male Normal Not Available
Blood Detected and Quantified
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146.0 +/- 22.0 uM Adult (>18 years old) Male Normal Not Available
Blood Detected and Quantified
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154.0 +/- 40.0 uM Adult (>18 years old) Female Normal Not Available
Blood Detected and Quantified
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260.0 +/- 10.0 uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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32.0 (4.00-60.0) uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
30 +/- 12 uM Not Specified Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
27.7 +/- 4.7 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
45.9 +/- 12.3 uM Adult (>18 years old) Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
37.4 +/- 7.6 uM Adult (>18 years old) Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
34.7 +/- 6.2 uM Adult (>18 years old) Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
26.5 +/- 4.2 uM Adult (>18 years old) Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
10.35 +/- 0.88 uM Adult (>18 years old) Both Normal Not Available
Saliva Detected and Quantified
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>10 uM Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
10.3 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
8.40-100.79 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
36.20 +/- 25.38 umol/mmol creatinine Infant (0-1 year old) Both Normal Not Available
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
13.3 (6.4-25.2) umol/mmol creatinine Adult (>18 years old) Both Normal urine by NMR
Urine Detected and not Quantified
Article_icon
Not Applicable Adult (>18 years old) Both Normal Urine compound detected by GC-MS
Urine Detected and Quantified
Article_icon
5.17-24.59 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
14.6 (6.6-29.3) umol/mmol creatinine Adult (>18 years old) Both Normal by LC-MS/MS (Biocrates kit)
Urine Detected and Quantified
Article_icon
1.0 (0.16-2.4) umol/mmol creatinine Newborn (0-30 days old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
4.9 +/- 2.5 umol/mmol creatinine Children (1-13 year old) Female Normal Not Available
Urine Detected and Quantified
Article_icon
18.0 +/- 9.6 umol/mmol creatinine Adult (>18 years old) Male Normal Not Available
Urine Detected and Quantified
Article_icon
16.0 +/- 9.0 umol/mmol creatinine Adult (>18 years old) Female Normal Not Available
Urine Detected and Quantified
Article_icon
12.7 (4.934-20.4) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
13.4 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
83.4 +/- 47.8 uM Adult (>18 years old) Not Specified Heart Transplant Not Available
Blood Detected and Quantified
Article_icon
114.0 +/- 9.2 uM Adult (>18 years old) Both Epilepsy Acute seizures
Blood Detected and Quantified
Article_icon
118.0 +/- 3.8 uM Adult (>18 years old) Both Epilepsy Refractory localization-related epilepsy (RLE)
Blood Detected and Quantified
Article_icon
227.0 +/- 10.0 uM Adult (>18 years old) Both Heart failure Non-diabetic patients with chronic heart failure
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
41.0 +/- 15.9 uM Children (1-13 year old) Not Specified Leukemia Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
30.2 +/- 9.8 uM Children (1-13 year old) Not Specified Leukemia Acute Lymphoblastic Leukemia (ALL) with Central...
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
9.68 +/- 2.22 uM Adult (>18 years old) Both Schizophrenia Not Available
Urine Detected and not Quantified
Article_icon
Not Applicable Adult (>18 years old) Both Autosomal dominant polycystic kidney disease Not Available
Urine Detected and Quantified
Article_icon
0.03 +/- 0.003 umol/mmol creatinine Adult (>18 years old) Both Alzheimer's disease Not Available
Associated Disorders and Diseases
Disease References
Epilepsy
  • Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. Pubmed: 14992292 Link_out
    Leukemia
    • Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. Pubmed: 15911239 Link_out
      Heart failure
      • Norrelund H, Wiggers H, Halbirk M, Frystyk J, Flyvbjerg A, Botker HE, Schmitz O, Jorgensen JO, Christiansen JS, Moller N: Abnormalities of whole body protein turnover, muscle metabolism and levels of metabolic hormones in patients with chronic heart failure. J Intern Med. 2006 Jul;260(1):11-21. Pubmed: 16789974 Link_out
        Schizophrenia
        • Do KQ, Lauer CJ, Schreiber W, Zollinger M, Gutteck-Amsler U, Cuenod M, Holsboer F: gamma-Glutamylglutamine and taurine concentrations are decreased in the cerebrospinal fluid of drug-naive patients with schizophrenic disorders. J Neurochem. 1995 Dec;65(6):2652-62. Pubmed: 7595563 Link_out
          Alzheimer's disease
          • Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. Pubmed: 17031479 Link_out
            Associated OMIM IDs
            DrugBank ID DB00156 Link_out
            Phenol Explorer Compound ID Not Available
            Phenol Explorer Metabolite ID Not Available
            FoodDB ID FDB011999
            KNApSAcK ID C00001394 Link_out
            Chemspider ID 6051 Link_out
            KEGG Compound ID C00188 Link_out
            BioCyc ID THR Link_out
            BiGG ID 34186 Link_out
            Wikipedia Link L-Threonine Link_out
            NuGOwiki Link HMDB00167 Link_out
            Metagene Link HMDB00167 Link_out
            METLIN ID 32 Link_out
            PubChem Compound 6288 Link_out
            PDB ID THR Link_out
            ChEBI ID 16857 Link_out
            References
            Synthesis Reference Fujita, Chuzo; Nara, Takashi; Samejima, Hirotoshi; Kinoshita, Shukuo. L-Threonine fermentation. I. Microbial conversion of L-homoserine to L-threonine. Nippon Nogei Kagaku Kaishi (1965), 39(6), 2
            Material Safety Data Sheet (MSDS) Download (PDF)
            General References
            1. Vold BS, Keith DE Jr, Slavik M: Urine levels of N-[9-(beta-D-ribofuranosyl)purin-6-ylcarbamoyl]-L-threonine, N6-(delta 2-isopentenyl)adenosine, and 2'-O-methylguanosine as determined by radioimmunoassay for normal subjects and cancer patients. Cancer Res. 1982 Dec;42(12):5265-9. Pubmed: 7139629 Link_out
            2. Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. Pubmed: 15911239 Link_out
            3. Hallgren P, Lundblad A, Svensson S: A new type of carbohydrate-protein linkage in a glycopeptide from normal human urine. J Biol Chem. 1975 Jul 25;250(14):5312-4. Pubmed: 1141232 Link_out
            4. Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. Pubmed: 12297216 Link_out
            5. Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. Pubmed: 14992292 Link_out
            6. Wevers RA, Engelke U, Wendel U, de Jong JG, Gabreels FJ, Heerschap A: Standardized method for high-resolution 1H-NMR of cerebrospinal fluid. Clin Chem. 1995 May;41(5):744-51. Pubmed: 7729054 Link_out
            7. Wulf G, Finn G, Suizu F, Lu KP: Phosphorylation-specific prolyl isomerization: is there an underlying theme? Nat Cell Biol. 2005 May;7(5):435-41. Pubmed: 15867923 Link_out
            8. Takeda DY, Parvin JD, Dutta A: Degradation of Cdt1 during S phase is Skp2-independent and is required for efficient progression of mammalian cells through S phase. J Biol Chem. 2005 Jun 17;280(24):23416-23. Epub 2005 Apr 25. Pubmed: 15855168 Link_out
            9. Nanda N, Bao M, Lin H, Clauser K, Komuves L, Quertermous T, Conley PB, Phillips DR, Hart MJ: Platelet endothelial aggregation receptor 1 (PEAR1), a novel epidermal growth factor repeat-containing transmembrane receptor, participates in platelet contact-induced activation. J Biol Chem. 2005 Jul 1;280(26):24680-9. Epub 2005 Apr 25. Pubmed: 15851471 Link_out
            10. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. Pubmed: 12097436 Link_out
            11. Boneh A, Korman SH, Sato K, Kanno J, Matsubara Y, Lerer I, Ben-Neriah Z, Kure S: A single nucleotide substitution that abolishes the initiator methionine codon of the GLDC gene is prevalent among patients with glycine encephalopathy in Jerusalem. J Hum Genet. 2005;50(5):230-4. Epub 2005 Apr 29. Pubmed: 15864413 Link_out
            12. Elzinga M, Maron BJ, Adelstein RS: Human heart and platelet actins are products of different genes. Science. 1976 Jan 9;191(4222):94-5. Pubmed: 1246600 Link_out
            13. Nicholson JK, O'Flynn MP, Sadler PJ, Macleod AF, Juul SM, Sonksen PH: Proton-nuclear-magnetic-resonance studies of serum, plasma and urine from fasting normal and diabetic subjects. Biochem J. 1984 Jan 15;217(2):365-75. Pubmed: 6696735 Link_out
            14. Rodriguez-Soriano J, Vallo A, Perez de Nanclares G, Bilbao JR, Castano L: A founder mutation in the CLCNKB gene causes Bartter syndrome type III in Spain. Pediatr Nephrol. 2005 Jul;20(7):891-6. Epub 2005 May 5. Pubmed: 15875219 Link_out
            15. Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7. Pubmed: 6198473 Link_out
            16. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411 Link_out
            Enzymes
            Name: Threonyl-tRNA synthetase, cytoplasmic
            Reactions:
            • ATP + L-threonine + tRNAThr = AMP + diphosphate + L-threonyl-tRNAThr [RN:R03663]
            Gene Name: TARS
            Uniprot ID: P26639 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Neutral amino acid transporter A
            Reactions:
            • --- []
            Gene Name: SLC1A4
            Uniprot ID: P43007 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Threonine synthase-like 1
            Reactions:
            • --- []
            Gene Name: THNSL1
            Uniprot ID: Q8IYQ7 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Acetolactate synthase-like protein
            Reactions:
              Gene Name: ILVBL
              Uniprot ID: A1L0T0 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Probable threonyl-tRNA synthetase 2, cytoplasmic
              Reactions:
              • ATP + L-threonine + tRNAThr = AMP + diphosphate + L-threonyl-tRNAThr [RN:R03663]
              Gene Name: TARSL2
              Uniprot ID: A2RTX5 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Threonyl-tRNA synthetase, mitochondrial
              Reactions:
              • ATP + L-threonine + tRNAThr = AMP + diphosphate + L-threonyl-tRNAThr [RN:R03663]
              Gene Name: TARS2
              Uniprot ID: Q9BW92 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Transporters
              Name: Monocarboxylate transporter 10
              Reactions:
                Gene Name: SLC16A10
                Uniprot ID: Q8TF71 Link_out
                Protein Sequence: FASTA
                Gene Sequence: FASTA