Epoxomicin
PubChem CID
11226684
Structure
Molecular Formula
Synonyms
- epoxomicin
- 134381-21-8
- BU-4061T
- EPOXOMYCIN
- BU 4061T
Molecular Weight
554.7 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2006-10-26
- Modify:2024-12-06
Description
Epoxomicin is a tripeptide consisting of an Ile-Ile-Thr-NH2 sequence N-substituted on the threonamide amidic nitrogen with a (2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-2-yl group and with acetyl and methyl groups on the nitrogen of the isoleucine residue distal to the threonamide; a naturally occurring selective proteasome inhibitor with anti-inflammatory activity. It has a role as a proteasome inhibitor. It is a member of morpholines and a tripeptide.
EPOXOMYCIN is a Protein drug.
Chemical Structure Depiction
Conformer generation is disallowed since too flexible
SVG Image
Sequence
IITL
(2S,3S)-2-[[(2S,3S)-2-[acetyl(methyl)amino]-3-methylpentanoyl]amino]-N-[(2S,3R)-3-hydroxy-1-[[(2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-2-yl]amino]-1-oxobutan-2-yl]-3-methylpentanamide
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
InChI=1S/C28H50N4O7/c1-11-16(5)21(30-27(38)23(17(6)12-2)32(10)19(8)34)25(36)31-22(18(7)33)26(37)29-20(13-15(3)4)24(35)28(9)14-39-28/h15-18,20-23,33H,11-14H2,1-10H3,(H,29,37)(H,30,38)(H,31,36)/t16-,17-,18+,20-,21-,22-,23-,28+/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
DOGIDQKFVLKMLQ-JTHVHQAWSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
CC[C@H](C)[C@@H](C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(C)C)C(=O)[C@]1(CO1)C)NC(=O)[C@H]([C@@H](C)CC)N(C)C(=O)C
Computed by OEChem 2.3.0 (PubChem release 2021.10.14)
C28H50N4O7
Computed by PubChem 2.2 (PubChem release 2021.10.14)
- epoxomicin
- L-threoninamide, N-acetyl-N-methyl-L-isoleucyl-L-isoleucyl-N-((1S)-3-methyl-1-(((2R)-2-methyl-2-oxiranyl)carbonyl)butyl)-
- N-acetyl-N-methyl-L-isoleucyl-L-isoleucyl-N-((1S)-3-methyl-1-(((2R)-2-methyl-2-oxiranyl)carbonyl)butyl)-L-threoninamide
- epoxomicin
- 134381-21-8
- BU-4061T
- EPOXOMYCIN
- BU 4061T
- UNII-Y0900I3U8U
- CHEBI:42265
- Y0900I3U8U
- EPOXOMICIN [MI]
- (2S,3S)-2-[[(2S,3S)-2-[acetyl(methyl)amino]-3-methylpentanoyl]amino]-N-[(2S,3R)-3-hydroxy-1-[[(2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-2-yl]amino]-1-oxobutan-2-yl]-3-methylpentanamide
- DTXSID5044073
- L-threoninamide, N-acetyl-N-methyl-L-isoleucyl-L-isoleucyl-N-((1S)-3-methyl-1-(((2R)-2-methyl-2-oxiranyl)carbonyl)butyl)-
- N-acetyl-N-methyl-L-isoleucyl-L-isoleucyl-N-((1S)-3-methyl-1-(((2R)-2-methyl-2-oxiranyl)carbonyl)butyl)-L-threoninamide
- N-Acetyl-N-methyl-L-isoleucyl-L-isoleucyl-N-(3-methyl-1-((2-methyloxiranyl)carbonyl)butyl)-L-threoninamide
- (2R,3S)-2-[acetyl(methyl)amino]-N-[(2S,3S)-1-{[(2S,3R)-3-hydroxy-1-({(2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-2-yl}amino)-1-oxobutan-2-yl]amino}-3-methyl-1-oxopentan-2-yl]-3-methylpentanamide
- L-Threoninamide, N-acetyl-N-methyl-L-isoleucyl-L-isoleucyl-N-((1S)-3-methyl-1-(((2R)-2-methyloxiranyl)carbonyl)butyl)-
- N-acetyl-N-methyl-L-isoleucyl-L-isoleucyl-N-{(2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-2-yl}-L-threoninamide
- Epoxomicin solution
- (2R,3S)-2-(Acetyl(methyl)amino)-N-((2S,3S)-1-(((2S,3R)-3-hydroxy-1-(((2S)-4-methyl-1-((2R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)amino)-1-oxobutan-2-yl)amino)-3-methyl-1-oxopentan-2-yl)-3-methylpentanamide
- (2S,3S)-2-(((2S,3S)-2-(acetyl(methyl)amino)-3-methylpentanoyl)amino)-N-((2S,3R)-3-hydroxy-1-(((2S)-4-methyl-1-((2R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)amino)-1-oxobutan-2-yl)-3-methylpentanamide
- N-acetyl-N-methyl-L-isoleucyl-L-isoleucyl-N-((2S)-4-methyl-1-((2R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)-L-threoninamide
- N-Acetyl-N-methyl-L-isoleucyl-L-isoleucyl-N-[(1S)-3-methyl-1-[[(2R)-2-methyloxiranyl]carbonyl]butyl]-L-threoninamide
- MFCD03791061
- SCHEMBL73907
- DTXCID80819894
- DOGIDQKFVLKMLQ-JTHVHQAWSA-N
- BCP13740
- EX-A1663
- N-Acetyl-N-methyl-L-isoleucyl-L-isoleucyl-N-((1S)-3-methyl-1-(((2R)-2-methyloxiranyl)carbonyl)butyl)-L-threoninamide
- AKOS025396426
- Epoxomicin, >=95% (HPLC), solid
- CS-3998
- NCGC00389337-01
- NCGC00389337-02
- NCGC00485955-01
- DA-63239
- HY-13821
- MS-30118
- Q5383826
- Y-100034
- (2S,3S)-N-[(1S,2R)-2-hydroxy-1-{[(2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-2-yl]carbamoyl}propyl]-3-methyl-2-[(2S,3S)-3-methyl-2-(N-methylacetamido)pentanamido]pentanamide
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
554.7 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
2.3
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
16
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
554.36794995 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
554.36794995 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
157Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
39
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
895
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
8
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)
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Parent, Connectivity Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
Proteasome Inhibitors
Compounds that inhibit the function or proteolytic action of the PROTEASOME. (See all compounds classified as Proteasome Inhibitors.)
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=DOGIDQKFVLKMLQ-JTHVHQAWSA-N
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- ChemIDplusChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- EPA DSSToxCompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
- FDA Global Substance Registration System (GSRS)LICENSEUnless 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
- ChEBI
- Open TargetsLICENSEDatasets generated by the Open Targets Platform are freely available for download.https://platform-docs.opentargets.org/licence
- ChEMBLLICENSEAccess 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.htmlChEMBL Protein Target Treehttps://www.ebi.ac.uk/chembl/g/#browse/targets
- Comparative Toxicogenomics Database (CTD)LICENSEIt 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
- Japan Chemical Substance Dictionary (Nikkaji)
- Metabolomics Workbench
- Springer Nature
- Thieme ChemistryLICENSEThe 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/
- WikidataEpoxomicinhttps://www.wikidata.org/wiki/Q5383826
- WikipediaEpoxomicinhttps://en.wikipedia.org/wiki/Epoxomicin
- PubChem
- Medical Subject Headings (MeSH)LICENSEWorks 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.htmlProteasome Inhibitorshttps://www.ncbi.nlm.nih.gov/mesh/68061988
- The Natural Products AtlasLICENSEThe Natural Products Atlas is licensed under a Creative Commons Attribution 4.0 International License.https://www.npatlas.org/termsThe Natural Products Atlas Classificationhttps://www.npatlas.org/
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 389690530https://pubchem.ncbi.nlm.nih.gov/substance/389690530
CONTENTS