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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-13 05:42:32 UTC

Update Date

2023-02-21 17:16:49 UTC

HMDB ID

HMDB0003840

Secondary Accession Numbers

HMDB0006407
HMDB03840
HMDB06407

Metabolite Identification

Common Name

Phosphoroselenoic acid

Description

Phosphoroselenoic acid, H3SePO3, is the activated selenium donor compound required for the biosynthesis of selenocysteyl-tRNA, the precursor of specific selenocysteine residues in bacterial and mammalian selenoproteins. Phosphoroselenoic acid is also the selenium donor used to synthesize selenocysteine (Sec), the 21st amino acid, which is co-translationally incorporated into selenoproteins at in-frame UGA codons. A number of enzymes have selenocysteine residues and, in some cases, the residues are located at their active sites. Proteins containing selenocysteine have been described in all three domains of life (PMID: 18156471 ). Selenophosphate synthetase (EC 2.7.9.3, human SPS1, the product of the selD gene) produces monoselenophosphate from selenide and ATP. The SPS1-encoded enzyme depends on a selenium salvage system that recycles L-selenocysteine. Selenophosphate synthetase genes play a role in a cancer cell's response to ionizing radiation and its reaction product, selenophosphate, might be involved in cancer prevention in a p53-dependent manner and could be applied to the development of a novel cancer therapy (PMID: 8986768 , 10609888 , 16786570 ).

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
[p(OH)3Se]	ChEBI
Selenophosphate	ChEBI
Selenophosphoric acid	Generator
Phosphoroselenoate	Generator
Monoselenophosphoric acid	HMDB
SePO3	HMDB
Trihydroxidoselenidophosphorus	HMDB

Chemical Formula

H₃O₃PSe

Average Molecular Weight

160.96

Monoisotopic Molecular Weight

161.898502302

IUPAC Name

hydroxy(selanylidene)phosphonous acid

Traditional Name

selenophosphoric acid

CAS Registry Number

25758-66-1

SMILES

OP(O)(O)=[Se]

InChI Identifier

InChI=1S/H3O3PSe/c1-4(2,3)5/h(H3,1,2,3,5)

InChI Key

JRPHGDYSKGJTKZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of inorganic compounds known as non-metal selenophosphates. These are inorganic compounds in which the largest oxoanion is selenophosphate, and in which the heaviest atom not in an oxoanion is a non-metal element.

Kingdom

Inorganic compounds

Super Class

Mixed metal/non-metal compounds

Class

Other mixed metal/non-metal oxoanionic compounds

Sub Class

Non-metal selenophosphates

Direct Parent

Non-metal selenophosphates

Alternative Parents

Not Available

Substituents

Non-metal selenophosphate

Molecular Framework

Not Available

External Descriptors

phosphoric acid derivative (CHEBI:29269 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0006407)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Selenoamino Acid Metabolism (HMDB: HMDB0006407)
Selenium Metabolism (PathBank: SMP0001908)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-1.1	ChemAxon
pKa (Strongest Acidic)	-6.3	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	26.32 m³·mol⁻¹	ChemAxon
Polarizability	7.23 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	113.546	30932474
DeepCCS	[M-H]-	111.651	30932474
DeepCCS	[M-2H]-	147.178	30932474
DeepCCS	[M+Na]+	121.712	30932474
AllCCS	[M+H]+	137.4	32859911
AllCCS	[M+H-H2O]+	133.5	32859911
AllCCS	[M+NH4]+	141.1	32859911
AllCCS	[M+Na]+	142.2	32859911
AllCCS	[M-H]-	154.3	32859911
AllCCS	[M+Na-2H]-	160.0	32859911
AllCCS	[M+HCOO]-	166.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phosphoroselenoic acid	OP(O)(O)=[Se]	2103.2	Standard polar	33892256
Phosphoroselenoic acid	OP(O)(O)=[Se]	1007.9	Standard non polar	33892256
Phosphoroselenoic acid	OP(O)(O)=[Se]	1275.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phosphoroselenoic acid,1TMS,isomer #1	C[Si](C)(C)OP(O)(O)=[Se]	1316.2	Semi standard non polar	33892256
Phosphoroselenoic acid,1TMS,isomer #1	C[Si](C)(C)OP(O)(O)=[Se]	1052.1	Standard non polar	33892256
Phosphoroselenoic acid,1TMS,isomer #1	C[Si](C)(C)OP(O)(O)=[Se]	1418.4	Standard polar	33892256
Phosphoroselenoic acid,2TMS,isomer #1	C[Si](C)(C)OP(O)(=[Se])O[Si](C)(C)C	1394.7	Semi standard non polar	33892256
Phosphoroselenoic acid,2TMS,isomer #1	C[Si](C)(C)OP(O)(=[Se])O[Si](C)(C)C	1185.0	Standard non polar	33892256
Phosphoroselenoic acid,2TMS,isomer #1	C[Si](C)(C)OP(O)(=[Se])O[Si](C)(C)C	1274.4	Standard polar	33892256
Phosphoroselenoic acid,3TMS,isomer #1	C[Si](C)(C)OP(=[Se])(O[Si](C)(C)C)O[Si](C)(C)C	1469.9	Semi standard non polar	33892256
Phosphoroselenoic acid,3TMS,isomer #1	C[Si](C)(C)OP(=[Se])(O[Si](C)(C)C)O[Si](C)(C)C	1301.1	Standard non polar	33892256
Phosphoroselenoic acid,3TMS,isomer #1	C[Si](C)(C)OP(=[Se])(O[Si](C)(C)C)O[Si](C)(C)C	1201.6	Standard polar	33892256
Phosphoroselenoic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(O)(O)=[Se]	1562.0	Semi standard non polar	33892256
Phosphoroselenoic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(O)(O)=[Se]	1289.9	Standard non polar	33892256
Phosphoroselenoic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(O)(O)=[Se]	1601.5	Standard polar	33892256
Phosphoroselenoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(O)(=[Se])O[Si](C)(C)C(C)(C)C	1873.4	Semi standard non polar	33892256
Phosphoroselenoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(O)(=[Se])O[Si](C)(C)C(C)(C)C	1629.1	Standard non polar	33892256
Phosphoroselenoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(O)(=[Se])O[Si](C)(C)C(C)(C)C	1562.8	Standard polar	33892256
Phosphoroselenoic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=[Se])(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2136.6	Semi standard non polar	33892256
Phosphoroselenoic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=[Se])(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1938.4	Standard non polar	33892256
Phosphoroselenoic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=[Se])(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1585.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phosphoroselenoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-08fr-1900000000-8bbadba0caff6a2e9bfc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phosphoroselenoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phosphoroselenoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphoroselenoic acid 10V, Negative-QTOF	splash10-03di-1900000000-7c4cc2e6d42e57db69e1	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphoroselenoic acid 20V, Negative-QTOF	splash10-004i-9400000000-26abcaf5c7c97fc49c19	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphoroselenoic acid 40V, Negative-QTOF	splash10-03di-3900000000-93b2ddc3ff356009e71c	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphoroselenoic acid 10V, Negative-QTOF	splash10-03di-0900000000-7a29d9af6cc1eab8dbe9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphoroselenoic acid 20V, Negative-QTOF	splash10-03di-0900000000-7a29d9af6cc1eab8dbe9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphoroselenoic acid 40V, Negative-QTOF	splash10-03di-0900000000-7a29d9af6cc1eab8dbe9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphoroselenoic acid 10V, Positive-QTOF	splash10-03di-0900000000-1f4443872a69e75b6bdb	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphoroselenoic acid 20V, Positive-QTOF	splash10-03di-0900000000-080a642c7d3be639b5e4	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphoroselenoic acid 40V, Positive-QTOF	splash10-03di-1900000000-3869630825a1dc7ee071	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphoroselenoic acid 10V, Positive-QTOF	splash10-03di-0900000000-dc2cdaa153ba7c67cfd0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphoroselenoic acid 20V, Positive-QTOF	splash10-03di-0900000000-c3c8ecde54e023841cfc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphoroselenoic acid 40V, Positive-QTOF	splash10-0006-2900000000-6b17f7962c7285173eb8	2021-09-23	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Selenocompound metabolism	Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023234

KNApSAcK ID

Not Available

Chemspider ID

1061

KEGG Compound ID

C05172

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1092

PDB ID

Not Available

ChEBI ID

29269

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Ephraim, F.; Majler, E. Selenophosphates. Berichte der Deutschen Chemischen Gesellschaft (1910), 43 277-85.

Material Safety Data Sheet (MSDS)

Not Available

General References

Guimaraes MJ, Peterson D, Vicari A, Cocks BG, Copeland NG, Gilbert DJ, Jenkins NA, Ferrick DA, Kastelein RA, Bazan JF, Zlotnik A: Identification of a novel selD homolog from eukaryotes, bacteria, and archaea: is there an autoregulatory mechanism in selenocysteine metabolism? Proc Natl Acad Sci U S A. 1996 Dec 24;93(26):15086-91. [PubMed:8986768 ]
Lacourciere GM: Biosynthesis of selenophosphate. Biofactors. 1999;10(2-3):237-44. [PubMed:10609888 ]
Chung HJ, Yoon SI, Shin SH, Koh YA, Lee SJ, Lee YS, Bae S: p53-Mediated enhancement of radiosensitivity by selenophosphate synthetase 1 overexpression. J Cell Physiol. 2006 Oct;209(1):131-41. [PubMed:16786570 ]
Lobanov AV, Hatfield DL, Gladyshev VN: Selenoproteinless animals: selenophosphate synthetase SPS1 functions in a pathway unrelated to selenocysteine biosynthesis. Protein Sci. 2008 Jan;17(1):176-82. [PubMed:18156471 ]

Enzymes

Enzyme Details

1. Selenide, water dikinase 1

General function:: Involved in catalytic activity
Specific function:: Synthesizes selenophosphate from selenide and ATP.
Gene Name:: SEPHS1
Uniprot ID:: P49903
Molecular weight:: 42910.325

Reactions

Adenosine triphosphate + Hydrogen selenide + Water → Adenosine monophosphate + Phosphoroselenoic acid + Phosphate	details

Enzyme Details

2. Selenide, water dikinase 2

General function:: Involved in catalytic activity
Specific function:: Synthesizes selenophosphate from selenide and ATP.
Gene Name:: SEPHS2
Uniprot ID:: Q99611
Molecular weight:: 47304.695

Reactions

Adenosine triphosphate + Hydrogen selenide + Water → Adenosine monophosphate + Phosphoroselenoic acid + Phosphate	details

Enzyme Details

3. O-phosphoseryl-tRNA(Sec) selenium transferase

General function:: Involved in catalytic activity
Specific function:: Converts O-phosphoseryl-tRNA(Sec) to selenocysteinyl-tRNA(Sec) required for selenoprotein biosynthesis.
Gene Name:: SEPSECS
Uniprot ID:: Q9HD40
Molecular weight:: 55725.69

Reactions

O-phospho-L-seryl-tRNA(Sec) + Phosphoroselenoic acid → L-selenocysteinyl-tRNA(Sec) + Phosphate	details
O-Phosphoseryl-tRNA(Sec) + Phosphoroselenoic acid + Water → L-Selenocysteinyl-tRNA(Sec) + Phosphate	details

Showing metabocard for Phosphoroselenoic acid (HMDB0003840)

MOL for HMDB0003840 (Phosphoroselenoic acid)

3D MOL for HMDB0003840 (Phosphoroselenoic acid)

3D SDF for HMDB0003840 (Phosphoroselenoic acid)

3D-SDF for HMDB0003840 (Phosphoroselenoic acid)

PDB for HMDB0003840 (Phosphoroselenoic acid)

3D PDB for HMDB0003840 (Phosphoroselenoic acid)

SMILES for HMDB0003840 (Phosphoroselenoic acid)

INCHI for HMDB0003840 (Phosphoroselenoic acid)

Structure for HMDB0003840 (Phosphoroselenoic acid)

3D Structure for HMDB0003840 (Phosphoroselenoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra

Enzymes

Reactions

Reactions

Reactions