Sigmoidin B

Details

• Internal ID: 025c4c4d-bf1d-4bd9-bf52-f2b351359d35
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 3-prenylated flavans > 3-prenylated flavanones
• IUPAC Name: (2S)-2-[3,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(=CCC1=C(C(=CC(=C1)C2CC(=O)C3=C(C=C(C=C3O2)O)O)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C(=CC(=C1)[C@@H]2CC(=O)C3=C(C=C(C=C3O2)O)O)O)O)C
• InChI: InChI=1S/C20H20O6/c1-10(2)3-4-11-5-12(6-16(24)20(11)25)17-9-15(23)19-14(22)7-13(21)8-18(19)26-17/h3,5-8,17,21-22,24-25H,4,9H2,1-2H3/t17-/m0/s1
• InChI Key: SFQIGPZCFNTPOD-KRWDZBQOSA-N
• Popularity: 15 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀O₆
• Molecular Weight: 356.40 g/mol
• Exact Mass: 356.12598835 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 4.00

Synonyms

• 87746-47-2
• Sigmoidin-B
• CHEMBL229454
• CHEBI:66483
• (2S)-2-[3,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
• (S)-2-(3,4-Dihydroxy-5-(3-methylbut-2-en-1-yl)phenyl)-5,7-dihydroxychroman-4-one
• (2s)-2-[3,4-dihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-5,7-dihydroxy-2,3-dihydro-4h-chromen-4-one
• D09HAX
• DTXSID60236606
• BDBM50212399
• XS161553
• 5,7,3',4'-tetrahydroxy-5'-prenylflavone
• Q27135084
• (2S)-2-[3,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-5,7-dihydroxy-chroman-4-one
• (2S)- 2-(3,4-dihydroxy-5-(3-methyl-2-butenyl)phenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one
• (2s)-2-[3,4-dihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-4-one
• 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxy-5-(3-methyl-2-butenyl)phenyl)-2,3-dihydro-5,7-di- hydroxy-, (S)-
• 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxy-5-(3-methyl-2-butenyl)phenyl)-2,3-dihydro-5,7-dihydroxy-, (S)-

2D Structure

ADMET Properties (via admetSAR 2)

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

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	19400 nM	IC50	PMID: 17489632

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.69%	91.11%
CHEMBL1929	P47989	Xanthine dehydrogenase	95.88%	96.12%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.67%	94.45%
CHEMBL2581	P07339	Cathepsin D	92.20%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.84%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	91.58%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.53%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.57%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.36%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.34%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.20%	99.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.92%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.85%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.61%	100.00%
CHEMBL4208	P20618	Proteasome component C5	85.60%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.36%	99.17%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	82.80%	92.68%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.16%	95.89%
CHEMBL4040	P28482	MAP kinase ERK2	80.05%	83.82%

Plants that contains it

• Erythrina abyssinica
• Erythrina abyssinica
• Erythrina latissima
• Erythrina sigmoidea
• Glycyrrhiza
• Glycyrrhiza glabra
• Glycyrrhiza inflata
• Glycyrrhiza uralensis
• Glycyrrhiza uralensis
• Mitracarpus hirtus

Cross-Links

• PubChem: 73205
• NPASS: NPC106976
• ChEMBL: CHEMBL229454
• LOTUS: LTS0120052
• wikiData: Q27135084