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Showing NP-Card for 4-hydroxy-4-methylglutamate (NP0326739)

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Record Information
Version1.0
Created at2022-09-12 08:36:54 UTC
Updated at2022-09-12 08:36:54 UTC
NP-MRD IDNP0326739
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-hydroxy-4-methylglutamate
Description(2S,4r)-4-hydroxy-4-methyl-glutamic acid 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. 4-hydroxy-4-methylglutamate is found in Caylusea abyssinica and Reseda luteola. It was first documented in 2022 (PMID: 36070101). Based on a literature review a significant number of articles have been published on (2s,4r)-4-hydroxy-4-methyl-glutamic acid (PMID: 35105225) (PMID: 35907257) (PMID: 35843358) (PMID: 35876282).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0326739 (4-hydroxy-4-methylglutamate)


  Mrv1652309122210362D          

 12 11  0  0  1  0            999 V2000
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9520    0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    2.1434    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4125    2.1434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    3.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
Download

3D MOL for NP0326739 (4-hydroxy-4-methylglutamate)

     RDKit          3D

 23 22  0  0  0  0  0  0  0  0999 V2000
   -2.0416   -1.2733   -0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9866   -0.6731    0.1214 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7418   -1.5726    1.1450 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2805   -0.3836   -0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2987    0.2199    0.3129 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8645    1.4188    0.9091 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5586    0.4784   -0.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0649    1.6084   -0.3984 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1810   -0.5488   -1.0608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4868    0.5966    0.7161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6279    0.7270    1.9524 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7950    1.6400   -0.1392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0790   -2.3895   -0.6424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8633   -1.0956   -1.8463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0535   -0.9194   -0.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1878   -1.2807    1.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0782    0.3297   -1.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6922   -1.2978   -1.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4556   -0.5667    1.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9889    2.2828    0.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0046    1.5193    1.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0010   -1.0489   -0.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6055    2.2290   -0.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  9  1  0
  7  8  2  0
  2 10  1  0
 10 12  1  0
 10 11  2  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  1
  6 20  1  0
  6 21  1  0
  9 22  1  0
 12 23  1  0
M  END
Download

3D SDF for NP0326739 (4-hydroxy-4-methylglutamate)


  Mrv1652309122210362D          

 12 11  0  0  1  0            999 V2000
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9520    0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    2.1434    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4125    2.1434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    3.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0326739

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@](O)(C[C@H](N)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H11NO5/c1-6(12,5(10)11)2-3(7)4(8)9/h3,12H,2,7H2,1H3,(H,8,9)(H,10,11)/t3-,6+/m0/s1

> <INCHI_KEY>
ONTAOGAXMOTXQW-BBIVZNJYSA-N

> <FORMULA>
C6H11NO5

> <MOLECULAR_WEIGHT>
177.156

> <EXACT_MASS>
177.063722458

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
16.049252404026866

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,4S)-4-amino-2-hydroxy-2-methylpentanedioic acid

> <JCHEM_LOGP>
-3.8036008460530093

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.6940483901810186

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8212301313509398

> <JCHEM_PKA_STRONGEST_BASIC>
9.152740155999414

> <JCHEM_POLAR_SURFACE_AREA>
120.85000000000001

> <JCHEM_REFRACTIVITY>
37.449600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,4S)-4-amino-2-hydroxy-2-methylpentanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0326739 (4-hydroxy-4-methylglutamate)

Download
PDB for NP0326739 (4-hydroxy-4-methylglutamate)
HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.644   0.564   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.080   2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.310   4.001   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       0.770   4.001   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       3.080   5.335   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.310   6.668   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.620   5.335   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   10                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    2   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

Download
3D PDB for NP0326739 (4-hydroxy-4-methylglutamate)
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SMILES for NP0326739 (4-hydroxy-4-methylglutamate)
C[C@@](O)(C[C@H](N)C(O)=O)C(O)=O
Download
INCHI for NP0326739 (4-hydroxy-4-methylglutamate)
InChI=1S/C6H11NO5/c1-6(12,5(10)11)2-3(7)4(8)9/h3,12H,2,7H2,1H3,(H,8,9)(H,10,11)/t3-,6+/m0/s1
Download
View in JSmol
Synonyms
ValueSource
(2S,4R)-4-Hydroxy-4-methyl-glutamateGenerator
Chemical FormulaC6H11NO5
Average Mass177.1560 Da
Monoisotopic Mass177.06372 Da
IUPAC Name(2R,4S)-4-amino-2-hydroxy-2-methylpentanedioic acid
Traditional Name(2R,4S)-4-amino-2-hydroxy-2-methylpentanedioic acid
CAS Registry NumberNot Available
SMILES
C[C@@](O)(C[C@H](N)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C6H11NO5/c1-6(12,5(10)11)2-3(7)4(8)9/h3,12H,2,7H2,1H3,(H,8,9)(H,10,11)/t3-,6+/m0/s1
InChI KeyONTAOGAXMOTXQW-BBIVZNJYSA-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
Caylusea abyssinicaLOTUS Database
Reseda luteolaLOTUS Database
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
    • 

  • Amino fatty acid
    • 

  • Branched fatty acid
    • 

  • Hydroxy fatty acid
    • 

  • Short-chain hydroxy acid
    • 

  • Methyl-branched fatty acid
    • 

  • Alpha-hydroxy acid
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Hydroxy acid
    • 

  • Fatty acid
    • 

  • Fatty acyl
    • 

  • Tertiary alcohol
    • 

  • 1,3-aminoalcohol
    • 

  • Amino acid
    • 

  • Carboxylic acid
    • 

  • Primary amine
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Primary aliphatic amine
    • 

  • Organic oxide
    • 

  • Alcohol
    • 

  • Carbonyl group
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Amine
    • 

  • 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-3.8ChemAxon
pKa (Strongest Acidic)1.82ChemAxon
pKa (Strongest Basic)9.15ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area120.85 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity37.45 m³·mol⁻¹ChemAxon
Polarizability16.05 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9249095  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11073946  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Viana EOR, da Silva MJ, da Silva BP, Tinoco LW, Parente JP: Two new triterpenoid saponins from the flowers of Albizia lebbeck. Nat Prod Res. 2022 Feb 1:1-10. doi: 10.1080/14786419.2022.2031184. [PubMed:35105225  ] 
  2. Gaur SS, Annapure US: Untargeted metabolite profiling of Enterococcus villorum SB2, isolated from the vagina of pregnant women, by HR-LCMS. World J Microbiol Biotechnol. 2022 Sep 7;38(12):219. doi:  10.1007/s11274-022-03404-3. [PubMed:36070101  ] 
  3. Yerra S, Pyata KB, Boju S, Sharma HK, Battula VR: Development and validation of a novel stability-indicating reverse phase HPLC method for the determination of sacubitril-valsartan premix stereoisomers: Cellulose tris(4-methyl benzoate) stationary phase. J Sep Sci. 2022 Oct;45(19):3714-3724. doi: 10.1002/jssc.202200363. Epub 2022 Sep  11. [PubMed:35907257  ] 
  4. Othman A, Amen Y, Nagata M, Shimizu K: Undescribed glucosylceramide, flavonol triglycoside, and oleanane saponin from the halophyte Agathophora alopecuroides: Promising candidates for stimulating ceramide synthesis. Phytochemistry. 2022 Oct;202:113320. doi: 10.1016/j.phytochem.2022.113320. Epub  2022 Jul 14. [PubMed:35843358  ] 
  5. Caporale A, O Loughlin J, Ortin Y, Rubini M: A convenient synthetic route to (2S,4S)-methylproline and its exploration for protein engineering of thioredoxin. Org Biomol Chem. 2022 Aug 17;20(32):6324-6328. doi: 10.1039/d2ob01011a. [PubMed:35876282  ] 
  6. LOTUS database [Link]