3,5,7-Trihydroxy-4\'-methoxy-8-prenylflavone 3-[rhamnosyl-(1->6)-galactoside] 7-galactoside



Compound IDCDAMM02782
Common name3,5,7-Trihydroxy-4\'-methoxy-8-prenylflavone 3-[rhamnosyl-(1->6)-galactoside] 7-galactoside
IUPAC name5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-2-yl]oxychromen-4-one
Molecular formulaC39H50O20

Experimental data

Retention time21.38
Adduct[M+H]+
Actual mz839.295
Theoretical mz839.297
Error2.47
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.1121

Identifiers and class information

Inchi keySFPBPCAQVDGNMT-UHFFFAOYNA-N
SmilesO=C1C(OC2OC(COC3OC(C)C(O)C(O)C3O)C(O)C(O)C2O)=C(OC=4C1=C(O)C=C(OC5OC(CO)C(O)C(O)C5O)C4CC=C(C)C)C=6C=CC(OC)=CC6
SuperclassPhenylpropanoids and polyketides
ClassFlavonoids

Pharmacokinetic properties

Number of descriptor values(#stars)14
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)22
Number of reactive functional groups (#rtvFG)3
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)838.812
Computed dipole moment(dipole)10.805
Total solvent accessible surface area (SASA)1041.6
Hydrophobic component of SASA (FOSA)522.265
Hydrophilic component of SASA (FISA)413.393
Pie component of the SASA (PISA)105.942
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)2177.14
Number of hydrogen bond donors (donorHB)10
Number of hydrogen bond acceptors (accptHB)28.3
Free energy of solvation of dipole (dip^2/V)0.0536275
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0859182
Globularity descriptor (glob)0.77993
Predicted polarizability in cubic angstroms (QPpolrz)67.861
Predicted hexadecane/gas partition coefficient (QPlogPC16)24.037
Predicted octanol/gas partition coefficient (QPlogPoct)54.313
Predicted water/gas partition coefficient (QPlogPw)43.427
Predicted octanol/water partition coefficient (QPlogPo/w)-2.208
Predicted aqueous solubility (QPlogS)-2.128
Conformation-independent predicted aqueous solubility (CIQPlogS)-5.384
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.598
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)1.19
Predicted brain/blood partition coefficient (QPlogBB)-5.293
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0.342
Predicted skin permeability, log Kp (QPlogKp)-6.653
PM3 calculated ionization potential (IP(ev))9.16
PM3 calculated electron affinity (EA(eV))0.707
Number of likely metabolic reactions (#metab)15
Prediction of binding to human serum albumin (QPlogKhsa)-1.687
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)0
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)306.879
Number of nitrogen and oxygen atoms (#NandO)20
Number of violations of Lipinski’s rule of five (RuleOfFive)3
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
P22303ACHEAcetylcholinesteraseT30082SwissTargetPrediction
O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction and SEA
P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
P16083NQO2Quinone reductase 2T75498SwissTargetPrediction
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
P43166CA7Carbonic anhydrase VIIT37541SwissTargetPrediction and SEA
P22748CA4Carbonic anhydrase IVT53378SwissTargetPrediction and SEA
P08913ADRA2AAlpha-2a adrenergic receptorT11448SwissTargetPrediction
P15121AKR1B1Aldose reductaseT26623SwissTargetPrediction
P35354PTGS2Cyclooxygenase-2T66665SwissTargetPrediction
P18825ADRA2CAdrenergic receptor alpha-2T01777SwissTargetPrediction
P01375TNFTNF-alphaT20178SwissTargetPrediction
O76074PDE5APhosphodiesterase 5AT07663SwissTargetPrediction
P60568IL2Interleukin-2T61698SwissTargetPrediction and SEA
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
P17931LGALS3Galectin-3T72038SEA
P04746AMY2APancreatic alpha-amylaseT86918SEA
P14679TYRTyrosinaseT97035SEA
P51812RPS6KA3Ribosomal protein S6 kinase alpha 3T03279SwissTargetPrediction
Q9NPH5NOX4NADPH oxidase 4T29741SwissTargetPrediction
Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SwissTargetPrediction and SEA
P47989XDHXanthine dehydrogenaseT40954SEA
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
P05231IL6Interleukin-6T32578SEA
P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T30082DI0025Alzheimer disease[ICD-11: 8A20]P22303ACHE
T30082DI0166Glaucoma[ICD-11: 9C61]P22303ACHE
T30082DI0282Myasthenia gravis[ICD-11: 8C6Y]P22303ACHE
T30082DI0313Oesophageal/gastroduodenal disorder[ICD-11: DD90]P22303ACHE
T30082DI0332Pediculosis[ICD-11: 1G00]P22303ACHE
T30082DI0421Unspecific substance harmful effect[ICD-11: NE6Z]P22303ACHE
T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
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
T75498DI0214Insomnia[ICD-11: 7A00-7A0Z]P16083NQO2
T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
T53378DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P22748CA4
T53378DI0166Glaucoma[ICD-11: 9C61]P22748CA4
T53378DI0372Seborrhoeic dermatitis[ICD-11: EA81]P22748CA4
T11448DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P08913ADRA2A
T11448DI0317Opioid use disorder[ICD-11: 6C43]P08913ADRA2A
T11448DI0396Substance abuse[ICD-11: 6C40]P08913ADRA2A
T26623DI0298Neuropathy[ICD-11: 8C0Z]P15121AKR1B1
T26623DI0366Rheumatoid arthritis[ICD-11: FA20]P15121AKR1B1
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
T01777DI0166Glaucoma[ICD-11: 9C61]P18825ADRA2C
T01777DI0190Hypertension[ICD-11: BA00-BA04]P18825ADRA2C
T01777DI0196Hypotension[ICD-11: BA20-BA21]P18825ADRA2C
T01777DI0308Obesity[ICD-11: 5B80-5B81]P18825ADRA2C
T01777DI0310Ocular disease[ICD-11: N.A.]P18825ADRA2C
T01777DI0396Substance abuse[ICD-11: 6C40]P18825ADRA2C
T20178DI0035Arterial occlusive disease[ICD-11: BD40]P01375TNF
T20178DI0274Multiple myeloma[ICD-11: 2A83]P01375TNF
T20178DI0351Psoriasis[ICD-11: EA90]P01375TNF
T20178DI0366Rheumatoid arthritis[ICD-11: FA20]P01375TNF
T07663DI0190Hypertension[ICD-11: BA00-BA04]O76074PDE5A
T07663DI0213Innate/adaptive immunodeficiency[ICD-11: 4A00]O76074PDE5A
T07663DI0378Sexual dysfunction[ICD-11: HA00-HA01]O76074PDE5A
T07663DI0411Tonus and reflex abnormality[ICD-11: MB47]O76074PDE5A
T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
T72038DI0190Hypertension[ICD-11: BA00-BA04]P17931LGALS3
T72038DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P17931LGALS3
T72038DI0252Melanoma[ICD-11: 2C30]P17931LGALS3
T72038DI0302Non-alcoholic fatty liver disease[ICD-11: DB92]P17931LGALS3
T72038DI0351Psoriasis[ICD-11: EA90]P17931LGALS3
T86918DI0110Cystic fibrosis[ICD-11: CA25]P04746AMY2A
T86918DI0328Pancreatic malfunction[ICD-11: DC30-DC3Z]P04746AMY2A
T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
T03279DI0249Mature B-cell leukaemia[ICD-11: 2A82]P51812RPS6KA3
T29741DI0146Fibrosis[ICD-11: GA14-GC01]Q9NPH5NOX4
T40954DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]P47989XDH
T40954DI0266Mineral deficiency[ICD-11: 5B5K]P47989XDH
T32578DI0028Anemia[ICD-11: 3A00-3A9Z]P05231IL6
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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