Basic information
- CAS
87746-47-2- Standard SMILES
CC(C)=CCc1cc([C@@H]2CC(=O)c3c(O)cc(O)cc3O2)cc(O)c1O- InChIKey
SFQIGPZCFNTPOD-KRWDZBQOSA-N- Molecular formula
- C20H20O6
- Average molar mass
- 356.4 g/mol
- Monoisotopic mass
- 356.12598835
Overview
Sigmoidin B is a tetrahydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 5, 7, 3' and 4' and a prenyl group at position 5'. Isolated from Erythrina sigmoidea, it exhibits anti-inflammatory and antioxidant activities. It has a role as a metabolite, an antibacterial agent, a radical scavenger and an anti-inflammatory agent. It is a member of 4'-hydroxyflavanones and a tetrahydroxyflavanone. It is functionally related to a (2S)-flavanone.
Names & identifiers
- Preferred name
- Sigmoidin B
- IUPAC
- (2S)-2-[3,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
- English name
- sigmoidin B
- Molecular formula
- C20H20O6
- Molecular weight
- 356.37
Names & synonyms
Sigmoidin B87746-47-2Sigmoidin-BCHEBI:66483DTXSID60236606(2S)-2-[3,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one4H-1-Benzopyran-4-one, 2-(3,4-dihydroxy-5-(3-methyl-2-butenyl)phenyl)-2,3-dihydro-5,7-dihydroxy-, (S)-(2S)-2-(3,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl)-5,7-dihydroxy-2,3-dihydrochromen-4-oneRefChem:182815DTXCID50159097CHEMBL229454(S)-2-(3,4-Dihydroxy-5-(3-methylbut-2-en-1-yl)phenyl)-5,7-dihydroxychroman-4-one
Show more names
(S)-2-[3,4-Dihydroxy-5-(3-methyl-2-butenyl)phenyl]-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one4H-1-Benzopyran-4-one, 2-[3,4-dihydroxy-5-(3-methyl-2-buten-1-yl)phenyl]-2,3-dihydro-5,7-dihydroxy-, (2S)-
(2S)-2-[3,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-5,7-dihydroxy-chroman-4-one(2s)-2-[3,4-dihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-5,7-dihydroxy-2,3-dihydro-4h-chromen-4-oneorb2943132SCHEMBL30266764BDBM50212399HY-N11845TN8923(2s)-2-[3,4-dihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-4-one
Database identifiers
- CAS
87746-47-2- PubChem CID
- 73205
- DTXSID
DTXSID60236606- ChEMBL
CHEMBL229454- ChEBI
CHEBI:66483- Nikkaji
- J184.475J
Properties
Computed structural properties
- XLogP
- 4
- Topological polar surface area
- 107 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 3
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 542
Chemistry & industry
Applications
UsesSigmoidin B, a prenylated flavanone, is a selective 5-lipoxygenase inhibitor. Sigmoidin B is a potent scavenger of the DPPH radical. Sigmoidin B has antigenotoxic activity that inhibits genotoxicity induced by Aflatoxin B1 (HY-N6615), with an IC50 of 18.7 μg/mL. Sigmoidin B has anti-inflammatory activity and antioxidant properties[1][2].
Suppliers1 total
宝欧信特生物科技（苏州）有限公司51288865780 · [email protected]
Additional notes
DefinitionChEBI: A tetrahydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 5, 7, 3' and 4' and a prenyl group at position 5'. Isolated from Erythrina sigmoidea, it exhibits anti-inflammatory and antioxidant acti ities.
Related reactions
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Compound notes
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