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Dinochrome A

PubChem CID
10032103
Structure
Dinochrome A_small.png
Dinochrome A_3D_Structure.png
Molecular Formula
Synonyms
  • Dinochrome A
  • CHEBI:65797
  • 74709-52-7
  • (3S,3'S,5R,5'R,6'R,8R,8'R,9cis)-3,5'-dihydroxy-6,7'-didehydro-5,5',6,8-tetrahydro-5,8-epoxy-beta,beta-caroten-3'-yl acetate
  • (3S,5R,6R,3'S,5'R,8'R)-5',8'-epoxy-6,7-didehydro-5,6,5',8'-tetrahydro-beta,beta- carotene-3,5,39-triol 3-O-acetate
Molecular Weight
642.9 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2006-10-25
  • Modify:
    2025-01-11
Description
Dinochrome A is a carotenoid that is 6,7'-didehydro-5,5',6,8-tetrahydro-5,8-epoxy-beta,beta-carotene substituted by acetyloxy group at position 3' and hydroxy groups at positions 3 and 5' respectively. Isolated from the fresh water red tide Peridinium bipes, it has been found to inhibit proliferation of human malignant tumor cells, such as GOTO, OST and HeLa cells. It has a role as a metabolite and an antineoplastic agent. It is a carotenoid, an acetate ester, a cyclic ether, a secondary alcohol, a tertiary alcohol and a member of allenes.
Dinochrome A has been reported in Peridinium bipes with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Dinochrome A.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(1S,3R)-4-[(3E,5E,7E,9E,11E,13E,15E)-16-[(2R,6S,7aR)-6-hydroxy-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-2-yl]-3,7,12-trimethylheptadeca-1,3,5,7,9,11,13,15-octaenylidene]-3-hydroxy-3,5,5-trimethylcyclohexyl] acetate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.05.07)

2.1.2 InChI

InChI=1S/C42H58O5/c1-29(18-14-19-31(3)22-23-37-40(8,9)27-35(46-33(5)43)28-41(37,10)45)16-12-13-17-30(2)20-15-21-32(4)36-24-38-39(6,7)25-34(44)26-42(38,11)47-36/h12-22,24,34-36,44-45H,25-28H2,1-11H3/b13-12+,18-14+,20-15+,29-16+,30-17+,31-19+,32-21+/t23?,34-,35-,36+,41+,42+/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.3 InChIKey

KXMXJSVCINTGDB-USNMBHGSSA-N
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.4 SMILES

C/C(=C\C=C\C=C(/C)\C=C\C=C(/C)\[C@H]1C=C2[C@](O1)(C[C@H](CC2(C)C)O)C)/C=C/C=C(\C)/C=C=C3[C@](C[C@H](CC3(C)C)OC(=O)C)(C)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C42H58O5
Computed by PubChem 2.1 (PubChem release 2021.05.07)

2.3 Other Identifiers

2.3.1 CAS

74709-52-7

2.3.2 ChEBI 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

  • (3S,5R,6R,3'S,5'R,8'R)-5',8'-epoxy-6,7-didehydro-5,6,5',8'-tetrahydro-beta,beta-carotene-3,5,3'-triol 3-O-acetate
  • dinochrome A

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
642.9 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
8.9
Reference
Computed by XLogP3 3.0 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Rotatable Bond Count
Property Value
10
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Exact Mass
Property Value
642.42842495 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
642.42842495 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
76 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Heavy Atom Count
Property Value
47
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
1500
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
5
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
7
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 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

Source of Spectrum
E2-50-1632-2
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.1.2 Other MS

1 of 2
Authors
Akimoto N, Graduate School of Pharmaceutical Sciences, Kyoto University and Maoka T, Research Institute for Production Development
Instrument
JMS-HX/HX 110A, JEOL
Instrument Type
FAB-EBEB
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
FAB
Collision Energy
3 kV
Precursor m/z
642.43
Precursor Adduct
[M]+*
Top 5 Peaks

642.3273 999

624.5381 999

42.996 638

562.3752 547

352.2355 545

Thumbnail
Thumbnail
License
CC BY-SA
Reference
Takashi Maoka, Miyuki Tsushima and Hoyoku Nishino, Isolation and Characterization of Dinochrome A and B, Anti-carcinogenic Active Carotenoids from the Fresh Water Red Tide Peridinium bipes, Chem. Pharm. Bull. 50, 1630-1633 (2002).
2 of 2
MoNA ID
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M]+*
Precursor m/z
642.43
Instrument
JMS-HX/HX 110A, JEOL
Instrument Type
FAB-EBEB
Ionization
FAB
Ionization Mode
positive
Collision Energy
3 kV
Top 5 Peaks

642.3273 99.96

624.5381 65.34

42.9960 41.76

562.3752 35.79

352.2355 35.63

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-Disease Co-Occurrences in Literature

8 Patents

8.1 Depositor-Supplied Patent Identifiers

9 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

10 Classification

10.1 MeSH Tree

10.2 ChEBI Ontology

10.3 EPA DSSTox Classification

10.4 LOTUS Tree

10.5 MolGenie Organic Chemistry Ontology

11 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. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. Japan Chemical Substance Dictionary (Nikkaji)
  5. Natural Product Activity and Species Source (NPASS)
  6. MassBank Europe
  7. 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
  8. Metabolomics Workbench
  9. SpectraBase
    Dinochrome A [(3S,5R,6R,3'S,5'R,8'R)-5',8'-epoxy-16,17-didehydro-5,6,5',8'-tetrahydro-.beta.,.beta.-carotene-3,5,3'-triol 3-O-acetate]
    https://spectrabase.com/spectrum/7RPjz2kAOSp
  10. Wikidata
  11. PubChem
  12. 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
  13. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS