5,7-dihydroxy-3-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one



Compound IDCDAMM00727
Common name5,7-dihydroxy-3-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
IUPAC name5,7-dihydroxy-3-(4-methoxyphenyl)-2,3-dihydrochromen-4-one
Molecular formulaC16H14O5

Experimental data

Retention time7.49
Adduct[M+H]+
Actual mz287.09
Theoretical mz287.091
Error4.44
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.9695

Identifiers and class information

Inchi keyXPZQBSCTDLGDBP-UHFFFAOYNA-N
SmilesO=C1C=2C(O)=CC(O)=CC2OCC1C3=CC=C(OC)C=C3
SuperclassPhenylpropanoids and polyketides
ClassIsoflavonoids

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)0
Predicted central nervous system activity (CNS)-1
Molecular weight (mol_MW)286.284
Computed dipole moment(dipole)3.691
Total solvent accessible surface area (SASA)509.038
Hydrophobic component of SASA (FOSA)148.321
Hydrophilic component of SASA (FISA)129.876
Pie component of the SASA (PISA)230.841
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)873.778
Number of hydrogen bond donors (donorHB)1
Number of hydrogen bond acceptors (accptHB)4
Free energy of solvation of dipole (dip^2/V)0.0155907
Index of cohesive interaction in solids (ACxDN^.5/SA)0.007858
Globularity descriptor (glob)0.868325
Predicted polarizability in cubic angstroms (QPpolrz)29.093
Predicted hexadecane/gas partition coefficient (QPlogPC16)9.12
Predicted octanol/gas partition coefficient (QPlogPoct)13.278
Predicted water/gas partition coefficient (QPlogPw)8.141
Predicted octanol/water partition coefficient (QPlogPo/w)2.468
Predicted aqueous solubility (QPlogS)-3.665
Conformation-independent predicted aqueous solubility (CIQPlogS)-4.264
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.764
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)581.143
Predicted brain/blood partition coefficient (QPlogBB)-0.766
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)275.149
Predicted skin permeability, log Kp (QPlogKp)-2.812
PM3 calculated ionization potential (IP(ev))9.076
PM3 calculated electron affinity (EA(eV))0.394
Number of likely metabolic reactions (#metab)4
Prediction of binding to human serum albumin (QPlogKhsa)0.113
Predicted qualitative human oral absorption (HumanOralAbsorption)3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)90.87
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)84.601
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
P21397MAOAMonoamine oxidase AT83875SEA
P43166CA7Carbonic anhydrase VIIT37541SEA
P22748CA4Carbonic anhydrase IVT53378SEA
P27338MAOBMonoamine oxidase BT83011SwissTargetPrediction and SEA
Q92731ESR2Estrogen receptor betaT80896SwissTargetPrediction and SEA
P11511CYP19A1Cytochrome P450 19A1T13260SwissTargetPrediction and SEA
P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction
P03372ESR1Estrogen receptor alphaT02506SwissTargetPrediction and SEA
O95718ESRRBEstrogen-related receptor betaT42025SEA
P16050ALOX15Arachidonate 15-lipoxygenaseT16042SwissTargetPrediction
P18054ALOX12Arachidonate 12-lipoxygenaseT35527SwissTargetPrediction and SEA
P20151KLK2Kallikrein 2T01908SEA
P25101EDNRAEndothelin receptor ET-AT23499SEA
P48736PIK3CGPI3-kinase p110-gamma subunitT95913SEA
P60568IL2Interleukin-2T61698SEA
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
P24530EDNRBEndothelin receptor ET-BT92828SEA
P37023ACVRL1Serine/threonine-protein kinase receptor R3T36959SEA
P14679TYRTyrosinaseT97035SEA
P52209PGD6-phosphogluconate dehydrogenaseT76497SEA
Q16678CYP1B1Cytochrome P450 1B1T92521SEA
P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA
Q15120PDK3Pyruvate dehydrogenase kinase isoform 3T99029SEA
O15427SLC16A3Monocarboxylate transporter 4T31788SEA
Q9NZ70TAK1TGF-beta-activated kinase 1T04361SEA
Q92887CMOATMultidrug resistance-associated protein 2T61792SEA
Q96HK3CALMCalmodulinT39610SEA
Q9UK17KCND3Voltage-gated potassium channel Kv4.3T74500SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T83875DI0117Depression[ICD-11: 6A70-6A7Z]P21397MAOA
T83875DI0331Parkinsonism[ICD-11: 8A00]P21397MAOA
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
T01908DI0213Innate/adaptive immunodeficiency[ICD-11: 4A00]P20151KLK2
T23499DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P25101EDNRA
T23499DI0356Pulmonary hypertension[ICD-11: BB01]P25101EDNRA
T23499DI0425Urinary system clinical symptom[ICD-11: MF8Y]P25101EDNRA
T95913DI0151Follicular lymphoma[ICD-11: 2A80]P48736PIK3CG
T95913DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P48736PIK3CG
T95913DI0249Mature B-cell leukaemia[ICD-11: 2A82]P48736PIK3CG
T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
T92828DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P24530EDNRB
T92828DI0356Pulmonary hypertension[ICD-11: BB01]P24530EDNRB
T36959DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P37023ACVRL1
T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
T76497DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P52209PGD
T70518DI0037Asthma[ICD-11: CA23]P16152CBR1
T04361DI0250Mature B-cell lymphoma[ICD-11: 2A85]Q9NZ70TAK1
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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