NP-MRD: Showing NP-Card for (2s,4s)-4-amino-2-hydroxy-2-methylpentanedioic acid (NP0150433)

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Record Information

Version

2.0

Created at

2022-09-02 06:32:14 UTC

Updated at

2022-09-02 06:32:14 UTC

NP-MRD ID

NP0150433

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,4s)-4-amino-2-hydroxy-2-methylpentanedioic acid

Description

4-Hydroxy-4-methylglutamate 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 a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. (2s,4s)-4-amino-2-hydroxy-2-methylpentanedioic acid is found in Apis cerana, Caylusea abyssinica, Daphnia pulex, Polystichum acrostichoides, Reseda luteola and Trypanosoma brucei. Based on a literature review very few articles have been published on 4-hydroxy-4-methylglutamate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-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

View in JSmol

Synonyms

Value	Source
4-Hydroxy-4-methylglutamic acid	Generator

Chemical Formula

C₆H₁₁NO₅

Average Mass

177.1560 Da

Monoisotopic Mass

177.06372 Da

IUPAC Name

(2S,4S)-4-amino-2-hydroxy-2-methylpentanedioic acid

Traditional Name

4-hydroxy-4-methylglutamate

CAS Registry Number

Not 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 Key

ONTAOGAXMOTXQW-DZSWIPIPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633
Caylusea abyssinica	LOTUS Database	35616633
Daphnia pulex	LOTUS Database	35616633
Polystichum acrostichoides	LOTUS Database	35616633
Reseda luteola	LOTUS Database	35616633
Trypanosoma brucei	LOTUS Database	35616633

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Amino fatty acid
Branched fatty acid
Methyl-branched fatty acid
Short-chain hydroxy acid
Hydroxy fatty acid
Alpha-hydroxy acid
Fatty acyl
Fatty acid
Dicarboxylic acid or derivatives
Hydroxy acid
1,3-aminoalcohol
Tertiary alcohol
Amino acid
Carboxylic acid
Organic nitrogen compound
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Amine
Organic oxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

tertiary alcohol (CHEBI:1848 )
non-proteinogenic L-alpha-amino acid (CHEBI:1848 )
amino dicarboxylic acid (CHEBI:1848 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-3.6	ALOGPS
logP	-3.8	ChemAxon
logS	-0.09	ALOGPS
pKa (Strongest Acidic)	1.82	ChemAxon
pKa (Strongest Basic)	9.15	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	120.85 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	37.45 m³·mol⁻¹	ChemAxon
Polarizability	15.88 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00052714

Chemspider ID

389724

KEGG Compound ID

C06034

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440894

PDB ID

Not Available

ChEBI ID

1848

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,4s)-4-amino-2-hydroxy-2-methylpentanedioic acid (NP0150433)

MOL for NP0150433 ((2s,4s)-4-amino-2-hydroxy-2-methylpentanedioic acid)

3D MOL for NP0150433 ((2s,4s)-4-amino-2-hydroxy-2-methylpentanedioic acid)

3D SDF for NP0150433 ((2s,4s)-4-amino-2-hydroxy-2-methylpentanedioic acid)

3D-SDF for NP0150433 ((2s,4s)-4-amino-2-hydroxy-2-methylpentanedioic acid)

PDB for NP0150433 ((2s,4s)-4-amino-2-hydroxy-2-methylpentanedioic acid)

3D PDB for NP0150433 ((2s,4s)-4-amino-2-hydroxy-2-methylpentanedioic acid)

SMILES for NP0150433 ((2s,4s)-4-amino-2-hydroxy-2-methylpentanedioic acid)

INCHI for NP0150433 ((2s,4s)-4-amino-2-hydroxy-2-methylpentanedioic acid)

Structure for NP0150433 ((2s,4s)-4-amino-2-hydroxy-2-methylpentanedioic acid)

3D Structure for NP0150433 ((2s,4s)-4-amino-2-hydroxy-2-methylpentanedioic acid)