Lophirone J



Compound IDCDAMM01647
Common nameLophirone J
IUPAC name7-methoxy-2-[2-(4-methoxyphenyl)-1-benzofuran-5-yl]-2,3-dihydrochromen-4-one
Molecular formulaC25H20O5

Experimental data

Retention time3.61
Adduct[M+H]+
Actual mz401.138
Theoretical mz401.138
Error0.69
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.9183

Identifiers and class information

Inchi keyGIIGHMRSPFEORX-FQKVKQEKNA-N
SmilesO=C1C2=CC=C(OC)C=C2OC(C3=CC=C4OC(=CC4=C3)C=5C=CC(OC)=CC5)C1
SuperclassPhenylpropanoids and polyketides
Class2-arylbenzofuran flavonoids

Pharmacokinetic properties

Number of descriptor values(#stars)1
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)0
Molecular weight (mol_MW)400.43
Computed dipole moment(dipole)2.189
Total solvent accessible surface area (SASA)706.113
Hydrophobic component of SASA (FOSA)234.749
Hydrophilic component of SASA (FISA)50.546
Pie component of the SASA (PISA)420.818
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1241.16
Number of hydrogen bond donors (donorHB)0
Number of hydrogen bond acceptors (accptHB)4.75
Free energy of solvation of dipole (dip^2/V)0.0038624
Index of cohesive interaction in solids (ACxDN^.5/SA)0
Globularity descriptor (glob)0.791
Predicted polarizability in cubic angstroms (QPpolrz)46.252
Predicted hexadecane/gas partition coefficient (QPlogPC16)13.127
Predicted octanol/gas partition coefficient (QPlogPoct)17.837
Predicted water/gas partition coefficient (QPlogPw)8.862
Predicted octanol/water partition coefficient (QPlogPo/w)5.222
Predicted aqueous solubility (QPlogS)-6.785
Conformation-independent predicted aqueous solubility (CIQPlogS)-6.742
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-6.921
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)3285.25
Predicted brain/blood partition coefficient (QPlogBB)-0.096
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)1789.37
Predicted skin permeability, log Kp (QPlogKp)-0.777
PM3 calculated ionization potential (IP(ev))8.56
PM3 calculated electron affinity (EA(eV))0.678
Number of likely metabolic reactions (#metab)5
Prediction of binding to human serum albumin (QPlogKhsa)0.866
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)100
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)59.971
Number of nitrogen and oxygen atoms (#NandO)5
Number of violations of Lipinski’s rule of five (RuleOfFive)1
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
P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction
P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
P05067APPBeta amyloid A4 proteinT87024SEA
P42336PIK3CAPI3-kinase p110-alpha subunitT80276SwissTargetPrediction
P22748CA4Carbonic anhydrase IVT53378SEA
P27338MAOBMonoamine oxidase BT83011SEA
P11926ODC1Ornithine decarboxylaseT60366SEA
P11511CYP19A1Cytochrome P450 19A1T13260SEA
P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction
P07195LDHBL-lactate dehydrogenase B chainT88057SEA
P42345MTORSerine/threonine-protein kinase mTORT75243SwissTargetPrediction
P00519ABL1Tyrosine-protein kinase ABLT63505SwissTargetPrediction
P36888FLT3Tyrosine-protein kinase receptor FLT3T74312SwissTargetPrediction
P56817BACE1Beta-secretase 1T79031SwissTargetPrediction
O14965AURKASerine/threonine-protein kinase Aurora-AT87675SwissTargetPrediction
Q9Y233PDE10APhosphodiesterase 10A (by homology)T84133SwissTargetPrediction
P25105PTAFRPlatelet activating factor receptorT87023SwissTargetPrediction
Q15858SCN9ASodium channel protein type IX alpha subunitT12119SwissTargetPrediction
P09619PDGFRBPlatelet-derived growth factor receptor betaT59102SwissTargetPrediction
P07333CSF1RMacrophage colony stimulating factor receptorT20333SwissTargetPrediction
O00763ACACBAcetyl-CoA carboxylase 2T08922SwissTargetPrediction
P60568IL2Interleukin-2T61698SEA
Q99683MAP3K5Mitogen-activated protein kinase kinase kinase 5T97589SwissTargetPrediction
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
Q9UHD2TBK1Serine/threonine-protein kinase TBK1T63024SwissTargetPrediction
P35557GCKHexokinase type IVT87166SwissTargetPrediction
P43490NAMPTNicotinamide phosphoribosyltransferaseT54582SwissTargetPrediction
P43003SLC1A3Excitatory amino acid transporter 1T86582SEA
Q9NZ70TAK1TGF-beta-activated kinase 1T04361SwissTargetPrediction
Q16678CYP1B1Cytochrome P450 1B1T92521SEA
Q04760GLO1Glyoxalase IT88285SwissTargetPrediction
O43497CACNA1GVoltage-gated T-type calcium channel alpha-1G subunitT64795SwissTargetPrediction
P16152CBR1Carbonyl reductase [NADPH] 1T70518SwissTargetPrediction and SEA
P41235HNF4AHepatocyte nuclear factor 4-alphaT15514SEA
Q13698CACNA1SVoltage-gated L-type calcium channel alpha-1S subunitT24965SEA
P16473TSHRThyroid stimulating hormone receptorT60606SwissTargetPrediction
O15427SLC16A3Monocarboxylate transporter 4T31788SEA
Q7RTX1TAS1R1Taste receptorT41263SEA
P43354NR4A2Orphan nuclear receptor NURR1T67163SEA
Q9UK17KCND3Voltage-gated potassium channel Kv4.3T74500SEA
P68104EEF1A1Elongation factor 1AT72269SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T77365DI0319Orthostatic hypotension[ICD-11: BA21]P29274ADORA2A
T77365DI0331Parkinsonism[ICD-11: 8A00]P29274ADORA2A
T77365DI0359Radionuclide imaging[ICD-11: N.A.]P29274ADORA2A
T92072DI0319Orthostatic hypotension[ICD-11: BA21]P30542ADORA1
T87024DI0025Alzheimer disease[ICD-11: 8A20]P05067APP
T87024DI0122Diagnostic imaging[ICD-11: N.A.]P05067APP
T80276DI0062Breast cancer[ICD-11: 2C60-2C6Y]P42336PIK3CA
T80276DI0151Follicular lymphoma[ICD-11: 2A80]P42336PIK3CA
T80276DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P42336PIK3CA
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
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
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
T75243DI0036Arteries/arterioles disorder[ICD-11: BD52]P42345MTOR
T75243DI0085Chronic myelomonocytic leukaemia[ICD-11: 2A40]P42345MTOR
T75243DI0274Multiple myeloma[ICD-11: 2A83]P42345MTOR
T75243DI0361Renal cell carcinoma[ICD-11: 2C90]P42345MTOR
T75243DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P42345MTOR
T75243DI0413Transplant rejection[ICD-11: NE84]P42345MTOR
T63505DI0062Breast cancer[ICD-11: 2C60-2C6Y]P00519ABL1
T63505DI0220Ischemia[ICD-11: 8B10-8B11]P00519ABL1
T63505DI0250Mature B-cell lymphoma[ICD-11: 2A85]P00519ABL1
T63505DI0306Nutritional deficiency[ICD-11: 5B50-5B71]P00519ABL1
T74312DI0012Acute myeloid leukaemia[ICD-11: 2A60]P36888FLT3
T74312DI0058Bone/articular cartilage neoplasm[ICD-11: 2F7B]P36888FLT3
T74312DI0095Colorectal cancer[ICD-11: 2B91]P36888FLT3
T74312DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]P36888FLT3
T74312DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P36888FLT3
T74312DI0248Mastocytosis[ICD-11: 2A21]P36888FLT3
T74312DI0250Mature B-cell lymphoma[ICD-11: 2A85]P36888FLT3
T74312DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P36888FLT3
T79031DI0025Alzheimer disease[ICD-11: 8A20]P56817BACE1
T87675DI0009Acute diabete complication[ICD-11: 5A2Y]O14965AURKA
T87675DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O14965AURKA
T84133DI0079Choreiform disorder[ICD-11: 8A01]Q9Y233PDE10A
T84133DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]Q9Y233PDE10A
T84133DI0218Irritable bowel syndrome[ICD-11: DD91]Q9Y233PDE10A
T84133DI0370Schizophrenia[ICD-11: 6A20]Q9Y233PDE10A
T84133DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9Y233PDE10A
T87023DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P25105PTAFR
T12119DI0051Bipolar disorder[ICD-11: 6A60]Q15858SCN9A
T12119DI0087Chronic pain[ICD-11: MG30]Q15858SCN9A
T12119DI0140Extremities vasodilatation[ICD-11: EG00]Q15858SCN9A
T12119DI0163General pain disorder[ICD-11: 8E43]Q15858SCN9A
T12119DI0320Osteoarthritis[ICD-11: FA00-FA05]Q15858SCN9A
T12119DI0324Pain[ICD-11: MG30-MG3Z]Q15858SCN9A
T12119DI0358Radiculopathy[ICD-11: 8B93]Q15858SCN9A
T12119DI0415Trigeminal nerve disorder[ICD-11: 8B82]Q15858SCN9A
T59102DI0009Acute diabete complication[ICD-11: 5A2Y]P09619PDGFRB
T59102DI0361Renal cell carcinoma[ICD-11: 2C90]P09619PDGFRB
T59102DI0403Thrombocytopenia[ICD-11: 3B64]P09619PDGFRB
T20333DI0058Bone/articular cartilage neoplasm[ICD-11: 2F7B]P07333CSF1R
T08922DI0417Type 2 diabetes mellitus[ICD-11: 5A11]O00763ACACB
T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
T97589DI0083Chronic kidney disease[ICD-11: GB61]Q99683MAP3K5
T97589DI0356Pulmonary hypertension[ICD-11: BB01]Q99683MAP3K5
T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
T87166DI0009Acute diabete complication[ICD-11: 5A2Y]P35557GCK
T87166DI0120Diabetes mellitus[ICD-11: 5A10]P35557GCK
T87166DI0308Obesity[ICD-11: 5B80-5B81]P35557GCK
T87166DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P35557GCK
T54582DI0231Leukaemia[ICD-11: 2A60-2B33]P43490NAMPT
T54582DI0241Lymphoma[ICD-11: 2A80-2A86]P43490NAMPT
T54582DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P43490NAMPT
T04361DI0250Mature B-cell lymphoma[ICD-11: 2A85]Q9NZ70TAK1
T88285DI0210Influenza[ICD-11: 1E30-1E32]Q04760GLO1
T64795DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]O43497CACNA1G
T64795DI0190Hypertension[ICD-11: BA00-BA04]O43497CACNA1G
T64795DI0276Multiple structural anomalies syndrome[ICD-11: LD2F]O43497CACNA1G
T64795DI0326Pancreatic cancer[ICD-11: 2C10]O43497CACNA1G
T64795DI0370Schizophrenia[ICD-11: 6A20]O43497CACNA1G
T70518DI0037Asthma[ICD-11: CA23]P16152CBR1
T60606DI0197Hypo-thyroidism[ICD-11: 5A00]P16473TSHR
T60606DI0407Thyroid cancer[ICD-11: 2D10]P16473TSHR
T41263DI0078Cholera[ICD-11: 1A00]Q7RTX1TAS1R1
T74500DI0004Acidosis[ICD-11: 5C73]Q9UK17KCND3
T72269DI0252Melanoma[ICD-11: 2C30]P68104EEF1A1

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