2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol



Compound IDCDAMM00833
Common name2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol
IUPAC name2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromene-3,4,5,7-tetrol
Molecular formulaC15H14O8

Experimental data

Retention time0.45
Adduct[M+H]+
Actual mz323.074
Theoretical mz323.076
Error5.5
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.8605

Identifiers and class information

Inchi keyZEACOKJOQLAYTD-UHFFFAOYNA-N
SmilesOC=1C=C(O)C2=C(OC(C3=CC(O)=C(O)C(O)=C3)C(O)C2O)C1
SuperclassPhenylpropanoids and polyketides
ClassFlavonoids

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)7
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)322.271
Computed dipole moment(dipole)3.554
Total solvent accessible surface area (SASA)527.588
Hydrophobic component of SASA (FOSA)43.995
Hydrophilic component of SASA (FISA)316.374
Pie component of the SASA (PISA)167.22
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)908.287
Number of hydrogen bond donors (donorHB)7
Number of hydrogen bond acceptors (accptHB)7.9
Free energy of solvation of dipole (dip^2/V)0.0139036
Index of cohesive interaction in solids (ACxDN^.5/SA)0.039617
Globularity descriptor (glob)0.85971
Predicted polarizability in cubic angstroms (QPpolrz)27.298
Predicted hexadecane/gas partition coefficient (QPlogPC16)11.648
Predicted octanol/gas partition coefficient (QPlogPoct)24.127
Predicted water/gas partition coefficient (QPlogPw)20.768
Predicted octanol/water partition coefficient (QPlogPo/w)-0.962
Predicted aqueous solubility (QPlogS)-2.088
Conformation-independent predicted aqueous solubility (CIQPlogS)-3.166
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.6
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)9.902
Predicted brain/blood partition coefficient (QPlogBB)-2.712
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)3.373
Predicted skin permeability, log Kp (QPlogKp)-6.089
PM3 calculated ionization potential (IP(ev))8.827
PM3 calculated electron affinity (EA(eV))-0.076
Number of likely metabolic reactions (#metab)8
Prediction of binding to human serum albumin (QPlogKhsa)-0.731
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)26.174
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)156.322
Number of nitrogen and oxygen atoms (#NandO)8
Number of violations of Lipinski’s rule of five (RuleOfFive)1
Number of violations of Jorgensen’s rule of three (RuleOfThree)2

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
Q12809KCNH2HERGT20251SwissTargetPrediction
O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction
Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction
P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
P05067APPBeta amyloid A4 proteinT87024SwissTargetPrediction
P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
P43166CA7Carbonic anhydrase VIIT37541SwissTargetPrediction
P23280CA6Carbonic anhydrase VIT06569SwissTargetPrediction
P22748CA4Carbonic anhydrase IVT53378SwissTargetPrediction
P14867GABRA1GABA-A receptor; alpha-1/beta-2/gamma-2T51487SwissTargetPrediction
Q5T7T8COX1Prostaglandin G/H synthase 1T60529SwissTargetPrediction
P35968KDRVascular endothelial growth factor receptor 2T80975SwissTargetPrediction
P08253MMP2Matrix metalloproteinase 2T68251SwissTargetPrediction
P14780MMP9Matrix metalloproteinase 9T54156SwissTargetPrediction
Q14534SQLESqualene monooxygenase (by homology)T93344SwissTargetPrediction
P08183ABCB1P-glycoprotein 1T25258SwissTargetPrediction
Q16539MAPK14MAP kinase p38 alphaT65864SwissTargetPrediction
P56817BACE1Beta-secretase 1T79031SwissTargetPrediction
P45452MMP13Matrix metalloproteinase 13T34296SwissTargetPrediction
P16050ALOX15Arachidonate 15-lipoxygenaseT16042SwissTargetPrediction
P18054ALOX12Arachidonate 12-lipoxygenaseT35527SwissTargetPrediction
O14746TERTTelomerase reverse transcriptaseT86052SwissTargetPrediction
P08581METHepatocyte growth factor receptorT40474SwissTargetPrediction
P10721KITStem cell growth factor receptorT57700SwissTargetPrediction
P12931SRCTyrosine-protein kinase SRCT85943SwissTargetPrediction
Q13627DYRK1ADual-specificity tyrosine-phosphorylation regulated kinase 1AT92803SwissTargetPrediction
P06870KLK1Kallikrein 1T40000SwissTargetPrediction
P20151KLK2Kallikrein 2T01908SwissTargetPrediction and SEA
P26358DNMT1DNA (cytosine-5)-methyltransferase 1 (by homology)T88304SwissTargetPrediction
P15692VEGFAVascular endothelial growth factor AT20761SwissTargetPrediction and SEA
P11362FGFR1Fibroblast growth factor receptor 1T47101SwissTargetPrediction
P39900MMP12Matrix metalloproteinase 12T03500SwissTargetPrediction
P49763PGFPlacenta growth factorT70792SwissTargetPrediction and SEA
P10415BCL2Apoptosis regulator Bcl-2T31309SwissTargetPrediction
P52209PGD6-phosphogluconate dehydrogenaseT76497SwissTargetPrediction and SEA
P22083FUT4Fucosyltransferase 4T51146SwissTargetPrediction
P42224STAT1Signal transducer and activator of transcription 1-alpha/betaT64205SwissTargetPrediction
Q16678CYP1B1Cytochrome P450 1B1T92521SwissTargetPrediction
P10636MAPTMicrotubule-associated protein tauT45593SwissTargetPrediction
Q16665HIF1AHypoxia-inducible factor 1 alphaT55610SwissTargetPrediction
P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T20251DI0175Heart failure[ICD-11: BD10-BD1Z]Q12809KCNH2
T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
T64567DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16790CA9
T13201DI0166Glaucoma[ICD-11: 9C61]P00915CA1
T13201DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00915CA1
T87024DI0025Alzheimer disease[ICD-11: 8A20]P05067APP
T87024DI0122Diagnostic imaging[ICD-11: N.A.]P05067APP
T20401DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P00918CA2
T20401DI0137Essential hypertension[ICD-11: BA00]P00918CA2
T20401DI0166Glaucoma[ICD-11: 9C61]P00918CA2
T20401DI0175Heart failure[ICD-11: BD10-BD1Z]P00918CA2
T20401DI0214Insomnia[ICD-11: 7A00-7A0Z]P00918CA2
T20401DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00918CA2
T06569DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P23280CA6
T06569DI0372Seborrhoeic dermatitis[ICD-11: EA81]P23280CA6
T53378DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P22748CA4
T53378DI0166Glaucoma[ICD-11: 9C61]P22748CA4
T53378DI0372Seborrhoeic dermatitis[ICD-11: EA81]P22748CA4
T51487DI0014Acute respiratory distress syndrome[ICD-11: CB00]P14867GABRA1
T51487DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]P14867GABRA1
T51487DI0082Chronic insomnia[ICD-11: 7A00]P14867GABRA1
T51487DI0087Chronic pain[ICD-11: MG30]P14867GABRA1
T51487DI0101Corneal disease[ICD-11: 9A76-9A78]P14867GABRA1
T51487DI0112Cystitis[ICD-11: GC00]P14867GABRA1
T51487DI0117Depression[ICD-11: 6A70-6A7Z]P14867GABRA1
T51487DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P14867GABRA1
T51487DI0173Headache[ICD-11: 8A80-8A84]P14867GABRA1
T51487DI0214Insomnia[ICD-11: 7A00-7A0Z]P14867GABRA1
T51487DI0243Malaria[ICD-11: 1F40-1F45]P14867GABRA1
T51487DI0256Mental/behavioural/neurodevelopmental disorder[ICD-11: 6E20-6E8Z]P14867GABRA1
T51487DI0411Tonus and reflex abnormality[ICD-11: MB47]P14867GABRA1
T60529DI0141Eye anterior segment structural developmental anomaly[ICD-11: LA11]Q5T7T8COX1
T60529DI0145Female pelvic pain[ICD-11: GA34]Q5T7T8COX1
T60529DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]Q5T7T8COX1
T60529DI0207Indeterminate colitis[ICD-11: DD72]Q5T7T8COX1
T60529DI0306Nutritional deficiency[ICD-11: 5B50-5B71]Q5T7T8COX1
T60529DI0320Osteoarthritis[ICD-11: FA00-FA05]Q5T7T8COX1
T60529DI0324Pain[ICD-11: MG30-MG3Z]Q5T7T8COX1
T60529DI0339Postoperative inflammation[ICD-11: 1A00-CA43]Q5T7T8COX1
T60529DI0366Rheumatoid arthritis[ICD-11: FA20]Q5T7T8COX1
T60529DI0372Seborrhoeic dermatitis[ICD-11: EA81]Q5T7T8COX1
T60529DI0416Tuberculosis[ICD-11: 1B10-1B12]Q5T7T8COX1
T60529DI0419Ulcerative colitis[ICD-11: DD71]Q5T7T8COX1
T80975DI0062Breast cancer[ICD-11: 2C60-2C6Y]P35968KDR
T80975DI0095Colorectal cancer[ICD-11: 2B91]P35968KDR
T80975DI0160Gastrointestinal stromal tumour[ICD-11: 2B5B]P35968KDR
T80975DI0244Malignant digestive organ neoplasm[ICD-11: 2C11]P35968KDR
T80975DI0361Renal cell carcinoma[ICD-11: 2C90]P35968KDR
T80975DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P35968KDR
T80975DI0395Stomach cancer[ICD-11: 2B72]P35968KDR
T80975DI0403Thrombocytopenia[ICD-11: 3B64]P35968KDR
T80975DI0407Thyroid cancer[ICD-11: 2D10]P35968KDR
T68251DI0238Lung cancer[ICD-11: 2C25]P08253MMP2
T54156DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P14780MMP9
T54156DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P14780MMP9
T54156DI0395Stomach cancer[ICD-11: 2B72]P14780MMP9
T54156DI0419Ulcerative colitis[ICD-11: DD71]P14780MMP9
T93344DI0118Dermatophytosis[ICD-11: 1F28]Q14534SQLE
T93344DI0385Skin fungal infection disorder[ICD-11: EA60]Q14534SQLE
T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
T65864DI0102Coronary atherosclerosis[ICD-11: BA52]Q16539MAPK14
T65864DI0287Myocardial infarction[ICD-11: BA41-BA43]Q16539MAPK14
T65864DI0366Rheumatoid arthritis[ICD-11: FA20]Q16539MAPK14
T65864DI0437Vitamin deficiency[ICD-11: 5B55-5B5F]Q16539MAPK14
T79031DI0025Alzheimer disease[ICD-11: 8A20]P56817BACE1
T34296DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45452MMP13
T86052DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]O14746TERT
T86052DI0284Myelodysplastic syndrome[ICD-11: 2A37]O14746TERT
T86052DI0326Pancreatic cancer[ICD-11: 2C10]O14746TERT
T40474DI0238Lung cancer[ICD-11: 2C25]P08581MET
T40474DI0303Non-small-cell lung cancer[ICD-11: 2C25]P08581MET
T40474DI0407Thyroid cancer[ICD-11: 2D10]P08581MET
T57700DI0058Bone/articular cartilage neoplasm[ICD-11: 2F7B]P10721KIT
T57700DI0095Colorectal cancer[ICD-11: 2B91]P10721KIT
T57700DI0160Gastrointestinal stromal tumour[ICD-11: 2B5B]P10721KIT
T57700DI0250Mature B-cell lymphoma[ICD-11: 2A85]P10721KIT
T57700DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P10721KIT
T57700DI0361Renal cell carcinoma[ICD-11: 2C90]P10721KIT
T57700DI0403Thrombocytopenia[ICD-11: 3B64]P10721KIT
T85943DI0062Breast cancer[ICD-11: 2C60-2C6Y]P12931SRC
T85943DI0220Ischemia[ICD-11: 8B10-8B11]P12931SRC
T85943DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P12931SRC
T85943DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P12931SRC
T92803DI0113Cytomegaloviral disease[ICD-11: 1D82]Q13627DYRK1A
T01908DI0213Innate/adaptive immunodeficiency[ICD-11: 4A00]P20151KLK2
T88304DI0012Acute myeloid leukaemia[ICD-11: 2A60]P26358DNMT1
T88304DI0284Myelodysplastic syndrome[ICD-11: 2A37]P26358DNMT1
T88304DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P26358DNMT1
T20761DI0095Colorectal cancer[ICD-11: 2B91]P15692VEGFA
T20761DI0365Retinopathy[ICD-11: 9B71]P15692VEGFA
T20761DI0430Vascular system developmental anomaly[ICD-11: LA90]P15692VEGFA
T47101DI0095Colorectal cancer[ICD-11: 2B91]P11362FGFR1
T47101DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P11362FGFR1
T47101DI0235Liver cancer[ICD-11: 2C12]P11362FGFR1
T47101DI0403Thrombocytopenia[ICD-11: 3B64]P11362FGFR1
T03500DI0037Asthma[ICD-11: CA23]P39900MMP12
T03500DI0238Lung cancer[ICD-11: 2C25]P39900MMP12
T03500DI0361Renal cell carcinoma[ICD-11: 2C90]P39900MMP12
T70792DI0095Colorectal cancer[ICD-11: 2B91]P49763PGF
T31309DI0062Breast cancer[ICD-11: 2C60-2C6Y]P10415BCL2
T31309DI0249Mature B-cell leukaemia[ICD-11: 2A82]P10415BCL2
T31309DI0273Motor neuron disease[ICD-11: 8B60]P10415BCL2
T31309DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P10415BCL2
T76497DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P52209PGD
T51146DI0441Appendicitis[ICD-11: DB10]P22083FUT4
T64205DI0383Skin and skin-structure infection[ICD-11: 1F28-1G0Z]P42224STAT1
T45593DI0012Acute myeloid leukaemia[ICD-11: 2A60]P10636MAPT
T45593DI0025Alzheimer disease[ICD-11: 8A20]P10636MAPT
T45593DI0265Mild neurocognitive disorder[ICD-11: 6D71]P10636MAPT
T55610DI0241Lymphoma[ICD-11: 2A80-2A86]Q16665HIF1A
T55610DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16665HIF1A
T70518DI0037Asthma[ICD-11: CA23]P16152CBR1

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