Sissotrin
PubChem CID
5280781
Structure
Molecular Formula
Synonyms
- Sissotrin
- 5928-26-7
- 5-Hydroxyl ononin
- Sissotrin [MI]
- biochanin A 7-O-beta-D-glucoside
Molecular Weight
446.4 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2004-09-16
- Modify:2025-01-18
Description
Biochanin A 7-O-beta-D-glucoside is a glycosyloxyisoflavone that is biochanin A attached to a beta-D-glucopyranosyl residue at position 7 via glycosidic linkage. It has a role as a phytoestrogen and a plant metabolite. It is a hydroxyisoflavone, a member of 4'-methoxyisoflavones and a 7-hydroxyisoflavones 7-O-beta-D-glucoside. It is functionally related to a biochanin A. It is a conjugate acid of a biochanin A 7-O-beta-D-glucoside(1-).
Sissotrin has been reported in Cicer microphyllum, Dalbergia sissoo, and other organisms with data available.
Chemical Structure Depiction
5-hydroxy-3-(4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
InChI=1S/C22H22O10/c1-29-11-4-2-10(3-5-11)13-9-30-15-7-12(6-14(24)17(15)18(13)25)31-22-21(28)20(27)19(26)16(8-23)32-22/h2-7,9,16,19-24,26-28H,8H2,1H3/t16-,19-,20+,21-,22-/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
LFEUICHQZGNOHD-RECXWPGBSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
COC1=CC=C(C=C1)C2=COC3=CC(=CC(=C3C2=O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C22H22O10
Computed by PubChem 2.2 (PubChem release 2021.10.14)
- Sissotrin
- 5928-26-7
- 5-Hydroxyl ononin
- Sissotrin [MI]
- biochanin A 7-O-beta-D-glucoside
- Biochanin A glucoside
- Biochanin A 7-glucoside
- 2F2SK16U1X
- 5-hydroxy-3-(4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
- CHEBI:28751
- 5-hydroxy-3-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl beta-D-glucopyranoside
- Biochanin A-beta-D-glucoside
- 4H-1-Benzopyran-4-one, 7-(.beta.-D-glucopyranosyloxy)-5-hydroxy-3-(4-methoxyphenyl)-
- 5-hydroxy-3-(4-methoxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
- 5-hydroxy-3-(4-methoxyphenyl)-7-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
- biochanin A-7-O-glucoside
- UNII-2F2SK16U1X
- Biochanin A 7-o-beta-glucoside
- NSC-289565
- Biochanin A 7-beta-D-glucopyranoside
- starbld0009535
- C05376
- Sissotrin, ~95% (TLC)
- MEGxp0_000435
- BIOCHANIN 7-O-GLUCOSIDE
- Biochanin A-.beta.-D-glucoside
- BIOCHANINA-7-O-GLUCOSIDE
- CHEMBL3426809
- ACon1_000323
- LFEUICHQZGNOHD-RECXWPGBSA-N
- HY-N1240
- STL564636
- AKOS030490964
- FS-8845
- NSC 289565
- 4H-1-Benzopyran-4-one, 7-(beta-D-glucopyranosyloxy)-5-hydroxy-3-(4-methoxyphenyl)-
- 7-(beta-D-Glucopyranosyloxy)-5-hydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one
- NCGC00169186-01
- BIOCHANIN A 7-O-.BETA.-GLUCOSIDE
- CS-0016641
- BIOCHANIN A 7-.BETA.-D-GLUCOPYRANOSIDE
- G90316
- BRD-K07506390-001-01-0
- Q23372518
- 5-Hydroxy-3-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl .beta.-D-glucopyranoside
- 7-(.BETA.-D-GLUCOPYRANOSYLOXY)-5-HYDROXY-3-(4-METHOXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
446.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
1.2
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
10
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
446.12129689 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
446.12129689 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
155 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
32
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
690
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
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
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)
Polyketides [PK] -> Flavonoids [PK12] -> Isoflavonoids [PK1205]
NIST Number
1118635
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M+H]+
Precursor m/z
447.1286
Total Peaks
1
m/z Top Peak
285.1
m/z 2nd Highest
0
m/z 3rd Highest
0
Thumbnail
Accession ID
Authors
Plant Biology, The Noble Foundation, Ardmore, OK, US/Dennis Fine, Daniel Wherritt, and Lloyd Sumner
Instrument
Bruker impact HD
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
30 eV
Column Name
Waters Acquity BEH C18 1.7um x 2.1 x 150 mm
Retention Time
613.8 sec
Precursor m/z
283.0601
Precursor Adduct
[M-H]-
Top 5 Peaks
268.0378 999
239.035 182
267.0294 181
269.0407 121
240.0413 84
License
CC BY-NC-SA
Accession ID
Authors
Plant Biology, The Noble Foundation, Ardmore, OK, US/Dennis Fine, Daniel Wherritt, and Lloyd Sumner
Instrument
Bruker impact HD
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
20 eV
Column Name
Waters Acquity BEH C18 1.7um x 2.1 x 150 mm
Retention Time
613.8 sec
Precursor m/z
491.12
Precursor Adduct
[M-H]-
Top 5 Peaks
283.0593 999
284.0617 113
268.0342 22
325.0685 20
445.1134 14
License
CC BY-NC-SA
MoNA ID
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
447.38
Instrument
TQD, Waters
Instrument Type
Flow-injection QqQ/MS
Ionization
ESI
Ionization Mode
positive
Collision Energy
40
Top 5 Peaks
285 100
284 33.20
283 5.30
MoNA ID
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
447.38
Instrument
TQD, Waters
Instrument Type
Flow-injection QqQ/MS
Ionization
ESI
Ionization Mode
positive
Collision Energy
50
Top 5 Peaks
285 100
284 43.69
283 7.77
286 4.47
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Parent, Connectivity Count
Same Parent, Exact Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=LFEUICHQZGNOHD-RECXWPGBSA-N
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
- CAS Common ChemistryLICENSEThe 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/
- ChemIDplusChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- FDA Global Substance Registration System (GSRS)LICENSEUnless 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
- ChEBIBiochanin A 7-O-beta-D-glucosidehttps://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28751
- LOTUS - the natural products occurrence databaseLICENSEThe code for LOTUS is released under the GNU General Public License v3.0.https://lotus.nprod.net/LOTUS Treehttps://lotus.naturalproducts.net/
- ChEMBLLICENSEAccess 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
- Japan Chemical Substance Dictionary (Nikkaji)
- KEGGLICENSEAcademic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial licensehttps://www.kegg.jp/kegg/legal.htmlPhytochemical compoundshttp://www.genome.jp/kegg-bin/get_htext?br08003.keg
- LIPID MAPSBiochanin A 7-O-glucosidehttps://lipidmaps.org/databases/lmsd/LMPK12050219Lipid Classificationhttps://www.lipidmaps.org/
- 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 WorkbenchBiochanin A 7-O-beta-D-glucosidehttps://www.metabolomicsworkbench.org/data/StructureData.php?RegNo=51834
- NIST Mass Spectrometry Data CenterLICENSEData covered by the Standard Reference Data Act of 1968 as amended.https://www.nist.gov/srd/public-lawSissotrinhttp://www.nist.gov/srd/nist1a.cfm
- SpectraBaseBIOCHANIN-7-O-BETA-D-GLUCOPYRANOSIDE;SISSOTRINhttps://spectrabase.com/spectrum/L5N1RGmnsYR5-hydroxy-3-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl hexopyranosidehttps://spectrabase.com/spectrum/2Pr1VlwZzq0
- Springer Nature
- Wikidata
- PubChem
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 403985117https://pubchem.ncbi.nlm.nih.gov/substance/403985117
- NCBI
CONTENTS