3-{3-[(2R,3S)-3-hydroxypiperidin-2-yl]-2-oxopropyl}quinazolin-4(3H)-one
Basic information
- CAS
24159-07-7- Standard SMILES
O=C(C[C@H]1NCCC[C@@H]1O)Cn1cnc2ccccc2c1=O- InChIKey
FWVHWDSCPKXMDB-CABCVRRESA-N- Molecular formula
- C16H19N3O3
- Average molar mass
- 301.34 g/mol
- Monoisotopic mass
- 301.14264148
Overview
febrifugine has been reported in Hydrangea macrophylla and Hydrangea febrifuga with data available.
Names & identifiers
- Preferred name
- 3-{3-[(2R,3S)-3-hydroxypiperidin-2-yl]-2-oxopropyl}quinazolin-4(3H)-one
- IUPAC
- 3-[3-[(2R,3S)-3-hydroxypiperidin-2-yl]-2-oxopropyl]quinazolin-4-one
- English name
- Febrifugine
- Molecular formula
- C16H19N3O3
- Molecular weight
- 301.34
Names & synonyms
24159-07-7CHEMBL3227823-{3-[(2R,3S)-3-hydroxypiperidin-2-yl]-2-oxopropyl}quinazolin-4(3H)-oneFerbifruginDichroin.beta.-Dichroine3-(3-((2R,3S)-3-hydroxypiperidin-2-yl)-2-oxopropyl)quinazolin-4(3H)-oneNSC 3155359SF.BETA.-DICHROINFEBRIFUGINE [MI]UNII-89UWD0FH2I
Show more names
β-dichroinefebrifuginferifugineFebrifugineβ-FebrifugineRadix Dichroae(+)-FebrifugineBETA-FebrifugineFebrifugine USP/EP/BPFebrifugine，Isofebrifugine
orb104700TRANS-(+)-FEBRIFUGINEorb3141504SCHEMBL9542831HY-N2384BDBM50606503TN1012AKOS040760109
Database identifiers
- CAS
24159-07-7- PubChem CID
- 9851692
- DTXSID
Properties
Computed structural properties
- XLogP
- 0.1
- Topological polar surface area
- 82 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 4
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 466
Physicochemical properties
- Melting point
- 139 · 139-140°; mp 154-156°
- alpha
- 25 · D25 +6° (c = 0.5 in chloroform); D25 +28° (c = 0.5 in ethanol)
- Density
- 1.39 · 1.39
- storage temp.
- 2 · 2-8°C
- solubility
- 1.5 mg/ml; · DMF: 1.5 mg/ml; DMSO: 3.0 mg/ml; Ethanol: 0.1 mg/ml; PBS (pH 7.2): 2.5 mg/ml
- form
- A crystalline solid
- Boiling point
- 508.2 · 508.2±60.0 °C(Predicted)
- pka
- 14.61 · 14.61±0.40(Predicted)
- color
- White to off-white
- InChI
- InChI=1S/C16H19N3O3/c20-11(8-14-15(21)6-3-7-17-14)9-19-10-18-13-5-2-1-4-12(13)16(19)22/h1-2,4-5,10,14-15,17,21H,3,6-9H2/t14-,15+/m1/s1
- InChIKey
- FWVHWDSCPKXMDB-CABCVRRESA-N
- SMILES
- N1C2=C(C=CC=C2)C(=O)N(CC(=O)C[C@@H]2[C@@H](O)CCCN2)C=1
- CAS DataBase Reference
- 24159 · 24159-07-7
- FDA UNII
- 89 UWD0FH2I · 89UWD0FH2I
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (97.4%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (97.4%)
Safety data
- Toxicity
- LD50 orally in white mice: 2.5-3.0 mg/kg (Koepfli, 1949)
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302
- Precautionary statements
- P264-P270-P301+P312-P330-P501
Chemistry & industry
Applications
DescriptionFebrifugine is a quinazolinone alkaloid originally isolated from D. febrifuga that has antimalarial activity. It reduces parasitemia and decreases mortality in mice infected with the P. berghei strain NK65 when administered at a dose of 1 mg/kg per day beginning prior to or on the day of infection.
UsesFebrifugine is a quinazoline alkaloid with significant antimalarial and anticancerous efficacy. Febrifugine is an NRF2 inhibitor, that works with halofuginone for the treatment of chemo- and radio-resistant forms of cancer. Febrifugine analogs also functions as antimalarial, anticancer agents and in the prevention of chicken coccidiosis.
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