Dinochrome A
PubChem CID
10032103
Structure
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.
Chemical Structure Depiction
[(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)
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)
KXMXJSVCINTGDB-USNMBHGSSA-N
Computed by InChI 1.0.6 (PubChem release 2021.05.07)
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)
C42H58O5
Computed by PubChem 2.1 (PubChem release 2021.05.07)
74709-52-7
- (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
- 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
- [(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
- ((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
- DTXSID301345757
- Q27134287
- (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
- (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
Property Name
Property Value
Reference
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)
Accession ID
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
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).
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
License
CC BY-SA
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Same Connectivity Count
Same Parent, Connectivity Count
Similar Compounds (2D)
Similar Conformers (3D)
Same Count
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
- ChEBI
- LOTUS - the natural products occurrence databaseLICENSEThe code for LOTUS is released under the GNU General Public License v3.0.https://lotus.nprod.net/Dinochrome Ahttps://www.wikidata.org/wiki/Q105147406LOTUS Treehttps://lotus.naturalproducts.net/
- EPA DSSToxCompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
- Japan Chemical Substance Dictionary (Nikkaji)
- Natural Product Activity and Species Source (NPASS)
- MassBank Europe
- MassBank of North America (MoNA)LICENSEThe content of the MoNA database is licensed under CC BY 4.0.https://mona.fiehnlab.ucdavis.edu/documentation/license
- Metabolomics Workbench
- SpectraBaseDinochrome 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
- WikidataDinochrome Ahttps://www.wikidata.org/wiki/Q105147406
- PubChem
- Medical Subject Headings (MeSH)LICENSEWorks 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.htmldinochrome Ahttps://www.ncbi.nlm.nih.gov/mesh/67474097
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
CONTENTS