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Aerucyclamide A

PubChem CID
24970830
Structure
Aerucyclamide A_small.png
Aerucyclamide A_3D_Structure.png
Molecular Formula
Synonyms
  • aerucyclamide A
  • (1S,4S,7R,8S,18R)-4,18-bis[(2S)-butan-2-yl]-7-methyl-6-oxa-13,20-dithia-3,10,17,22,23,24-hexazatetracyclo[17.2.1.15,8.112,15]tetracosa-5(24),12(23),14,19(22)-tetraene-2,9,16-trione
  • (1S,4S,7R,8S,18R)-4,18-bis((2S)-butan-2-yl)-7-methyl-6-oxa-13,20-dithia-3,10,17,22,23,24-hexazatetracyclo(17.2.1.15,8.112,15)tetracosa-5(24),12(23),14,19(22)-tetraene-2,9,16-trione
  • CHEMBL479808
  • CHEBI:184019
Molecular Weight
534.7 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2008-10-20
  • Modify:
    2024-12-07
Description
Aerucyclamide a is a cyclic peptide.
aerucyclamide A has been reported in Microcystis aeruginosa with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Aerucyclamide A.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1S,4S,7R,8S,18R)-4,18-bis[(2S)-butan-2-yl]-7-methyl-6-oxa-13,20-dithia-3,10,17,22,23,24-hexazatetracyclo[17.2.1.15,8.112,15]tetracosa-5(24),12(23),14,19(22)-tetraene-2,9,16-trione
Computed by Lexichem TK 2.7.0 (PubChem release 2021.05.07)

2.1.2 InChI

InChI=1S/C24H34N6O4S2/c1-6-11(3)17-23-30-19(13(5)34-23)22(33)25-8-16-26-14(9-35-16)20(31)29-18(12(4)7-2)24-27-15(10-36-24)21(32)28-17/h9,11-13,15,17-19H,6-8,10H2,1-5H3,(H,25,33)(H,28,32)(H,29,31)/t11-,12-,13+,15+,17-,18+,19-/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.3 InChIKey

VJFRQMMMXJJUSM-VZGZUROSSA-N
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.4 SMILES

CC[C@H](C)[C@H]1C2=N[C@@H]([C@H](O2)C)C(=O)NCC3=NC(=CS3)C(=O)N[C@@H](C4=N[C@H](CS4)C(=O)N1)[C@@H](C)CC
Computed by OEChem 2.3.0 (PubChem release 2021.05.07)

2.2 Molecular Formula

C24H34N6O4S2
Computed by PubChem 2.1 (PubChem release 2021.05.07)

2.3 Other Identifiers

2.3.1 ChEBI ID

2.3.2 ChEMBL ID

2.3.3 DSSTox Substance ID

2.3.4 Metabolomics Workbench ID

2.3.5 Nikkaji Number

2.3.6 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

aerucyclamide A

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
534.7 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
2.9
Reference
Computed by XLogP3 3.0 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Acceptor Count
Property Value
9
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Exact Mass
Property Value
534.20829593 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
534.20829593 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
188Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Heavy Atom Count
Property Value
36
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
930
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
7
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)

3.2 Chemical Classes

Cyclamide
S75 | CyanoMetDB | Comprehensive database of secondary metabolites from cyanobacteria | DOI:10.5281/zenodo.4551528 | DOI:10.1021/np800118g PMID:18558743

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 LC-MS

1 of 12
View All
Authors
E. Janssen [dtc], B. Lauper [com]
Instrument
Q Exactive Plus Orbitrap Thermo Scientific
Instrument Type
LC-ESI-QFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
15 % (nominal)
Fragmentation Mode
HCD
Column Name
XBridge C18 3.5um, 2.1x50mm, Waters
Retention Time
10.697 min
Precursor m/z
535.2156
Precursor Adduct
[M+H]+
Top 5 Peaks

535.2152 999

517.2058 6

Thumbnail
Thumbnail
License
CC BY-SA
2 of 12
View All
Authors
E. Janssen [dtc], B. Lauper [com]
Instrument
Q Exactive Plus Orbitrap Thermo Scientific
Instrument Type
LC-ESI-QFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
30 % (nominal)
Fragmentation Mode
HCD
Column Name
XBridge C18 3.5um, 2.1x50mm, Waters
Retention Time
10.697 min
Precursor m/z
535.2156
Precursor Adduct
[M+H]+
Top 5 Peaks

535.2153 999

517.2048 708

424.1835 277

86.0964 123

490.1936 96

Thumbnail
Thumbnail
License
CC BY-SA

6 Chemical Vendors

7 Literature

7.1 Consolidated References

7.2 NLM Curated PubMed Citations

7.3 Chemical Co-Occurrences in Literature

7.4 Chemical-Gene Co-Occurrences in Literature

7.5 Chemical-Disease Co-Occurrences in Literature

8 Patents

8.1 Depositor-Supplied Patent Identifiers

8.2 Chemical Co-Occurrences in Patents

8.3 Chemical-Disease Co-Occurrences in Patents

9 Biological Test Results

9.1 BioAssay Results

10 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
S75 | CyanoMetDB | Comprehensive database of secondary metabolites from cyanobacteria | DOI:10.5281/zenodo.4551528

11 Classification

11.1 MeSH Tree

11.2 ChEBI Ontology

11.3 NORMAN Suspect List Exchange Classification

11.4 EPA DSSTox Classification

11.5 The Natural Products Atlas Classification

11.6 LOTUS Tree

11.7 MolGenie Organic Chemistry Ontology

12 Information Sources

  1. ChEBI
  2. 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/
  3. 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
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. Japan Chemical Substance Dictionary (Nikkaji)
  6. Natural Product Activity and Species Source (NPASS)
  7. 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/
    Aerucyclamide A
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  8. The Natural Products Atlas
    LICENSE
    The Natural Products Atlas is licensed under a Creative Commons Attribution 4.0 International License.
    https://www.npatlas.org/terms
    The Natural Products Atlas Classification
    https://www.npatlas.org/
  9. MassBank Europe
  10. 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
  11. Metabolomics Workbench
  12. Wikidata
  13. PubChem
  14. 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
  15. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS