Basic information
- CAS
87746-48-3- Standard SMILES
CC(C)=CCc1cc([C@@H]2CC(=O)c3c(O)cc(O)cc3O2)c(CC=C(C)C)c(O)c1O- InChIKey
BVHLNRAYBCPKOY-NRFANRHFSA-N- Molecular formula
- C25H28O6
- Average molar mass
- 424.5 g/mol
- Monoisotopic mass
- 424.18858861
Overview
Sigmoidin A is a tetrahydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 5, 7, 3' and 4' and prenyl groups at positions 2' and 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, an anti-inflammatory agent and an anti-obesity agent. It is a member of 4'-hydroxyflavanones and a tetrahydroxyflavanone. It is functionally related to a (2S)-flavanone.
Names & identifiers
- Preferred name
- Sigmoidin A
- IUPAC
- (2S)-2-[3,4-dihydroxy-2,5-bis(3-methylbut-2-enyl)phenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
- English name
- sigmoidin A
- Molecular formula
- C25H28O6
- Molecular weight
- 0
Names & synonyms
Sigmoidin A87746-48-3Sigmoidin-A(2S)-2-[3,4-dihydroxy-2,5-bis(3-methylbut-2-enyl)phenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-oneCHEBI:66482DTXSID202366074H-1-Benzopyran-4-one, 2-(3,4-dihydroxy-2,5-bis(3-methyl-2-butenyl)phenyl)-2,3-dihydro-5,7-dihydroxy-, (S)-(2S)-2-(3,4-dihydroxy-2,5-bis(3-methylbut-2-enyl)phenyl)-5,7-dihydroxy-2,3-dihydrochromen-4-oneRefChem:182814DTXCID10159098CHEMBL229506(2S)-2-[3,4-dihydroxy-2,5-bis(3-methylbut-2-enyl)phenyl]-5,7-dihydroxy-chroman-4-one
Show more names
(2s)-2-[3,4-dihydroxy-2,5-bis(3-methylbut-2-en-1-yl)phenyl]-5,7-dihydroxy-2,3-dihydro-4h-chromen-4-oneSM3QN39TDCSCHEMBL31502307BDBM50212392(S)-2-[3,4-Dihydroxy-2,5-bis(3-methyl-2-butenyl)phenyl]-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-oneXS1615545,7,3',4'-tetrahydroxy-2',5'-diprenylflavoneQ27135083
Database identifiers
- CAS
87746-48-3
Properties
Computed structural properties
- XLogP
- 5.9
- Topological polar surface area
- 107 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 5
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 692
Chemistry & industry
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 prenyl groups at positions 2' and 5'. Isolated from Erythrina sigmoidea, it exhibits anti-inflammatory and antioxid nt activities.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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