NP-MRD: Showing NP-Card for O-Phospho-DL-threonine (NP0002825)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2020-11-23 19:41:23 UTC

Updated at

2021-08-12 19:52:15 UTC

NP-MRD ID

NP0002825

Secondary Accession Numbers

None

Natural Product Identification

Common Name

O-Phospho-DL-threonine

Provided By

BMRB

Description

O-Phosphothreonine, also known as L-threonine phosphate, 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. O-Phosphothreonine exists in all living organisms, ranging from bacteria to humans. O-Phosphothreonine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. O-Phospho-DL-threonine is found in Daphnia pulex and Medicago sativa. It was first documented in 1993 (PMID: 7693088). Based on a literature review a significant number of articles have been published on O-Phosphothreonine (PMID: 17984079) (PMID: 11782793) (PMID: 15022197) (PMID: 15745821).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


     RDKit          2D

 22 21  0  0  0  0  0  0  0  0999 V2000
    1.6863   -1.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4068   -0.3136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3762   -1.5930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8757   -1.5546    0.0000 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.9141   -3.0541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8373   -0.0551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3752   -1.5162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1898    0.9658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4693    0.1828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0896    1.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4849    1.1983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0512    3.2483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9033   -2.3760    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2545   -0.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8607   -2.0297    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9585    0.3076    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1167    0.7279    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0917   -0.1984    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9728    2.2453    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7871    0.8993    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9709   -1.2308    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3306    4.0313    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  4  3  1  6
  4  5  2  0
  4  6  1  0
  4  7  1  0
  2  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
  1 13  1  6
  1 14  1  0
  1 15  1  0
  2 16  1  6
  6 17  1  0
  7 18  1  0
  8 19  1  6
  9 20  1  0
  9 21  1  0
 12 22  1  0
M  END
> <DATABASE_ID>
NP0002825

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H10NO6P/c1-2(3(5)4(6)7)11-12(8,9)10/h2-3H,5H2,1H3,(H,6,7)(H2,8,9,10)/t2-,3+/m1/s1

> <INCHI_KEY>
USRGIUJOYOXOQJ-GBXIJSLDSA-N

> <FORMULA>
C4H10NO6P

> <MOLECULAR_WEIGHT>
199.0991

> <EXACT_MASS>
199.024573569

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
15.432093653557242

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R)-2-amino-3-(phosphonooxy)butanoic acid

> <ALOGPS_LOGP>
-1.86

> <JCHEM_LOGP>
-2.7024999243079155

> <ALOGPS_LOGS>
-0.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.1480381470609275

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2107285190080166

> <JCHEM_PKA_STRONGEST_BASIC>
9.465326155390212

> <JCHEM_POLAR_SURFACE_AREA>
130.08

> <JCHEM_REFRACTIVITY>
37.3327

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.35e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phosphothreonine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      13.743  -5.851   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.410  -6.597   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.078  -5.825   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.105  -4.279   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      15.075  -6.597   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      12.410  -8.116   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0      13.769  -4.279   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       9.772  -6.571   0.000  0.00  0.00           O+0
HETATM    9  P   UNK     0       8.440  -5.825   0.000  0.00  0.00           P+0
HETATM   10  O   UNK     0       7.667  -7.157   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       7.081  -5.052   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       9.186  -4.466   0.000  0.00  0.00           O+0
CONECT    1    2    5    7                                                  
CONECT    2    1    3    6                                                  
CONECT    3    2    8    4                                                  
CONECT    4    3                                                            
CONECT    5    1                                                            
CONECT    6    2                                                            
CONECT    7    1                                                            
CONECT    8    3    9                                                       
CONECT    9    8   11   12   10                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R)-2-Amino-3-hydroxybutanoic acid 3-phosphate	ChEBI
L-Threonine O-3-phosphate	ChEBI
L-Threonine phosphate	ChEBI
O3-Phosphothreonine	ChEBI
Phosphothreonine	ChEBI
Threonine phosphate ester	ChEBI
Threoninium dihydrogen phosphate	ChEBI
O-Phospho-L-threonine	Kegg
(2S,3R)-2-Amino-3-hydroxybutanoate 3-phosphate	Generator
(2S,3R)-2-Amino-3-hydroxybutanoic acid 3-phosphoric acid	Generator
L-Threonine O-3-phosphoric acid	Generator
L-Threonine phosphoric acid	Generator
Threonine phosphoric acid ester	Generator
Threoninium dihydrogen phosphoric acid	Generator
Phosphate, threonine	MeSH, HMDB
Threonine phosphate	MeSH, HMDB

Chemical Formula

C₄H₁₀NO₆P

Average Mass

199.0991 Da

Monoisotopic Mass

199.02457 Da

IUPAC Name

(2S,3R)-2-amino-3-(phosphonooxy)butanoic acid

Traditional Name

phosphothreonine

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C4H10NO6P/c1-2(3(5)4(6)7)11-12(8,9)10/h2-3H,5H2,1H3,(H,6,7)(H2,8,9,10)/t2-,3+/m1/s1

InChI Key

USRGIUJOYOXOQJ-GBXIJSLDSA-N

Experimental Spectra

truetrue

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Daphnia pulex	LOTUS Database	35616633
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Medicago sativa	LOTUS Database	35616633
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

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	-1.9	ALOGPS
logP	-2.7	ChemAxon
logS	-0.93	ALOGPS
pKa (Strongest Acidic)	1.21	ChemAxon
pKa (Strongest Basic)	9.47	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	130.08 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	37.33 m³·mol⁻¹	ChemAxon
Polarizability	15.43 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

HMDB0011185

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB027954

KNApSAcK ID

Not Available

Chemspider ID

2497038

KEGG Compound ID

C12147

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Threonine

METLIN ID

Not Available

PubChem Compound

3246323

PDB ID

TPO

ChEBI ID

37525

Good Scents ID

Not Available

References

General References

Kataoka H, Nakai K, Katagiri Y, Makita M: Analysis of free and bound O-phosphoamino acids in urine by gas chromatography with flame photometric detection. Biomed Chromatogr. 1993 Jul-Aug;7(4):184-8. [PubMed:7693088 ]
Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
Arsenov DV, Golubeva MB, Kisel' MA, Konoplya NA, Lyubin GS, Kuz'mitskii BB, Strel'chenok OA: Modification of humoral immune response in C57Bl/6 mice with a complex of alpha-fetoprotein and retinoid acid derivatives. Bull Exp Biol Med. 2001 Oct;132(4):963-5. doi: 10.1023/a:1013615211043. [PubMed:11782793 ]
Iuga A, Brunner E: Phosphorylated amino acids: model compounds for solid-state 31P NMR spectroscopic studies of proteins. Magn Reson Chem. 2004 Apr;42(4):369-72. doi: 10.1002/mrc.1356. [PubMed:15022197 ]
Winum JY, Innocenti A, Gagnard V, Montero JL, Scozzafava A, Vullo D, Supuran CT: Carbonic anhydrase inhibitors. Interaction of isozymes I, II, IV, V, and IX with organic phosphates and phosphonates. Bioorg Med Chem Lett. 2005 Mar 15;15(6):1683-6. doi: 10.1016/j.bmcl.2005.01.049. [PubMed:15745821 ]

Showing NP-Card for O-Phospho-DL-threonine (NP0002825)

MOL for NP0002825 (O-Phospho-DL-threonine)

3D MOL for NP0002825 (O-Phospho-DL-threonine)

3D SDF for NP0002825 (O-Phospho-DL-threonine)

3D-SDF for NP0002825 (O-Phospho-DL-threonine)

PDB for NP0002825 (O-Phospho-DL-threonine)

3D PDB for NP0002825 (O-Phospho-DL-threonine)

SMILES for NP0002825 (O-Phospho-DL-threonine)

INCHI for NP0002825 (O-Phospho-DL-threonine)

Structure for NP0002825 (O-Phospho-DL-threonine)

3D Structure for NP0002825 (O-Phospho-DL-threonine)