Lilaline



Compound IDCDAMM01050
Common nameLilaline
IUPAC name3-methyl-5-[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]pyrrolidin-2-one
Molecular formulaC20H17NO7

Experimental data

Retention time20.31
Adduct[M+H]+
Actual mz384.114
Theoretical mz384.108
Error14.9
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.7051

Identifiers and class information

Inchi keyYDCRQLJCXBNURP-UHFFFAOYNA-N
SmilesO=C1C(O)=C(OC=2C1=C(O)C=C(O)C2C3NC(=O)C(C)C3)C=4C=CC(O)=CC4
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)1
Number of rotatable bonds (#rotor)4
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)383.357
Computed dipole moment(dipole)6.5
Total solvent accessible surface area (SASA)579.888
Hydrophobic component of SASA (FOSA)121.821
Hydrophilic component of SASA (FISA)279.626
Pie component of the SASA (PISA)178.441
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1064.61
Number of hydrogen bond donors (donorHB)4
Number of hydrogen bond acceptors (accptHB)7
Free energy of solvation of dipole (dip^2/V)0.0396861
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0241426
Globularity descriptor (glob)0.869523
Predicted polarizability in cubic angstroms (QPpolrz)35.587
Predicted hexadecane/gas partition coefficient (QPlogPC16)12.312
Predicted octanol/gas partition coefficient (QPlogPoct)22.548
Predicted water/gas partition coefficient (QPlogPw)18.455
Predicted octanol/water partition coefficient (QPlogPo/w)0.351
Predicted aqueous solubility (QPlogS)-2.644
Conformation-independent predicted aqueous solubility (CIQPlogS)-4.463
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-3.12
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)12.334
Predicted brain/blood partition coefficient (QPlogBB)-2.143
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)8.029
Predicted skin permeability, log Kp (QPlogKp)-5.66
PM3 calculated ionization potential (IP(ev))8.786
PM3 calculated electron affinity (EA(eV))0.83
Number of likely metabolic reactions (#metab)6
Prediction of binding to human serum albumin (QPlogKhsa)-0.348
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)48.529
Solvent-accessible surface area of fluorine atoms (SAFluorine)0
Solvent-accessible surface area of amide oxygen atoms (SAamideO)31.798
Van der Waals surface area (PSA)155.481
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
Q96KS0EIT6HIF-prolyl hydroxylase 1T53904SwissTargetPrediction
P24864CCNE1Cyclin-dependent kinase 2/cyclin E1T10052SEA
O14684PTGESProstaglandin E synthaseT02562SwissTargetPrediction
P33527ABCC1Multidrug resistance-associated protein 1T11288SEA
P08183ABCB1P-glycoprotein 1T25258SwissTargetPrediction and SEA
P04626ERBB2Receptor protein-tyrosine kinase erbB-2T14597SwissTargetPrediction
P11474ESRRAEstrogen-related receptor alphaT72841SEA
O14757CHEK1Serine/threonine-protein kinase Chk1T62449SwissTargetPrediction
P30291WEE1Serine/threonine-protein kinase WEE1T69991SwissTargetPrediction
P24941CDK2Cyclin-dependent kinase 2T70176SEA
Q9Y233PDE10APhosphodiesterase 10A (by homology)T84133SwissTargetPrediction
P00742F10Thrombin and coagulation factor XT84631SwissTargetPrediction
P49356FNTBFarnesyl protein transferaseT13127SwissTargetPrediction
P31749AKT1Serine/threonine-protein kinase AKTT67619SwissTargetPrediction
P08238HSP90AB1Heat shock protein HSP 90-betaT96623SwissTargetPrediction
P07900HSP90AA1Heat shock protein HSP 90-alphaT18477SwissTargetPrediction
P47871GCGRGlucagon receptorT60182SwissTargetPrediction
P05186ALPLAlkaline phosphatase, tissue-nonspecific isozymeT09538SwissTargetPrediction
Q15078CDK5R1Cyclin-dependent kinase 5/CDK5 activator 1T09513SwissTargetPrediction and SEA
P24385CCND1Cyclin-dependent kinase 4/cyclin D1T12355SEA
P49759CLK1Dual specificty protein kinase CLK1T46685SwissTargetPrediction
Q96EB6SIRT1NAD-dependent deacetylase sirtuin 1T14731SwissTargetPrediction
P06493CDK1Cyclin-dependent kinase 1/cyclin B1T49898SwissTargetPrediction
Q07002CDK18Serine/threonine-protein kinase PCTAIRE-3T27577SEA
O76074PDE5APhosphodiesterase 5AT07663SwissTargetPrediction
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
Q9NPH5NOX4NADPH oxidase 4T29741SEA
P47989XDHXanthine dehydrogenaseT40954SEA
Q16678CYP1B1Cytochrome P450 1B1T92521SEA
Q04760GLO1Glyoxalase IT88285SEA
P20248CCNA2CDK2/Cyclin AT58470SEA
Q14004CDK13Cyclin-dependent kinase 13T74839SEA
P51679CCR4C-C chemokine receptor type 4T06955SwissTargetPrediction
P14625HSP90B1EndoplasminT81311SwissTargetPrediction
Q16512PKN1Protein kinase N1T60003SEA
Q9HC98NEK6Serine/threonine-protein kinase NEK6T78992SEA
Q13332PTPRSReceptor-type tyrosine-protein phosphatase ST10147SEA
P21860ERBB3Receptor tyrosine-protein kinase erbB-3T86350SEA
Q13705ACVR2BActivin receptor type-2BT80338SEA
Q99417MYCBPMYCBP messenger RNAT37298SEA
Q15717ELAVL1ELAV-like protein 1T78349SEA
P27037ACVR2AActivin receptor type IIAT47366SEA
P14635CCNB1G2/mitotic-specific cyclin B1T98459SEA
Q9GZT9EGLN1Egl nine homolog 1T32880SwissTargetPrediction

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T53904DI0010Acute disease anaemia[ICD-11: 3A90]Q96KS0EIT6
T02562DI0025Alzheimer disease[ICD-11: 8A20]O14684PTGES
T11288DI0167Gout[ICD-11: FA25]P33527ABCC1
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
T72841DI0366Rheumatoid arthritis[ICD-11: FA20]P11474ESRRA
T62449DI0027Anal cancer[ICD-11: 2C00]O14757CHEK1
T62449DI0172Head and neck cancer[ICD-11: 2D42]O14757CHEK1
T62449DI0183Hodgkin lymphoma[ICD-11: 2B30]O14757CHEK1
T62449DI0238Lung cancer[ICD-11: 2C25]O14757CHEK1
T62449DI0241Lymphoma[ICD-11: 2A80-2A86]O14757CHEK1
T62449DI0321Ovarian cancer[ICD-11: 2C73]O14757CHEK1
T62449DI0326Pancreatic cancer[ICD-11: 2C10]O14757CHEK1
T62449DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O14757CHEK1
T69991DI0321Ovarian cancer[ICD-11: 2C73]P30291WEE1
T69991DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P30291WEE1
T69991DI0429Uterine ligament/parametrium/uterine adnexa neoplasm[ICD-11: 2C72]P30291WEE1
T70176DI0060Brain cancer[ICD-11: 2A00]P24941CDK2
T70176DI0062Breast cancer[ICD-11: 2C60-2C6Y]P24941CDK2
T70176DI0238Lung cancer[ICD-11: 2C25]P24941CDK2
T70176DI0241Lymphoma[ICD-11: 2A80-2A86]P24941CDK2
T70176DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P24941CDK2
T70176DI0303Non-small-cell lung cancer[ICD-11: 2C25]P24941CDK2
T70176DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P24941CDK2
T70176DI0406Thymoma[ICD-11: 2C27]P24941CDK2
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
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
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
T60182DI0193Hypo-glycaemia[ICD-11: 5A41]P47871GCGR
T09538DI0164Genetic prion disease[ICD-11: 8E02]P05186ALPL
T09538DI0330Parasitic infection[ICD-11: 1D0Y-1G2Z]P05186ALPL
T12355DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P24385CCND1
T14731DI0366Rheumatoid arthritis[ICD-11: FA20]Q96EB6SIRT1
T14731DI0399Systemic sclerosis[ICD-11: 4A42]Q96EB6SIRT1
T14731DI0431Vasculitis[ICD-11: 4A44]Q96EB6SIRT1
T49898DI0062Breast cancer[ICD-11: 2C60-2C6Y]P06493CDK1
T49898DI0238Lung cancer[ICD-11: 2C25]P06493CDK1
T49898DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P06493CDK1
T49898DI0250Mature B-cell lymphoma[ICD-11: 2A85]P06493CDK1
T49898DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P06493CDK1
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
T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
T29741DI0146Fibrosis[ICD-11: GA14-GC01]Q9NPH5NOX4
T40954DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]P47989XDH
T40954DI0266Mineral deficiency[ICD-11: 5B5K]P47989XDH
T88285DI0210Influenza[ICD-11: 1E30-1E32]Q04760GLO1
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
T10147DI0057Bone paget disease[ICD-11: FB85]Q13332PTPRS
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
T47366DI0012Acute myeloid leukaemia[ICD-11: 2A60]P27037ACVR2A
T47366DI0198Idiopathic inflammatory myopathy[ICD-11: 4A41]P27037ACVR2A

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