Goniolactone E



Compound IDCDAMM01614
Common nameGoniolactone E
IUPAC name5-hydroxy-7-[(3-hydroxy-5-oxo-3,3a,6,6a-tetrahydro-2H-furo[3,2-b]furan-2-yl)-phenylmethoxy]-2-phenyl-2,3-dihydrochromen-4-one
Molecular formulaC28H24O8

Experimental data

Retention time7.35
Adduct[M+H]+
Actual mz489.159
Theoretical mz489.154
Error8.64
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.1087

Identifiers and class information

Inchi keyZUODXHTXKPNRSK-WRBCOIOGNA-N
SmilesO=C1OC2C(O)C(OC2C1)C(OC=3C=C(O)C=4C(=O)CC(OC4C3)C=5C=CC=CC5)C=6C=CC=CC6
SuperclassPhenylpropanoids and polyketides
ClassFlavonoids

Pharmacokinetic properties

Number of descriptor values(#stars)1
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)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)488.493
Computed dipole moment(dipole)11.433
Total solvent accessible surface area (SASA)754.917
Hydrophobic component of SASA (FOSA)187.939
Hydrophilic component of SASA (FISA)176.068
Pie component of the SASA (PISA)390.91
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1407.35
Number of hydrogen bond donors (donorHB)1
Number of hydrogen bond acceptors (accptHB)9.65
Free energy of solvation of dipole (dip^2/V)0.0928783
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0127829
Globularity descriptor (glob)0.804515
Predicted polarizability in cubic angstroms (QPpolrz)50.049
Predicted hexadecane/gas partition coefficient (QPlogPC16)15.54
Predicted octanol/gas partition coefficient (QPlogPoct)25.043
Predicted water/gas partition coefficient (QPlogPw)15.039
Predicted octanol/water partition coefficient (QPlogPo/w)3.283
Predicted aqueous solubility (QPlogS)-5.37
Conformation-independent predicted aqueous solubility (CIQPlogS)-6.594
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-6.559
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)211.957
Predicted brain/blood partition coefficient (QPlogBB)-1.612
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)92.492
Predicted skin permeability, log Kp (QPlogKp)-2.811
PM3 calculated ionization potential (IP(ev))9.135
PM3 calculated electron affinity (EA(eV))0.171
Number of likely metabolic reactions (#metab)10
Prediction of binding to human serum albumin (QPlogKhsa)0.237
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)87.806
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)130.199
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)1

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
Q12809KCNH2HERGT20251SwissTargetPrediction
P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction
P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction
P04818TYMSThymidylate synthase (by homology)T98397SwissTargetPrediction
P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
P42338PIK3CBPI3-kinase p110-beta subunitT05031SwissTargetPrediction
P42336PIK3CAPI3-kinase p110-alpha subunitT80276SwissTargetPrediction
P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
P43405SYKTyrosine-protein kinase SYKT62431SwissTargetPrediction
P43166CA7Carbonic anhydrase VIIT37541SwissTargetPrediction
P22748CA4Carbonic anhydrase IVT53378SwissTargetPrediction
P27338MAOBMonoamine oxidase BT83011SEA
P07949RETKinesin-1 heavy chain/ Tyrosine-protein kinase receptor RETT60631SwissTargetPrediction
P11511CYP19A1Cytochrome P450 19A1T13260SwissTargetPrediction and SEA
P08253MMP2Matrix metalloproteinase 2T68251SwissTargetPrediction
Q14534SQLESqualene monooxygenase (by homology)T93344SwissTargetPrediction
P08183ABCB1P-glycoprotein 1T25258SwissTargetPrediction
P42345MTORSerine/threonine-protein kinase mTORT75243SwissTargetPrediction
P45452MMP13Matrix metalloproteinase 13T34296SwissTargetPrediction
Q9Y233PDE10APhosphodiesterase 10A (by homology)T84133SwissTargetPrediction
P62942FKBP1AFK506-binding protein 1AT76059SwissTargetPrediction
P23458JAK1Tyrosine-protein kinase JAK1T62460SwissTargetPrediction
O00329PIK3CDPI3-kinase p110-delta subunitT67849SwissTargetPrediction
Q15078CDK5R1Cyclin-dependent kinase 5/CDK5 activator 1T09513SwissTargetPrediction
Q13627DYRK1ADual-specificity tyrosine-phosphorylation regulated kinase 1AT92803SwissTargetPrediction
P49759CLK1Dual specificty protein kinase CLK1T46685SwissTargetPrediction
Q9Y463DYRK1BDual specificity tyrosine-phosphorylation-regulated kinase 1BT82720SwissTargetPrediction
P29597TYK2Tyrosine-protein kinase TYK2T78932SwissTargetPrediction
P20151KLK2Kallikrein 2T01908SEA
Q9NWZ3IRAK4Interleukin-1 receptor-associated kinase 4T55398SwissTargetPrediction
P39900MMP12Matrix metalloproteinase 12T03500SwissTargetPrediction
P25024CXCR1Interleukin-8 receptor AT00884SwissTargetPrediction
P50613CDK7Cyclin-dependent kinase 7T58449SwissTargetPrediction
P49760CLK2Dual specificity protein kinase CLK2T73725SwissTargetPrediction
P49761CLK3Dual specificity protein kinase CLK3T21585SwissTargetPrediction
P06737PYGLLiver glycogen phosphorylaseT19184SwissTargetPrediction
Q99558MAP3K14Mitogen-activated protein kinase kinase kinase 14T95736SwissTargetPrediction
P25025CXCR2Interleukin-8 receptor BT56923SwissTargetPrediction
P50281MMP14Matrix metalloproteinase 14T65019SwissTargetPrediction
P48736PIK3CGPI3-kinase p110-gamma subunitT95913SwissTargetPrediction
P01112HRASTransforming protein p21/H-Ras-1T71081SwissTargetPrediction
P78527PRKDCDNA-dependent protein kinaseT81735SwissTargetPrediction
P68400CSNK2A1Casein kinase II alphaT51565SwissTargetPrediction
P19784CSNK2A2Casein kinase II alpha (prime)T80526SwissTargetPrediction
P04049RAF1Serine/threonine-protein kinase RAFT51883SwissTargetPrediction
P15056BRAFSerine/threonine-protein kinase B-rafT99089SwissTargetPrediction
P53671LIMK2LIM domain kinase 2T09133SwissTargetPrediction
P35557GCKHexokinase type IVT87166SwissTargetPrediction
P60842EIF4A1Eukaryotic initiation factor 4A-IT86805SwissTargetPrediction
P21452TACR2Neurokinin 2 receptorT52790SwissTargetPrediction
O15111CHUKInhibitor of NF-kappa-B kinase (IKK)T78429SwissTargetPrediction
Q13153PAK1Serine/threonine-protein kinase PAK 1T37961SwissTargetPrediction
Q92630DYRK2Dual-specificity tyrosine-phosphorylation regulated kinase 2T39486SwissTargetPrediction
Q15746MYLKMyosin light chain kinase, smooth muscleT97141SwissTargetPrediction
O43293DAPK3Death-associated protein kinase 3T81623SwissTargetPrediction
Q9UBF8PI4KBPI4-kinase beta subunitT12541SwissTargetPrediction
P52209PGD6-phosphogluconate dehydrogenaseT76497SwissTargetPrediction
P22083FUT4Fucosyltransferase 4T51146SwissTargetPrediction
P42224STAT1Signal transducer and activator of transcription 1-alpha/betaT64205SwissTargetPrediction
Q16678CYP1B1Cytochrome P450 1B1T92521SEA
P10636MAPTMicrotubule-associated protein tauT45593SwissTargetPrediction
Q5VT25CDC42BPASerine or threonine-protein kinase MRCK-AT00075SwissTargetPrediction
P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA
P06734FCER2Immunoglobulin epsilon Fc receptorT67207SwissTargetPrediction
Q13177PAK2Serine/threonine-protein kinase PAK 2T07766SwissTargetPrediction
Q9BZ11ADAM33Disintegrin and metalloproteinase domain-containing protein 33T11192SwissTargetPrediction
Q9H2X6HIPK2Homeodomain-interacting protein kinase 2T53952SwissTargetPrediction
Q56UN5MAP3K19SPS1/STE20-related protein kinase YSK4T42157SwissTargetPrediction

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T20251DI0175Heart failure[ICD-11: BD10-BD1Z]Q12809KCNH2
T77365DI0319Orthostatic hypotension[ICD-11: BA21]P29274ADORA2A
T77365DI0331Parkinsonism[ICD-11: 8A00]P29274ADORA2A
T77365DI0359Radionuclide imaging[ICD-11: N.A.]P29274ADORA2A
T92072DI0319Orthostatic hypotension[ICD-11: BA21]P30542ADORA1
T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
T98397DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P04818TYMS
T98397DI0395Stomach cancer[ICD-11: 2B72]P04818TYMS
T36059DI0351Psoriasis[ICD-11: EA90]P0DMS8ADORA3
T36059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMS8ADORA3
T05031DI0062Breast cancer[ICD-11: 2C60-2C6Y]P42338PIK3CB
T80276DI0062Breast cancer[ICD-11: 2C60-2C6Y]P42336PIK3CA
T80276DI0151Follicular lymphoma[ICD-11: 2A80]P42336PIK3CA
T80276DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P42336PIK3CA
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
T62431DI0403Thrombocytopenia[ICD-11: 3B64]P43405SYK
T53378DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P22748CA4
T53378DI0166Glaucoma[ICD-11: 9C61]P22748CA4
T53378DI0372Seborrhoeic dermatitis[ICD-11: EA81]P22748CA4
T83011DI0115Dementia[ICD-11: 6D80-6D8Z]P27338MAOB
T83011DI0117Depression[ICD-11: 6A70-6A7Z]P27338MAOB
T83011DI0190Hypertension[ICD-11: BA00-BA04]P27338MAOB
T83011DI0243Malaria[ICD-11: 1F40-1F45]P27338MAOB
T83011DI0264Migraine[ICD-11: 8A80]P27338MAOB
T83011DI0331Parkinsonism[ICD-11: 8A00]P27338MAOB
T60631DI0095Colorectal cancer[ICD-11: 2B91]P07949RET
T60631DI0238Lung cancer[ICD-11: 2C25]P07949RET
T60631DI0250Mature B-cell lymphoma[ICD-11: 2A85]P07949RET
T60631DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P07949RET
T60631DI0403Thrombocytopenia[ICD-11: 3B64]P07949RET
T60631DI0407Thyroid cancer[ICD-11: 2D10]P07949RET
T13260DI0062Breast cancer[ICD-11: 2C60-2C6Y]P11511CYP19A1
T13260DI0108Cushing syndrome[ICD-11: 5A70]P11511CYP19A1
T68251DI0238Lung cancer[ICD-11: 2C25]P08253MMP2
T93344DI0118Dermatophytosis[ICD-11: 1F28]Q14534SQLE
T93344DI0385Skin fungal infection disorder[ICD-11: EA60]Q14534SQLE
T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
T75243DI0036Arteries/arterioles disorder[ICD-11: BD52]P42345MTOR
T75243DI0085Chronic myelomonocytic leukaemia[ICD-11: 2A40]P42345MTOR
T75243DI0274Multiple myeloma[ICD-11: 2A83]P42345MTOR
T75243DI0361Renal cell carcinoma[ICD-11: 2C90]P42345MTOR
T75243DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P42345MTOR
T75243DI0413Transplant rejection[ICD-11: NE84]P42345MTOR
T34296DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45452MMP13
T84133DI0079Choreiform disorder[ICD-11: 8A01]Q9Y233PDE10A
T84133DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]Q9Y233PDE10A
T84133DI0218Irritable bowel syndrome[ICD-11: DD91]Q9Y233PDE10A
T84133DI0370Schizophrenia[ICD-11: 6A20]Q9Y233PDE10A
T84133DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9Y233PDE10A
T76059DI0331Parkinsonism[ICD-11: 8A00]P62942FKBP1A
T76059DI0349Pruritus[ICD-11: EC90]P62942FKBP1A
T76059DI0413Transplant rejection[ICD-11: NE84]P62942FKBP1A
T62460DI0039Atopic eczema[ICD-11: EA80]P23458JAK1
T62460DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P23458JAK1
T62460DI0366Rheumatoid arthritis[ICD-11: FA20]P23458JAK1
T62460DI0404Thrombocytosis[ICD-11: 3B63]P23458JAK1
T67849DI0151Follicular lymphoma[ICD-11: 2A80]O00329PIK3CD
T67849DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]O00329PIK3CD
T67849DI0249Mature B-cell leukaemia[ICD-11: 2A82]O00329PIK3CD
T67849DI0250Mature B-cell lymphoma[ICD-11: 2A85]O00329PIK3CD
T67849DI0395Stomach cancer[ICD-11: 2B72]O00329PIK3CD
T92803DI0113Cytomegaloviral disease[ICD-11: 1D82]Q13627DYRK1A
T78932DI0351Psoriasis[ICD-11: EA90]P29597TYK2
T01908DI0213Innate/adaptive immunodeficiency[ICD-11: 4A00]P20151KLK2
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
T03500DI0037Asthma[ICD-11: CA23]P39900MMP12
T03500DI0238Lung cancer[ICD-11: 2C25]P39900MMP12
T03500DI0361Renal cell carcinoma[ICD-11: 2C90]P39900MMP12
T00884DI0324Pain[ICD-11: MG30-MG3Z]P25024CXCR1
T58449DI0062Breast cancer[ICD-11: 2C60-2C6Y]P50613CDK7
T58449DI0238Lung cancer[ICD-11: 2C25]P50613CDK7
T58449DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P50613CDK7
T58449DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P50613CDK7
T56923DI0155Fungal infection[ICD-11: 1F29-1F2F]P25025CXCR2
T56923DI0324Pain[ICD-11: MG30-MG3Z]P25025CXCR2
T65019DI0178Hepatic fibrosis/cirrhosis[ICD-11: DB93]P50281MMP14
T95913DI0151Follicular lymphoma[ICD-11: 2A80]P48736PIK3CG
T95913DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P48736PIK3CG
T95913DI0249Mature B-cell leukaemia[ICD-11: 2A82]P48736PIK3CG
T81735DI0360Rectum cancer[ICD-11: 2B92]P78527PRKDC
T81735DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P78527PRKDC
T51565DI0104Coronavirus infection[ICD-11: 1D92]P68400CSNK2A1
T51565DI0235Liver cancer[ICD-11: 2C12]P68400CSNK2A1
T51565DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P68400CSNK2A1
T51883DI0252Melanoma[ICD-11: 2C30]P04049RAF1
T51883DI0303Non-small-cell lung cancer[ICD-11: 2C25]P04049RAF1
T51883DI0321Ovarian cancer[ICD-11: 2C73]P04049RAF1
T51883DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P04049RAF1
T99089DI0252Melanoma[ICD-11: 2C30]P15056BRAF
T87166DI0009Acute diabete complication[ICD-11: 5A2Y]P35557GCK
T87166DI0120Diabetes mellitus[ICD-11: 5A10]P35557GCK
T87166DI0308Obesity[ICD-11: 5B80-5B81]P35557GCK
T87166DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P35557GCK
T86805DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P60842EIF4A1
T52790DI0218Irritable bowel syndrome[ICD-11: DD91]P21452TACR2
T78429DI0250Mature B-cell lymphoma[ICD-11: 2A85]O15111CHUK
T97141DI0127Duodenal ulcer[ICD-11: DA63]Q15746MYLK
T12541DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]Q9UBF8PI4KB
T12541DI0440Zoonotic viral diseaseICD-11: 1D6YQ9UBF8PI4KB
T76497DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P52209PGD
T51146DI0441Appendicitis[ICD-11: DB10]P22083FUT4
T64205DI0383Skin and skin-structure infection[ICD-11: 1F28-1G0Z]P42224STAT1
T45593DI0012Acute myeloid leukaemia[ICD-11: 2A60]P10636MAPT
T45593DI0025Alzheimer disease[ICD-11: 8A20]P10636MAPT
T45593DI0265Mild neurocognitive disorder[ICD-11: 6D71]P10636MAPT
T70518DI0037Asthma[ICD-11: CA23]P16152CBR1
T67207DI0231Leukaemia[ICD-11: 2A60-2B33]P06734FCER2
T42157DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q56UN5MAP3K19

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