MiMeDB: Showing metabocard for L-Threonine O-3-phosphate (MMDBc0030319)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 00:03:19 UTC

Update Date

2024-04-30 19:45:06 UTC

Metabolite ID

MMDBc0030319

Metabolite Identification

Common Name

L-Threonine O-3-phosphate

Description

In E. coli, acid phosphatase / phosphotransferase and alkaline phosphatase are the enzymes that catalyze the chemical reaction L-threonine 3-O-phosphate[periplasmic space] + H2O[periplasmic space] -> L-threonine[periplasmic space] + phosphate[periplasmic space], where L-Threonine O-3-phosphate is a substrate (EcoCyc compound: L-THREONINE-O-3-PHOSPHATE).

Structure

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

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

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
Threonine phosphate	MeSH

Molecular Formula

C₄H₁₀NO₆P

Average Mass

199.0991

Monoisotopic Mass

199.024573569

IUPAC Name

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

Traditional Name

phosphothreonine

CAS Registry Number

1114-81-4

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

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
Phosphoethanolamine
Monoalkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Fatty acid
Alkyl phosphate
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Amine
Primary amine
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Primary aliphatic amine
Organic nitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:37525 )
L-threonine derivative (CHEBI:37525 )
O-phosphoamino acid (CHEBI:37525 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	23.5 g/L	ALOGPS
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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9200000000-7e906e7246b3ef636b98	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0002-9110000000-0b27bac67efac2895d49	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-6900000000-6cd4ab972cda9b9e8854	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0pb9-9300000000-7755990490f9b0d090c2	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9100000000-f7e90830423c5451204b	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-6900000000-ad7260fbe15d44575ebf	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9500000000-c0ec684a681c34652a92	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-d20cfbbcad9f78ca2901	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002b-9000000000-9908dfcad99a8b2ecd13	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-9aaf147a652fb60749b4	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0pb9-9510000000-8d5b2fb7fb7bb01b3bec	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9100000000-726f690c1820afc5c14c	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-6ad9948041570cedf47e	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0006977	L-Threonine O-3-phosphate	D-1-Aminopropan-2-ol O-phosphate	Not Available		VMH	30371894
MMDBr0007890	L-Threonine	L-Threonine O-3-phosphate	Not Available		VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	58	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown; Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Bacteria	Firmicutes	171	Human feces; Human ; Human stool; Human saliva	Metabolic reconstruction
Bacteria	Bacteroidetes	62	Human feces; Human	Metabolic reconstruction
Bacteria	Actinobacteria	29	Human feces; Human	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	19	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	3		Metabolic reconstruction
Bacteria	Spirochaetes	1

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Urine	Detected and Quantified	0.036	0.0009	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	7688003
Human Blood	Detected but not Quantified							HMDB

External Links

HMDB ID

HMDB0011185

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

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. doi: 10.1002/bmc.1130070403. [PubMed:7693088 ]

Showing metabocard for L-Threonine O-3-phosphate (MMDBc0030319)

MOL for #<Metabolite:0x0000556b65943f38>

3D MOL for #<Metabolite:0x0000556b65943f38>

3D SDF for #<Metabolite:0x0000556b65943f38>

3D-SDF for #<Metabolite:0x0000556b65943f38>

PDB for #<Metabolite:0x0000556b65943f38>

3D PDB for #<Metabolite:0x0000556b65943f38>

SMILES for #<Metabolite:0x0000556b65943f38>

INCHI for #<Metabolite:0x0000556b65943f38>

Structure for #<Metabolite:0x0000556b65943f38>

3D Structure for #<Metabolite:0x0000556b65943f38>