(-)-Fisetinidol
Basic information
- CAS
490-49-3- Standard SMILES
Oc1ccc2c(c1)O[C@H](c1ccc(O)c(O)c1)[C@@H](O)C2- InChIKey
VFZYLYJWCROVLO-DZGCQCFKSA-N- Molecular formula
- C15H14O5
- Average molar mass
- 274.27 g/mol
- Monoisotopic mass
- 274.08412354
Overview
Fisetinidol is a tetrahydroxyflavan that is (2S)-flavan substituted by hydroxy groups at positions 3, 7, 3' and 4'. It has a role as an EC 3.2.1.20 (alpha-glucosidase) inhibitor and a plant metabolite. It is a catechin and a tetrahydroxyflavan. It derives from a hydride of a (2S)-flavan.
Names & identifiers
- Preferred name
- (-)-Fisetinidol
- IUPAC
- (2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,7-diol
- English name
- (-)-FISETINIDOL
- Molecular formula
- C15H14O5
- Molecular weight
- 274.27
Names & synonyms
Fisetinidol490-49-33,7,3',4'-Tetrahydroxyflavan(2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,7-diolCHEBI:5066(-)-FisetinidolRefChem:934644Spectrum_001710SpecPlus_000717Spectrum2_000423Spectrum3_000237Spectrum4_001574
Show more names
3,4-Dihydro-2α-(3,4-dihydroxyphenyl)-2H-1-benzopyran-3β,7-diol(2R)-2α-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3β,7-diol2H-1-Benzopyran-3,7-diol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R,3S)-
Spectrum5_000228C09735BSPBio_001913KBioGR_002128KBioSS_002190SPECTRUM210014DivK1c_006813SPBio_000406
Database identifiers
- CAS
490-49-3- PubChem CID
- 442397
- DTXSID
DTXSID401028831
Properties
Computed structural properties
- XLogP
- 0.7
- Topological polar surface area
- 90.2 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 1
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 336
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavans, Flavanols and Leucoanthocyanidins [PK1202]
Physicochemical properties
- Melting point
- 205 · 205-206 °C(Solv: ethyl acetate (141-78-6); ligroine (8032-32-4))
- Boiling point
- 568.2 · 568.2±50.0 °C(Predicted)
- Density
- 1.492 · 1.492±0.06 g/cm3(Predicted)
- pka
- 9.56 · 9.56±0.10(Predicted)
Chemistry & industry
Additional notes
DefinitionChEBI: A tetrahydroxyflavan that is (2S)-flavan substituted by hydroxy groups at positions 3, 7, 3' and 4'.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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