6-(3,4-Dihydroxyphenyl)-6a,12b-dihydro-3,10,11,12-tetrahydroxy-[2]benzopyrano[3,4-c]benzopyran-8(6H)-one



Compound IDCDAMM02642
Common name6-(3,4-Dihydroxyphenyl)-6a,12b-dihydro-3,10,11,12-tetrahydroxy-[2]benzopyrano[3,4-c]benzopyran-8(6H)-one
IUPAC name6-(3,4-dihydroxyphenyl)-3,10,11,12-tetrahydroxy-6a,12b-dihydro-6H-isochromeno[3,4-c]chromen-8-one
Molecular formulaC22H16O9

Experimental data

Retention time6.48
Adduct[M+H]+
Actual mz425.091
Theoretical mz425.086
Error12.05
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.5147

Identifiers and class information

Inchi keyWEZKOSOKVUPYJW-XLPVHSHMNA-N
SmilesO=C1OC2C(OC3=CC(O)=CC=C3C2C4=C(O)C(O)=C(O)C=C14)C5=CC=C(O)C(O)=C5
SuperclassPhenylpropanoids and polyketides
ClassFlavonoids

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)6
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)424.363
Computed dipole moment(dipole)8.22
Total solvent accessible surface area (SASA)613.339
Hydrophobic component of SASA (FOSA)44.637
Hydrophilic component of SASA (FISA)329.711
Pie component of the SASA (PISA)238.992
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1120.32
Number of hydrogen bond donors (donorHB)6
Number of hydrogen bond acceptors (accptHB)8.25
Free energy of solvation of dipole (dip^2/V)0.0603065
Index of cohesive interaction in solids (ACxDN^.5/SA)0.032948
Globularity descriptor (glob)0.850535
Predicted polarizability in cubic angstroms (QPpolrz)37.111
Predicted hexadecane/gas partition coefficient (QPlogPC16)14.015
Predicted octanol/gas partition coefficient (QPlogPoct)27.181
Predicted water/gas partition coefficient (QPlogPw)20.654
Predicted octanol/water partition coefficient (QPlogPo/w)0.246
Predicted aqueous solubility (QPlogS)-3.427
Conformation-independent predicted aqueous solubility (CIQPlogS)-5.435
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.09
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)7.4
Predicted brain/blood partition coefficient (QPlogBB)-2.837
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)2.462
Predicted skin permeability, log Kp (QPlogKp)-6.178
PM3 calculated ionization potential (IP(ev))8.779
PM3 calculated electron affinity (EA(eV))0.81
Number of likely metabolic reactions (#metab)8
Prediction of binding to human serum albumin (QPlogKhsa)-0.271
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)30.988
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)170.375
Number of nitrogen and oxygen atoms (#NandO)9
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
P00533EGFREpidermal growth factor receptor erbB1T59328SwissTargetPrediction
Q12809KCNH2HERGT20251SwissTargetPrediction
P36544CHRNA7Neuronal acetylcholine receptor protein alpha-7 subunitT34429SwissTargetPrediction
P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction
P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction
P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
P05067APPBeta amyloid A4 proteinT87024SwissTargetPrediction
P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
P43166CA7Carbonic anhydrase VIIT37541SwissTargetPrediction
Q9ULX7CA14Carbonic anhydrase XIVT31992SwissTargetPrediction
P22748CA4Carbonic anhydrase IVT53378SEA
P14867GABRA1GABA-A receptor; alpha-1/beta-2/gamma-2T51487SwissTargetPrediction
Q92731ESR2Estrogen receptor betaT80896SEA
P28845HSD11B111-beta-hydroxysteroid dehydrogenase 1T65200SwissTargetPrediction
P08253MMP2Matrix metalloproteinase 2T68251SwissTargetPrediction
P14780MMP9Matrix metalloproteinase 9T54156SwissTargetPrediction
P03372ESR1Estrogen receptor alphaT02506SEA
Q14534SQLESqualene monooxygenase (by homology)T93344SwissTargetPrediction
P33527ABCC1Multidrug resistance-associated protein 1T11288SwissTargetPrediction
P08183ABCB1P-glycoprotein 1T25258SwissTargetPrediction
P10827THRAThyroid hormone receptor alphaT79591SwissTargetPrediction
P10828THRBThyroid hormone receptor beta-1T98933SwissTargetPrediction
Q16539MAPK14MAP kinase p38 alphaT65864SwissTargetPrediction
P56817BACE1Beta-secretase 1T79031SwissTargetPrediction
O14746TERTTelomerase reverse transcriptaseT86052SwissTargetPrediction
P07900HSP90AA1Heat shock protein HSP 90-alphaT18477SwissTargetPrediction
P08581METHepatocyte growth factor receptorT40474SwissTargetPrediction
Q15078CDK5R1Cyclin-dependent kinase 5/CDK5 activator 1T09513SwissTargetPrediction
Q13627DYRK1ADual-specificity tyrosine-phosphorylation regulated kinase 1AT92803SwissTargetPrediction
P40763STAT3Signal transducer and activator of transcription 3T29130SwissTargetPrediction
P20151KLK2Kallikrein 2T01908SEA
P26358DNMT1DNA (cytosine-5)-methyltransferase 1 (by homology)T88304SwissTargetPrediction
P15692VEGFAVascular endothelial growth factor AT20761SEA
P39900MMP12Matrix metalloproteinase 12T03500SwissTargetPrediction
P50281MMP14Matrix metalloproteinase 14T65019SwissTargetPrediction
P49763PGFPlacenta growth factorT70792SEA
P08151GLI1Zinc finger protein GLI1T40890SwissTargetPrediction
P04049RAF1Serine/threonine-protein kinase RAFT51883SwissTargetPrediction
P15056BRAFSerine/threonine-protein kinase B-rafT99089SwissTargetPrediction
O60760HPGDSHematopoietic prostaglandin D synthaseT19433SwissTargetPrediction
Q9NPH5NOX4NADPH oxidase 4T29741SwissTargetPrediction
P10415BCL2Apoptosis regulator Bcl-2T31309SwissTargetPrediction
P52209PGD6-phosphogluconate dehydrogenaseT76497SwissTargetPrediction and SEA
P22083FUT4Fucosyltransferase 4T51146SwissTargetPrediction
P42224STAT1Signal transducer and activator of transcription 1-alpha/betaT64205SwissTargetPrediction
P10636MAPTMicrotubule-associated protein tauT45593SwissTargetPrediction
P37840SNCAAlpha-synucleinT03644SwissTargetPrediction
P10070GLI2Zinc finger protein GLI2T29672SwissTargetPrediction
Q16236NFE2L2Nuclear factor erythroid 2-related factor 2T88505SwissTargetPrediction
P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA
P05231IL6Interleukin-6T32578SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T59328DI0030Angina pectoris[ICD-11: BA40]P00533EGFR
T59328DI0062Breast cancer[ICD-11: 2C60-2C6Y]P00533EGFR
T59328DI0095Colorectal cancer[ICD-11: 2B91]P00533EGFR
T59328DI0121Diabetic foot ulcer[ICD-11: BD54]P00533EGFR
T59328DI0220Ischemia[ICD-11: 8B10-8B11]P00533EGFR
T59328DI0238Lung cancer[ICD-11: 2C25]P00533EGFR
T59328DI0303Non-small-cell lung cancer[ICD-11: 2C25]P00533EGFR
T59328DI0361Renal cell carcinoma[ICD-11: 2C90]P00533EGFR
T59328DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P00533EGFR
T59328DI0420Unspecific body region injury[ICD-11: ND56]P00533EGFR
T20251DI0175Heart failure[ICD-11: BD10-BD1Z]Q12809KCNH2
T34429DI0101Corneal disease[ICD-11: 9A76-9A78]P36544CHRNA7
T34429DI0370Schizophrenia[ICD-11: 6A20]P36544CHRNA7
T77365DI0319Orthostatic hypotension[ICD-11: BA21]P29274ADORA2A
T77365DI0331Parkinsonism[ICD-11: 8A00]P29274ADORA2A
T77365DI0359Radionuclide imaging[ICD-11: N.A.]P29274ADORA2A
T92072DI0319Orthostatic hypotension[ICD-11: BA21]P30542ADORA1
T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
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
T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
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
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
T65200DI0210Influenza[ICD-11: 1E30-1E32]P28845HSD11B1
T65200DI0239Lupus erythematosus[ICD-11: 4A40]P28845HSD11B1
T65200DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P28845HSD11B1
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
T02506DI0106COVID-19[ICD-11: 1D6Y]P03372ESR1
T93344DI0118Dermatophytosis[ICD-11: 1F28]Q14534SQLE
T93344DI0385Skin fungal infection disorder[ICD-11: EA60]Q14534SQLE
T11288DI0167Gout[ICD-11: FA25]P33527ABCC1
T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
T79591DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]P10827THRA
T79591DI0197Hypo-thyroidism[ICD-11: 5A00]P10827THRA
T98933DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]P10828THRB
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
T86052DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]O14746TERT
T86052DI0284Myelodysplastic syndrome[ICD-11: 2A37]O14746TERT
T86052DI0326Pancreatic cancer[ICD-11: 2C10]O14746TERT
T18477DI0015Acute upper respiratory infection[ICD-11: CA07]P07900HSP90AA1
T18477DI0037Asthma[ICD-11: CA23]P07900HSP90AA1
T40474DI0238Lung cancer[ICD-11: 2C25]P08581MET
T40474DI0303Non-small-cell lung cancer[ICD-11: 2C25]P08581MET
T40474DI0407Thyroid cancer[ICD-11: 2D10]P08581MET
T92803DI0113Cytomegaloviral disease[ICD-11: 1D82]Q13627DYRK1A
T29130DI0351Psoriasis[ICD-11: EA90]P40763STAT3
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
T03500DI0037Asthma[ICD-11: CA23]P39900MMP12
T03500DI0238Lung cancer[ICD-11: 2C25]P39900MMP12
T03500DI0361Renal cell carcinoma[ICD-11: 2C90]P39900MMP12
T65019DI0178Hepatic fibrosis/cirrhosis[ICD-11: DB93]P50281MMP14
T70792DI0095Colorectal cancer[ICD-11: 2B91]P49763PGF
T51883DI0252Melanoma[ICD-11: 2C30]P04049RAF1
T51883DI0303Non-small-cell lung cancer[ICD-11: 2C25]P04049RAF1
T51883DI0321Ovarian cancer[ICD-11: 2C73]P04049RAF1
T51883DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P04049RAF1
T99089DI0252Melanoma[ICD-11: 2C30]P15056BRAF
T19433DI0148Flatworm infection[ICD-11: 1F70-1F86]O60760HPGDS
T29741DI0146Fibrosis[ICD-11: GA14-GC01]Q9NPH5NOX4
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
T03644DI0025Alzheimer disease[ICD-11: 8A20]P37840SNCA
T03644DI0044Autonomic nervous system disorder[ICD-11: 8D87]P37840SNCA
T03644DI0331Parkinsonism[ICD-11: 8A00]P37840SNCA
T88505DI0038Ataxic disorder[ICD-11: 8A03]Q16236NFE2L2
T70518DI0037Asthma[ICD-11: CA23]P16152CBR1
T32578DI0028Anemia[ICD-11: 3A00-3A9Z]P05231IL6

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