Xanthoxoline



Compound IDCDAMM00539
Common nameXanthoxoline
IUPAC name1-hydroxy-2,3-dimethoxy-10H-acridin-9-one
Molecular formulaC15H13NO4

Experimental data

Retention time6.65
Adduct[2M+Na]+
Actual mz565.156
Theoretical mz565.157
Error2.16
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.8114

Identifiers and class information

Inchi keyCYPILPIHKOUTNO-UHFFFAOYSA-N
SmilesO=C1C=2C=CC=CC2NC3=CC(OC)=C(OC)C(O)=C13
SuperclassOrganoheterocyclic compounds
ClassQuinolines and derivatives

Plant source

  • Piper longum 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)0
    Number of non-conjugated amide groups (#amide)0
    Number of rotatable bonds (#rotor)3
    Number of reactive functional groups (#rtvFG)0
    Predicted central nervous system activity (CNS)0
    Molecular weight (mol_MW)271.272
    Computed dipole moment(dipole)7.498
    Total solvent accessible surface area (SASA)490.42
    Hydrophobic component of SASA (FOSA)175.123
    Hydrophilic component of SASA (FISA)93.03
    Pie component of the SASA (PISA)222.267
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)836.704
    Number of hydrogen bond donors (donorHB)1
    Number of hydrogen bond acceptors (accptHB)3.75
    Free energy of solvation of dipole (dip^2/V)0.0671839
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0076465
    Globularity descriptor (glob)0.875612
    Predicted polarizability in cubic angstroms (QPpolrz)27.527
    Predicted hexadecane/gas partition coefficient (QPlogPC16)8.473
    Predicted octanol/gas partition coefficient (QPlogPoct)13.117
    Predicted water/gas partition coefficient (QPlogPw)7.541
    Predicted octanol/water partition coefficient (QPlogPo/w)2.583
    Predicted aqueous solubility (QPlogS)-3.775
    Conformation-independent predicted aqueous solubility (CIQPlogS)-4.067
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.605
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)1299.27
    Predicted brain/blood partition coefficient (QPlogBB)-0.426
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)656.518
    Predicted skin permeability, log Kp (QPlogKp)-2.163
    PM3 calculated ionization potential (IP(ev))8.328
    PM3 calculated electron affinity (EA(eV))0.46
    Number of likely metabolic reactions (#metab)5
    Prediction of binding to human serum albumin (QPlogKhsa)0.063
    Predicted qualitative human oral absorption (HumanOralAbsorption)3
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)100
    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)74.099
    Number of nitrogen and oxygen atoms (#NandO)5
    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
    P34903GABRA3GABA A receptor alpha-3/beta-2/gamma-2T62292SEA
    P47869GABRA2GABA A receptor alpha-2/beta-2/gamma-2T51452SEA
    P21397MAOAMonoamine oxidase AT83875SEA
    P43166CA7Carbonic anhydrase VIIT37541SEA
    P23280CA6Carbonic anhydrase VIT06569SEA
    P22748CA4Carbonic anhydrase IVT53378SEA
    P14867GABRA1GABA-A receptor; alpha-1/beta-2/gamma-2T51487SEA
    P05164MPOMyeloperoxidaseT23471SEA
    P14920DAOD-amino-acid oxidaseT33124SEA
    P11926ODC1Ornithine decarboxylaseT60366SEA
    P09917ALOX5Arachidonate 5-lipoxygenaseT00140SEA
    O00206TLR4Toll-like receptor 4 (by homology)T81443SEA
    P08183ABCB1P-glycoprotein 1T25258SEA
    P52732KIF11Kinesin-like protein 1T28484SEA
    O14757CHEK1Serine/threonine-protein kinase Chk1T62449SEA
    P30291WEE1Serine/threonine-protein kinase WEE1T69991SEA
    P36888FLT3Tyrosine-protein kinase receptor FLT3T74312SEA
    P35916FLT4Vascular endothelial growth factor receptor 3T07303SEA
    P24385CCND1Cyclin-dependent kinase 4/cyclin D1T12355SEA
    P09619PDGFRBPlatelet-derived growth factor receptor betaT59102SEA
    P31644GABRA5GABA receptor alpha-5 subunitT26368SEA
    P12268IMPDH2Inosine-5'-monophosphate dehydrogenase 2T89360SEA
    P08151GLI1Zinc finger protein GLI1T40890SEA
    Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
    P08236GUSBBeta-glucuronidaseT96413SEA
    P47989XDHXanthine dehydrogenaseT40954SEA
    Q04771ACVR1Activin receptor type-1T12091SEA
    P55786NPEPPSPuromycin-sensitive aminopeptidaseT15610SEA
    Q16678CYP1B1Cytochrome P450 1B1T92521SEA
    P30281CCND3Cyclin-dependent kinase 4/cyclin DT72507SEA
    O60911CTSVCathepsin (V and K)T93653SEA
    O60285NUAK1NUAK family SNF1-like kinase 1T21653SEA
    Q9UQB9AURKCSerine/threonine-protein kinase Aurora-CT97592SEA
    Q13332PTPRSReceptor-type tyrosine-protein phosphatase ST10147SEA
    Q13882PTK6Tyrosine-protein kinase BRKT73694SEA
    P18507GABRG2GABA-A receptor; alpha-6/beta-3/gamma-2T08910SEA
    P23284PPIBCyclophilin BT25847SEA
    Q9H4B7TUBB1Tubulin beta-1 chainT84397SEA
    P09936UCHL1Ubiquitin thioesterase L1T56051SEA
    P16220CREB1Cyclic AMP-responsive element-binding proteinT92098SEA
    P38936CAP20Melanoma differentiation-associated protein 6T39855SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T62292DI0216Intentional self-harm[ICD-11: PC91]P34903GABRA3
    T51452DI0216Intentional self-harm[ICD-11: PC91]P47869GABRA2
    T83875DI0117Depression[ICD-11: 6A70-6A7Z]P21397MAOA
    T83875DI0331Parkinsonism[ICD-11: 8A00]P21397MAOA
    T06569DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P23280CA6
    T06569DI0372Seborrhoeic dermatitis[ICD-11: EA81]P23280CA6
    T53378DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P22748CA4
    T53378DI0166Glaucoma[ICD-11: 9C61]P22748CA4
    T53378DI0372Seborrhoeic dermatitis[ICD-11: EA81]P22748CA4
    T51487DI0014Acute respiratory distress syndrome[ICD-11: CB00]P14867GABRA1
    T51487DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]P14867GABRA1
    T51487DI0082Chronic insomnia[ICD-11: 7A00]P14867GABRA1
    T51487DI0087Chronic pain[ICD-11: MG30]P14867GABRA1
    T51487DI0101Corneal disease[ICD-11: 9A76-9A78]P14867GABRA1
    T51487DI0112Cystitis[ICD-11: GC00]P14867GABRA1
    T51487DI0117Depression[ICD-11: 6A70-6A7Z]P14867GABRA1
    T51487DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P14867GABRA1
    T51487DI0173Headache[ICD-11: 8A80-8A84]P14867GABRA1
    T51487DI0214Insomnia[ICD-11: 7A00-7A0Z]P14867GABRA1
    T51487DI0243Malaria[ICD-11: 1F40-1F45]P14867GABRA1
    T51487DI0256Mental/behavioural/neurodevelopmental disorder[ICD-11: 6E20-6E8Z]P14867GABRA1
    T51487DI0411Tonus and reflex abnormality[ICD-11: MB47]P14867GABRA1
    T23471DI0229Left ventricular failure[ICD-11: BD11]P05164MPO
    T23471DI0339Postoperative inflammation[ICD-11: 1A00-CA43]P05164MPO
    T33124DI0038Ataxic disorder[ICD-11: 8A03]P14920DAO
    T33124DI0370Schizophrenia[ICD-11: 6A20]P14920DAO
    T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
    T00140DI0037Asthma[ICD-11: CA23]P09917ALOX5
    T00140DI0147Filariasis[ICD-11: 1F66]P09917ALOX5
    T00140DI0403Thrombocytopenia[ICD-11: 3B64]P09917ALOX5
    T81443DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]O00206TLR4
    T81443DI0346Prostate cancer[ICD-11: 2C82]O00206TLR4
    T81443DI0375Sepsis[ICD-11: 1G40-1G41]O00206TLR4
    T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
    T28484DI0012Acute myeloid leukaemia[ICD-11: 2A60]P52732KIF11
    T28484DI0172Head and neck cancer[ICD-11: 2D42]P52732KIF11
    T28484DI0241Lymphoma[ICD-11: 2A80-2A86]P52732KIF11
    T28484DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P52732KIF11
    T28484DI0274Multiple myeloma[ICD-11: 2A83]P52732KIF11
    T28484DI0321Ovarian cancer[ICD-11: 2C73]P52732KIF11
    T28484DI0361Renal cell carcinoma[ICD-11: 2C90]P52732KIF11
    T28484DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P52732KIF11
    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
    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
    T07303DI0361Renal cell carcinoma[ICD-11: 2C90]P35916FLT4
    T12355DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P24385CCND1
    T59102DI0009Acute diabete complication[ICD-11: 5A2Y]P09619PDGFRB
    T59102DI0361Renal cell carcinoma[ICD-11: 2C90]P09619PDGFRB
    T59102DI0403Thrombocytopenia[ICD-11: 3B64]P09619PDGFRB
    T26368DI0216Intentional self-harm[ICD-11: PC91]P31644GABRA5
    T89360DI0413Transplant rejection[ICD-11: NE84]P12268IMPDH2
    T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
    T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
    T96413DI0242Lysosomal disease[ICD-11: 5C56]P08236GUSB
    T40954DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]P47989XDH
    T40954DI0266Mineral deficiency[ICD-11: 5B5K]P47989XDH
    T12091DI0028Anemia[ICD-11: 3A00-3A9Z]Q04771ACVR1
    T12091DI0274Multiple myeloma[ICD-11: 2A83]Q04771ACVR1
    T12091DI0284Myelodysplastic syndrome[ICD-11: 2A37]Q04771ACVR1
    T12091DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q04771ACVR1
    T15610DI0012Acute myeloid leukaemia[ICD-11: 2A60]P55786NPEPPS
    T15610DI0284Myelodysplastic syndrome[ICD-11: 2A37]P55786NPEPPS
    T93653DI0055Bone cancer[ICD-11: 2B5Z]O60911CTSV
    T93653DI0087Chronic pain[ICD-11: MG30]O60911CTSV
    T97592DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]Q9UQB9AURKC
    T97592DI0346Prostate cancer[ICD-11: 2C82]Q9UQB9AURKC
    T97592DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9UQB9AURKC
    T10147DI0057Bone paget disease[ICD-11: FB85]Q13332PTPRS
    T73694DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]Q13882PTK6
    T73694DI0339Postoperative inflammation[ICD-11: 1A00-CA43]Q13882PTK6
    T08910DI0117Depression[ICD-11: 6A70-6A7Z]P18507GABRG2
    T08910DI0256Mental/behavioural/neurodevelopmental disorder[ICD-11: 6E20-6E8Z]P18507GABRG2
    T08910DI0411Tonus and reflex abnormality[ICD-11: MB47]P18507GABRG2
    T25847DI0306Nutritional deficiency[ICD-11: 5B50-5B71]P23284PPIB
    T84397DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9H4B7TUBB1
    T56051DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P09936UCHL1

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