NP-MRD: Showing NP-Card for 4-fluoro-threonine (NP0019327)

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Record Information

Version

2.0

Created at

2021-01-06 04:52:23 UTC

Updated at

2021-07-15 17:30:40 UTC

NP-MRD ID

NP0019327

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-fluoro-threonine

Provided By

NPAtlas

Description

4-fluoro-threonine is found in Streptomyces asterosporus, Streptomyces cattleya and Streptomyces xinghaiensis. 4-fluoro-threonine was first documented in 1986 (PMID: 3082840). Based on a literature review very few articles have been published on 4-fluoro-L-threonine (PMID: 25728393).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242120153D          

 17 16  0  0  0  0            999 V2000
    0.1409    1.4714   -1.1191 N   0  0  2  0  0  0  0  0  0  0  0  0
    0.3874    0.6725    0.0669 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5520   -0.2150   -0.0987 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1858   -0.2027   -1.1776 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9621   -1.0621    0.9104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8562   -0.0690    0.4967 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6128   -0.8327    1.6356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4067   -0.9538   -0.5915 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7388   -0.2063   -1.7049 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.8366    2.2399   -1.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8407    1.8279   -1.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5947    1.4169    0.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9189   -1.3890    1.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6223    0.6857    0.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4027   -0.2028    2.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7446   -1.7824   -0.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3537   -1.3983   -0.2221 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  1  0  0  0
  7 15  1  0  0  0  0
  8 16  1  0  0  0  0
  8 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0019327

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H8FNO3/c5-1-2(7)3(6)4(8)9/h2-3,7H,1,6H2,(H,8,9)/t2-,3+/m1/s1

> <INCHI_KEY>
GTFWIYJIEXNAOL-GBXIJSLDSA-N

> <FORMULA>
C4H8FNO3

> <MOLECULAR_WEIGHT>
137.11

> <EXACT_MASS>
137.048821285

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
11.234829796482197

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-3.10

> <JCHEM_LOGP>
-3.627040033000521

> <ALOGPS_LOGS>
-0.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.559720892505446

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9614039470323021

> <JCHEM_PKA_STRONGEST_BASIC>
8.913931920902582

> <JCHEM_POLAR_SURFACE_AREA>
83.55000000000001

> <JCHEM_REFRACTIVITY>
26.311399999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-fluorothreonine

> <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       0.141   1.471  -1.119  0.00  0.00           N+0
HETATM    2  C   UNK     0       0.387   0.673   0.067  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.552  -0.215  -0.099  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.186  -0.203  -1.178  0.00  0.00           O+0
HETATM    5  O   UNK     0       1.962  -1.062   0.910  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.856  -0.069   0.497  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.613  -0.833   1.636  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.407  -0.954  -0.592  0.00  0.00           C+0
HETATM    9  F   UNK     0      -1.739  -0.206  -1.705  0.00  0.00           F+0
HETATM   10  H   UNK     0       0.837   2.240  -1.228  0.00  0.00           H+0
HETATM   11  H   UNK     0      -0.841   1.828  -1.143  0.00  0.00           H+0
HETATM   12  H   UNK     0       0.595   1.417   0.890  0.00  0.00           H+0
HETATM   13  H   UNK     0       2.919  -1.389   1.013  0.00  0.00           H+0
HETATM   14  H   UNK     0      -1.622   0.686   0.764  0.00  0.00           H+0
HETATM   15  H   UNK     0      -0.403  -0.203   2.363  0.00  0.00           H+0
HETATM   16  H   UNK     0      -0.745  -1.782  -0.855  0.00  0.00           H+0
HETATM   17  H   UNK     0      -2.354  -1.398  -0.222  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                                                            
CONECT   10    1                                                            
CONECT   11    1                                                            
CONECT   12    2                                                            
CONECT   13    5                                                            
CONECT   14    6                                                            
CONECT   15    7                                                            
CONECT   16    8                                                            
CONECT   17    8                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2S,3S)-2-Amino-4-fluoro-3-hydroxybutanoic acid	ChEBI
4-Fluorothreonine	ChEBI
(2S,3S)-2-Amino-4-fluoro-3-hydroxybutanoate	Generator

Chemical Formula

C₄H₈FNO₃

Average Mass

137.1100 Da

Monoisotopic Mass

137.04882 Da

IUPAC Name

(2S,3S)-2-amino-4-fluoro-3-hydroxybutanoic acid

Traditional Name

4-fluorothreonine

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C4H8FNO3/c5-1-2(7)3(6)4(8)9/h2-3,7H,1,6H2,(H,8,9)/t2-,3+/m1/s1

InChI Key

GTFWIYJIEXNAOL-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 calvus	LOTUS Database	35616633
Streptomyces cattleya	NPAtlas	3082840
Streptomyces xinghaiensis	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	-3.1	ALOGPS
logP	-3.6	ChemAxon
logS	-0.03	ALOGPS
pKa (Strongest Acidic)	1.96	ChemAxon
pKa (Strongest Basic)	8.91	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	83.55 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	26.31 m³·mol⁻¹	ChemAxon
Polarizability	11.23 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

NPA020062

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

113553

KEGG Compound ID

C15533

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

4-Fluoro-L-threonine

METLIN ID

Not Available

PubChem Compound

128057

PDB ID

Not Available

ChEBI ID

11986

Good Scents ID

Not Available

References

General References

Sanada M, Miyano T, Iwadare S, Williamson JM, Arison BH, Smith JL, Douglas AW, Liesch JM, Inamine E: Biosynthesis of fluorothreonine and fluoroacetic acid by the thienamycin producer, Streptomyces cattleya. J Antibiot (Tokyo). 1986 Feb;39(2):259-65. doi: 10.7164/antibiotics.39.259. [PubMed:3082840 ]
Odar C, Winkler M, Wiltschi B: Fluoro amino acids: a rarity in nature, yet a prospect for protein engineering. Biotechnol J. 2015 Mar;10(3):427-46. doi: 10.1002/biot.201400587. Epub 2015 Mar 2. [PubMed:25728393 ]

Showing NP-Card for 4-fluoro-threonine (NP0019327)

MOL for NP0019327 (4-fluoro-threonine)

3D MOL for NP0019327 (4-fluoro-threonine)

3D SDF for NP0019327 (4-fluoro-threonine)

3D-SDF for NP0019327 (4-fluoro-threonine)

PDB for NP0019327 (4-fluoro-threonine)

3D PDB for NP0019327 (4-fluoro-threonine)

SMILES for NP0019327 (4-fluoro-threonine)

INCHI for NP0019327 (4-fluoro-threonine)

Structure for NP0019327 (4-fluoro-threonine)

3D Structure for NP0019327 (4-fluoro-threonine)