(R)-(+)-4-Methoxydalbergione
Basic information
- CAS
4646-86-0- Standard SMILES
C=C[C@@H](C1=CC(=O)C(OC)=CC1=O)c1ccccc1- InChIKey
RGSUZUQISVAJJF-GFCCVEGCSA-N- Molecular formula
- C16H14O3
- Average molar mass
- 254.28 g/mol
- Monoisotopic mass
- 254.0942943
Overview
(R)-4''-methoxydalbergione is a member of the class of 1,4-benzoquinones that is p-benzoquinone substituted by a methoxy group at position 2 and a 1-phenylallyl group at position 5. Isolated from the heartwood of Dalbergia louveli, it exhibits antiplasmodial activity. It has a role as a metabolite and an antiplasmodial drug. It is a member of 1,4-benzoquinones and an enol ether.
Names & identifiers
- Preferred name
- (R)-(+)-4-Methoxydalbergione
- IUPAC
- 2-methoxy-5-[(1R)-1-phenylprop-2-enyl]cyclohexa-2,5-diene-1,4-dione
- English name
- (R)-4-Methoxydalbergione
- Molecular formula
- C16H14O3
- Molecular weight
- 254.28
Names & synonyms
(R)-4-Methoxydalbergione4646-86-0(R)-(+)-4-methoxydalbergione2-methoxy-5-[(1R)-1-phenylprop-2-enyl]cyclohexa-2,5-diene-1,4-dioneDTXSID103319582-methoxy-5-((1R)-1-phenylprop-2-enyl)cyclohexa-2,5-diene-1,4-dioneRefChem:1051043DTXCID40283052(R)-4''-methoxydalbergione2-methoxy-5-[(1R)-1-phenylprop-2-en-1-yl]cyclohexa-2,5-diene-1,4-dioneSCHEMBL716867CHEMBL466581
Show more names
(+)-4-Methoxydalbergione2-[(αR)-α-Vinylbenzyl]-5-methoxy-1,4-benzoquinone2-[(R)-1-Phenyl-2-propenyl]-5-methoxy-1,4-benzoquinone2-[(1R)-1-Phenyl-2-propenyl]-5-methoxy-1,4-benzoquinone2,5-Cyclohexadiene-1,4-dione, 2-methoxy-5-[(1R)-1-phenyl-2-propen-1-yl]-
orb1680936CHEBI:66703HY-N9746LMPK12100072TN5798AKOS040762945DA-69188CS-0203739
Database identifiers
- CAS
4646-86-0- PubChem CID
- 442809
- DTXSID
DTXSID10331958- ChEMBL
CHEMBL466581- ChEBI
CHEBI:66703- Nikkaji
- J107.387G
Properties
Computed structural properties
- XLogP
- 2.7
- Topological polar surface area
- 43.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 4
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 451
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Neoflavonoids [PK1210]
Physicochemical properties
- Melting point
- 112 · 112-113 °C
- Boiling point
- 395.7 · 395.7±42.0 °C(Predicted)
- Density
- 1.16 · 1.16±0.1 g/cm3(Predicted)
Chemistry & industry
Applications
Description(R)-4-Methoxy dalbergione is the main allergen of Dalbergia nigra and Dalbergia latifolia Roxb. (East Indian rosewood, palissandre). Occupational sensitization occurs in timberworkers.
Uses(R)-4-Methoxydalbergione is a urease inhibitor with IC50s of 59.72 and 67.33 μM for Bacillus pasteurii urease and Jack bean urease. (R)-4-Methoxydalbergione also has antiplasmodial activity. (R)-4-Methoxydalbergione can be isolated from Ranunculus repens[1][2].
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: (R)-4''-methoxydalbergione is a member of the class of 1,4-benzoquinones that is p-benzoquinone substituted by a methoxy group at position 2 and a 1-phenylallyl group at position 5. Isolated from the heartwood of Dalbergia louveli, it exhibits antiplasmodial activity. It has a role as a metabolite and an antiplasmodial drug. It is an enol ether and a member of 1,4-benzoquinones.
Related reactions
0 records
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Compound notes
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