6,4\'-Dihydroxy-7-methylaurone 6-rhamnoside



Compound IDCDAMM00753
Common name6,4\'-Dihydroxy-7-methylaurone 6-rhamnoside
IUPAC name2-[(4-hydroxyphenyl)methylidene]-7-methyl-6-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-1-benzofuran-3-one
Molecular formulaC22H22O8

Experimental data

Retention time8.21
Adduct[M+K]+
Actual mz453.099
Theoretical mz453.094
Error10.25
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.9451

Identifiers and class information

Inchi keyQAHBZNNBXKMITG-GAVWZHHSNA-N
SmilesO=C1C(OC=2C1=CC=C(OC3OC(C)C(O)C(O)C3O)C2C)=CC4=CC=C(O)C=C4
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)8
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)414.411
Computed dipole moment(dipole)1.597
Total solvent accessible surface area (SASA)674.088
Hydrophobic component of SASA (FOSA)217.592
Hydrophilic component of SASA (FISA)217.869
Pie component of the SASA (PISA)238.627
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1226.6
Number of hydrogen bond donors (donorHB)4
Number of hydrogen bond acceptors (accptHB)10.8
Free energy of solvation of dipole (dip^2/V)0.002078
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0320433
Globularity descriptor (glob)0.822086
Predicted polarizability in cubic angstroms (QPpolrz)40.077
Predicted hexadecane/gas partition coefficient (QPlogPC16)13.742
Predicted octanol/gas partition coefficient (QPlogPoct)25.195
Predicted water/gas partition coefficient (QPlogPw)19.178
Predicted octanol/water partition coefficient (QPlogPo/w)1.031
Predicted aqueous solubility (QPlogS)-3.631
Conformation-independent predicted aqueous solubility (CIQPlogS)-4.254
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.549
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)85.083
Predicted brain/blood partition coefficient (QPlogBB)-2.068
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)34.486
Predicted skin permeability, log Kp (QPlogKp)-3.926
PM3 calculated ionization potential (IP(ev))8.755
PM3 calculated electron affinity (EA(eV))1.021
Number of likely metabolic reactions (#metab)6
Prediction of binding to human serum albumin (QPlogKhsa)-0.399
Predicted qualitative human oral absorption (HumanOralAbsorption)3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)67.524
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)133.689
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)0

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction
Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction
P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
P15121AKR1B1Aldose reductaseT26623SwissTargetPrediction
P13726F3Coagulation factor VII/tissue factorT72702SwissTargetPrediction
P11387TOP1DNA topoisomerase IT09826SwissTargetPrediction
P07900HSP90AA1Heat shock protein HSP 90-alphaT18477SwissTargetPrediction
P10721KITStem cell growth factor receptorT57700SwissTargetPrediction
P55263ADKAdenosine kinaseT91661SwissTargetPrediction
P60568IL2Interleukin-2T61698SwissTargetPrediction and SEA
P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SwissTargetPrediction
Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SEA
P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T92072DI0319Orthostatic hypotension[ICD-11: BA21]P30542ADORA1
T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
T64567DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16790CA9
T36059DI0351Psoriasis[ICD-11: EA90]P0DMS8ADORA3
T36059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMS8ADORA3
T13201DI0166Glaucoma[ICD-11: 9C61]P00915CA1
T13201DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00915CA1
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
T26623DI0298Neuropathy[ICD-11: 8C0Z]P15121AKR1B1
T26623DI0366Rheumatoid arthritis[ICD-11: FA20]P15121AKR1B1
T72702DI0075Cervical cancer[ICD-11: 2C77]P13726F3
T09826DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P11387TOP1
T09826DI0095Colorectal cancer[ICD-11: 2B91]P11387TOP1
T09826DI0238Lung cancer[ICD-11: 2C25]P11387TOP1
T09826DI0321Ovarian cancer[ICD-11: 2C73]P11387TOP1
T09826DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11387TOP1
T18477DI0015Acute upper respiratory infection[ICD-11: CA07]P07900HSP90AA1
T18477DI0037Asthma[ICD-11: CA23]P07900HSP90AA1
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
T91661DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P55263ADK
T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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