Showing metabocard for L-Threonine (MMDBc0000053)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:28:40 UTC
Update Date2022-08-30 23:23:38 UTC
Metabolite IDMMDBc0000053
Metabolite Identification
Common NameL-Threonine
DescriptionThreonine 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 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f5abc4a6848>


  Mrv1652309272007332D          

  8  7  0  0  0  0            999 V2000
    0.7145    0.9281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.3094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.3094    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -1.1344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.1031    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    0.9281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  4  5  1  1  0  0  0
  6  4  1  0  0  0  0
  8  6  1  0  0  0  0
  6  7  1  1  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f5abc4a6848>

HMDB0000167
     RDKit          3D
L-Threonine
 17 16  0  0  0  0  0  0  0  0999 V2000
   -1.8249   -0.6671    0.0317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7314    0.1925   -0.5656 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0445    1.5339   -0.5448 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5460   -0.1279    0.1824 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4521    0.2534    1.5719 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7330    0.4408   -0.4653 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5588    1.1725    0.1381 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792    0.1757   -1.8015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4459   -1.3442    0.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3372   -1.2962   -0.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6188   -0.0143    0.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6077   -0.1187   -1.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9660    1.9624    0.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6436   -1.2404    0.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4468    0.3949    1.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0874   -0.5430    2.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1296   -0.7744   -2.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  6
  3 13  1  0
  4 14  1  1
  5 15  1  0
  5 16  1  0
  8 17  1  0
M  END
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3D SDF for #<Metabolite:0x00007f5abc4a6848>


  Mrv1652309272007332D          

  8  7  0  0  0  0            999 V2000
    0.7145    0.9281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.3094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.3094    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -1.1344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.1031    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    0.9281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  4  5  1  1  0  0  0
  6  4  1  0  0  0  0
  8  6  1  0  0  0  0
  6  7  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000053

> <DATABASE_NAME>
MIME

> <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

> <FORMULA>
C4H9NO3

> <MOLECULAR_WEIGHT>
119.1192

> <EXACT_MASS>
119.058243159

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
11.078258022254147

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R)-2-amino-3-hydroxybutanoic acid

> <ALOGPS_LOGP>
-3.01

> <JCHEM_LOGP>
-3.4709635238772347

> <ALOGPS_LOGS>
0.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.953369305664726

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.207432028688761

> <JCHEM_PKA_STRONGEST_BASIC>
9.002504827404067

> <JCHEM_POLAR_SURFACE_AREA>
83.55

> <JCHEM_REFRACTIVITY>
26.4598

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.77e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-threonine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007f5abc4a6848>

HMDB0000167
     RDKit          3D
L-Threonine
 17 16  0  0  0  0  0  0  0  0999 V2000
   -1.8249   -0.6671    0.0317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7314    0.1925   -0.5656 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0445    1.5339   -0.5448 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5460   -0.1279    0.1824 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4521    0.2534    1.5719 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7330    0.4408   -0.4653 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5588    1.1725    0.1381 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792    0.1757   -1.8015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4459   -1.3442    0.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3372   -1.2962   -0.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6188   -0.0143    0.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6077   -0.1187   -1.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9660    1.9624    0.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6436   -1.2404    0.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4468    0.3949    1.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0874   -0.5430    2.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1296   -0.7744   -2.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  6
  3 13  1  0
  4 14  1  1
  5 15  1  0
  5 16  1  0
  8 17  1  0
M  END
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PDB for #<Metabolite:0x00007f5abc4a6848>

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0       1.334   1.732   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334   0.192   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667  -0.578   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000  -0.578   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       0.000  -2.118   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -1.334   0.192   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.334   1.732   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.667  -0.578   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    8    7                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for #<Metabolite:0x00007f5abc4a6848>

COMPND    HMDB0000167
HETATM    1  C1  UNL     1      -1.825  -0.667   0.032  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.731   0.193  -0.566  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.044   1.534  -0.545  1.00  0.00           O  
HETATM    4  C3  UNL     1       0.546  -0.128   0.182  1.00  0.00           C  
HETATM    5  N1  UNL     1       0.452   0.253   1.572  1.00  0.00           N  
HETATM    6  C4  UNL     1       1.733   0.441  -0.465  1.00  0.00           C  
HETATM    7  O2  UNL     1       2.559   1.172   0.138  1.00  0.00           O  
HETATM    8  O3  UNL     1       1.979   0.176  -1.801  1.00  0.00           O  
HETATM    9  H1  UNL     1      -1.446  -1.344   0.824  1.00  0.00           H  
HETATM   10  H2  UNL     1      -2.337  -1.296  -0.715  1.00  0.00           H  
HETATM   11  H3  UNL     1      -2.619  -0.014   0.490  1.00  0.00           H  
HETATM   12  H4  UNL     1      -0.608  -0.119  -1.616  1.00  0.00           H  
HETATM   13  H5  UNL     1      -0.966   1.962   0.325  1.00  0.00           H  
HETATM   14  H6  UNL     1       0.644  -1.240   0.163  1.00  0.00           H  
HETATM   15  H7  UNL     1       1.447   0.395   1.917  1.00  0.00           H  
HETATM   16  H8  UNL     1       0.087  -0.543   2.166  1.00  0.00           H  
HETATM   17  H9  UNL     1       2.130  -0.774  -2.101  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    4   12
CONECT    3   13
CONECT    4    5    6   14
CONECT    5   15   16
CONECT    6    7    7    8
CONECT    8   17
END
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SMILES for #<Metabolite:0x00007f5abc4a6848>

C[C@@H](O)[C@H](N)C(O)=O
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INCHI for #<Metabolite:0x00007f5abc4a6848>

InChI=1S/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3+/m1/s1
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Synonyms
ValueSource
(2S)-ThreonineChEBI
(2S,3R)-(-)-ThreonineChEBI
(2S,3R)-2-Amino-3-hydroxybutanoic acidChEBI
2-Amino-3-hydroxybutyric acidChEBI
L-(-)-ThreonineChEBI
L-2-Amino-3-hydroxybutyric acidChEBI
L-alpha-Amino-beta-hydroxybutyric acidChEBI
L-ThreoninChEBI
TChEBI
ThrChEBI
THREONINEChEBI
(2S,3R)-2-Amino-3-hydroxybutanoateGenerator
2-Amino-3-hydroxybutyrateGenerator
L-2-Amino-3-hydroxybutyrateGenerator
L-a-Amino-b-hydroxybutyrateGenerator
L-a-Amino-b-hydroxybutyric acidGenerator
L-alpha-Amino-beta-hydroxybutyrateGenerator
L-Α-amino-β-hydroxybutyrateGenerator
L-Α-amino-β-hydroxybutyric acidGenerator
(2S,3R)-2-Amino-3-hydroxybutyrateHMDB
(2S,3R)-2-Amino-3-hydroxybutyric acidHMDB
(R-(R*,s*))-2-amino-3-hydroxybutanoateHMDB
(R-(R*,s*))-2-amino-3-hydroxybutanoic acidHMDB
(S)-ThreonineHMDB
2-Amino-3-hydroxybutanoateHMDB
2-Amino-3-hydroxybutanoic acidHMDB
ThreoninHMDB
[R-(R*,s*)]-2-amino-3-hydroxy-butanoateHMDB
[R-(R*,s*)]-2-amino-3-hydroxy-butanoic acidHMDB
[R-(R*,s*)]-2-amino-3-hydroxybutanoateHMDB
[R-(R*,s*)]-2-amino-3-hydroxybutanoic acidHMDB
L ThreonineHMDB
Molecular FormulaC4H9NO3
Average Mass119.1192
Monoisotopic Mass119.058243159
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