Lophirone I



Compound IDCDAMM02764
Common nameLophirone I
IUPAC name7-hydroxy-2-[2-(4-hydroxyphenyl)-1-benzofuran-5-yl]-2,3-dihydrochromen-4-one
Molecular formulaC23H16O5

Experimental data

Retention time1.76
Adduct[M+H]+
Actual mz373.107
Theoretical mz373.107
Error0.74
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.0372

Identifiers and class information

Inchi keyFKAOXSDPCYTXNP-ANBDAQEENA-N
SmilesO=C1C2=CC=C(O)C=C2OC(C3=CC=C4OC(=CC4=C3)C=5C=CC(O)=CC5)C1
SuperclassPhenylpropanoids and polyketides
Class2-arylbenzofuran flavonoids

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)2
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)372.376
Computed dipole moment(dipole)1.546
Total solvent accessible surface area (SASA)655.171
Hydrophobic component of SASA (FOSA)48.285
Hydrophilic component of SASA (FISA)159.837
Pie component of the SASA (PISA)447.049
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1134.38
Number of hydrogen bond donors (donorHB)2
Number of hydrogen bond acceptors (accptHB)4.75
Free energy of solvation of dipole (dip^2/V)0.0021081
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0102531
Globularity descriptor (glob)0.802879
Predicted polarizability in cubic angstroms (QPpolrz)42.229
Predicted hexadecane/gas partition coefficient (QPlogPC16)13.482
Predicted octanol/gas partition coefficient (QPlogPoct)19.921
Predicted water/gas partition coefficient (QPlogPw)12.591
Predicted octanol/water partition coefficient (QPlogPo/w)3.655
Predicted aqueous solubility (QPlogS)-6.042
Conformation-independent predicted aqueous solubility (CIQPlogS)-6.177
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-6.854
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)302.111
Predicted brain/blood partition coefficient (QPlogBB)-1.21
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)135.666
Predicted skin permeability, log Kp (QPlogKp)-2.698
PM3 calculated ionization potential (IP(ev))8.602
PM3 calculated electron affinity (EA(eV))0.706
Number of likely metabolic reactions (#metab)5
Prediction of binding to human serum albumin (QPlogKhsa)0.631
Predicted qualitative human oral absorption (HumanOralAbsorption)3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)92.736
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)88.832
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)1

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
P05067APPBeta amyloid A4 proteinT87024SEA
P22748CA4Carbonic anhydrase IVT53378SEA
P27338MAOBMonoamine oxidase BT83011SEA
P11086PNMTPhenylethanolamine N-methyltransferaseT56496SwissTargetPrediction
Q92731ESR2Estrogen receptor betaT80896SEA
P11511CYP19A1Cytochrome P450 19A1T13260SEA
P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction
P03372ESR1Estrogen receptor alphaT02506SEA
P14061HSD17B1Estradiol 17-beta-dehydrogenase 1T44011SwissTargetPrediction
P56817BACE1Beta-secretase 1T79031SwissTargetPrediction
O14965AURKASerine/threonine-protein kinase Aurora-AT87675SwissTargetPrediction
P20151KLK2Kallikrein 2T01908SEA
P15692VEGFAVascular endothelial growth factor AT20761SEA
P49763PGFPlacenta growth factorT70792SEA
P47989XDHXanthine dehydrogenaseT40954SEA
Q16678CYP1B1Cytochrome P450 1B1T92521SwissTargetPrediction and SEA
P16152CBR1Carbonyl reductase [NADPH] 1T70518SwissTargetPrediction and SEA
Q13332PTPRSReceptor-type tyrosine-protein phosphatase ST10147SEA
P27169PON1Serum paraoxonase/arylesterase 1T34562SEA
Q99417MYCBPMYCBP messenger RNAT37298SEA
Q96HK3CALMCalmodulinT39610SEA
Q9UK17KCND3Voltage-gated potassium channel Kv4.3T74500SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T87024DI0025Alzheimer disease[ICD-11: 8A20]P05067APP
T87024DI0122Diagnostic imaging[ICD-11: N.A.]P05067APP
T53378DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P22748CA4
T53378DI0166Glaucoma[ICD-11: 9C61]P22748CA4
T53378DI0372Seborrhoeic dermatitis[ICD-11: EA81]P22748CA4
T83011DI0115Dementia[ICD-11: 6D80-6D8Z]P27338MAOB
T83011DI0117Depression[ICD-11: 6A70-6A7Z]P27338MAOB
T83011DI0190Hypertension[ICD-11: BA00-BA04]P27338MAOB
T83011DI0243Malaria[ICD-11: 1F40-1F45]P27338MAOB
T83011DI0264Migraine[ICD-11: 8A80]P27338MAOB
T83011DI0331Parkinsonism[ICD-11: 8A00]P27338MAOB
T80896DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q92731ESR2
T80896DI0108Cushing syndrome[ICD-11: 5A70]Q92731ESR2
T80896DI0254Menopausal disorder[ICD-11: GA30]Q92731ESR2
T80896DI0432Vasomotor/allergic rhinitis[ICD-11: CA08]Q92731ESR2
T13260DI0062Breast cancer[ICD-11: 2C60-2C6Y]P11511CYP19A1
T13260DI0108Cushing syndrome[ICD-11: 5A70]P11511CYP19A1
T16347DI0009Acute diabete complication[ICD-11: 5A2Y]P18031PTPN1
T16347DI0062Breast cancer[ICD-11: 2C60-2C6Y]P18031PTPN1
T16347DI0308Obesity[ICD-11: 5B80-5B81]P18031PTPN1
T16347DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P18031PTPN1
T02506DI0106COVID-19[ICD-11: 1D6Y]P03372ESR1
T79031DI0025Alzheimer disease[ICD-11: 8A20]P56817BACE1
T87675DI0009Acute diabete complication[ICD-11: 5A2Y]O14965AURKA
T87675DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O14965AURKA
T01908DI0213Innate/adaptive immunodeficiency[ICD-11: 4A00]P20151KLK2
T20761DI0095Colorectal cancer[ICD-11: 2B91]P15692VEGFA
T20761DI0365Retinopathy[ICD-11: 9B71]P15692VEGFA
T20761DI0430Vascular system developmental anomaly[ICD-11: LA90]P15692VEGFA
T70792DI0095Colorectal cancer[ICD-11: 2B91]P49763PGF
T40954DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]P47989XDH
T40954DI0266Mineral deficiency[ICD-11: 5B5K]P47989XDH
T70518DI0037Asthma[ICD-11: CA23]P16152CBR1
T10147DI0057Bone paget disease[ICD-11: FB85]Q13332PTPRS
T37298DI0235Liver cancer[ICD-11: 2C12]Q99417MYCBP
T39610DI0068Cardiac arrhythmia[ICD-11: BC9Z]Q96HK3CALM
T39610DI0243Malaria[ICD-11: 1F40-1F45]Q96HK3CALM
T39610DI0370Schizophrenia[ICD-11: 6A20]Q96HK3CALM
T74500DI0004Acidosis[ICD-11: 5C73]Q9UK17KCND3

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