Yakuchinone A
Basic information
- CAS
78954-23-1- Standard SMILES
COc1cc(CCC(=O)CCCCc2ccccc2)ccc1O- InChIKey
TXELARZTKDBEKS-UHFFFAOYSA-N- Molecular formula
- C20H24O3
- Average molar mass
- 312.4 g/mol
- Monoisotopic mass
- 312.17254462
Overview
1-(4'-hydroxy-3'-methoxyphenyl)-7-phenyl-3-heptanone is a ketone that is heptan-3-one substituted by a 4-hydroxy-3-methoxyphenyl group at position 1 and a phenyl group at position 7. Isolated from in Alpinia oxyphylla, it exhibits antineoplastic and inhibitory activities against COX-1, COX-2 and NO synthase. It has a role as a metabolite, an antineoplastic agent, a cyclooxygenase 2 inhibitor, a cyclooxygenase 1 inhibitor and an EC 1.14.13.39 (nitric oxide synthase) inhibitor. It is a ketone, a monomethoxybenzene and a member of phenols.
Names & identifiers
- Preferred name
- Yakuchinone A
- IUPAC
- 1-(4-hydroxy-3-methoxyphenyl)-7-phenylheptan-3-one
- English name
- yakuchinone-A
- Molecular formula
- C20H24O3
- Molecular weight
- 312.4
Names & synonyms
yakuchinone A78954-23-1Yakuchinone-A3-Heptanone, 1-(4-hydroxy-3-methoxyphenyl)-7-phenyl-2X58Y9JC7LDTXSID50229406RefChem:195587DTXCID301518971-(4-hydroxy-3-methoxyphenyl)-7-phenylheptan-3-one1-(4'-Hydroxy-3'-methoxyphenyl)-7-phenyl-3-heptanoneCHEMBL45451941-(4-Hydroxy-3-methoxyphenyl)-7-phenyl-3-heptanone
Show more names
Yakuchinone A, 10 mM in DMSO
1-(4-hydroxy-3-methoxy-phenyl)-7-phenyl-heptan-3-one1-[4-hydroxy-3-methoxyphenyl]-7-phenyl-3-heptanoneMFCD30533823UNII-2X58Y9JC7Lorb1217650orb1305481SCHEMBL3677507SCHEMBL29497123
Database identifiers
- CAS
78954-23-1- PubChem CID
- 133145
- DTXSID
DTXSID50229406- ChEMBL
CHEMBL4545194- ChEBI
CHEBI:66033- UNII
- 2X58Y9JC7L
- Nikkaji
- J576.152B
Properties
Computed structural properties
- XLogP
- 3.6
- Topological polar surface area
- 46.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 9
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 336
Physicochemical properties
- Boiling point
- 212 · 212-214 °C(Press: 2 Torr)
- Density
- 1.095 · 1.095±0.06 g/cm3(Predicted)
- solubility
- 0 · DMSO:0.0(Max Conc. mg/mL);0.0(Max Conc. mM)
- pka
- 10.02 · 10.02±0.20(Predicted)
- form
- Liquid
- color
- Colorless to off-white
- InChI
- InChI=1S/C20H24O3/c1-23-20-15-17(12-14-19(20)22)11-13-18(21)10-6-5-9-16-7-3-2-4-8-16/h2-4,7-8,12,14-15,22H,5-6,9-11,13H2,1H3
- InChIKey
- TXELARZTKDBEKS-UHFFFAOYSA-N
- SMILES
- C(C1=CC=C(O)C(OC)=C1)CC(=O)CCCCC1=CC=CC=C1
- LogP
- 3.72 · 3.720 (est)
- FDA UNII
- 2 X58Y9JC7L · 2X58Y9JC7L
Chemistry & industry
Applications
UsesYakuchinone A is a natural product isolated from the fruit of Alpinia oxyphylla, which can induce apoptosis and has anticancer and anti-inflammatory activities[1].
Additional notes
DefinitionChEBI: A ketone that is heptan-3-one substituted by a 4-hydroxy-3-methoxyphenyl group at position 1 and a phenyl group at position 7. Isolated from in Alpinia oxyphylla, it exhibits antineoplastic and inhibitory activities against COX-1, COX-2 and NO synthase.
Suppliers
Loading…
Open inquiries
Loading…
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…