2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one



Compound IDCDAMM00571
Common name2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one
IUPAC name2,4-dihydroxy-1,4-benzoxazin-3-one
Molecular formulaC8H7NO4

Experimental data

Retention time9.64
Adduct[M+H]+
Actual mz182.043
Theoretical mz182.045
Error12.5
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.7763

Identifiers and class information

Inchi keyCOVOPZQGJGUPEY-UHFFFAOYNA-N
SmilesO=C1N(O)C=2C=CC=CC2OC1O
SuperclassOrganoheterocyclic compounds
ClassBenzoxazines

Plant source

  • Piper longum L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)0
    Number of non-conjugated amine groups (#amine)0
    Number of amidine and guanidine groups (#amidine)0
    Number of carboxylic acid groups (#acid)0
    Number of non-conjugated amide groups (#amide)0
    Number of rotatable bonds (#rotor)3
    Number of reactive functional groups (#rtvFG)1
    Predicted central nervous system activity (CNS)-1
    Molecular weight (mol_MW)181.148
    Computed dipole moment(dipole)1.341
    Total solvent accessible surface area (SASA)354.129
    Hydrophobic component of SASA (FOSA)0
    Hydrophilic component of SASA (FISA)156.377
    Pie component of the SASA (PISA)197.752
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)556.332
    Number of hydrogen bond donors (donorHB)3
    Number of hydrogen bond acceptors (accptHB)2.7
    Free energy of solvation of dipole (dip^2/V)0.0032316
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0132057
    Globularity descriptor (glob)0.923761
    Predicted polarizability in cubic angstroms (QPpolrz)16.073
    Predicted hexadecane/gas partition coefficient (QPlogPC16)6.706
    Predicted octanol/gas partition coefficient (QPlogPoct)10.918
    Predicted water/gas partition coefficient (QPlogPw)9.372
    Predicted octanol/water partition coefficient (QPlogPo/w)0.445
    Predicted aqueous solubility (QPlogS)-1.178
    Conformation-independent predicted aqueous solubility (CIQPlogS)-2.282
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-3.709
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)325.821
    Predicted brain/blood partition coefficient (QPlogBB)-0.839
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)147.21
    Predicted skin permeability, log Kp (QPlogKp)-3.417
    PM3 calculated ionization potential (IP(ev))8.171
    PM3 calculated electron affinity (EA(eV))0.027
    Number of likely metabolic reactions (#metab)3
    Prediction of binding to human serum albumin (QPlogKhsa)-0.598
    Predicted qualitative human oral absorption (HumanOralAbsorption)2
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)74.529
    Solvent-accessible surface area of fluorine atoms (SAFluorine)0
    Solvent-accessible surface area of amide oxygen atoms (SAamideO)0
    Van der Waals surface area (PSA)79.979
    Number of nitrogen and oxygen atoms (#NandO)5
    Number of violations of Lipinski’s rule of five (RuleOfFive)0
    Number of violations of Jorgensen’s rule of three (RuleOfThree)0

    Compound-target network

    Cytoscape Graph

    Protein targets associated with phytocompound

    Uniprot ID Gene name Target name TTD_ID Prediction source
    Q8N5Z0AADATKynurenine/alpha-aminoadipate aminotransferase, mitochondrialT82668SEA
    P51575P2RX1P2X purinoceptor 1T69091SEA
    Q99571P2RX4P2X purinoceptor 4T60330SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T82668DI0265Mild neurocognitive disorder[ICD-11: 6D71]Q8N5Z0AADAT
    T82668DI0370Schizophrenia[ICD-11: 6A20]Q8N5Z0AADAT

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