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Record Information
Version1.0
Created at2020-03-18 23:26:05 UTC
Updated at2022-12-13 23:36:22 UTC
CannabisDB IDCDB000135
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameL-Threonine
DescriptionThreonine, 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. L-Threonine is also found in Cannabis plants (PMID: 6991645 ). 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
Structure
Thumb
Synonyms
Chemical FormulaC4H9NO3
Average Molecular Weight119.12
Monoisotopic Molecular Weight119.0582
IUPAC Name(2S,3R)-2-amino-3-hydroxybutanoic acid
Traditional NameL-threonine
CAS Registry Number72-19-5
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 KeyAYFVYJQAPQTCCC-GBXIJSLDSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point256 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility97 mg/mLNot Available
logP-2.94HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP-3ALOGPS
logP-3.5ChemAxon
logS0.6ALOGPS
pKa (Strongest Acidic)2.21ChemAxon
pKa (Strongest Basic)9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.46 m³·mol⁻¹ChemAxon
Polarizability11.08 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
MS/MS
NMR
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Threonine--tRNA ligase, cytoplasmicTARS5p13.2P26639 details
L-serine dehydratase/L-threonine deaminaseSDS12q24.13P20132 details
Threonine synthase-like 1THNSL110p12.1Q8IYQ7 details
Acetolactate synthase-like proteinILVBL19p13.1A1L0T0 details
Serine dehydratase-likeSDSL12q24.13Q96GA7 details
Probable threonine--tRNA ligase 2, cytoplasmicTARSL215q26.3A2RTX5 details
Threonine--tRNA ligase, mitochondrialTARS21q21.3Q9BW92 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Neutral amino acid transporter ASLC1A42p15-p13P43007 details
Monocarboxylate transporter 10SLC16A106q21-q22Q8TF71 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Acetolactate synthase-like proteinILVBL19p13.1A1L0T0 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.281 mg/g dry wt
    • David S. Wishart,...
details
GabriolaDetected and Quantified0.241 mg/g dry wt
    • David S. Wishart,...
details
Island HoneyDetected and Quantified0.201 mg/g dry wt
    • David S. Wishart,...
details
QuadraDetected and Quantified0.240 mg/g dry wt
    • David S. Wishart,...
details
Sensi StarDetected and Quantified0.129 mg/g dry wt
    • David S. Wishart,...
details
Tangerine DreamDetected and Quantified0.175 mg/g dry wt
    • David S. Wishart,...
details
HMDB IDHMDB0000167
DrugBank IDDB00156
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011999
KNApSAcK IDC00001394
Chemspider ID6051
KEGG Compound IDC00188
BioCyc IDTHR
BiGG ID34186
Wikipedia LinkThreonine
METLIN ID32
PubChem Compound6288
PDB IDNot Available
ChEBI ID16857
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Boehm G, Cervantes H, Georgi G, Jelinek J, Sawatzki G, Wermuth B, Colombo JP: Effect of increasing dietary threonine intakes on amino acid metabolism of the central nervous system and peripheral tissues in growing rats. Pediatr Res. 1998 Dec;44(6):900-6. doi: 10.1203/00006450-199812000-00013. [PubMed:9853925 ]

Enzymes

General function:
Involved in nucleotide binding
Specific function:
Not Available
Gene Name:
TARS
Uniprot ID:
P26639
Molecular weight:
83434.5
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
SDS
Uniprot ID:
P20132
Molecular weight:
34625.105
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
THNSL1
Uniprot ID:
Q8IYQ7
Molecular weight:
83069.5
General function:
Involved in magnesium ion binding
Specific function:
Not Available
Gene Name:
ILVBL
Uniprot ID:
A1L0T0
Molecular weight:
67867.2
General function:
Involved in catalytic activity
Specific function:
Has low serine dehydratase and threonine dehydratase activity.
Gene Name:
SDSL
Uniprot ID:
Q96GA7
Molecular weight:
34674.01
General function:
Involved in nucleotide binding
Specific function:
Not Available
Gene Name:
TARSL2
Uniprot ID:
A2RTX5
Molecular weight:
92644.755
General function:
Involved in nucleotide binding
Specific function:
Not Available
Gene Name:
TARS2
Uniprot ID:
Q9BW92
Molecular weight:
81035.345

Transporters

General function:
Involved in sodium:dicarboxylate symporter activity
Specific function:
Transporter for alanine, serine, cysteine, and threonine. Exhibits sodium dependence
Gene Name:
SLC1A4
Uniprot ID:
P43007
Molecular weight:
55722.5
General function:
Involved in transmembrane transport
Specific function:
Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells
Gene Name:
SLC16A10
Uniprot ID:
Q8TF71
Molecular weight:
55492.1