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O-benzyl-L-serine

PubChem CID
78457
Structure
O-benzyl-L-serine_small.png
O-benzyl-L-serine_3D_Structure.png
Molecular Formula
Synonyms
  • O-benzyl-L-serine
  • 4726-96-9
  • H-Ser(Bzl)-OH
  • benzylserine
  • (S)-2-Amino-3-(benzyloxy)propanoic acid
Molecular Weight
195.21 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-07-19
  • Modify:
    2025-01-18
Description
O-BENZYL-l-SERINE is a L-alpha-amino acid.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
O-benzyl-L-serine.png

1.2 3D Conformer

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
H-Ser(Bn)-OH
Sequence
X
HELM
PEPTIDE1{[c1ccc(cc1)COC[C@@H](C(=O)O)N]}$$$$
IUPAC
O-benzyl-L-serine

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

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

3.1.2 InChI

InChI=1S/C10H13NO3/c11-9(10(12)13)7-14-6-8-4-2-1-3-5-8/h1-5,9H,6-7,11H2,(H,12,13)/t9-/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.3 InChIKey

IDGQXGPQOGUGIX-VIFPVBQESA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.4 SMILES

C1=CC=C(C=C1)COC[C@@H](C(=O)O)N
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C10H13NO3
Computed by PubChem 2.2 (PubChem release 2021.10.14)

3.3 Other Identifiers

3.3.1 CAS

3.3.3 Deprecated CAS

1445593-41-8, 1682647-45-5, 1683583-31-4, 27485-53-6

3.3.4 European Community (EC) Number

3.3.5 ChEBI ID

3.3.6 DSSTox Substance ID

3.3.7 Metabolomics Workbench ID

3.3.8 Nikkaji Number

3.3.9 Pharos Ligand ID

3.3.10 Wikidata

3.4 Synonyms

3.4.1 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
195.21 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
-2
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
195.08954328 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
195.08954328 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
72.6 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
14
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
178
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
1
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
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 Collision Cross Section

147.84 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

141.17 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

143.46 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Ross et al. JASMS 2022; 33; 1061-1072. DOI:10.1021/jasms.2c00111
142.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

5 Spectral Information

5.1 1D NMR Spectra

5.1.1 13C NMR Spectra

Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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5.2 Mass Spectrometry

5.2.1 GC-MS

1 of 2
NIST Number
231014
Library
Main library
Total Peaks
83
m/z Top Peak
91
m/z 2nd Highest
74
m/z 3rd Highest
89
Thumbnail
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2 of 2
NIST Number
188040
Library
Replicate library
Total Peaks
83
m/z Top Peak
91
m/z 2nd Highest
44
m/z 3rd Highest
108
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5.2.2 MS-MS

1 of 2
NIST Number
1053406
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M+H]+
Precursor m/z
196.0968
Total Peaks
8
m/z Top Peak
91
m/z 2nd Highest
150.1
m/z 3rd Highest
178.1
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2 of 2
NIST Number
1053408
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M-H]-
Precursor m/z
194.0823
Total Peaks
7
m/z Top Peak
107.1
m/z 2nd Highest
77.1
m/z 3rd Highest
105.1
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5.2.3 Other MS

1 of 3
View All
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
196.096817016602
Instrument
Agilent 6550 iFunnel
Instrument Type
Q-TOF
Ionization Mode
ESI
Collision Energy
20
Top 5 Peaks
91.05479 100
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License
CC-BY
2 of 3
View All
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
196.096817016602
Instrument
Agilent 6550 iFunnel
Instrument Type
Q-TOF
Ionization Mode
ESI
Collision Energy
30
Top 5 Peaks

91.05496 100

65.03884 6.56

Thumbnail
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License
CC-BY

5.3 IR Spectra

5.3.1 ATR-IR Spectra

Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Forensic Spectral Research
Source of Sample
Indofine Chemical Company, Inc.
Catalog Number
04-468
Lot Number
12226
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
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5.4 Raman Spectra

Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Indofine Chemical Company, Inc.
Catalog Number
04-468
Lot Number
12226
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
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7 Chemical Vendors

8 Use and Manufacturing

8.1 General Manufacturing Information

EPA TSCA Commercial Activity Status
L-Serine, O-(phenylmethyl)-: ACTIVE

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

Note
This chemical does not meet GHS hazard criteria for 66.7% (2 of 3) of all reports. Pictograms displayed are for 33.3% (1 of 3) of reports that indicate hazard statements.
Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H315 (33.3%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (33.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (33.3%): 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 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 2 of 3 reports by companies. For more detailed information, please visit ECHA C&L website.

There is 1 notification provided by 1 of 3 reports by companies with hazard statement code(s).

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.

9.1.2 Hazard Classes and Categories

Skin Irrit. 2 (33.3%)

Eye Irrit. 2A (33.3%)

STOT SE 3 (33.3%)

10 Literature

10.1 Consolidated References

10.2 Springer Nature References

10.3 Thieme References

10.4 Chemical Co-Occurrences in Literature

10.5 Chemical-Gene Co-Occurrences in Literature

10.6 Chemical-Disease Co-Occurrences in Literature

11 Patents

11.1 Depositor-Supplied Patent Identifiers

11.2 WIPO PATENTSCOPE

11.3 Chemical Co-Occurrences in Patents

11.4 Chemical-Disease Co-Occurrences in Patents

11.5 Chemical-Gene Co-Occurrences in Patents

12 Interactions and Pathways

12.1 Protein Bound 3D Structures

12.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

12.2 Chemical-Target Interactions

13 Biological Test Results

13.1 BioAssay Results

14 Classification

14.1 ChEBI Ontology

14.2 ChemIDplus

14.3 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

14.4 UN GHS Classification

14.5 NORMAN Suspect List Exchange Classification

14.6 CCSBase Classification

14.7 EPA DSSTox Classification

14.8 EPA TSCA and CDR Classification

14.9 EPA Substance Registry Services Tree

14.10 MolGenie Organic Chemistry Ontology

15 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/
    L-Serine, O-(phenylmethyl)-, homopolymer
    https://commonchemistry.cas.org/detail?cas_rn=30916-68-8
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA Chemicals under the TSCA
    L-Serine, O-(phenylmethyl)-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  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. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  7. ChEBI
  8. IUPHAR/BPS Guide to PHARMACOLOGY
    LICENSE
    The Guide to PHARMACOLOGY database is licensed under the Open Data Commons Open Database License (ODbL) https://opendatacommons.org/licenses/odbl/. Its contents are licensed under a Creative Commons Attribution-ShareAlike 4.0 International License (http://creativecommons.org/licenses/by-sa/4.0/)
    https://www.guidetopharmacology.org/about.jsp#license
    Guide to Pharmacology Target Classification
    https://www.guidetopharmacology.org/targets.jsp
  9. Therapeutic Target Database (TTD)
  10. Japan Chemical Substance Dictionary (Nikkaji)
  11. 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
  12. Metabolomics Workbench
  13. 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
    L-Serine, O-(phenylmethyl)-
    http://www.nist.gov/srd/nist1a.cfm
  14. Pharos
    LICENSE
    Data accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.
    https://pharos.nih.gov/about
  15. Protein Data Bank in Europe (PDBe)
  16. RCSB Protein Data Bank (RCSB PDB)
    LICENSE
    Data files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.
    https://www.rcsb.org/pages/policies
  17. SpectraBase
  18. Springer Nature
  19. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  20. Wikidata
  21. PubChem
  22. GHS Classification (UNECE)
  23. 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/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  24. EPA Substance Registry Services
  25. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  26. PATENTSCOPE (WIPO)
CONTENTS