8-Acetoxy-4\'-methoxypinoresinol



Compound IDCDAMM01247
Common name8-Acetoxy-4\'-methoxypinoresinol
IUPAC name(3-hepta-1,3,5-trienyl-7-methyl-6,8-dioxo-1aH-oxireno[2,3-j]isochromen-7-yl) 3,5-dihydroxyhexanoate
Molecular formulaC23H26O8

Experimental data

Retention time0.45
Adduct[M+K]+
Actual mz469.119
Theoretical mz469.126
Error14.41
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.9677

Identifiers and class information

Inchi keyZVILPMKYRJCFAE-UHFFFAOYNA-N
SmilesO=C(OC1(C(=O)C=C2C=C(OC3OC23C1=O)C=CC=CC=CC)C)CC(O)CC(O)C
SuperclassLignans, neolignans and related compounds
ClassFuranoid lignans

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)12
Number of reactive functional groups (#rtvFG)4
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)430.454
Computed dipole moment(dipole)7.269
Total solvent accessible surface area (SASA)790.473
Hydrophobic component of SASA (FOSA)466.899
Hydrophilic component of SASA (FISA)171.36
Pie component of the SASA (PISA)152.213
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1393.86
Number of hydrogen bond donors (donorHB)1
Number of hydrogen bond acceptors (accptHB)11.15
Free energy of solvation of dipole (dip^2/V)0.0379104
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0141055
Globularity descriptor (glob)0.763408
Predicted polarizability in cubic angstroms (QPpolrz)43.377
Predicted hexadecane/gas partition coefficient (QPlogPC16)13.902
Predicted octanol/gas partition coefficient (QPlogPoct)21.946
Predicted water/gas partition coefficient (QPlogPw)13.623
Predicted octanol/water partition coefficient (QPlogPo/w)2.277
Predicted aqueous solubility (QPlogS)-4.413
Conformation-independent predicted aqueous solubility (CIQPlogS)-3.757
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-6.086
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)234.903
Predicted brain/blood partition coefficient (QPlogBB)-2.12
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)103.361
Predicted skin permeability, log Kp (QPlogKp)-2.989
PM3 calculated ionization potential (IP(ev))8.765
PM3 calculated electron affinity (EA(eV))1.545
Number of likely metabolic reactions (#metab)4
Prediction of binding to human serum albumin (QPlogKhsa)-0.401
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)82.71
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)143.447
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
P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction
P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
P29275ADORA2BAdenosine A2b receptorT86679SwissTargetPrediction
Q99705MCHR1Melanin-concentrating hormone receptor 1T09572SwissTargetPrediction
P00519ABL1Tyrosine-protein kinase ABLT63505SwissTargetPrediction
Q16539MAPK14MAP kinase p38 alphaT65864SwissTargetPrediction
P45452MMP13Matrix metalloproteinase 13T34296SwissTargetPrediction
P00742F10Thrombin and coagulation factor XT84631SwissTargetPrediction
P12931SRCTyrosine-protein kinase SRCT85943SwissTargetPrediction
P04062GBABeta-glucocerebrosidaseT84173SwissTargetPrediction
Q9NWZ3IRAK4Interleukin-1 receptor-associated kinase 4T55398SwissTargetPrediction
P28482MAPK1MAP kinase ERK2T58970SwissTargetPrediction
P11362FGFR1Fibroblast growth factor receptor 1T47101SwissTargetPrediction
P04406GAPDHGlyceraldehyde-3-phosphate dehydrogenase liverT39321SwissTargetPrediction
Q99808SLC29A1Equilibrative nucleoside transporter 1T13491SwissTargetPrediction
O43868SLC28A2Sodium/nucleoside cotransporter 2T94627SwissTargetPrediction
P04629NTRK1Nerve growth factor receptor Trk-AT07173SwissTargetPrediction
P31639SLC5A2Sodium/glucose cotransporter 2T30085SwissTargetPrediction
Q00987MDM2p53-binding protein Mdm-2T00176SwissTargetPrediction
P16455MGMT6-O-methylguanine-DNA methyltransferaseT24587SwissTargetPrediction
P20839IMPDH1Inosine-5'-monophosphate dehydrogenase 1T40111SwissTargetPrediction
P12268IMPDH2Inosine-5'-monophosphate dehydrogenase 2T89360SwissTargetPrediction
P17931LGALS3Galectin-3T72038SwissTargetPrediction
P16234PDGFRAPlatelet-derived growth factor receptorT53524SwissTargetPrediction
O15151MDM4Protein Mdm4T36741SwissTargetPrediction
P09382LGALS1Galectin-1T09544SwissTargetPrediction
O00142TK2Thymidine kinase, mitochondrialT22976SwissTargetPrediction

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T77365DI0319Orthostatic hypotension[ICD-11: BA21]P29274ADORA2A
T77365DI0331Parkinsonism[ICD-11: 8A00]P29274ADORA2A
T77365DI0359Radionuclide imaging[ICD-11: N.A.]P29274ADORA2A
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
T86679DI0180Herpes simplex infection[ICD-11: 1F00]P29275ADORA2B
T86679DI0397Supraventricular tachyarrhythmia[ICD-11: BC81]P29275ADORA2B
T09572DI0308Obesity[ICD-11: 5B80-5B81]Q99705MCHR1
T63505DI0062Breast cancer[ICD-11: 2C60-2C6Y]P00519ABL1
T63505DI0220Ischemia[ICD-11: 8B10-8B11]P00519ABL1
T63505DI0250Mature B-cell lymphoma[ICD-11: 2A85]P00519ABL1
T63505DI0306Nutritional deficiency[ICD-11: 5B50-5B71]P00519ABL1
T65864DI0102Coronary atherosclerosis[ICD-11: BA52]Q16539MAPK14
T65864DI0287Myocardial infarction[ICD-11: BA41-BA43]Q16539MAPK14
T65864DI0366Rheumatoid arthritis[ICD-11: FA20]Q16539MAPK14
T65864DI0437Vitamin deficiency[ICD-11: 5B55-5B5F]Q16539MAPK14
T34296DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45452MMP13
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
T85943DI0062Breast cancer[ICD-11: 2C60-2C6Y]P12931SRC
T85943DI0220Ischemia[ICD-11: 8B10-8B11]P12931SRC
T85943DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P12931SRC
T85943DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P12931SRC
T84173DI0257Metabolic disorder[ICD-11: 5C50-5D2Z]P04062GBA
T55398DI0039Atopic eczema[ICD-11: EA80]Q9NWZ3IRAK4
T55398DI0109Cutaneous lupus erythematosus[ICD-11: EB50-EB5Z]Q9NWZ3IRAK4
T55398DI0241Lymphoma[ICD-11: 2A80-2A86]Q9NWZ3IRAK4
T55398DI0339Postoperative inflammation[ICD-11: 1A00-CA43]Q9NWZ3IRAK4
T55398DI0351Psoriasis[ICD-11: EA90]Q9NWZ3IRAK4
T55398DI0366Rheumatoid arthritis[ICD-11: FA20]Q9NWZ3IRAK4
T58970DI0036Arteries/arterioles disorder[ICD-11: BD52]P28482MAPK1
T58970DI0252Melanoma[ICD-11: 2C30]P28482MAPK1
T58970DI0326Pancreatic cancer[ICD-11: 2C10]P28482MAPK1
T58970DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P28482MAPK1
T47101DI0095Colorectal cancer[ICD-11: 2B91]P11362FGFR1
T47101DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P11362FGFR1
T47101DI0235Liver cancer[ICD-11: 2C12]P11362FGFR1
T47101DI0403Thrombocytopenia[ICD-11: 3B64]P11362FGFR1
T39321DI0279Muscular atrophy[ICD-11: 8B61]P04406GAPDH
T39321DI0280Muscular dystrophy[ICD-11: 8C70]P04406GAPDH
T13491DI0030Angina pectoris[ICD-11: BA40]Q99808SLC29A1
T07173DI0303Non-small-cell lung cancer[ICD-11: 2C25]P04629NTRK1
T07173DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P04629NTRK1
T30085DI0120Diabetes mellitus[ICD-11: 5A10]P31639SLC5A2
T30085DI0175Heart failure[ICD-11: BD10-BD1Z]P31639SLC5A2
T30085DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P31639SLC5A2
T00176DI0012Acute myeloid leukaemia[ICD-11: 2A60]Q00987MDM2
T00176DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q00987MDM2
T24587DI0369Sarcoma[ICD-11: 2A60-2C35]P16455MGMT
T40111DI0062Breast cancer[ICD-11: 2C60-2C6Y]P20839IMPDH1
T40111DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]P20839IMPDH1
T40111DI0250Mature B-cell lymphoma[ICD-11: 2A85]P20839IMPDH1
T40111DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P20839IMPDH1
T40111DI0413Transplant rejection[ICD-11: NE84]P20839IMPDH1
T89360DI0413Transplant rejection[ICD-11: NE84]P12268IMPDH2
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
T53524DI0160Gastrointestinal stromal tumour[ICD-11: 2B5B]P16234PDGFRA
T53524DI0225Kaposi sarcoma[ICD-11: 2B57]P16234PDGFRA
T53524DI0403Thrombocytopenia[ICD-11: 3B64]P16234PDGFRA
T36741DI0012Acute myeloid leukaemia[ICD-11: 2A60]O15151MDM4
T36741DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]O15151MDM4
T36741DI0284Myelodysplastic syndrome[ICD-11: 2A37]O15151MDM4
T36741DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O15151MDM4
T22976DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]O00142TK2

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