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Carubicin

PubChem CID
443831
Structure
Carubicin_small.png
Carubicin_3D_Structure.png
Molecular Formula
Synonyms
  • Carubicin
  • Carminomycin
  • 50935-04-1
  • Carminomicin I
  • 39472-31-6
Molecular Weight
513.5 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-06-24
  • Modify:
    2025-01-04
Description
Carminomycin is a toxic anthracycline antibiotic that is produced by Actinomadura carminata and also has potent antineoplastic activity. It has a role as an antineoplastic agent and an apoptosis inducer. It is an anthracycline antibiotic, an aminoglycoside antibiotic, a member of tetracenequinones, a member of p-quinones and a tertiary alpha-hydroxy ketone. It is a conjugate base of a carminomycin(1+). It derives from a hydride of a tetracene.
Carubicin is an anthracycline antineoplastic antibiotic isolated from the bacterium Actinomadura carminata. Carubicin intercalates into DNA and interacts with topoisomerase II, thereby inhibiting DNA replication and repair and RNA and protein synthesis.
A very toxic anthracycline-type antineoplastic related to DAUNORUBICIN, obtained from Actinomadura carminata.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Carubicin.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-4,6,9,11-tetrahydroxy-8,10-dihydro-7H-tetracene-5,12-dione
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C26H27NO10/c1-9-21(30)13(27)6-16(36-9)37-15-8-26(35,10(2)28)7-12-18(15)25(34)20-19(23(12)32)22(31)11-4-3-5-14(29)17(11)24(20)33/h3-5,9,13,15-16,21,29-30,32,34-35H,6-8,27H2,1-2H3/t9-,13-,15-,16-,21+,26-/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

XREUEWVEMYWFFA-CSKJXFQVSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)O)O)(C(=O)C)O)N)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C26H27NO10
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DSSTox Substance ID

2.3.7 KEGG ID

2.3.8 Metabolomics Workbench ID

2.3.9 NCI Thesaurus Code

2.3.10 Nikkaji Number

2.3.11 Wikidata

2.3.12 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Carminomicin
  • Carminomycin
  • Carminomycin I
  • Carminomycin II
  • Carminomycin III
  • Carubicin
  • Carubicin Hydrochloride
  • Demethyldaunomycin
  • Demethyldaunorubicin
  • Hydrochloride, Carubicin
  • Karminomicin
  • Karminomycin
  • NSC 180,024
  • NSC 180024
  • NSC-180,024
  • NSC-180024
  • NSC180,024
  • NSC180024
  • Rubeomycin A
  • Rubeomycin A1

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
513.5 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
1.5
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
11
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
513.16349606 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
513.16349606 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
197 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
37
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
944
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
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 2021.10.14)

3.2 Chemical Classes

3.2.1 Drugs

Pharmaceuticals -> Antibiotics
S6 | ITNANTIBIOTIC | Antibiotic List from the ITN MSCA ANSWER | DOI:10.5281/zenodo.2621956

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 LC-MS

1 of 8
View All
Authors
Nogawa T, Okano A, CSRS, RIKEN
Instrument
ABSciex API3200 LC/MS system
Instrument Type
LC-ESI-QQQ
MS Level
MS
Ionization Mode
POSITIVE
Precursor Adduct
[M+H]+
Top 5 Peaks

129.9 999

513.8 955

513.9 937

513.7 906

513.6 895

Thumbnail
Thumbnail
License
CC BY
2 of 8
View All
Authors
Nogawa T, Okano A, CSRS, RIKEN
Instrument
Agilent 6410 Triple Quadrupole LC/MS system
Instrument Type
LC-ESI-QQQ
MS Level
MS2
Ionization Mode
POSITIVE
Precursor Adduct
[M+H]+
Top 5 Peaks

130.1 99

130 95

130.2 93

130.3 79

129.9 77

Thumbnail
Thumbnail
License
CC BY

6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 MeSH Pharmacological Classification

Antibiotics, Antineoplastic
Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)
Topoisomerase II Inhibitors
Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II. (See all compounds classified as Topoisomerase II Inhibitors.)

8 Toxicity

8.1 Toxicological Information

8.1.1 Acute Effects

9 Literature

9.1 Consolidated References

9.2 NLM Curated PubMed Citations

9.3 Springer Nature References

9.4 Chemical Co-Occurrences in Literature

9.5 Chemical-Gene Co-Occurrences in Literature

9.6 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 NCI Thesaurus Tree

13.3 ChEBI Ontology

13.4 KEGG: Lipid

13.5 ChemIDplus

13.6 ChEMBL Target Tree

13.7 NORMAN Suspect List Exchange Classification

13.8 EPA DSSTox Classification

13.9 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/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. FDA Global Substance Registration System (GSRS)
    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
  5. ChEBI
  6. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  7. 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
  8. Drug Gene Interaction database (DGIdb)
    LICENSE
    The data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.
    http://www.dgidb.org/downloads
  9. Japan Chemical Substance Dictionary (Nikkaji)
  10. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  11. MassBank Europe
  12. 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
  13. Metabolomics Workbench
  14. 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/
    Carminomycin
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  15. Springer Nature
  16. Wikidata
  17. Wikipedia
  18. 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
  19. PubChem
  20. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  21. PATENTSCOPE (WIPO)
CONTENTS