An official website of the United States government

O-Phospho-DL-serine

PubChem CID
106
Structure
O-Phospho-DL-serine_small.png
O-Phospho-DL-serine_3D_Structure.png
Molecular Formula
Synonyms
  • 17885-08-4
  • dl-O-Phosphoserine
  • O-Phospho-DL-serine
  • DL-Serine dihydrogen phosphate
  • Serophen
Molecular Weight
185.07 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-27
  • Modify:
    2025-01-25
Description
O-phosphoserine is a serine derivative that is serine substituted at the oxygen atom by a phosphono group. It has a role as a human metabolite. It is a non-proteinogenic alpha-amino acid, a serine derivative and an O-phosphoamino acid. It is a conjugate acid of an O-phosphonatooxyserine(2-).
DL-O-Phosphoserine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
dl-O-Phosphoserine has been reported in Mycoplasma gallisepticum, Arabidopsis thaliana, and Claviceps purpurea with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
O-Phospho-DL-serine.png

1.2 3D Conformer

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
H-DL-Ser(PO3H2)-OH
Sequence
X
HELM
PEPTIDE1{[C(C(C(=O)O)N)OP(=O)(O)O]}$$$$
IUPAC
O-phosphono-DL-serine

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

2-amino-3-phosphonooxypropanoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

3.1.2 InChI

InChI=1S/C3H8NO6P/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.3 InChIKey

BZQFBWGGLXLEPQ-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.4 SMILES

C(C(C(=O)O)N)OP(=O)(O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C3H8NO6P
Computed by PubChem 2.2 (PubChem release 2021.10.14)

3.3 Other Identifiers

3.3.1 CAS

3.3.2 European Community (EC) Number

3.3.3 UNII

3.3.4 ChEBI ID

3.3.5 ChEMBL ID

3.3.6 DSSTox Substance ID

3.3.7 HMDB ID

3.3.8 Metabolomics Workbench ID

3.3.9 Nikkaji Number

3.3.10 NSC Number

3.3.11 Wikidata

3.4 Synonyms

3.4.1 MeSH Entry Terms

  • Phosphate, Serine
  • Phosphate, Seryl
  • Phosphorylserine
  • Phosphoserine
  • Serine Phosphate
  • Seryl Phosphate

3.4.2 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
185.07 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
-5.1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
7
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
185.00892397 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
185.00892397 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
130 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
11
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
186
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

4.2 Experimental Properties

4.2.1 Physical Description

Solid

4.2.2 Melting Point

228 °C

4.3 Chemical Classes

4.3.1 Drugs

Pharmaceuticals
S10 | SWISSPHARMA | Pharmaceutical List with Consumption Data | DOI:10.5281/zenodo.2623484

5 Spectral Information

5.1 1D NMR Spectra

5.1.1 1H NMR Spectra

Spectra ID
Instrument Type
Varian
Frequency
500 MHz
Solvent
Water
pH
5.5
Shifts [ppm]:Intensity
4.22:35.98, 3.97:87.74, 4.21:43.60, 3.96:84.46, 3.95:71.96, 4.12:69.30, 4.20:58.26, 4.14:48.21, 4.21:59.03, 3.96:92.67, 4.23:33.20, 4.19:54.37, 4.09:34.60, 4.10:63.50, 4.23:37.82, 4.20:60.18, 4.13:100.00
Thumbnail
Thumbnail

5.1.2 13C NMR Spectra

1 of 2
Source of Sample
Fluka AG, Buchs, Switzerland
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
Bruker HX-90
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
Thumbnail

5.2 2D NMR Spectra

5.2.1 1H-13C NMR Spectra

2D NMR Spectra Type
1H-13C HSQC
Spectra ID
Instrument Type
Bruker
Frequency
600 MHz
Solvent
Water
pH
7.00
Shifts [ppm] (F2:F1):Intensity
3.94:58.53:1.00, 4.06:65.50:0.58, 4.17:65.50:0.65
Thumbnail
Thumbnail

5.3 Mass Spectrometry

5.3.1 GC-MS

Source of Spectrum
NP-3-2464-0
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

5.3.2 MS-MS

1 of 7
View All
Spectra ID
Instrument Type
Quattro_QQQ
Ionization Mode
Positive
Top 5 Peaks

88.297 100

185.999 9.16

70.378 4.83

Thumbnail
Thumbnail
Notes
delivery=Flow_Injectionanalyzer=Triple_Quad
2 of 7
View All
Spectra ID
Instrument Type
Quattro_QQQ
Ionization Mode
Positive
Top 5 Peaks

70.37 100

88.282 64.42

42.662 46.88

Thumbnail
Thumbnail
Notes
delivery=Flow_Injectionanalyzer=Triple_Quad

5.3.3 LC-MS

1 of 17
View All
Authors
da Silva KM, Iturrospe E, van de Lavoir M, Robeyns R, University of Antwerp, Belgium
Instrument
Agilent 6530 QTOF
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
20 eV
Fragmentation Mode
CID
Retention Time
0.359 min
Precursor m/z
186.0162
Precursor Adduct
[M+H]+
Top 5 Peaks

42.0344 999

88.039 762

70.0297 566

114.0087 21

106.0418 2

Thumbnail
Thumbnail
License
CC BY
2 of 17
View All
Authors
da Silva KM, Iturrospe E, van de Lavoir M, Robeyns R, University of Antwerp, Belgium
Instrument
Agilent 6530 QTOF
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
10 eV
Fragmentation Mode
CID
Retention Time
0.353 min
Precursor m/z
186.0162
Precursor Adduct
[M+H]+
Top 5 Peaks

88.0383 999

70.0286 224

42.0341 202

140.0105 25

Thumbnail
Thumbnail
License
CC BY

5.3.4 Other MS

1 of 2
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
184.001
Instrument
qTof
Ionization Mode
negative
Top 5 Peaks

78.959717 100

96.972252 21.60

96.969467 20.09

78.974777 8.16

96.976433 6.19

Thumbnail
Thumbnail
2 of 2
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
184.002
Instrument
Orbitrap
Ionization Mode
negative
Top 5 Peaks

96.968231 100

78.957741 28.41

156.953979 4.17

140.959488 2.83

184.949387 2.33

Thumbnail
Thumbnail

5.4 IR Spectra

5.4.1 FTIR Spectra

Technique
KBr WAFER
Source of Sample
Fluka Chemie AG, Buchs, Switzerland
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

7 Chemical Vendors

8 Food Additives and Ingredients

8.1 Associated Foods

9 Pharmacology and Biochemistry

9.1 Human Metabolite Information

9.1.1 Tissue Locations

  • Epidermis
  • Testis

9.1.2 Cellular Locations

Cytoplasm

9.2 Biochemical Reactions

10 Use and Manufacturing

10.1 Uses

Use (kg; approx.) in Germany (2009): >1000

Consumption (g per capita; approx.) in Germany (2009): 0.0122

Excretion rate: 1

Calculated removal (%): 75.1

11 Safety and Hazards

11.1 Hazards Identification

11.1.1 GHS Classification

Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H315 (97.5%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (97.5%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (97.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

11.1.2 Hazard Classes and Categories

Skin Irrit. 2 (97.5%)

Eye Irrit. 2 (97.5%)

STOT SE 3 (97.5%)

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Wiley References

12.5 Chemical Co-Occurrences in Literature

12.6 Chemical-Gene Co-Occurrences in Literature

12.7 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

13.5 Chemical-Gene Co-Occurrences in Patents

14 Interactions and Pathways

14.1 Chemical-Target Interactions

14.2 Pathways

15 Biological Test Results

15.1 BioAssay Results

16 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

17 Classification

17.1 MeSH Tree

17.2 ChEBI Ontology

17.3 ChemIDplus

17.4 UN GHS Classification

17.5 NORMAN Suspect List Exchange Classification

17.6 EPA DSSTox Classification

17.7 LOTUS Tree

17.8 MolGenie Organic Chemistry Ontology

18 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. DTP/NCI
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  6. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  7. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  8. ChEBI
  9. E. coli Metabolome Database (ECMDB)
    LICENSE
    ECMDB is offered to the public as a freely available resource.
    https://ecmdb.ca/citations
  10. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
  11. Yeast Metabolome Database (YMDB)
    LICENSE
    YMDB is offered to the public as a freely available resource.
    http://www.ymdb.ca/downloads
  12. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  13. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  14. Natural Product Activity and Species Source (NPASS)
  15. FooDB
    LICENSE
    FooDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (FooDB) and the original publication.
    https://foodb.ca/about
  16. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  17. Japan Chemical Substance Dictionary (Nikkaji)
  18. MassBank Europe
  19. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  20. Metabolomics Workbench
  21. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    SERINE PHOSPHATE
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  22. SpectraBase
    DL-SERINE, DIHYDROGEN PHOSPHATE (ESTER)
    https://spectrabase.com/spectrum/CgxBWkkoNQW
    DL-SERINE, DIHYDROGEN PHOSPHATE (ESTER)
    https://spectrabase.com/spectrum/LbrgYUV4W9t
  23. Springer Nature
  24. Wikidata
  25. Wiley
  26. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  27. PubChem
  28. GHS Classification (UNECE)
  29. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  30. PATENTSCOPE (WIPO)
CONTENTS