Eupatin 3-O-sulfate



Compound IDCDAMM02948
Common nameEupatin 3-O-sulfate
IUPAC name[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,7-dimethoxy-4-oxochromen-3-yl] hydrogen sulfate
Molecular formulaC18H16O11S

Experimental data

Retention time15.1
Adduct[M+H]+
Actual mz441.054
Theoretical mz441.048
Error12.3
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.1383

Identifiers and class information

Inchi keyNSLLNIWBDJKTNH-UHFFFAOYSA-N
SmilesO=C1C(OS(=O)(=O)O)=C(OC2=CC(OC)=C(OC)C(O)=C12)C=3C=CC(OC)=C(O)C3
SuperclassPhenylpropanoids and polyketides
ClassFlavonoids

Plant source

  • Clitoria ternatea L.

    • 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)1
    Number of non-conjugated amide groups (#amide)0
    Number of rotatable bonds (#rotor)8
    Number of reactive functional groups (#rtvFG)0
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)440.378
    Computed dipole moment(dipole)3.576
    Total solvent accessible surface area (SASA)654.809
    Hydrophobic component of SASA (FOSA)268.33
    Hydrophilic component of SASA (FISA)244.674
    Pie component of the SASA (PISA)140.237
    Weakly polar component of the SASA (WPSA)1.567
    Total solvent accesible volume (volume)1167.95
    Number of hydrogen bond donors (donorHB)2
    Number of hydrogen bond acceptors (accptHB)9.75
    Free energy of solvation of dipole (dip^2/V)0.0109483
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0210574
    Globularity descriptor (glob)0.819092
    Predicted polarizability in cubic angstroms (QPpolrz)36.79
    Predicted hexadecane/gas partition coefficient (QPlogPC16)12.244
    Predicted octanol/gas partition coefficient (QPlogPoct)20.641
    Predicted water/gas partition coefficient (QPlogPw)14.682
    Predicted octanol/water partition coefficient (QPlogPo/w)1.493
    Predicted aqueous solubility (QPlogS)-3.527
    Conformation-independent predicted aqueous solubility (CIQPlogS)-5.218
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-3.321
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)12.002
    Predicted brain/blood partition coefficient (QPlogBB)-2.346
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)5.386
    Predicted skin permeability, log Kp (QPlogKp)-4.767
    PM3 calculated ionization potential (IP(ev))8.734
    PM3 calculated electron affinity (EA(eV))0.861
    Number of likely metabolic reactions (#metab)5
    Prediction of binding to human serum albumin (QPlogKhsa)-0.556
    Predicted qualitative human oral absorption (HumanOralAbsorption)2
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)42.047
    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)163.096
    Number of nitrogen and oxygen atoms (#NandO)11
    Number of violations of Lipinski’s rule of five (RuleOfFive)1
    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
    P22303ACHEAcetylcholinesteraseT30082SwissTargetPrediction
    O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction
    P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
    P04054PLA2G1BPhospholipase A2 group 1BT31479SwissTargetPrediction
    P43166CA7Carbonic anhydrase VIIT37541SEA
    P23280CA6Carbonic anhydrase VIT06569SwissTargetPrediction
    Q9ULX7CA14Carbonic anhydrase XIVT31992SwissTargetPrediction
    P22748CA4Carbonic anhydrase IVT53378SwissTargetPrediction and SEA
    P00747PLGPlasminogenT89034SwissTargetPrediction
    P05164MPOMyeloperoxidaseT23471SwissTargetPrediction
    P42330AKR1C3Aldo-keto-reductase family 1 member C3T60857SwissTargetPrediction
    Q6B0I6KDM4DLysine-specific demethylase 4DT17036SwissTargetPrediction
    P11926ODC1Ornithine decarboxylaseT60366SEA
    P11511CYP19A1Cytochrome P450 19A1T13260SwissTargetPrediction
    P09917ALOX5Arachidonate 5-lipoxygenaseT00140SEA
    P08069IGF1RInsulin-like growth factor I receptorT48069SwissTargetPrediction
    Q9UM73ALKALK tyrosine kinase receptorT56418SwissTargetPrediction
    Q9HC97GPR35G-protein coupled receptor 35T56143SwissTargetPrediction
    P33527ABCC1Multidrug resistance-associated protein 1T11288SwissTargetPrediction and SEA
    P08183ABCB1P-glycoprotein 1T25258SEA
    P27695APEX1DNA-(apurinic or apyrimidinic site) lyaseT13348SwissTargetPrediction
    P06213INSRInsulin receptorT85435SwissTargetPrediction
    P36888FLT3Tyrosine-protein kinase receptor FLT3T74312SwissTargetPrediction
    P56817BACE1Beta-secretase 1T79031SwissTargetPrediction
    P18054ALOX12Arachidonate 12-lipoxygenaseT35527SEA
    P30518AVPR2Vasopressin V2 receptor (by homology)T66237SwissTargetPrediction
    P41143OPRD1Delta opioid receptorT58992SwissTargetPrediction
    P00742F10Thrombin and coagulation factor XT84631SwissTargetPrediction
    O14746TERTTelomerase reverse transcriptaseT86052SEA
    P11388TOP2ADNA topoisomerase II alphaT17048SwissTargetPrediction
    P31749AKT1Serine/threonine-protein kinase AKTT67619SwissTargetPrediction
    P49841GSK3BGlycogen synthase kinase-3 betaT70977SwissTargetPrediction
    P51955NEK2Serine/threonine-protein kinase NEK2T49102SwissTargetPrediction
    P06493CDK1Cyclin-dependent kinase 1/cyclin B1T49898SwissTargetPrediction
    P06737PYGLLiver glycogen phosphorylaseT19184SwissTargetPrediction
    P60568IL2Interleukin-2T61698SEA
    P53350PLK1Serine/threonine-protein kinase PLK1T40694SwissTargetPrediction
    Q96GD4AURKBSerine/threonine-protein kinase Aurora-BT46781SwissTargetPrediction
    Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
    Q9NPH5NOX4NADPH oxidase 4T29741SEA
    Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SEA
    P47989XDHXanthine dehydrogenaseT40954SwissTargetPrediction and SEA
    Q16678CYP1B1Cytochrome P450 1B1T92521SwissTargetPrediction and SEA
    P10636MAPTMicrotubule-associated protein tauT45593SwissTargetPrediction
    Q04760GLO1Glyoxalase IT88285SwissTargetPrediction and SEA
    Q16512PKN1Protein kinase N1T60003SwissTargetPrediction
    Q9UQM7CAMK2ACaM kinase II alphaT18299SwissTargetPrediction
    Q9HC98NEK6Serine/threonine-protein kinase NEK6T78992SwissTargetPrediction and SEA
    O60285NUAK1NUAK family SNF1-like kinase 1T21653SwissTargetPrediction
    P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA
    Q13332PTPRSReceptor-type tyrosine-protein phosphatase ST10147SEA
    Q9H4B7TUBB1Tubulin beta-1 chainT84397SEA
    P16220CREB1Cyclic AMP-responsive element-binding proteinT92098SEA
    Q15717ELAVL1ELAV-like protein 1T78349SEA
    Q9UK17KCND3Voltage-gated potassium channel Kv4.3T74500SEA

    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
    T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
    T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
    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
    T31479DI0230Leishmaniasis[ICD-11: 1F54]P04054PLA2G1B
    T31479DI0335Peroxisomal disease[ICD-11: 5C57]P04054PLA2G1B
    T31479DI0367Rosacea[ICD-11: ED90]P04054PLA2G1B
    T31479DI0398Synthesis disorder[ICD-11: 5C52-5C59]P04054PLA2G1B
    T06569DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P23280CA6
    T06569DI0372Seborrhoeic dermatitis[ICD-11: EA81]P23280CA6
    T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
    T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
    T53378DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P22748CA4
    T53378DI0166Glaucoma[ICD-11: 9C61]P22748CA4
    T53378DI0372Seborrhoeic dermatitis[ICD-11: EA81]P22748CA4
    T89034DI0030Angina pectoris[ICD-11: BA40]P00747PLG
    T89034DI0052Bleeding disorder[ICD-11: GA20-GA21]P00747PLG
    T89034DI0254Menopausal disorder[ICD-11: GA30]P00747PLG
    T89034DI0287Myocardial infarction[ICD-11: BA41-BA43]P00747PLG
    T89034DI0345Procedure injury[ICD-11: NE81]P00747PLG
    T89034DI0357Pulmonary thromboembolism[ICD-11: BB00]P00747PLG
    T23471DI0229Left ventricular failure[ICD-11: BD11]P05164MPO
    T23471DI0339Postoperative inflammation[ICD-11: 1A00-CA43]P05164MPO
    T60857DI0145Female pelvic pain[ICD-11: GA34]P42330AKR1C3
    T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
    T13260DI0062Breast cancer[ICD-11: 2C60-2C6Y]P11511CYP19A1
    T13260DI0108Cushing syndrome[ICD-11: 5A70]P11511CYP19A1
    T00140DI0037Asthma[ICD-11: CA23]P09917ALOX5
    T00140DI0147Filariasis[ICD-11: 1F66]P09917ALOX5
    T00140DI0403Thrombocytopenia[ICD-11: 3B64]P09917ALOX5
    T48069DI0276Multiple structural anomalies syndrome[ICD-11: LD2F]P08069IGF1R
    T48069DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P08069IGF1R
    T48069DI0408Thyrotoxicosis[ICD-11: 5A02]P08069IGF1R
    T56418DI0238Lung cancer[ICD-11: 2C25]Q9UM73ALK
    T56418DI0251Mature T-cell lymphoma[ICD-11: 2A90]Q9UM73ALK
    T56418DI0303Non-small-cell lung cancer[ICD-11: 2C25]Q9UM73ALK
    T11288DI0167Gout[ICD-11: FA25]P33527ABCC1
    T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
    T13348DI0365Retinopathy[ICD-11: 9B71]P27695APEX1
    T13348DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P27695APEX1
    T85435DI0009Acute diabete complication[ICD-11: 5A2Y]P06213INSR
    T85435DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P06213INSR
    T74312DI0012Acute myeloid leukaemia[ICD-11: 2A60]P36888FLT3
    T74312DI0058Bone/articular cartilage neoplasm[ICD-11: 2F7B]P36888FLT3
    T74312DI0095Colorectal cancer[ICD-11: 2B91]P36888FLT3
    T74312DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]P36888FLT3
    T74312DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P36888FLT3
    T74312DI0248Mastocytosis[ICD-11: 2A21]P36888FLT3
    T74312DI0250Mature B-cell lymphoma[ICD-11: 2A85]P36888FLT3
    T74312DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P36888FLT3
    T79031DI0025Alzheimer disease[ICD-11: 8A20]P56817BACE1
    T66237DI0009Acute diabete complication[ICD-11: 5A2Y]P30518AVPR2
    T66237DI0041Autism spectrum disorder[ICD-11: 6A02]P30518AVPR2
    T66237DI0131Enuresis[ICD-11: 6C00]P30518AVPR2
    T66237DI0194Hypo-osmolality/hyponatraemia[ICD-11: 5C72]P30518AVPR2
    T66237DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P30518AVPR2
    T66237DI0338Polyuria[ICD-11: MF55]P30518AVPR2
    T58992DI0059Bowel habit change[ICD-11: ME05]P41143OPRD1
    T58992DI0218Irritable bowel syndrome[ICD-11: DD91]P41143OPRD1
    T58992DI0324Pain[ICD-11: MG30-MG3Z]P41143OPRD1
    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
    T86052DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]O14746TERT
    T86052DI0284Myelodysplastic syndrome[ICD-11: 2A37]O14746TERT
    T86052DI0326Pancreatic cancer[ICD-11: 2C10]O14746TERT
    T17048DI0012Acute myeloid leukaemia[ICD-11: 2A60]P11388TOP2A
    T17048DI0225Kaposi sarcoma[ICD-11: 2B57]P11388TOP2A
    T17048DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11388TOP2A
    T67619DI0062Breast cancer[ICD-11: 2C60-2C6Y]P31749AKT1
    T70977DI0288Myotonic disorder[ICD-11: 8C71]P49841GSK3B
    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
    T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
    T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
    T40694DI0012Acute myeloid leukaemia[ICD-11: 2A60]P53350PLK1
    T40694DI0284Myelodysplastic syndrome[ICD-11: 2A37]P53350PLK1
    T40694DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P53350PLK1
    T46781DI0009Acute diabete complication[ICD-11: 5A2Y]Q96GD4AURKB
    T46781DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q96GD4AURKB
    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
    T45593DI0012Acute myeloid leukaemia[ICD-11: 2A60]P10636MAPT
    T45593DI0025Alzheimer disease[ICD-11: 8A20]P10636MAPT
    T45593DI0265Mild neurocognitive disorder[ICD-11: 6D71]P10636MAPT
    T88285DI0210Influenza[ICD-11: 1E30-1E32]Q04760GLO1
    T18299DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UQM7CAMK2A
    T70518DI0037Asthma[ICD-11: CA23]P16152CBR1
    T10147DI0057Bone paget disease[ICD-11: FB85]Q13332PTPRS
    T84397DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9H4B7TUBB1
    T74500DI0004Acidosis[ICD-11: 5C73]Q9UK17KCND3

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