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Showing metabocard for L-Allothreonine (HMDB0004041)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 09:32:39 UTC
Update Date2023-02-21 17:16:51 UTC
HMDB IDHMDB0004041
Secondary Accession Numbers
  • HMDB04041
Metabolite Identification
Common NameL-Allothreonine
DescriptionL-allothreonine is the L-enantiomer of allothreonine. It has a role as an Escherichia coli metabolite and a Saccharomyces cerevisiae metabolite. It is an enantiomer of a D-allothreonine. It is a tautomer of a L-allothreonine zwitterion. Allothreonine is the substrate of the enzyme Serine hydroxymethyltransferase1 (SHMT, EC 2.1.2.1), a human cytoplasmic mRNA binding protein. SHMT uses pyridoxal 5'-phosphate (PLP) and tetrahydropteroylglutamate (H4PteGlu) as coenzymes and catalyzes the reversible interconversion of serine and glycine. In addition to these physiological reactions, SHMT also catalyzes, in the absence of H4PteGlu, the retroaldol cleavage of several 3-hydroxyamino acids, such as allothreonine. Allothreonine is a plant metabolite that appears in the human diet in variable concentrations depending on: plant species, physiological changes during plant growth, senescence, and reactions to environmental stress or to changes due to plant transformation (PMID:10858298 , 10952545 ).
Structure
Data?1676999811
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0004041 (L-Allothreonine)


  Mrv1652308122017452D          

  8  7  0  0  1  0            999 V2000
   28.6880  -12.1837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8301  -12.1837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5446  -10.9461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2591  -13.0087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9736  -11.7712    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   27.2591  -12.1837    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   27.9736  -10.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5446  -11.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  6  0  0  0
  2  8  1  0  0  0  0
  3  8  2  0  0  0  0
  6  4  1  6  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
M  END
Download

3D MOL for HMDB0004041 (L-Allothreonine)

HMDB0004041
     RDKit          3D
L-Allothreonine
 17 16  0  0  0  0  0  0  0  0999 V2000
    1.4434    0.7857   -0.4586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8046    0.0968    0.7312 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6399   -0.8850    1.2589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4754   -0.5725    0.2596 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1793   -1.5699   -0.7662 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4281    0.4344   -0.2493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9132    0.4259   -1.4101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8129    1.4544    0.6063 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7931    1.7859   -0.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7002    0.9243   -1.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3090    0.2069   -0.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5143    0.8223    1.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1100   -1.6075    1.7041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8653   -1.1381    1.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0926   -1.0959   -1.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0166   -2.1897   -0.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5309    2.1220    0.4110 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  1
  3 13  1  0
  4 14  1  1
  5 15  1  0
  5 16  1  0
  8 17  1  0
M  END
Download

3D SDF for HMDB0004041 (L-Allothreonine)


  Mrv1652308122017452D          

  8  7  0  0  1  0            999 V2000
   28.6880  -12.1837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8301  -12.1837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5446  -10.9461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2591  -13.0087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9736  -11.7712    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   27.2591  -12.1837    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   27.9736  -10.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5446  -11.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  6  0  0  0
  2  8  1  0  0  0  0
  3  8  2  0  0  0  0
  6  4  1  6  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004041

> <DATABASE_NAME>
hmdb

> <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-/m0/s1

> <INCHI_KEY>
AYFVYJQAPQTCCC-HRFVKAFMSA-N

> <FORMULA>
C4H9NO3

> <MOLECULAR_WEIGHT>
119.1192

> <EXACT_MASS>
119.058243159

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
11.080603006345182

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S)-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-allothreonine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0004041 (L-Allothreonine)

HMDB0004041
     RDKit          3D
L-Allothreonine
 17 16  0  0  0  0  0  0  0  0999 V2000
    1.4434    0.7857   -0.4586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8046    0.0968    0.7312 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6399   -0.8850    1.2589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4754   -0.5725    0.2596 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1793   -1.5699   -0.7662 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4281    0.4344   -0.2493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9132    0.4259   -1.4101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8129    1.4544    0.6063 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7931    1.7859   -0.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7002    0.9243   -1.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3090    0.2069   -0.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5143    0.8223    1.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1100   -1.6075    1.7041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8653   -1.1381    1.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0926   -1.0959   -1.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0166   -2.1897   -0.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5309    2.1220    0.4110 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  1
  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 HMDB0004041 (L-Allothreonine)

HEADER    PROTEIN                                 12-AUG-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-AUG-20         0                                  
HETATM    1  O   UNK     0      53.551 -22.743   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      48.216 -22.743   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      49.550 -20.433   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      50.884 -24.283   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      52.217 -21.973   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      50.884 -22.743   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      52.217 -20.433   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      49.550 -21.973   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2    8                                                            
CONECT    3    8                                                            
CONECT    4    6                                                            
CONECT    5    1    6    7                                                  
CONECT    6    4    5    8                                                  
CONECT    7    5                                                            
CONECT    8    2    3    6                                                  
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for HMDB0004041 (L-Allothreonine)

COMPND    HMDB0004041
HETATM    1  C1  UNL     1       1.443   0.786  -0.459  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.805   0.097   0.731  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.640  -0.885   1.259  1.00  0.00           O  
HETATM    4  C3  UNL     1      -0.475  -0.572   0.260  1.00  0.00           C  
HETATM    5  N1  UNL     1      -0.179  -1.570  -0.766  1.00  0.00           N  
HETATM    6  C4  UNL     1      -1.428   0.434  -0.249  1.00  0.00           C  
HETATM    7  O2  UNL     1      -1.913   0.426  -1.410  1.00  0.00           O  
HETATM    8  O3  UNL     1      -1.813   1.454   0.606  1.00  0.00           O  
HETATM    9  H1  UNL     1       1.793   1.786  -0.133  1.00  0.00           H  
HETATM   10  H2  UNL     1       0.700   0.924  -1.246  1.00  0.00           H  
HETATM   11  H3  UNL     1       2.309   0.207  -0.852  1.00  0.00           H  
HETATM   12  H4  UNL     1       0.514   0.822   1.515  1.00  0.00           H  
HETATM   13  H5  UNL     1       1.110  -1.608   1.704  1.00  0.00           H  
HETATM   14  H6  UNL     1      -0.865  -1.138   1.131  1.00  0.00           H  
HETATM   15  H7  UNL     1      -0.093  -1.096  -1.682  1.00  0.00           H  
HETATM   16  H8  UNL     1      -1.017  -2.190  -0.819  1.00  0.00           H  
HETATM   17  H9  UNL     1      -2.531   2.122   0.411  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 HMDB0004041 (L-Allothreonine)

C[C@H](O)[C@H](N)C(O)=O
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INCHI for HMDB0004041 (L-Allothreonine)

InChI=1S/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3-/m0/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(2S,3S)-2-Amino-3-hydroxybutanoic acidChEBI
Allo-L-threonineChEBI
ALLO-threonineChEBI
L-Allo-threonineChEBI
(2S,3S)-2-Amino-3-hydroxybutanoateGenerator
D-AllothreonineHMDB
Chemical FormulaC4H9NO3
Average Molecular Weight119.1192
Monoisotopic Molecular Weight119.058243159
IUPAC Name(2S,3S)-2-amino-3-hydroxybutanoic acid
Traditional NameL-allothreonine
CAS Registry Number24830-94-2
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-/m0/s1
InChI KeyAYFVYJQAPQTCCC-HRFVKAFMSA-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 effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point256 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available119.9http://allccs.zhulab.cn/database/detail?ID=AllCCS00002062
Predicted Molecular Properties
PropertyValueSource
Water Solubility477 g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+124.3631661259
DarkChem[M-H]-121.17131661259
DeepCCS[M+H]+124.98630932474
DeepCCS[M-H]-121.1230932474
DeepCCS[M-2H]-158.46930932474
DeepCCS[M+Na]+133.90730932474
AllCCS[M+H]+130.432859911
AllCCS[M+H-H2O]+126.232859911
AllCCS[M+NH4]+134.332859911
AllCCS[M+Na]+135.432859911
AllCCS[M-H]-121.932859911
AllCCS[M+Na-2H]-125.232859911
AllCCS[M+HCOO]-128.832859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.1.06 minutes32390414
Predicted by Siyang on May 30, 20229.3787 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20228.01 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid405.4 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid493.7 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid353.3 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid39.3 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid223.1 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid85.5 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid292.2 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid227.8 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)827.7 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid593.1 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid39.5 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid644.5 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid208.5 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid330.0 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate695.0 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA524.7 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water412.5 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
L-AllothreonineC[C@H](O)[C@H](N)C(O)=O2204.6Standard polar33892256
L-AllothreonineC[C@H](O)[C@H](N)C(O)=O1140.3Standard non polar33892256
L-AllothreonineC[C@H](O)[C@H](N)C(O)=O1720.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
L-Allothreonine,1TMS,isomer #1C[C@H](O[Si](C)(C)C)[C@H](N)C(=O)O1245.8Semi standard non polar33892256
L-Allothreonine,1TMS,isomer #2C[C@H](O)[C@H](N)C(=O)O[Si](C)(C)C1169.6Semi standard non polar33892256
L-Allothreonine,1TMS,isomer #3C[C@H](O)[C@H](N[Si](C)(C)C)C(=O)O1269.5Semi standard non polar33892256
L-Allothreonine,2TMS,isomer #1C[C@H](O[Si](C)(C)C)[C@H](N)C(=O)O[Si](C)(C)C1281.3Semi standard non polar33892256
L-Allothreonine,2TMS,isomer #2C[C@H](O[Si](C)(C)C)[C@H](N[Si](C)(C)C)C(=O)O1344.5Semi standard non polar33892256
L-Allothreonine,2TMS,isomer #3C[C@H](O)[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C1295.4Semi standard non polar33892256
L-Allothreonine,2TMS,isomer #4C[C@H](O)[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1462.8Semi standard non polar33892256
L-Allothreonine,3TMS,isomer #1C[C@H](O[Si](C)(C)C)[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C1409.5Semi standard non polar33892256
L-Allothreonine,3TMS,isomer #1C[C@H](O[Si](C)(C)C)[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C1396.4Standard non polar33892256
L-Allothreonine,3TMS,isomer #1C[C@H](O[Si](C)(C)C)[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C1465.4Standard polar33892256
L-Allothreonine,3TMS,isomer #2C[C@H](O[Si](C)(C)C)[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1535.8Semi standard non polar33892256
L-Allothreonine,3TMS,isomer #2C[C@H](O[Si](C)(C)C)[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1418.8Standard non polar33892256
L-Allothreonine,3TMS,isomer #2C[C@H](O[Si](C)(C)C)[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1539.1Standard polar33892256
L-Allothreonine,3TMS,isomer #3C[C@H](O)[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1489.9Semi standard non polar33892256
L-Allothreonine,3TMS,isomer #3C[C@H](O)[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1417.2Standard non polar33892256
L-Allothreonine,3TMS,isomer #3C[C@H](O)[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1578.1Standard polar33892256
L-Allothreonine,4TMS,isomer #1C[C@H](O[Si](C)(C)C)[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1610.6Semi standard non polar33892256
L-Allothreonine,4TMS,isomer #1C[C@H](O[Si](C)(C)C)[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1526.2Standard non polar33892256
L-Allothreonine,4TMS,isomer #1C[C@H](O[Si](C)(C)C)[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1435.9Standard polar33892256
L-Allothreonine,1TBDMS,isomer #1C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](N)C(=O)O1472.7Semi standard non polar33892256
L-Allothreonine,1TBDMS,isomer #2C[C@H](O)[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C1388.8Semi standard non polar33892256
L-Allothreonine,1TBDMS,isomer #3C[C@H](O)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O1524.1Semi standard non polar33892256
L-Allothreonine,2TBDMS,isomer #1C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C1733.6Semi standard non polar33892256
L-Allothreonine,2TBDMS,isomer #2C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O1786.0Semi standard non polar33892256
L-Allothreonine,2TBDMS,isomer #3C[C@H](O)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1716.7Semi standard non polar33892256
L-Allothreonine,2TBDMS,isomer #4C[C@H](O)[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1898.5Semi standard non polar33892256
L-Allothreonine,3TBDMS,isomer #1C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2028.1Semi standard non polar33892256
L-Allothreonine,3TBDMS,isomer #1C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2022.7Standard non polar33892256
L-Allothreonine,3TBDMS,isomer #1C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1904.4Standard polar33892256
L-Allothreonine,3TBDMS,isomer #2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2173.4Semi standard non polar33892256
L-Allothreonine,3TBDMS,isomer #2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2086.3Standard non polar33892256
L-Allothreonine,3TBDMS,isomer #2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1916.1Standard polar33892256
L-Allothreonine,3TBDMS,isomer #3C[C@H](O)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2113.1Semi standard non polar33892256
L-Allothreonine,3TBDMS,isomer #3C[C@H](O)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2081.0Standard non polar33892256
L-Allothreonine,3TBDMS,isomer #3C[C@H](O)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1946.9Standard polar33892256
L-Allothreonine,4TBDMS,isomer #1C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2414.5Semi standard non polar33892256
L-Allothreonine,4TBDMS,isomer #1C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2327.4Standard non polar33892256
L-Allothreonine,4TBDMS,isomer #1C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1973.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - L-Allothreonine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00xr-8940000000-61137c228f750ff5411e2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-Allothreonine GC-EI-TOF (Non-derivatized)splash10-00xr-8940000000-61137c228f750ff5411e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-Allothreonine GC-EI-TOF (Non-derivatized)splash10-0gb9-0920000000-edebe0b2d1f6b0331fd82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-Allothreonine GC-EI-TOF (Non-derivatized)splash10-0159-0900000000-6a1aac793b872dd501912017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Allothreonine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9000000000-a05d200d324c3242c2392016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Allothreonine GC-MS (2 TMS) - 70eV, Positivesplash10-0002-7910000000-e87d0898bf497885fb9f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Allothreonine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Allothreonine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-014i-1900000000-363df736fd62d53cc4db2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Allothreonine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-00di-9100000000-7f4010640f9aaa91fc322012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Allothreonine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-00di-9000000000-b74fb2510f41c62a6d3e2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Allothreonine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-00di-9000000000-e4e5e42d8f9c5a7e24992012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Allothreonine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-00di-3900000000-3af5982aae7c0d1d4c1d2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Allothreonine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-00di-9100000000-96f9fd8a735417bb1ac52012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Allothreonine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-0ab9-9000000000-eaa990f46fd8a493c0972012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Allothreonine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-0a4i-9000000000-105c4ce290165725b91e2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Allothreonine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-0a4i-9000000000-b63cc65df0fddbb42eb62012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Allothreonine CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positive-QTOFsplash10-00di-0900000000-cc2f28c096c87aa9d2742012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Allothreonine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-00di-9400000000-c73aeffbd76d76ccd3122012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Allothreonine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-0fk9-9700000000-af60cc91d30ce48f55f02012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Allothreonine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-00xr-9500000000-dd28c7e04ef0ceb1e7bb2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Allothreonine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-00xr-9500000000-b69e5e49d69cc04d88f72012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Allothreonine LC-ESI-QQ , negative-QTOFsplash10-014i-1900000000-363df736fd62d53cc4db2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Allothreonine LC-ESI-QQ , negative-QTOFsplash10-00di-9100000000-7f4010640f9aaa91fc322017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Allothreonine LC-ESI-QQ , negative-QTOFsplash10-00di-9000000000-b74fb2510f41c62a6d3e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Allothreonine LC-ESI-QQ , negative-QTOFsplash10-00di-9000000000-e4e5e42d8f9c5a7e24992017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Allothreonine LC-ESI-QTOF , negative-QTOFsplash10-00xr-9500000000-dd28c7e04ef0ceb1e7bb2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Allothreonine 10V, Positive-QTOFsplash10-0uk9-6900000000-d30fcc60bda11aeb88b42016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Allothreonine 20V, Positive-QTOFsplash10-0ab9-9200000000-182ac9ea6ada1c0a3a852016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Allothreonine 40V, Positive-QTOFsplash10-0a4i-9000000000-95f5b00b8a7eea104a342016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Allothreonine 10V, Negative-QTOFsplash10-01b9-6900000000-c89f1ad4eeed98ad609e2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Allothreonine 20V, Negative-QTOFsplash10-0fk9-9400000000-4018f60617aa408e59aa2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Allothreonine 40V, Negative-QTOFsplash10-05fr-9000000000-4dd50d3bdda9c01c92202016-09-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Epidermis
  • Eye Lens
  • Fibroblasts
  • Intestine
  • Pancreas
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
UrineDetected and Quantified0.5 (0.0-1.0) umol/mmol creatinineAdult (>18 years old)Both
Prostate Cancer		 details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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 ]
  2. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  3. 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 ]
Prostate cancer
  1. 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. doi: 10.1038/nature07762. [PubMed:19212411 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023287
KNApSAcK IDC00054661
Chemspider ID89699
KEGG Compound IDC05519
BioCyc IDL-ALLO-THREONINE
BiGG IDNot Available
Wikipedia LinkThreonine
METLIN ID7007
PubChem Compound99289
PDB IDNot Available
ChEBI ID28718
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceShiraiwa, Tadashi; Fukuda, Keiji; Kubo, Motoki. Preparation of optically active allothreonine via optical resolution by replacing crystallization. Chemical & Pharmaceutical Bulletin (2002), 50(2), 287-291.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Baier LJ, Sacchettini JC, Knowler WC, Eads J, Paolisso G, Tataranni PA, Mochizuki H, Bennett PH, Bogardus C, Prochazka M: An amino acid substitution in the human intestinal fatty acid binding protein is associated with increased fatty acid binding, increased fat oxidation, and insulin resistance. J Clin Invest. 1995 Mar;95(3):1281-7. [PubMed:7883976 ]
  2. 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. doi: 10.1038/nature07762. [PubMed:19212411 ]
  3. 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 ]
  4. Wishart MJ, Denu JM, Williams JA, Dixon JE: A single mutation converts a novel phosphotyrosine binding domain into a dual-specificity phosphatase. J Biol Chem. 1995 Nov 10;270(45):26782-5. [PubMed:7592916 ]
  5. Meyer W, Poehling HM, Neurand K: Intraepidermal distribution of free amino acids in porcine skin. J Dermatol Sci. 1991 Sep;2(5):383-92. [PubMed:1742249 ]
  6. Farhana L, Dawson MI, Huang Y, Zhang Y, Rishi AK, Reddy KB, Freeman RS, Fontana JA: Apoptosis signaling by the novel compound 3-Cl-AHPC involves increased EGFR proteolysis and accompanying decreased phosphatidylinositol 3-kinase and AKT kinase activities. Oncogene. 2004 Mar 11;23(10):1874-84. [PubMed:14981538 ]
  7. Parimi PS, Gruca LL, Kalhan SC: Metabolism of threonine in newborn infants. Am J Physiol Endocrinol Metab. 2005 Dec;289(6):E981-5. Epub 2005 Jul 19. [PubMed:16030066 ]
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