NP-MRD: Showing NP-Card for L-threo-α-amino-β, γ-dihydroxybutyric acid (NP0021678)

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Record Information

Version

2.0

Created at

2021-01-06 06:57:18 UTC

Updated at

2021-07-15 17:36:59 UTC

NP-MRD ID

NP0021678

Secondary Accession Numbers

None

Natural Product Identification

Common Name

L-threo-α-amino-β, γ-dihydroxybutyric acid

Provided By

NPAtlas

Description

L-threo-α-amino-β, γ-dihydroxybutyric acid is found in Streptomyces. Based on a literature review very few articles have been published on 4-Hydroxy-L-threonine.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105173D          

 18 17  0  0  0  0            999 V2000
    1.3553    1.2821    0.7472 N   0  0  2  0  0  0  0  0  0  0  0  0
    0.7217    0.0191    0.4190 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5795   -0.7147   -0.4997 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2473   -1.8410   -0.9218 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7753   -0.1822   -0.9226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6383    0.3471   -0.1302 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3600    1.0438    0.8660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604   -0.8457   -0.4925 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6956   -0.3471   -0.9700 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9261    1.6743    1.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1235    1.9362   -0.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5642   -0.5195    1.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6761   -0.5808   -0.7206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5996    1.0262   -1.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2332    0.5909    1.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0287   -1.4808   -1.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7348   -1.4428    0.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2184    0.0348   -0.2094 H   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  2  0  0  0  0
  3  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  1 10  1  0  0  0  0
  1 11  1  0  0  0  0
  2 12  1  1  0  0  0
  5 13  1  0  0  0  0
  6 14  1  6  0  0  0
  7 15  1  0  0  0  0
  8 16  1  0  0  0  0
  8 17  1  0  0  0  0
  9 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021678

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H9NO4/c5-3(4(8)9)2(7)1-6/h2-3,6-7H,1,5H2,(H,8,9)/t2-,3+/m1/s1

> <INCHI_KEY>
JBNUARFQOCGDRK-GBXIJSLDSA-N

> <FORMULA>
C4H9NO4

> <MOLECULAR_WEIGHT>
135.1186

> <EXACT_MASS>
135.053157781

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
12.037439893689232

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S)-2-amino-3,4-dihydroxybutanoic acid

> <ALOGPS_LOGP>
-3.36

> <JCHEM_LOGP>
-4.517531650626965

> <ALOGPS_LOGS>
0.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.797735282478573

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9232639848113715

> <JCHEM_PKA_STRONGEST_BASIC>
8.62379843972846

> <JCHEM_POLAR_SURFACE_AREA>
103.78

> <JCHEM_REFRACTIVITY>
28.0035

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.57e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydroxythreonine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  N   UNK     0       1.355   1.282   0.747  0.00  0.00           N+0
HETATM    2  C   UNK     0       0.722   0.019   0.419  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.579  -0.715  -0.500  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.247  -1.841  -0.922  0.00  0.00           O+0
HETATM    5  O   UNK     0       2.775  -0.182  -0.923  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.638   0.347  -0.130  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.360   1.044   0.866  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.460  -0.846  -0.493  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.696  -0.347  -0.970  0.00  0.00           O+0
HETATM   10  H   UNK     0       0.926   1.674   1.617  0.00  0.00           H+0
HETATM   11  H   UNK     0       1.123   1.936  -0.041  0.00  0.00           H+0
HETATM   12  H   UNK     0       0.564  -0.520   1.392  0.00  0.00           H+0
HETATM   13  H   UNK     0       3.676  -0.581  -0.721  0.00  0.00           H+0
HETATM   14  H   UNK     0      -0.600   1.026  -1.004  0.00  0.00           H+0
HETATM   15  H   UNK     0      -1.233   0.591   1.737  0.00  0.00           H+0
HETATM   16  H   UNK     0      -1.029  -1.481  -1.283  0.00  0.00           H+0
HETATM   17  H   UNK     0      -1.735  -1.443   0.418  0.00  0.00           H+0
HETATM   18  H   UNK     0      -3.218   0.035  -0.209  0.00  0.00           H+0
CONECT    1    2   10   11                                                  
CONECT    2    1    3    6   12                                             
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3   13                                                       
CONECT    6    2    7    8   14                                             
CONECT    7    6   15                                                       
CONECT    8    6    9   16   17                                             
CONECT    9    8   18                                                       
CONECT   10    1                                                            
CONECT   11    1                                                            
CONECT   12    2                                                            
CONECT   13    5                                                            
CONECT   14    6                                                            
CONECT   15    7                                                            
CONECT   16    8                                                            
CONECT   17    8                                                            
CONECT   18    9                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Hydroxythreonine	ChEBI
alpha-Amino-beta,gamma-dihydroxybutyric acid	MeSH

Chemical Formula

C₄H₉NO₄

Average Mass

135.1186 Da

Monoisotopic Mass

135.05316 Da

IUPAC Name

(2S,3S)-2-amino-3,4-dihydroxybutanoic acid

Traditional Name

hydroxythreonine

CAS Registry Number

Not Available

SMILES

N[C@@H]([C@H](O)CO)C(O)=O

InChI Identifier

InChI=1S/C4H9NO4/c5-3(4(8)9)2(7)1-6/h2-3,6-7H,1,5H2,(H,8,9)/t2-,3+/m1/s1

InChI Key

JBNUARFQOCGDRK-GBXIJSLDSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Streptomyces	NPAtlas	5581354

Chemical Taxonomy

Description

This compound 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
Beta-hydroxy acid
Short-chain hydroxy acid
Hydroxy acid
Fatty acid
1,3-aminoalcohol
1,2-diol
Amino acid
Secondary alcohol
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Primary amine
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Amine
Alcohol
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:28330 )
L-threonine derivative (CHEBI:28330 )
hydroxy-amino acid (CHEBI:28330 )

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	-3.4	ALOGPS
logP	-4.5	ChemAxon
logS	0.42	ALOGPS
pKa (Strongest Acidic)	1.92	ChemAxon
pKa (Strongest Basic)	8.62	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	103.78 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	28 m³·mol⁻¹	ChemAxon
Polarizability	12.04 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

NPAtlas ID

NPA007501

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

167988

KEGG Compound ID

C06056

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

193577

PDB ID

Not Available

ChEBI ID

28330

Good Scents ID

Not Available

References

General References

Showing NP-Card for L-threo-α-amino-β, γ-dihydroxybutyric acid (NP0021678)

MOL for NP0021678 (L-threo-α-amino-β, γ-dihydroxybutyric acid)

3D MOL for NP0021678 (L-threo-α-amino-β, γ-dihydroxybutyric acid)

3D SDF for NP0021678 (L-threo-α-amino-β, γ-dihydroxybutyric acid)

3D-SDF for NP0021678 (L-threo-α-amino-β, γ-dihydroxybutyric acid)

PDB for NP0021678 (L-threo-α-amino-β, γ-dihydroxybutyric acid)

3D PDB for NP0021678 (L-threo-α-amino-β, γ-dihydroxybutyric acid)

SMILES for NP0021678 (L-threo-α-amino-β, γ-dihydroxybutyric acid)

INCHI for NP0021678 (L-threo-α-amino-β, γ-dihydroxybutyric acid)

Structure for NP0021678 (L-threo-α-amino-β, γ-dihydroxybutyric acid)

3D Structure for NP0021678 (L-threo-α-amino-β, γ-dihydroxybutyric acid)