1,5-Dihydroxyxanthone



Compound IDCDAMM02167
Common name1,5-Dihydroxyxanthone
IUPAC name1,5-dihydroxyxanthen-9-one
Molecular formulaC13H8O4

Experimental data

Retention time0.51
Adduct[2M+Na]+
Actual mz479.073
Theoretical mz479.073
Error0.59
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.3507

Identifiers and class information

Inchi keyAPIPFXZYOMIJQG-UHFFFAOYSA-N
SmilesO=C1C=2C=CC=C(O)C2OC=3C=CC=C(O)C13
SuperclassOrganoheterocyclic compounds
ClassBenzopyrans

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)-1
Molecular weight (mol_MW)228.204
Computed dipole moment(dipole)2.972
Total solvent accessible surface area (SASA)425.466
Hydrophobic component of SASA (FOSA)0
Hydrophilic component of SASA (FISA)138.723
Pie component of the SASA (PISA)286.742
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)700.975
Number of hydrogen bond donors (donorHB)1
Number of hydrogen bond acceptors (accptHB)3
Free energy of solvation of dipole (dip^2/V)0.0126004
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0070511
Globularity descriptor (glob)0.896952
Predicted polarizability in cubic angstroms (QPpolrz)23.353
Predicted hexadecane/gas partition coefficient (QPlogPC16)8.028
Predicted octanol/gas partition coefficient (QPlogPoct)10.897
Predicted water/gas partition coefficient (QPlogPw)7.615
Predicted octanol/water partition coefficient (QPlogPo/w)1.796
Predicted aqueous solubility (QPlogS)-2.669
Conformation-independent predicted aqueous solubility (CIQPlogS)-3.483
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.567
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)479.058
Predicted brain/blood partition coefficient (QPlogBB)-0.707
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)223.299
Predicted skin permeability, log Kp (QPlogKp)-2.874
PM3 calculated ionization potential (IP(ev))8.96
PM3 calculated electron affinity (EA(eV))0.687
Number of likely metabolic reactions (#metab)2
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)85.434
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)76.689
Number of nitrogen and oxygen atoms (#NandO)4
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 AT83875SwissTargetPrediction and SEA
P35354PTGS2Cyclooxygenase-2T66665SwissTargetPrediction
Q6B0I6KDM4DLysine-specific demethylase 4DT17036SEA
Q92731ESR2Estrogen receptor betaT80896SEA
P03372ESR1Estrogen receptor alphaT02506SEA
Q9HC97GPR35G-protein coupled receptor 35T56143SEA
P16050ALOX15Arachidonate 15-lipoxygenaseT16042SEA
P18054ALOX12Arachidonate 12-lipoxygenaseT35527SEA
P11388TOP2ADNA topoisomerase II alphaT17048SEA
Q15078CDK5R1Cyclin-dependent kinase 5/CDK5 activator 1T09513SwissTargetPrediction
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
Q9NPH5NOX4NADPH oxidase 4T29741SEA
P47989XDHXanthine dehydrogenaseT40954SEA
Q16549PCSK7Subtilisin/kexin type 7T33211SEA
Q16678CYP1B1Cytochrome P450 1B1T92521SEA
Q04760GLO1Glyoxalase IT88285SEA
Q9UNI1CELA1Elastase 1T22839SEA
O60911CTSVCathepsin (V and K)T93653SEA
Q9HC98NEK6Serine/threonine-protein kinase NEK6T78992SEA
O60285NUAK1NUAK family SNF1-like kinase 1T21653SEA
P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA
Q13332PTPRSReceptor-type tyrosine-protein phosphatase ST10147SEA
P09172DBHDopamine beta hydroxylaseT74937SEA
O35273SMAD3Mothers against decapentaplegic homolog 3T35445SEA
P16220CREB1Cyclic AMP-responsive element-binding proteinT92098SEA
Q15717ELAVL1ELAV-like protein 1T78349SEA

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
T66665DI0087Chronic pain[ICD-11: MG30]P35354PTGS2
T66665DI0145Female pelvic pain[ICD-11: GA34]P35354PTGS2
T66665DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]P35354PTGS2
T66665DI0207Indeterminate colitis[ICD-11: DD72]P35354PTGS2
T66665DI0227Knee osteoarthritis[ICD-11: FA01]P35354PTGS2
T66665DI0320Osteoarthritis[ICD-11: FA00-FA05]P35354PTGS2
T66665DI0324Pain[ICD-11: MG30-MG3Z]P35354PTGS2
T66665DI0366Rheumatoid arthritis[ICD-11: FA20]P35354PTGS2
T66665DI0416Tuberculosis[ICD-11: 1B10-1B12]P35354PTGS2
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
T02506DI0106COVID-19[ICD-11: 1D6Y]P03372ESR1
T17048DI0012Acute myeloid leukaemia[ICD-11: 2A60]P11388TOP2A
T17048DI0225Kaposi sarcoma[ICD-11: 2B57]P11388TOP2A
T17048DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11388TOP2A
T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
T29741DI0146Fibrosis[ICD-11: GA14-GC01]Q9NPH5NOX4
T40954DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]P47989XDH
T40954DI0266Mineral deficiency[ICD-11: 5B5K]P47989XDH
T88285DI0210Influenza[ICD-11: 1E30-1E32]Q04760GLO1
T22839DI0024Alpha-1-antitrypsin deficiency[ICD-11: 5C5A]Q9UNI1CELA1
T22839DI0065Bronchitis[ICD-11: CA20]Q9UNI1CELA1
T93653DI0055Bone cancer[ICD-11: 2B5Z]O60911CTSV
T93653DI0087Chronic pain[ICD-11: MG30]O60911CTSV
T70518DI0037Asthma[ICD-11: CA23]P16152CBR1
T10147DI0057Bone paget disease[ICD-11: FB85]Q13332PTPRS
T74937DI0175Heart failure[ICD-11: BD10-BD1Z]P09172DBH
T74937DI0341Post-traumatic stress disorder[ICD-11: 6B40]P09172DBH
T35445DI0226Kidney fibrosis[ICD-11: GC01]O35273SMAD3

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