Artonin E



Compound IDCDAMM01476
Common nameArtonin E
IUPAC name5-hydroxy-8,8-dimethyl-3-(3-methylbut-2-enyl)-2-(2,4,5-trihydroxyphenyl)pyrano[2,3-h]chromen-4-one
Molecular formulaC25H24O7

Experimental data

Retention time5.65
Adduct[M+H]+
Actual mz437.156
Theoretical mz437.159
Error7.72
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.8002

Identifiers and class information

Inchi keyHDHRTQZSBFUBMJ-UHFFFAOYSA-N
SmilesO=C1C2=C(O)C=C3OC(C=CC3=C2OC(C=4C=C(O)C(O)=CC4O)=C1CC=C(C)C)(C)C
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)0
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)436.46
Computed dipole moment(dipole)4.793
Total solvent accessible surface area (SASA)734.102
Hydrophobic component of SASA (FOSA)327.18
Hydrophilic component of SASA (FISA)198.298
Pie component of the SASA (PISA)208.625
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1326.33
Number of hydrogen bond donors (donorHB)3
Number of hydrogen bond acceptors (accptHB)5.25
Free energy of solvation of dipole (dip^2/V)0.0173223
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0123869
Globularity descriptor (glob)0.795261
Predicted polarizability in cubic angstroms (QPpolrz)45.066
Predicted hexadecane/gas partition coefficient (QPlogPC16)14.151
Predicted octanol/gas partition coefficient (QPlogPoct)22.539
Predicted water/gas partition coefficient (QPlogPw)12.495
Predicted octanol/water partition coefficient (QPlogPo/w)3.913
Predicted aqueous solubility (QPlogS)-6.436
Conformation-independent predicted aqueous solubility (CIQPlogS)-6.934
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.84
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)130.449
Predicted brain/blood partition coefficient (QPlogBB)-1.888
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)54.733
Predicted skin permeability, log Kp (QPlogKp)-3.863
PM3 calculated ionization potential (IP(ev))8.761
PM3 calculated electron affinity (EA(eV))0.502
Number of likely metabolic reactions (#metab)7
Prediction of binding to human serum albumin (QPlogKhsa)0.792
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)87.719
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)122.395
Number of nitrogen and oxygen atoms (#NandO)7
Number of violations of Lipinski’s rule of five (RuleOfFive)0
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
P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
P35228NOS2Nitric oxide synthase, inducibleT02703SwissTargetPrediction
P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SwissTargetPrediction and SEA
P17612PRKACAcAMP-dependent protein kinase alpha-catalytic subunitT12808SwissTargetPrediction
P35354PTGS2Cyclooxygenase-2T66665SwissTargetPrediction
P11926ODC1Ornithine decarboxylaseT60366SEA
O14684PTGESProstaglandin E synthaseT02562SwissTargetPrediction
P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction and SEA
Q14534SQLESqualene monooxygenase (by homology)T93344SwissTargetPrediction
Q15118PDK1Pyruvate dehydrogenase kinase isoform 1T20891SwissTargetPrediction
P06276BCHEButyrylcholinesteraseT99799SwissTargetPrediction
P56817BACE1Beta-secretase 1T79031SwissTargetPrediction
P49327FASNFatty acid synthaseT16514SwissTargetPrediction
O75874IDH1Isocitrate dehydrogenase [NADP] cytoplasmicT69563SwissTargetPrediction
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SwissTargetPrediction and SEA
P00742F10Thrombin and coagulation factor XT84631SwissTargetPrediction
P24723PRKCHProtein kinase C etaT40149SwissTargetPrediction
P10276RARARetinoic acid receptor alphaT94085SEA
P35222CTNNB1Axin1/beta-cateninT82795SwissTargetPrediction
P07900HSP90AA1Heat shock protein HSP 90-alphaT18477SwissTargetPrediction
P05771PRKCBProtein kinase C betaT40276SwissTargetPrediction
Q02156PRKCEProtein kinase C epsilonT00895SwissTargetPrediction
P06870KLK1Kallikrein 1T40000SwissTargetPrediction
P20151KLK2Kallikrein 2T01908SwissTargetPrediction
P34972CNR2Cannabinoid receptor 2T37693SwissTargetPrediction
Q05655PRKCDProtein kinase C deltaT44861SwissTargetPrediction
Q96EB6SIRT1NAD-dependent deacetylase sirtuin 1T14731SwissTargetPrediction
O14980XPO1Exportin-1T51407SEA
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SwissTargetPrediction and SEA
Q14680MELKMaternal embryonic leucine zipper kinaseT96892SwissTargetPrediction
Q16678CYP1B1Cytochrome P450 1B1T92521SwissTargetPrediction
P05129PRKCGProtein kinase C gammaT47107SwissTargetPrediction
P63316TNNC1Troponin, cardiac muscleT12966SwissTargetPrediction
P14625HSP90B1EndoplasminT81311SwissTargetPrediction
O60911CTSVCathepsin (V and K)T93653SEA

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
T92072DI0319Orthostatic hypotension[ICD-11: BA21]P30542ADORA1
T02703DI0083Chronic kidney disease[ICD-11: GB61]P35228NOS2
T02703DI0320Osteoarthritis[ICD-11: FA00-FA05]P35228NOS2
T02703DI0375Sepsis[ICD-11: 1G40-1G41]P35228NOS2
T02703DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P35228NOS2
T36059DI0351Psoriasis[ICD-11: EA90]P0DMS8ADORA3
T36059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMS8ADORA3
T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
T12808DI0279Muscular atrophy[ICD-11: 8B61]P17612PRKACA
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
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
T02562DI0025Alzheimer disease[ICD-11: 8A20]O14684PTGES
T16347DI0009Acute diabete complication[ICD-11: 5A2Y]P18031PTPN1
T16347DI0062Breast cancer[ICD-11: 2C60-2C6Y]P18031PTPN1
T16347DI0308Obesity[ICD-11: 5B80-5B81]P18031PTPN1
T16347DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P18031PTPN1
T93344DI0118Dermatophytosis[ICD-11: 1F28]Q14534SQLE
T93344DI0385Skin fungal infection disorder[ICD-11: EA60]Q14534SQLE
T20891DI0241Lymphoma[ICD-11: 2A80-2A86]Q15118PDK1
T99799DI0324Pain[ICD-11: MG30-MG3Z]P06276BCHE
T99799DI0411Tonus and reflex abnormality[ICD-11: MB47]P06276BCHE
T79031DI0025Alzheimer disease[ICD-11: 8A20]P56817BACE1
T16514DI0096concerning food/fluid intake symptom[ICD-11: MG43]P49327FASN
T69563DI0012Acute myeloid leukaemia[ICD-11: 2A60]O75874IDH1
T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
T84631DI0053Blood-forming organ disease[ICD-11: 3C0Z]P00742F10
T84631DI0080Christmas disease[ICD-11: 3B11]P00742F10
T84631DI0091Coagulation defect[ICD-11: 3B10]P00742F10
T84631DI0103Coronary thrombosis[ICD-11: BA43]P00742F10
T84631DI0114Deep vein thrombosis[ICD-11: BD71]P00742F10
T84631DI0397Supraventricular tachyarrhythmia[ICD-11: BC81]P00742F10
T84631DI0405Thrombosis[ICD-11: DB61-GB90]P00742F10
T84631DI0433Venous thromboembolism[ICD-11: BD72]P00742F10
T40149DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]P24723PRKCH
T94085DI0025Alzheimer disease[ICD-11: 8A20]P10276RARA
T94085DI0251Mature T-cell lymphoma[ICD-11: 2A90]P10276RARA
T82795DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P35222CTNNB1
T18477DI0015Acute upper respiratory infection[ICD-11: CA07]P07900HSP90AA1
T18477DI0037Asthma[ICD-11: CA23]P07900HSP90AA1
T40276DI0123Diffuse large B-cell lymphoma[ICD-11: 2A81]P05771PRKCB
T40276DI0241Lymphoma[ICD-11: 2A80-2A86]P05771PRKCB
T40276DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P05771PRKCB
T00895DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]Q02156PRKCE
T00895DI0243Malaria[ICD-11: 1F40-1F45]Q02156PRKCE
T01908DI0213Innate/adaptive immunodeficiency[ICD-11: 4A00]P20151KLK2
T37693DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P34972CNR2
T37693DI0214Insomnia[ICD-11: 7A00-7A0Z]P34972CNR2
T44861DI0287Myocardial infarction[ICD-11: BA41-BA43]Q05655PRKCD
T14731DI0366Rheumatoid arthritis[ICD-11: FA20]Q96EB6SIRT1
T14731DI0399Systemic sclerosis[ICD-11: 4A42]Q96EB6SIRT1
T14731DI0431Vasculitis[ICD-11: 4A44]Q96EB6SIRT1
T51407DI0234Liposarcoma[ICD-11: 2B59]O14980XPO1
T51407DI0274Multiple myeloma[ICD-11: 2A83]O14980XPO1
T51407DI0395Stomach cancer[ICD-11: 2B72]O14980XPO1
T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
T96892DI0012Acute myeloid leukaemia[ICD-11: 2A60]Q14680MELK
T96892DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q14680MELK
T96892DI0249Mature B-cell leukaemia[ICD-11: 2A82]Q14680MELK
T96892DI0250Mature B-cell lymphoma[ICD-11: 2A85]Q14680MELK
T96892DI0284Myelodysplastic syndrome[ICD-11: 2A37]Q14680MELK
T96892DI0286Myeloproliferative neoplasm[ICD-11: 2A20]Q14680MELK
T47107DI0012Acute myeloid leukaemia[ICD-11: 2A60]P05129PRKCG
T47107DI0248Mastocytosis[ICD-11: 2A21]P05129PRKCG
T12966DI0006Acquired cutaneous blood vessel malformation[ICD-11: EF20]P63316TNNC1
T12966DI0175Heart failure[ICD-11: BD10-BD1Z]P63316TNNC1
T81311DI0238Lung cancer[ICD-11: 2C25]P14625HSP90B1
T93653DI0055Bone cancer[ICD-11: 2B5Z]O60911CTSV
T93653DI0087Chronic pain[ICD-11: MG30]O60911CTSV

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