Sissotrin

Details

• Internal ID: 2dea20f3-a8ac-4469-9d9c-32d6447701dd
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid O-glycosides
• IUPAC Name: 5-hydroxy-3-(4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): COC1=CC=C(C=C1)C2=COC3=CC(=CC(=C3C2=O)O)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): 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
• InChI: 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
• InChI Key: LFEUICHQZGNOHD-RECXWPGBSA-N
• Popularity: 48 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₁₀
• Molecular Weight: 446.40 g/mol
• Exact Mass: 446.12129689 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: 1.20

Synonyms

• 5928-26-7
• Biochanin A glucoside
• 5-Hydroxyl ononin
• Biochanin A 7-glucoside
• 2F2SK16U1X
• Biochanin A 7-o-beta-glucoside
• Biochanin A 7-beta-D-glucopyranoside
• 5-hydroxy-3-(4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• 7-(beta-D-Glucopyranosyloxy)-5-hydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one
• NSC-289565
• 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)oxan-2-yl)oxychromen-4-one
• RefChem:1098573
• 5-hydroxy-3-(4-methoxyphenyl)-7-((2S,4R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxychromen-4-one
• biochanin A 7-O-beta-D-glucoside
• Sissotrin [MI]
• 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
• Biochanin A-beta-D-glucoside
• biochanin A-7-O-glucoside
• 5-hydroxy-3-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl beta-D-glucopyranoside
• 4H-1-Benzopyran-4-one, 7-(.beta.-D-glucopyranosyloxy)-5-hydroxy-3-(4-methoxyphenyl)-
• 5-hydroxy-3-(4-methoxyphenyl)-7-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• UNII-2F2SK16U1X
• starbld0009535
• C05376
• Sissotrin, ~95% (TLC)
• MEGxp0_000435
• orb1681676
• BIOCHANIN 7-O-GLUCOSIDE
• Biochanin A-.beta.-D-glucoside
• BIOCHANINA-7-O-GLUCOSIDE
• CHEMBL3426809
• SCHEMBL30089411
• ACon1_000323
• CHEBI:28751
• LFEUICHQZGNOHD-RECXWPGBSA-N
• HY-N1240
• Sissotrin;Biochanin A-7-O-glucoside
• STL564636
• AKOS030490964
• FB65335
• FS-8845
• NSC 289565
• 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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.20%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.50%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.70%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.69%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.17%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	93.40%	86.92%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.04%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.95%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.25%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.59%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.58%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.14%	99.17%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.99%	96.21%
CHEMBL4208	P20618	Proteasome component C5	87.26%	90.00%
CHEMBL1907	P15144	Aminopeptidase N	86.93%	93.31%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.06%	97.28%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.75%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.90%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	80.97%	94.73%

Plants that contains it

• Astragalus mongholicus
• Calicotome villosa
• Cicer flexuosum
• Cicer mogoltavicum
• Cicer songaricum
• Dalbergia sissoo
• Genista pichisermolliana
• Ipomoea muricata
• Medicago truncatula
• Murraya paniculata
• Murraya paniculata
• Pueraria montana var. lobata
• Styphnolobium japonicum
• Trifolium aureum
• Trifolium diffusum
• Trifolium pratense
• Trifolium subterraneum

Cross-Links

• PubChem: 5280781
• NPASS: NPC13473
• LOTUS: LTS0126321
• wikiData: Q23372518