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Showing NP-Card for hydroxyglutamic acid (NP0234540)

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Record Information
Version2.0
Created at2022-09-06 16:37:58 UTC
Updated at2022-09-06 16:37:58 UTC
NP-MRD IDNP0234540
Secondary Accession NumbersNone
Natural Product Identification
Common Namehydroxyglutamic acid
Description4-Hydroxy-L-glutamic acid, also known as 4-hydroxy-L-glutamate or erythro-L-bhga, belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Specifically 4-Hydroxy-L-glutamic acid combines with 2-oxoglutarate to produce 4-hydroxy-2-oxoglutarate and glutamate. 4-Hydroxy-L-glutamic acid is an intermediate in the metabolism of gamma-hydroxyglutamic acid. 4-Hydroxy-L-glutamic acid is a very strong basic compound (based on its pKa). 4-Hydroxy-L-glutamic acid exists in all living organisms, ranging from bacteria to humans. Within humans, 4-hydroxy-L-glutamic acid participates in a number of enzymatic reactions. In particular, 4-hydroxy-L-glutamic acid can be biosynthesized from pyrroline hydroxycarboxylic acid through its interaction with the enzyme Delta-1-pyrroline-5-carboxylate dehydrogenase, mitochondrial. In addition, 4-hydroxy-L-glutamic acid can be converted into L-4-hydroxyglutamate semialdehyde through the action of the enzyme proline dehydrogenase 1, mitochondrial. In humans, 4-hydroxy-L-glutamic acid is involved in the metabolic disorder called hyperprolinemia type II. This reaction is catalyzed by 4-hydroxyglutamate aminotransferase (PMID 13948827 ). hydroxyglutamic acid is found in Hemerocallis fulva and Linaria vulgaris. hydroxyglutamic acid was first documented in 1962 (PMID: 13948827). The reaction can be described as: 4-Hydroxy-L-glutamic acid + 2-Oxoglutarate <=> 4-Hydroxy-2-oxoglutarate + L-Glutamate.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0234540 (hydroxyglutamic acid)


  Mrv1652305171806192D          

 11 10  0  0  0  0            999 V2000
    4.6184    2.6664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  6  1  0  0  0  0
 11  8  1  0  0  0  0
M  END
Download

3D MOL for NP0234540 (hydroxyglutamic acid)

     RDKit          3D

 20 19  0  0  0  0  0  0  0  0999 V2000
    0.5407   -1.6400   -0.7269 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0959   -0.3642   -0.3762 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1708    0.7849   -0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0283    0.7883    0.4265 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7061    2.0057    0.1500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9870   -0.3039    0.2541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6694   -1.4683    0.5655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2452   -0.0548   -0.2526 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8320   -0.4469    0.9192 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8607   -1.5636    1.4908 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4621    0.6559    1.4788 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5079   -1.8307   -1.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0041   -2.4407   -0.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9143   -0.1750   -1.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1012    0.9580   -1.5063 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7644    1.7041   -0.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7265    0.8836    1.4992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5858    2.2288   -0.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5387   -0.3270   -1.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4353    0.6057    1.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  8  1  0
  6  7  2  0
  2  9  1  0
  9 11  1  0
  9 10  2  0
  1 12  1  0
  1 13  1  0
  2 14  1  6
  3 15  1  0
  3 16  1  0
  4 17  1  1
  5 18  1  0
  8 19  1  0
 11 20  1  0
M  END
Download

3D SDF for NP0234540 (hydroxyglutamic acid)


  Mrv1652305171806192D          

 11 10  0  0  0  0            999 V2000
    4.6184    2.6664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  6  1  0  0  0  0
 11  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0234540

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CC(O)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H9NO5/c6-2(4(8)9)1-3(7)5(10)11/h2-3,7H,1,6H2,(H,8,9)(H,10,11)

> <INCHI_KEY>
HBDWQSHEVMSFGY-UHFFFAOYSA-N

> <FORMULA>
C5H9NO5

> <MOLECULAR_WEIGHT>
163.129

> <EXACT_MASS>
163.048072394

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
14.24479229894592

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-4-hydroxypentanedioic acid

> <ALOGPS_LOGP>
-3.67

> <JCHEM_LOGP>
-4.246000214409296

> <ALOGPS_LOGS>
-0.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.6117381883773465

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.6839758422188176

> <JCHEM_PKA_STRONGEST_BASIC>
9.160931011999752

> <JCHEM_POLAR_SURFACE_AREA>
120.85000000000001

> <JCHEM_REFRACTIVITY>
32.7363

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.43e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydroxyglutamic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0234540 (hydroxyglutamic acid)

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PDB for NP0234540 (hydroxyglutamic acid)
HEADER    PROTEIN                                 17-MAY-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-MAY-18         0                                  
HETATM    1  N   UNK     0       8.621   4.977   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.954   4.977   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.286   3.437   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.620   1.127   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   10                                                  
CONECT    7    6                                                            
CONECT    8    2    9   11                                                  
CONECT    9    8                                                            
CONECT   10    6                                                            
CONECT   11    8                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for NP0234540 (hydroxyglutamic acid)
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SMILES for NP0234540 (hydroxyglutamic acid)
NC(CC(O)C(O)=O)C(O)=O
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INCHI for NP0234540 (hydroxyglutamic acid)
InChI=1S/C5H9NO5/c6-2(4(8)9)1-3(7)5(10)11/h2-3,7H,1,6H2,(H,8,9)(H,10,11)
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View in JSmol
Synonyms
ValueSource
4-Hydroxy-L-glutamateGenerator
beta-HydroxyglutamateHMDB
beta-Hydroxyglutamic acidHMDB
Erythro-L-bhgaHMDB
Hydroxyglutamic acid, (DL)-isomerHMDB
Hydroxyglutamic acid, erythro-(DL)-isomerHMDB
Hydroxyglutamic acid, erythro-(L)-isomerHMDB
Hydroxyglutamic acid, sodium saltHMDB
Threo-L-bhgaHMDB
Chemical FormulaC5H9NO5
Average Mass163.1290 Da
Monoisotopic Mass163.04807 Da
IUPAC Name2-amino-4-hydroxypentanedioic acid
Traditional Namehydroxyglutamic acid
CAS Registry NumberNot Available
SMILES
NC(CC(O)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C5H9NO5/c6-2(4(8)9)1-3(7)5(10)11/h2-3,7H,1,6H2,(H,8,9)(H,10,11)
InChI KeyHBDWQSHEVMSFGY-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Hemerocallis fulvaLOTUS Database
Linaria vulgarisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentGlutamic acid and derivatives  
Alternative Parents
Substituents
  • Glutamic acid or derivatives
    • 

  • Alpha-amino acid
    • 

  • Amino fatty acid
    • 

  • Hydroxy fatty acid
    • 

  • Short-chain hydroxy acid
    • 

  • Alpha-hydroxy acid
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Hydroxy acid
    • 

  • Fatty acid
    • 

  • Fatty acyl
    • 

  • 1,3-aminoalcohol
    • 

  • Secondary alcohol
    • 

  • Amino acid
    • 

  • Carboxylic acid
    • 

  • Primary amine
    • 

  • Primary aliphatic amine
    • 

  • Organopnictogen compound
    • 

  • Alcohol
    • 

  • Organonitrogen compound
    • 

  • Carbonyl group
    • 

  • Organic oxygen compound
    • 

  • Amine
    • 

  • Organic oxide
    • 

  • Organic nitrogen compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-3.7ALOGPS
logP-4.2ChemAxon
logS-0.34ALOGPS
pKa (Strongest Acidic)1.68ChemAxon
pKa (Strongest Basic)9.16ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area120.85 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity32.74 m³·mol⁻¹ChemAxon
Polarizability14.24 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002273  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022938  
KNApSAcK IDNot Available
Chemspider ID816  
KEGG Compound IDC03079  
BioCyc IDL-ERYTHRO-4-HYDROXY-GLUTAMATE  
BiGG ID1447439  
Wikipedia LinkNot Available
METLIN ID6586  
PubChem Compound5460078  
PDB IDNot Available
ChEBI ID16338  
Good Scents IDNot Available
References
General References
  1. GOLDSTONE A, ADAMS E: Metabolism of gamma-hydroxyglutamic acid. I. Conversion to alpha-hydroxy-gamma-ketoglutarate by purified glutamic-aspartic transaminase to rat liver. J Biol Chem. 1962 Nov;237:3476-85. [PubMed:13948827  ] 
  2. LOTUS database [Link]