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benzyl N-[1-[(4-fluoro-3-oxobutan-2-yl)amino]-1-oxo-3-phenylpropan-2-yl]carbamate

PubChem CID
122019
Structure
benzyl N-[1-[(4-fluoro-3-oxobutan-2-yl)amino]-1-oxo-3-phenylpropan-2-yl]carbamate_small.png
benzyl N-[1-[(4-fluoro-3-oxobutan-2-yl)amino]-1-oxo-3-phenylpropan-2-yl]carbamate_3D_Structure.png
Molecular Formula
Synonyms
  • Z-FA-FMK
  • 96922-64-4
  • 105637-38-5
  • MDL 201053
  • Zfa-fmk
Molecular Weight
386.4 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2005-08-08
  • Modify:
    2025-01-18
See also: Z-FA-Fmk (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
benzyl N-[1-[(4-fluoro-3-oxobutan-2-yl)amino]-1-oxo-3-phenylpropan-2-yl]carbamate.png

1.2 3D Conformer

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
Cbz-DL-Phe-DL-Ala-CH2F
Sequence
FA

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

benzyl N-[1-[(4-fluoro-3-oxobutan-2-yl)amino]-1-oxo-3-phenylpropan-2-yl]carbamate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.05.07)

3.1.2 InChI

InChI=1S/C21H23FN2O4/c1-15(19(25)13-22)23-20(26)18(12-16-8-4-2-5-9-16)24-21(27)28-14-17-10-6-3-7-11-17/h2-11,15,18H,12-14H2,1H3,(H,23,26)(H,24,27)
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

3.1.3 InChIKey

ASXVEBPEZMSPHB-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

3.1.4 SMILES

CC(C(=O)CF)NC(=O)C(CC1=CC=CC=C1)NC(=O)OCC2=CC=CC=C2
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C21H23FN2O4
Computed by PubChem 2.1 (PubChem release 2021.05.07)

3.3 Other Identifiers

3.3.1 CAS

105637-38-5

3.3.2 ChEMBL ID

3.3.3 DSSTox Substance ID

3.3.4 HMDB ID

3.3.5 Wikidata

3.3.6 Wikipedia

3.4 Synonyms

3.4.1 MeSH Entry Terms

  • benzyloxycarbonyl-Phe-Ala-fluormethylketone
  • benzyloxycarbonylphenylalanyl-alanine fluoromethyl ketone
  • carbobenzoxy-L-phenylalanyl-(D,L)-alanyl fluoromethyl ketone
  • MDL 201053
  • MDL 201053, (R-(R*,S*))-isomer
  • MDL 201053, (S-(R*,R*))-isomer
  • MDL 201117
  • MDL-201053
  • MDL-201117
  • Z-FA-FMK
  • Z-Phe-Ala-CH2F
  • Z-Phe-Ala-FMK
  • Z-Phe-AlaCH2F
  • ZFA-fmk

3.4.2 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
386.4 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
3.3
Reference
Computed by XLogP3 3.0 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Rotatable Bond Count
Property Value
10
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Exact Mass
Property Value
386.16418538 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
386.16418538 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
84.5 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Heavy Atom Count
Property Value
28
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
517
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
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
2
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 2021.05.07)

6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 MeSH Pharmacological Classification

Cysteine Proteinase Inhibitors
Exogenous and endogenous compounds which inhibit CYSTEINE ENDOPEPTIDASES. (See all compounds classified as Cysteine Proteinase Inhibitors.)

8 Associated Disorders and Diseases

9 Literature

9.1 Consolidated References

9.2 NLM Curated PubMed Citations

9.3 Chemical Co-Occurrences in Literature

9.4 Chemical-Gene Co-Occurrences in Literature

9.5 Chemical-Disease Co-Occurrences in Literature

10 Patents

10.1 Depositor-Supplied Patent Identifiers

10.2 WIPO PATENTSCOPE

10.3 Chemical Co-Occurrences in Patents

10.4 Chemical-Disease Co-Occurrences in Patents

10.5 Chemical-Gene Co-Occurrences in Patents

11 Interactions and Pathways

11.1 Chemical-Target Interactions

12 Biological Test Results

12.1 BioAssay Results

13 Classification

13.1 MeSH Tree

13.2 ChemIDplus

13.3 ChEMBL Target Tree

13.4 EPA DSSTox Classification

13.5 PFAS and Fluorinated Organic Compounds in PubChem

13.6 MolGenie Organic Chemistry Ontology

14 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/
    Carbamic acid, [2-[(3-fluoro-1-methyl-2-oxopropyl)amino]-2-oxo-1-(phenylmethyl)ethyl]-, phenylmethyl ester
    https://commonchemistry.cas.org/detail?cas_rn=96922-64-4
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA DSSTox
    2-{[(Benzyloxy)(hydroxy)methylidene]amino}-N-(4-fluoro-3-oxobutan-2-yl)-3-phenylpropanimidic acid
    https://comptox.epa.gov/dashboard/DTXSID60909641
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. 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
  5. 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
  6. 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
  7. Wikidata
    Benzyloxycarbonylphenylalanyl-alanine fluoromethyl ketone
    https://www.wikidata.org/wiki/Q18390589
  8. Wikipedia
  9. PubChem
  10. 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
    Cysteine Proteinase Inhibitors
    https://www.ncbi.nlm.nih.gov/mesh/68015853
  11. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  12. PATENTSCOPE (WIPO)
  13. NCBI
CONTENTS