Artocarpetin B



Compound IDCDAMM00872
Common nameArtocarpetin B
IUPAC name5-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-7-methoxy-8-(3-methylbut-2-enyl)chromen-4-one
Molecular formulaC22H22O6

Experimental data

Retention time0.41
Adduct[M+NH4]+
Actual mz400.18
Theoretical mz400.176
Error11.19
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.0651

Identifiers and class information

Inchi keyAGQBGLZQKDLJAR-UHFFFAOYSA-N
SmilesO=C1C=C(OC=2C1=C(O)C=C(OC)C2CC=C(C)C)C=3C=CC(O)=CC3OC
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)382.412
Computed dipole moment(dipole)4.777
Total solvent accessible surface area (SASA)644.353
Hydrophobic component of SASA (FOSA)301.586
Hydrophilic component of SASA (FISA)149.267
Pie component of the SASA (PISA)193.5
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1182.74
Number of hydrogen bond donors (donorHB)1
Number of hydrogen bond acceptors (accptHB)4.5
Free energy of solvation of dipole (dip^2/V)0.0192942
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0069837
Globularity descriptor (glob)0.839395
Predicted polarizability in cubic angstroms (QPpolrz)39.174
Predicted hexadecane/gas partition coefficient (QPlogPC16)11.85
Predicted octanol/gas partition coefficient (QPlogPoct)17.058
Predicted water/gas partition coefficient (QPlogPw)8.175
Predicted octanol/water partition coefficient (QPlogPo/w)4.023
Predicted aqueous solubility (QPlogS)-5.391
Conformation-independent predicted aqueous solubility (CIQPlogS)-6.149
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.054
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)380.541
Predicted brain/blood partition coefficient (QPlogBB)-1.21
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)174.106
Predicted skin permeability, log Kp (QPlogKp)-3.013
PM3 calculated ionization potential (IP(ev))8.917
PM3 calculated electron affinity (EA(eV))0.474
Number of likely metabolic reactions (#metab)7
Prediction of binding to human serum albumin (QPlogKhsa)0.711
Predicted qualitative human oral absorption (HumanOralAbsorption)3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)96.686
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)88.542
Number of nitrogen and oxygen atoms (#NandO)6
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
P00533EGFREpidermal growth factor receptor erbB1T59328SwissTargetPrediction
P22303ACHEAcetylcholinesteraseT30082SwissTargetPrediction
P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
Q07820MCL1Induced myeloid leukemia cell differentiation protein Mcl-1T14912SwissTargetPrediction
P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
P02766TTRTransthyretinT86462SEA
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
P15121AKR1B1Aldose reductaseT26623SwissTargetPrediction
P35354PTGS2Cyclooxygenase-2T66665SwissTargetPrediction
P11926ODC1Ornithine decarboxylaseT60366SwissTargetPrediction and SEA
Q92731ESR2Estrogen receptor betaT80896SwissTargetPrediction
P11511CYP19A1Cytochrome P450 19A1T13260SwissTargetPrediction
P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction and SEA
P08183ABCB1P-glycoprotein 1T25258SwissTargetPrediction and SEA
P04626ERBB2Receptor protein-tyrosine kinase erbB-2T14597SwissTargetPrediction
Q15118PDK1Pyruvate dehydrogenase kinase isoform 1T20891SwissTargetPrediction
P06276BCHEButyrylcholinesteraseT99799SwissTargetPrediction
P56817BACE1Beta-secretase 1T79031SwissTargetPrediction
P37231PPARGPeroxisome proliferator-activated receptor gammaT58921SwissTargetPrediction
P49356FNTBFarnesyl protein transferaseT13127SwissTargetPrediction
P31749AKT1Serine/threonine-protein kinase AKTT67619SwissTargetPrediction
P08238HSP90AB1Heat shock protein HSP 90-betaT96623SwissTargetPrediction
P07900HSP90AA1Heat shock protein HSP 90-alphaT18477SwissTargetPrediction
P15692VEGFAVascular endothelial growth factor AT20761SEA
P34972CNR2Cannabinoid receptor 2T37693SwissTargetPrediction
Q96EB6SIRT1NAD-dependent deacetylase sirtuin 1T14731SwissTargetPrediction
Q07002CDK18Serine/threonine-protein kinase PCTAIRE-3T27577SEA
O76074PDE5APhosphodiesterase 5AT07663SwissTargetPrediction
P49763PGFPlacenta growth factorT70792SEA
P00749PLAUUrokinase-type plasminogen activatorT17758SwissTargetPrediction
O14980XPO1Exportin-1T51407SEA
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SwissTargetPrediction and SEA
P14679TYRTyrosinaseT97035SEA
P00374DHFRDihydrofolate reductaseT17345SwissTargetPrediction
Q9NPH5NOX4NADPH oxidase 4T29741SEA
P47989XDHXanthine dehydrogenaseT40954SEA
Q14680MELKMaternal embryonic leucine zipper kinaseT96892SwissTargetPrediction
Q16678CYP1B1Cytochrome P450 1B1T92521SwissTargetPrediction and SEA
P20248CCNA2CDK2/Cyclin AT58470SEA
Q14004CDK13Cyclin-dependent kinase 13T74839SEA
P51679CCR4C-C chemokine receptor type 4T06955SwissTargetPrediction
P14625HSP90B1EndoplasminT81311SwissTargetPrediction
O60911CTSVCathepsin (V and K)T93653SEA
P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA
Q13332PTPRSReceptor-type tyrosine-protein phosphatase ST10147SEA
Q9NQS5GPR84G-protein coupled receptor 84T98091SwissTargetPrediction
P21860ERBB3Receptor tyrosine-protein kinase erbB-3T86350SEA
Q13705ACVR2BActivin receptor type-2BT80338SEA
Q99417MYCBPMYCBP messenger RNAT37298SEA
P16220CREB1Cyclic AMP-responsive element-binding proteinT92098SEA
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
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
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
T14912DI0012Acute myeloid leukaemia[ICD-11: 2A60]Q07820MCL1
T14912DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]Q07820MCL1
T14912DI0250Mature B-cell lymphoma[ICD-11: 2A85]Q07820MCL1
T14912DI0252Melanoma[ICD-11: 2C30]Q07820MCL1
T14912DI0274Multiple myeloma[ICD-11: 2A83]Q07820MCL1
T14912DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q07820MCL1
T36059DI0351Psoriasis[ICD-11: EA90]P0DMS8ADORA3
T36059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMS8ADORA3
T86462DI0026Amyloidosis[ICD-11: 5D00]P02766TTR
T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
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
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
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
T13260DI0062Breast cancer[ICD-11: 2C60-2C6Y]P11511CYP19A1
T13260DI0108Cushing syndrome[ICD-11: 5A70]P11511CYP19A1
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
T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
T14597DI0062Breast cancer[ICD-11: 2C60-2C6Y]P04626ERBB2
T14597DI0238Lung cancer[ICD-11: 2C25]P04626ERBB2
T14597DI0346Prostate cancer[ICD-11: 2C82]P04626ERBB2
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
T58921DI0009Acute diabete complication[ICD-11: 5A2Y]P37231PPARG
T58921DI0025Alzheimer disease[ICD-11: 8A20]P37231PPARG
T58921DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P37231PPARG
T13127DI0342Premature ageing appearance[ICD-11: LD2B]P49356FNTB
T67619DI0062Breast cancer[ICD-11: 2C60-2C6Y]P31749AKT1
T96623DI0062Breast cancer[ICD-11: 2C60-2C6Y]P08238HSP90AB1
T96623DI0238Lung cancer[ICD-11: 2C25]P08238HSP90AB1
T96623DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P08238HSP90AB1
T96623DI0249Mature B-cell leukaemia[ICD-11: 2A82]P08238HSP90AB1
T96623DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P08238HSP90AB1
T96623DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P08238HSP90AB1
T96623DI0395Stomach cancer[ICD-11: 2B72]P08238HSP90AB1
T18477DI0015Acute upper respiratory infection[ICD-11: CA07]P07900HSP90AA1
T18477DI0037Asthma[ICD-11: CA23]P07900HSP90AA1
T20761DI0095Colorectal cancer[ICD-11: 2B91]P15692VEGFA
T20761DI0365Retinopathy[ICD-11: 9B71]P15692VEGFA
T20761DI0430Vascular system developmental anomaly[ICD-11: LA90]P15692VEGFA
T37693DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P34972CNR2
T37693DI0214Insomnia[ICD-11: 7A00-7A0Z]P34972CNR2
T14731DI0366Rheumatoid arthritis[ICD-11: FA20]Q96EB6SIRT1
T14731DI0399Systemic sclerosis[ICD-11: 4A42]Q96EB6SIRT1
T14731DI0431Vasculitis[ICD-11: 4A44]Q96EB6SIRT1
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
T70792DI0095Colorectal cancer[ICD-11: 2B91]P49763PGF
T17758DI0211Inherited coagulation factor deficiency[ICD-11: 3B14]P00749PLAU
T17758DI0287Myocardial infarction[ICD-11: BA41-BA43]P00749PLAU
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
T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
T17345DI0207Indeterminate colitis[ICD-11: DD72]P00374DHFR
T17345DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P00374DHFR
T17345DI0416Tuberculosis[ICD-11: 1B10-1B12]P00374DHFR
T17345DI0427Urinary tract infection[ICD-11: GC08]P00374DHFR
T29741DI0146Fibrosis[ICD-11: GA14-GC01]Q9NPH5NOX4
T40954DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]P47989XDH
T40954DI0266Mineral deficiency[ICD-11: 5B5K]P47989XDH
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
T58470DI0363Retina cancer[ICD-11: 2D02]P20248CCNA2
T74839DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q14004CDK13
T06955DI0283Mycosis fungoides[ICD-11: 2B01]P51679CCR4
T06955DI0379Sezary syndrome[ICD-11: 2B02]P51679CCR4
T81311DI0238Lung cancer[ICD-11: 2C25]P14625HSP90B1
T93653DI0055Bone cancer[ICD-11: 2B5Z]O60911CTSV
T93653DI0087Chronic pain[ICD-11: MG30]O60911CTSV
T70518DI0037Asthma[ICD-11: CA23]P16152CBR1
T10147DI0057Bone paget disease[ICD-11: FB85]Q13332PTPRS
T98091DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]Q9NQS5GPR84
T98091DI0417Type 2 diabetes mellitus[ICD-11: 5A11]Q9NQS5GPR84
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
T74500DI0004Acidosis[ICD-11: 5C73]Q9UK17KCND3
T47366DI0012Acute myeloid leukaemia[ICD-11: 2A60]P27037ACVR2A
T47366DI0198Idiopathic inflammatory myopathy[ICD-11: 4A41]P27037ACVR2A

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