Torosaflavone A



Compound IDCDAMM02416
Common nameTorosaflavone A
IUPAC name6-(4,5-dihydroxy-6-methyloxan-2-yl)-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Molecular formulaC21H20O8

Experimental data

Retention time0.49
Adduct[M+K]+
Actual mz439.079
Theoretical mz439.079
Error0.32
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.2637

Identifiers and class information

Inchi keyNORMTIXLPBZOKX-KPZLMBSHNA-N
SmilesO=C1C=C(OC2=CC(O)=C(C(O)=C12)C3OC(C)C(O)C(O)C3)C=4C=CC(O)=CC4
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)5
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)400.384
Computed dipole moment(dipole)7.387
Total solvent accessible surface area (SASA)656.227
Hydrophobic component of SASA (FOSA)167.806
Hydrophilic component of SASA (FISA)240.619
Pie component of the SASA (PISA)247.802
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1167.46
Number of hydrogen bond donors (donorHB)4
Number of hydrogen bond acceptors (accptHB)8.85
Free energy of solvation of dipole (dip^2/V)0.0467438
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0269724
Globularity descriptor (glob)0.817094
Predicted polarizability in cubic angstroms (QPpolrz)39.724
Predicted hexadecane/gas partition coefficient (QPlogPC16)13.413
Predicted octanol/gas partition coefficient (QPlogPoct)24.82
Predicted water/gas partition coefficient (QPlogPw)18.093
Predicted octanol/water partition coefficient (QPlogPo/w)1.223
Predicted aqueous solubility (QPlogS)-4.295
Conformation-independent predicted aqueous solubility (CIQPlogS)-4.726
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.673
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)51.774
Predicted brain/blood partition coefficient (QPlogBB)-2.141
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)20.158
Predicted skin permeability, log Kp (QPlogKp)-4.601
PM3 calculated ionization potential (IP(ev))9.125
PM3 calculated electron affinity (EA(eV))0.709
Number of likely metabolic reactions (#metab)7
Prediction of binding to human serum albumin (QPlogKhsa)-0.142
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)64.788
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)144.656
Number of nitrogen and oxygen atoms (#NandO)8
Number of violations of Lipinski’s rule of five (RuleOfFive)0
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
P02766TTRTransthyretinT86462SEA
P43166CA7Carbonic anhydrase VIIT37541SEA
P22748CA4Carbonic anhydrase IVT53378SEA
P15121AKR1B1Aldose reductaseT26623SEA
P05164MPOMyeloperoxidaseT23471SEA
Q6B0I6KDM4DLysine-specific demethylase 4DT17036SEA
Q9HC97GPR35G-protein coupled receptor 35T56143SEA
P33527ABCC1Multidrug resistance-associated protein 1T11288SEA
P08183ABCB1P-glycoprotein 1T25258SEA
O95271TNKSTankyrase-1T83059SEA
P18054ALOX12Arachidonate 12-lipoxygenaseT35527SEA
P15692VEGFAVascular endothelial growth factor AT20761SEA
Q07002CDK18Serine/threonine-protein kinase PCTAIRE-3T27577SEA
P60568IL2Interleukin-2T61698SEA
P49763PGFPlacenta growth factorT70792SEA
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
Q9NPH5NOX4NADPH oxidase 4T29741SEA
Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SEA
P47989XDHXanthine dehydrogenaseT40954SEA
Q16678CYP1B1Cytochrome P450 1B1T92521SEA
Q04760GLO1Glyoxalase IT88285SEA
P20248CCNA2CDK2/Cyclin AT58470SEA
Q14004CDK13Cyclin-dependent kinase 13T74839SEA
Q16512PKN1Protein kinase N1T60003SEA
Q9HC98NEK6Serine/threonine-protein kinase NEK6T78992SEA
P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA
Q13564NAE1NEDD8-activating enzyme E1 regulatory subunitT01447SEA
Q13332PTPRSReceptor-type tyrosine-protein phosphatase ST10147SEA
P21860ERBB3Receptor tyrosine-protein kinase erbB-3T86350SEA
Q13705ACVR2BActivin receptor type-2BT80338SEA
Q99417MYCBPMYCBP messenger RNAT37298SEA
P16220CREB1Cyclic AMP-responsive element-binding proteinT92098SEA
Q15717ELAVL1ELAV-like protein 1T78349SEA
Q96HK3CALMCalmodulinT39610SEA
Q9UK17KCND3Voltage-gated potassium channel Kv4.3T74500SEA
P27037ACVR2AActivin receptor type IIAT47366SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T86462DI0026Amyloidosis[ICD-11: 5D00]P02766TTR
T53378DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P22748CA4
T53378DI0166Glaucoma[ICD-11: 9C61]P22748CA4
T53378DI0372Seborrhoeic dermatitis[ICD-11: EA81]P22748CA4
T26623DI0298Neuropathy[ICD-11: 8C0Z]P15121AKR1B1
T26623DI0366Rheumatoid arthritis[ICD-11: FA20]P15121AKR1B1
T23471DI0229Left ventricular failure[ICD-11: BD11]P05164MPO
T23471DI0339Postoperative inflammation[ICD-11: 1A00-CA43]P05164MPO
T11288DI0167Gout[ICD-11: FA25]P33527ABCC1
T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
T83059DI0060Brain cancer[ICD-11: 2A00]O95271TNKS
T83059DI0062Breast cancer[ICD-11: 2C60-2C6Y]O95271TNKS
T83059DI0321Ovarian cancer[ICD-11: 2C73]O95271TNKS
T83059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O95271TNKS
T20761DI0095Colorectal cancer[ICD-11: 2B91]P15692VEGFA
T20761DI0365Retinopathy[ICD-11: 9B71]P15692VEGFA
T20761DI0430Vascular system developmental anomaly[ICD-11: LA90]P15692VEGFA
T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
T70792DI0095Colorectal cancer[ICD-11: 2B91]P49763PGF
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
T58470DI0363Retina cancer[ICD-11: 2D02]P20248CCNA2
T74839DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q14004CDK13
T70518DI0037Asthma[ICD-11: CA23]P16152CBR1
T01447DI0284Myelodysplastic syndrome[ICD-11: 2A37]Q13564NAE1
T10147DI0057Bone paget disease[ICD-11: FB85]Q13332PTPRS
T86350DI0062Breast cancer[ICD-11: 2C60-2C6Y]P21860ERBB3
T86350DI0095Colorectal cancer[ICD-11: 2B91]P21860ERBB3
T86350DI0172Head and neck cancer[ICD-11: 2D42]P21860ERBB3
T86350DI0238Lung cancer[ICD-11: 2C25]P21860ERBB3
T86350DI0246Malignant mesenchymal neoplasm[ICD-11: 2B5D-2B5Y]P21860ERBB3
T86350DI0259Metastatic lymph node neoplasm[ICD-11: 2D60]P21860ERBB3
T86350DI0326Pancreatic cancer[ICD-11: 2C10]P21860ERBB3
T86350DI0351Psoriasis[ICD-11: EA90]P21860ERBB3
T86350DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P21860ERBB3
T86350DI0393Squamous cell carcinoma[ICD-11: 2B60-2D01]P21860ERBB3
T80338DI0295Nervous system paraneoplastic/autoimmune disorder[ICD-11: 8E4A]Q13705ACVR2B
T37298DI0235Liver cancer[ICD-11: 2C12]Q99417MYCBP
T39610DI0068Cardiac arrhythmia[ICD-11: BC9Z]Q96HK3CALM
T39610DI0243Malaria[ICD-11: 1F40-1F45]Q96HK3CALM
T39610DI0370Schizophrenia[ICD-11: 6A20]Q96HK3CALM
T74500DI0004Acidosis[ICD-11: 5C73]Q9UK17KCND3
T47366DI0012Acute myeloid leukaemia[ICD-11: 2A60]P27037ACVR2A
T47366DI0198Idiopathic inflammatory myopathy[ICD-11: 4A41]P27037ACVR2A

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