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1,4-Naphthalenedione, 2-(1-(acetyloxy)-4-methyl-3-pentenyl)-5,8-dihydroxy-, (R)-

PubChem CID
135565816
Structure
1,4-Naphthalenedione, 2-(1-(acetyloxy)-4-methyl-3-pentenyl)-5,8-dihydroxy-, (R)-_small.png
1,4-Naphthalenedione, 2-(1-(acetyloxy)-4-methyl-3-pentenyl)-5,8-dihydroxy-, (R)-_3D_Structure.png
Molecular Formula
Synonyms
  • acetyl shikonin
  • ST04094S3X
  • 1,4-Naphthalenedione, 2-[(1R)-1-(acetyloxy)-4-methyl-3-penten-1-yl]-5,8-dihydroxy-
  • 1,4-Naphthalenedione, 2-(1-(acetyloxy)-4-methyl-3-pentenyl)-5,8-dihydroxy-, (R)-
  • 1,4-Naphthoquinone, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, 2-acetate, (+)-
Molecular Weight
330.3 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2019-01-15
  • Modify:
    2024-12-27

1 Structures

1.1 2D Structure

Chemical Structure Depiction
1,4-Naphthalenedione, 2-(1-(acetyloxy)-4-methyl-3-pentenyl)-5,8-dihydroxy-, (R)-.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(1R)-1-(1,4-dihydroxy-5,8-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] acetate
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

2.1.2 InChI

InChI=1S/C18H18O6/c1-9(2)4-7-15(24-10(3)19)11-8-14(22)16-12(20)5-6-13(21)17(16)18(11)23/h4-6,8,15,22-23H,7H2,1-3H3/t15-/m1/s1
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.3 InChIKey

ZSHRYNLKHZXANX-OAHLLOKOSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.4 SMILES

CC(=CC[C@H](C1=CC(=C2C(=O)C=CC(=O)C2=C1O)O)OC(=O)C)C
Computed by OEChem 2.1.5 (PubChem release 2019.06.18)

2.2 Molecular Formula

C18H18O6
Computed by PubChem 2.1 (PubChem release 2019.06.18)

2.3 Other Identifiers

2.3.1 CAS

24502-78-1

2.3.2 UNII

2.3.3 ChEMBL ID

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • (1R)-1-(5,8-Dihydroxy-1,4-dioxo-1,4-dihydro-2-naphthalenyl)-4-methyl-3-penten-1-yl acetate
  • acetylshikonin
  • acetylshikonin, (+-)-isomer
  • acetylshikonin, (R)-isomer
  • acetylshikonin, (S)-isomer

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
330.3 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
3.5
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
6
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
5
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
330.11033829 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
330.11033829 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
101Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
24
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
586
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
1
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)

5 Chemical Vendors

6 Toxicity

6.1 Toxicological Information

6.1.1 Acute Effects

7 Literature

7.1 Consolidated References

7.2 NLM Curated PubMed Citations

8 Biological Test Results

8.1 BioAssay Results

9 Classification

9.1 MeSH Tree

9.2 ChemIDplus

9.3 ChEMBL Target Tree

10 Information Sources

  1. 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
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. 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
  4. PubChem
  5. 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
CONTENTS