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Acetyl hexapeptide-3

PubChem CID
71587772
Structure
Acetyl hexapeptide-3_small.png
Molecular Formula
Synonyms
  • Acetyl hexapeptide-3
  • Acetyl Hexapeptide-8
  • Argireline NP
  • Hexapeptide 3
  • Acetyl hexapeptide 3
Molecular Weight
887.0 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2013-07-08
  • Modify:
    2025-01-18
Description
Argireline has been used in trials studying the treatment of wrinkles.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Acetyl hexapeptide-3.png

1.2 3D Status

Conformer generation is disallowed since too many atoms, too flexible

2 Biologic Description

SVG Image
SVG Image
Sequence
EMQRR

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

(4S)-4-acetamido-5-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-amino-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]hex-5-enoic acid
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

3.1.2 InChI

InChI=1S/C35H62N14O11S/c1-18(20(45-19(2)50)9-12-27(52)53)44-23(10-13-28(54)55)31(58)49-25(14-17-61-3)33(60)48-24(8-11-26(36)51)32(59)47-22(7-5-16-43-35(40)41)30(57)46-21(29(37)56)6-4-15-42-34(38)39/h20-25,44H,1,4-17H2,2-3H3,(H2,36,51)(H2,37,56)(H,45,50)(H,46,57)(H,47,59)(H,48,60)(H,49,58)(H,52,53)(H,54,55)(H4,38,39,42)(H4,40,41,43)/t20-,21-,22-,23-,24-,25-/m0/s1
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

3.1.3 InChIKey

AJLNZWYOJAWBCR-OOPVGHQCSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

3.1.4 SMILES

CC(=O)N[C@@H](CCC(=O)O)C(=C)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C35H62N14O11S
Computed by PubChem 2.1 (PubChem release 2019.06.18)

3.3 Other Identifiers

3.3.1 CAS

616204-22-9

3.3.2 European Community (EC) Number

3.3.3 DrugBank ID

3.3.4 DSSTox Substance ID

3.3.5 Metabolomics Workbench ID

3.3.6 RXCUI

3.3.7 Wikipedia

3.4 Synonyms

3.4.1 MeSH Entry Terms

  • Ac-EEMQRR-NH2
  • acetyl hexapeptide-8
  • acetyl-glutamyl-glutamyl-methionyl-glutaminyl-arginyl-argininamide
  • argireline

3.4.2 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
887.0 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
-5.2
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
14
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
15
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
33
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
886.44432002 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
886.44432002 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
472 Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
61
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
1610
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
6
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 2019.01.04)

4.2 Chemical Classes

4.2.1 Drugs

Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749

4.2.2 Cosmetics

Cosmetic ingredients (Acetyl Hexapeptide-8) -> CIR (Cosmetic Ingredient Review)

6 Chemical Vendors

7 Drug and Medication Information

7.1 FDA National Drug Code Directory

7.2 Drug Labels

Active ingredient and drug
Active ingredient and drug

7.3 Clinical Trials

7.3.1 ClinicalTrials.gov

8 Use and Manufacturing

8.1 Uses

Cosmetic Ingredient Review Link
CIR ingredient: Acetyl Hexapeptide-8
EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125

8.1.1 Household Products

Household & Commercial/Institutional Products

Information on 2 consumer products that contain Acetyl Hexapeptide-8 in the following categories is provided:

• Inside the Home

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

Note
This chemical does not meet GHS hazard criteria for 100% (89 of 89) of all reports. Pictograms displayed are for < 0.1% (0 of 89) of reports that indicate hazard statements.
GHS Hazard Statements

Not Classified

Reported as not meeting GHS hazard criteria by 89 of 89 companies. For more detailed information, please visit ECHA C&L website.

ECHA C&L Notifications Summary

Aggregated GHS information provided per 89 reports by companies from 1 notifications to the ECHA C&L Inventory.

Reported as not meeting GHS hazard criteria per 89 of 89 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 0 notifications provided by 0 of 89 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

Not Classified

10 Literature

10.1 Consolidated References

10.2 NLM Curated PubMed Citations

10.3 Chemical Co-Occurrences in Literature

10.4 Chemical-Gene Co-Occurrences in Literature

10.5 Chemical-Disease Co-Occurrences in Literature

11 Patents

11.1 Depositor-Supplied Patent Identifiers

11.2 Chemical Co-Occurrences in Patents

11.3 Chemical-Disease Co-Occurrences in Patents

11.4 Chemical-Gene Co-Occurrences in Patents

12 Classification

12.1 MeSH Tree

12.2 ChemIDplus

12.3 UN GHS Classification

12.4 EPA CPDat Classification

12.5 NORMAN Suspect List Exchange Classification

12.6 EPA DSSTox Classification

12.7 Consumer Product Information Database Classification

12.8 MolGenie Organic Chemistry Ontology

13 Information Sources

  1. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  2. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  3. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. 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
  5. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  6. Consumer Product Information Database (CPID)
    LICENSE
    Copyright (c) 2024 DeLima Associates. All rights reserved. Unless otherwise indicated, all materials from CPID are copyrighted by DeLima Associates. No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://www.whatsinproducts.com/contents/view/1/6
    Consumer Products Category Classification
    https://www.whatsinproducts.com/
  7. Cosmetic Ingredient Review (CIR)
  8. EPA Chemical and Products Database (CPDat)
  9. DailyMed
  10. Metabolomics Workbench
  11. National Drug Code (NDC) Directory
    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
  12. NLM RxNorm Terminology
    LICENSE
    The RxNorm Terminology is created by the National Library of Medicine (NLM) and is in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from NLM. Credit to the U.S. National Library of Medicine as the source is appreciated but not required. The full RxNorm dataset requires a free license.
    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
  13. 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/
    5-{[1-({1-[(3-carbamoyl-1-{[1-({1-carbamoyl-4-[(diaminomethylidene)amino]butyl}carbamoyl)-4-[(diaminomethylidene)amino]butyl]carbamoyl}propyl)carbamoyl]-3-(methylsulfanyl)propyl}carbamoyl)-3-carboxypropyl]amino}-4-acetamidohex-5-enoic acid
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  14. Wikipedia
  15. PubChem
  16. 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
    acetyl-glutamyl-glutamyl-methionyl-glutaminyl-arginyl-argininamide
    https://www.ncbi.nlm.nih.gov/mesh/67582852
  17. GHS Classification (UNECE)
  18. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS