warangalone

Iupac Name：5-hydroxy-7-(4-hydroxyphenyl)-2,
2-dimethyl-10-(3-methylbut-2-enyl)pyrano[3,2-g]chromen-6-one

Molecular Weight：404.45506

Modify Date.: 2022-11-29 12:54

Introduction:

Warangalone is an anti-malarial compound which can inhibit the growth of both strains of parasite 3D7 (chloroquine sensitive) and K1 (chloroquine resistant) with IC50s of 4.8 μg/mL and 3.7 μg/mL, respectively. Warangalone can also inhibit cyclic AMP-dependent protein kinase catalytic subunit (cAK) with an IC50 of 3.5 μM.

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1. Names and Identifiers

1.1 Name: warangalone
1.2 Synonyms: 2H,6H-Benzo[1,2-b:5,4-b′]dipyran-6-one, 5-hydroxy-7-(4-hydroxyphenyl)-2,2-dimethyl-10-(3-methyl-2-buten-1-yl)- 2H,6H-Benzo[1,2-b:5,4-b′]dipyran-6-one, 5-hydroxy-7-(4-hydroxyphenyl)-2,2-dimethyl-10-(3-methyl-2-butenyl)- 2H,6H-Benzo[1,2-b:5,4-b′]dipyran-6-one, 5-hydroxy-7-(p-hydroxyphenyl)-2,2-dimethyl-10-(3-methyl-2-butenyl)- 5-Hydroxy-7-(4-hydroxyphenyl)-2,2-dimethyl-10-(3-methyl-2-buten-1-yl)-2H,6H-benzo[1,2-b:5,4-b′]dipyran-6-one 5-hydroxy-7-(4-hydroxyphenyl)-2,2-dimethyl-10-(3-methylbut-2-enyl)-6-pyrano[3,2-g][1]benzopyranone 5-hydroxy-7-(4-hydroxyphenyl)-2,2-dimethyl-10-(3-methylbut-2-enyl)pyrano[3,2-g]chromen-6-one Scandenolone Scandenone Warangalon Warangalone (Scandenolone)

1.3 CAS No.: 4449-55-2

1.4 CID: 5379679

1.5 Molecular Formula: C25H24O5 (isomer)

1.6 Inchi: InChI=1S/C25H24O5/c1-14(2)5-10-18-23-17(11-12-25(3,4)30-23)21(27)20-22(28)19(13-29-24(18)20)15-6-8-16(26)9-7-15/h5-9,11-13,26-27H,10H2,1-4H3

1.7 InChkey: HGHOPAZIUPORIN-UHFFFAOYSA-N

1.8 Canonical Smiles: CC(=CCC1=C2C(=C(C3=C1OC=C(C3=O)C4=CC=C(C=C4)O)O)C=CC(O2)(C)C)C

1.9 Isomers Smiles: CC(=CCC1=C2C(=C(C3=C1OC=C(C3=O)C4=CC=C(C=C4)O)O)C=CC(O2)(C)C)C

2. Properties

2.1 Density: 1.258

2.1 Melting point: 164-165 °C

2.1 Boiling point: 627°Cat760mmHg

2.1 Refractive index: 1.627

2.1 Flash Point: 216.7°C

2.1 PSA: 79.90000

2.1 logP: 5.56410

2.1 Color/Form: Yellow powder

2.2 pKa: 6.39±0.40(Predicted)

3. Synthesis Route

4449-55-2Total: 1 Synthesis Route

51225-28-6 6 Suppliers

4449-55-2 9 Suppliers

482-53-1 11 Suppliers

Literatures:
Singhal, Ashok K.; Sharma, Ram P.; Thyagarajan, Gopalakrishna; Herz, Werner; Govindan, Serengolam V. Phytochemistry (Elsevier), 1980 , vol. 19, p. 929 - 934
Yield: null

4. Other Information

4.0 Mesh Entry Terms: warangalone

4.1 Use Classification: Polyketides [PK] -> Flavonoids [PK12] -> Isoflavonoids [PK1205]

5. Computational chemical data

Molecular Weight: 404.45506g/mol
Molecular Formula: C₂₅H₂₄O₅
Compound Is Canonicalized: True
XLogP3-AA: 5.9
Exact Mass: 404.16237386
Monoisotopic Mass: 404.16237386
Complexity: 752
Rotatable Bond Count: 3
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 5
Topological Polar Surface Area: 76
Heavy Atom Count: 30
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceB4OAAAAAAAAAAAAAAAAAAAAAAAAAAwYIEAAAAAAACBQAAAGgAACAAADESgmAIyBoAABgCIAqBSAAACCAAkIAAIiAEGCMgMJzaGNRqCeWCl4BUIuYeI7PzOIAACCAAIAABAAAQQABAAAAAAAAAAAA==