MiMeDB: Showing metabocard for O-Phospho-4-hydroxy-L-threonine (MMDBc0029840)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:43:48 UTC

Update Date

2022-08-31 17:19:14 UTC

Metabolite ID

MMDBc0029840

Metabolite Identification

Common Name

O-Phospho-4-hydroxy-L-threonine

Description

O-Phospho-4-hydroxy-L-threonine is involved in the vitamin B6 metabolism system. O-Phospho-4-hydroxy-L-threonine is a precursor for pyridoxine. O-Phospho-4-hydroxy-L-threonine can be converted to 4-hydroxy-L-threonine and 2-Amino-3-oxo-4-phosphonooxybutyrate by threonine synthase [EC:4.2.3.1] and 4-hydroxythreonine-4-phosphate dehydrogenase [EC:1.1.1.262], respectively.

Structure

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


  Mrv1652309042000322D          

 13 12  0  0  1  0            999 V2000
   19.3189   -4.4276    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   18.6044   -4.0151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1754   -3.1900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0319   -4.4276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7464   -3.1900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0334   -4.8401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7314   -3.7131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9064   -5.1420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4609   -5.2526    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1754   -4.0151    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.4609   -4.4276    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.8898   -4.4276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7464   -4.0151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  1  8  2  0  0  0  0
  2 12  1  0  0  0  0
 10  3  1  6  0  0  0
  4 13  1  0  0  0  0
  5 13  2  0  0  0  0
 11  9  1  6  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029840

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H10NO7P/c5-3(4(7)8)2(6)1-12-13(9,10)11/h2-3,6H,1,5H2,(H,7,8)(H2,9,10,11)/t2-,3+/m1/s1

> <INCHI_KEY>
FKHAKIJOKDGEII-GBXIJSLDSA-N

> <FORMULA>
C4H10NO7P

> <MOLECULAR_WEIGHT>
215.0985

> <EXACT_MASS>
215.019488191

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
16.597838646165975

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S)-2-amino-3-hydroxy-4-(phosphonooxy)butanoic acid

> <ALOGPS_LOGP>
-2.40

> <JCHEM_LOGP>
-3.876164191197906

> <ALOGPS_LOGS>
-0.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.0740868709070774

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.313786360081051

> <JCHEM_PKA_STRONGEST_BASIC>
8.926715134721942

> <JCHEM_POLAR_SURFACE_AREA>
150.31

> <JCHEM_REFRACTIVITY>
38.876400000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.27e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(phosphonooxy)-L-threonine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  P   UNK     0      36.062  -8.265   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0      34.728  -7.495   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      32.061  -5.955   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      28.060  -8.265   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      29.393  -5.955   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      37.396  -9.035   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      36.832  -6.931   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      35.292  -9.598   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      30.727  -9.805   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      32.061  -7.495   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.727  -8.265   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      33.394  -8.265   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      29.393  -7.495   0.000  0.00  0.00           C+0
CONECT    1    2    6    7    8                                             
CONECT    2    1   12                                                       
CONECT    3   10                                                            
CONECT    4   13                                                            
CONECT    5   13                                                            
CONECT    6    1                                                            
CONECT    7    1                                                            
CONECT    8    1                                                            
CONECT    9   11                                                            
CONECT   10    3   11   12                                                  
CONECT   11    9   10   13                                                  
CONECT   12    2   10                                                       
CONECT   13    4    5   11                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

Synonyms

Value	Source
4-(Phosphonooxy)-threonine	ChEBI
4-(Phosphonooxy)-L-threonine	Kegg
4-Phosphooxy-L-threonine	Kegg
4-Phosphonooxy-L-threonine	HMDB
4-Phospho-hydroxy-threonine	HMDB
4-(Phosphohydroxy)-L-threonine	HMDB
4-Phosphohydroxythreonine	HMDB
4-Phosphothreonine	HMDB

Molecular Formula

C₄H₁₀NO₇P

Average Mass

215.0985

Monoisotopic Mass

215.019488191

IUPAC Name

(2S,3S)-2-amino-3-hydroxy-4-(phosphonooxy)butanoic acid

Traditional Name

4-(phosphonooxy)-L-threonine

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C4H10NO7P/c5-3(4(7)8)2(6)1-12-13(9,10)11/h2-3,6H,1,5H2,(H,7,8)(H2,9,10,11)/t2-,3+/m1/s1

InChI Key

FKHAKIJOKDGEII-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
Beta-hydroxy acid
Short-chain hydroxy acid
Monoalkyl phosphate
Hydroxy acid
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acid
Amino acid
Secondary alcohol
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Amine
Organooxygen compound
Organonitrogen compound
Primary amine
Primary aliphatic amine
Alcohol
Organic oxygen compound
Organopnictogen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

L-threonine derivative (CHEBI:18336 )
O-phosphoamino acid (CHEBI:18336 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	22.7 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-3.9	ChemAxon
logS	-0.98	ALOGPS
pKa (Strongest Acidic)	1.31	ChemAxon
pKa (Strongest Basic)	8.93	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	150.31 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	38.88 m³·mol⁻¹	ChemAxon
Polarizability	16.6 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-a8f91387710592709ff8	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-01ow-9711000000-89a880807057686a60b1	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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00r2-2920000000-c23edaafe01dd32ccd6a	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9600000000-fd8c6ec273c259b6d693	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9300000000-42e18773c2868e50da83	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03mj-9850000000-0cd651cd24395dbae4a1	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9100000000-a925d7c6b56522b6d34b	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-5c41cf86b2bcca517868	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-2590000000-a9146bba129194b49abb	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9200000000-e8dbc889a8d9573cd396	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001j-9000000000-9eec4757ad69989237c0	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01ta-9030000000-a684f48886db0724b48e	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-177256aadc387d9ad236	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

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
MMDBp0192471	Phosphoserine aminotransferase	Enzyme	Q9Y617	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0007526	O-Phospho-4-hydroxy-L-threonine	2-Amino-3-oxo-4-phosphonooxybutyrate	Not Available		VMH	30371894
MMDBr0008035	1-Deoxy-D-xylulose 5-phosphate	Pyridoxine 5'-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	163	Human feces; Human sputum; Human ; Human unknown; Human pleural fluid plaque; Human feces; pleural fluid plaque; bal; Human stool; Pig ; Human dental plaque; Human nasal swab	Unknown; Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	116	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria	Synergistetes	1		Metabolic reconstruction
Bacteria	Firmicutes	76	Human feces; Human ; Cattle	Metabolic reconstruction
Bacteria	Actinobacteria	21	Human feces; Human ; Human supragingival plaque	Metabolic reconstruction
Bacteria	Fusobacteria	12	Human feces; Human	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0006802

DrugBank ID

DB02609

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB024088

KNApSAcK ID

Not Available

Chemspider ID

389731

KEGG Compound ID

C06055

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440901

PDB ID

Not Available

ChEBI ID

18336

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for O-Phospho-4-hydroxy-L-threonine (MMDBc0029840)

MOL for #<Metabolite:0x00007f66b78b3150>

3D MOL for #<Metabolite:0x00007f66b78b3150>

3D SDF for #<Metabolite:0x00007f66b78b3150>

3D-SDF for #<Metabolite:0x00007f66b78b3150>

PDB for #<Metabolite:0x00007f66b78b3150>

3D PDB for #<Metabolite:0x00007f66b78b3150>

SMILES for #<Metabolite:0x00007f66b78b3150>

INCHI for #<Metabolite:0x00007f66b78b3150>

Structure for #<Metabolite:0x00007f66b78b3150>

3D Structure for #<Metabolite:0x00007f66b78b3150>