Physalin B



Compound IDCDAMM00528
Common namePhysalin B
IUPAC name5-hydroxy-2,9,26-trimethyl-3,19,23,28-tetraoxaoctacyclo[16.9.1.118,27.01,5.02,24.08,17.09,14.021,26]nonacosa-11,14-diene-4,10,22,29-tetrone
Molecular formulaC28H30O9

Experimental data

Retention time13.05
Adduct[M+Na]+
Actual mz533.179
Theoretical mz533.178
Error2.03
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.2889

Identifiers and class information

Inchi keyHVTFEHJSUSPQBK-UHFFFAOYNA-N
SmilesO=C1OC2CC3(C)C1COC45OC6(C3C4=O)C(O)(C(=O)OC26C)CCC7C5CC=C8CC=CC(=O)C87C
SuperclassLipids and lipid-like molecules
ClassSteroids and steroid 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)1
    Number of reactive functional groups (#rtvFG)2
    Predicted central nervous system activity (CNS)-1
    Molecular weight (mol_MW)510.54
    Computed dipole moment(dipole)6.063
    Total solvent accessible surface area (SASA)636.504
    Hydrophobic component of SASA (FOSA)353.614
    Hydrophilic component of SASA (FISA)182.19
    Pie component of the SASA (PISA)100.7
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1301.85
    Number of hydrogen bond donors (donorHB)1
    Number of hydrogen bond acceptors (accptHB)12.25
    Free energy of solvation of dipole (dip^2/V)0.028237
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0192457
    Globularity descriptor (glob)0.905883
    Predicted polarizability in cubic angstroms (QPpolrz)46.266
    Predicted hexadecane/gas partition coefficient (QPlogPC16)12.564
    Predicted octanol/gas partition coefficient (QPlogPoct)24.324
    Predicted water/gas partition coefficient (QPlogPw)16.485
    Predicted octanol/water partition coefficient (QPlogPo/w)1.233
    Predicted aqueous solubility (QPlogS)-3.224
    Conformation-independent predicted aqueous solubility (CIQPlogS)-5.013
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-3.535
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)185.436
    Predicted brain/blood partition coefficient (QPlogBB)-0.977
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)80.049
    Predicted skin permeability, log Kp (QPlogKp)-4.427
    PM3 calculated ionization potential (IP(ev))9.793
    PM3 calculated electron affinity (EA(eV))0.492
    Number of likely metabolic reactions (#metab)5
    Prediction of binding to human serum albumin (QPlogKhsa)-0.272
    Predicted qualitative human oral absorption (HumanOralAbsorption)3
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)61.806
    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)145.589
    Number of nitrogen and oxygen atoms (#NandO)9
    Number of violations of Lipinski’s rule of five (RuleOfFive)1
    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
    P08173CHRM4Muscarinic acetylcholine receptor M4T20709SwissTargetPrediction
    P08912CHRM5Muscarinic acetylcholine receptor M5T79961SwissTargetPrediction
    P11229CHRM1Muscarinic acetylcholine receptor M1T28893SwissTargetPrediction
    P20309CHRM3Muscarinic acetylcholine receptor M3T67684SwissTargetPrediction
    P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction
    P00734F2ThrombinT94033SwissTargetPrediction
    P41594GRM5Metabotropic glutamate receptor 5T99347SwissTargetPrediction
    P17612PRKACAcAMP-dependent protein kinase alpha-catalytic subunitT12808SwissTargetPrediction
    O60341KDM1ALysine-specific histone demethylase 1T16739SwissTargetPrediction
    P10275ARAndrogen ReceptorT11211SwissTargetPrediction
    P04150NR3C1Glucocorticoid receptorT40016SwissTargetPrediction
    P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction
    P14902IDO1Indoleamine 2,3-dioxygenaseT89697SwissTargetPrediction
    P28845HSD11B111-beta-hydroxysteroid dehydrogenase 1T65200SwissTargetPrediction
    P08253MMP2Matrix metalloproteinase 2T68251SwissTargetPrediction
    P08254MMP3Matrix metalloproteinase 3T86702SwissTargetPrediction
    P14780MMP9Matrix metalloproteinase 9T54156SwissTargetPrediction
    P03956MMP1Matrix metalloproteinase 1T52450SwissTargetPrediction
    Q14534SQLESqualene monooxygenase (by homology)T93344SwissTargetPrediction
    P11309PIM1Serine/threonine-protein kinase PIM1T50594SwissTargetPrediction
    P06276BCHEButyrylcholinesteraseT99799SwissTargetPrediction
    P06213INSRInsulin receptorT85435SwissTargetPrediction
    Q9P1W9PIM2Serine/threonine-protein kinase PIM2T07279SwissTargetPrediction
    P45452MMP13Matrix metalloproteinase 13T34296SwissTargetPrediction
    P78536ADAM17ADAM17T82393SwissTargetPrediction
    P09237MMP7Matrix metalloproteinase 7T73475SwissTargetPrediction
    P08172CHRM2Muscarinic acetylcholine receptor M2T46185SwissTargetPrediction
    P80365HSD11B211-beta-hydroxysteroid dehydrogenase 2T43721SwissTargetPrediction
    P29466CASP1Caspase-1T98269SwissTargetPrediction
    O00311CDC7CDC7/DBF4 (Cell division cycle 7-related protein kinase/Activator of S phase kinase)T81358SwissTargetPrediction
    P62136PPP1CASerine/threonine protein phosphatase PP1-alpha catalytic subunitT59845SwissTargetPrediction
    P25025CXCR2Interleukin-8 receptor BT56923SwissTargetPrediction
    P42574CASP3Caspase-3T57943SwissTargetPrediction
    P55210CASP7Caspase-7T72252SwissTargetPrediction
    Q9UQ81MCH5Caspase-8T15700SwissTargetPrediction
    P12268IMPDH2Inosine-5'-monophosphate dehydrogenase 2T89360SwissTargetPrediction
    P08151GLI1Zinc finger protein GLI1T40890SwissTargetPrediction and SEA
    P28074PSMB5Proteasome Macropain subunit MB1T49031SwissTargetPrediction
    O60706ABCC9Sulfonylurea receptor 2T02777SwissTargetPrediction

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T20709DI0037Asthma[ICD-11: CA23]P08173CHRM4
    T20709DI0141Eye anterior segment structural developmental anomaly[ICD-11: LA11]P08173CHRM4
    T20709DI0166Glaucoma[ICD-11: 9C61]P08173CHRM4
    T20709DI0293Nausea/vomiting[ICD-11: MD90]P08173CHRM4
    T20709DI0362Respiratory system disease[ICD-11: CB40-CB7Z]P08173CHRM4
    T79961DI0002Abnormal micturition[ICD-11: MF50]P08912CHRM5
    T79961DI0032Anterior uveitis[ICD-11: 9A96]P08912CHRM5
    T79961DI0034Appearance/behaviour symptom[ICD-11: MB23]P08912CHRM5
    T79961DI0037Asthma[ICD-11: CA23]P08912CHRM5
    T79961DI0061Brain disease[ICD-11: 8C70-8E61]P08912CHRM5
    T79961DI0071Central and peripheral nervous disease[ICD-11: 8A04-8E7Z]P08912CHRM5
    T79961DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P08912CHRM5
    T79961DI0093Cognition symptoms/signs/clinical symptom[ICD-11: MB21]P08912CHRM5
    T79961DI0105Cough[ICD-11: MD12]P08912CHRM5
    T79961DI0124Digestive system disease[ICD-11: DE2Z]P08912CHRM5
    T79961DI0145Female pelvic pain[ICD-11: GA34]P08912CHRM5
    T79961DI0154Functional bladder disorder[ICD-11: GC50]P08912CHRM5
    T79961DI0158Gastritis[ICD-11: DA42]P08912CHRM5
    T79961DI0162General examination[ICD-11: QA00]P08912CHRM5
    T79961DI0166Glaucoma[ICD-11: 9C61]P08912CHRM5
    T79961DI0190Hypertension[ICD-11: BA00-BA04]P08912CHRM5
    T79961DI0208Infectious gastroenteritis/colitis[ICD-11: 1A40]P08912CHRM5
    T79961DI0218Irritable bowel syndrome[ICD-11: DD91]P08912CHRM5
    T79961DI0307Nystagmus[ICD-11: 9C84]P08912CHRM5
    T79961DI0315Oesophagus motility disorder[ICD-11: DA21]P08912CHRM5
    T79961DI0324Pain[ICD-11: MG30-MG3Z]P08912CHRM5
    T79961DI0329Pancreatitis[ICD-11: DC31-DC34]P08912CHRM5
    T79961DI0331Parkinsonism[ICD-11: 8A00]P08912CHRM5
    T79961DI0333Peptic ulcer[ICD-11: DA61]P08912CHRM5
    T79961DI0338Polyuria[ICD-11: MF55]P08912CHRM5
    T79961DI0411Tonus and reflex abnormality[ICD-11: MB47]P08912CHRM5
    T79961DI0421Unspecific substance harmful effect[ICD-11: NE6Z]P08912CHRM5
    T79961DI0424Urgency[ICD-11: N.A.]P08912CHRM5
    T28893DI0001Abdominal pelvic pain[ICD-11: MD81]P11229CHRM1
    T28893DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P11229CHRM1
    T28893DI0101Corneal disease[ICD-11: 9A76-9A78]P11229CHRM1
    T28893DI0129Dystonic disorder[ICD-11: 8A02]P11229CHRM1
    T28893DI0154Functional bladder disorder[ICD-11: GC50]P11229CHRM1
    T28893DI0157Gastric ulcer[ICD-11: DA60]P11229CHRM1
    T28893DI0166Glaucoma[ICD-11: 9C61]P11229CHRM1
    T28893DI0186Hyperhidrosis[ICD-11: EE00]P11229CHRM1
    T28893DI0218Irritable bowel syndrome[ICD-11: DD91]P11229CHRM1
    T28893DI0331Parkinsonism[ICD-11: 8A00]P11229CHRM1
    T28893DI0333Peptic ulcer[ICD-11: DA61]P11229CHRM1
    T28893DI0371Sebaceous gland disorder[ICD-11: ED91]P11229CHRM1
    T67684DI0037Asthma[ICD-11: CA23]P20309CHRM3
    T67684DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P20309CHRM3
    T67684DI0154Functional bladder disorder[ICD-11: GC50]P20309CHRM3
    T67684DI0166Glaucoma[ICD-11: 9C61]P20309CHRM3
    T67684DI0293Nausea/vomiting[ICD-11: MD90]P20309CHRM3
    T67684DI0333Peptic ulcer[ICD-11: DA61]P20309CHRM3
    T67684DI0362Respiratory system disease[ICD-11: CB40-CB7Z]P20309CHRM3
    T67684DI0371Sebaceous gland disorder[ICD-11: ED91]P20309CHRM3
    T67684DI0382Sjogren syndrome[ICD-11: 4A43]P20309CHRM3
    T67684DI0411Tonus and reflex abnormality[ICD-11: MB47]P20309CHRM3
    T77365DI0319Orthostatic hypotension[ICD-11: BA21]P29274ADORA2A
    T77365DI0331Parkinsonism[ICD-11: 8A00]P29274ADORA2A
    T77365DI0359Radionuclide imaging[ICD-11: N.A.]P29274ADORA2A
    T94033DI0052Bleeding disorder[ICD-11: GA20-GA21]P00734F2
    T94033DI0091Coagulation defect[ICD-11: 3B10]P00734F2
    T94033DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P00734F2
    T94033DI0275Multiple sclerosis[ICD-11: 8A40]P00734F2
    T94033DI0287Myocardial infarction[ICD-11: BA41-BA43]P00734F2
    T94033DI0306Nutritional deficiency[ICD-11: 5B50-5B71]P00734F2
    T94033DI0403Thrombocytopenia[ICD-11: 3B64]P00734F2
    T94033DI0405Thrombosis[ICD-11: DB61-GB90]P00734F2
    T99347DI0152Fragile X chromosome[ICD-11: LD55]P41594GRM5
    T99347DI0331Parkinsonism[ICD-11: 8A00]P41594GRM5
    T12808DI0279Muscular atrophy[ICD-11: 8B61]P17612PRKACA
    T16739DI0012Acute myeloid leukaemia[ICD-11: 2A60]O60341KDM1A
    T16739DI0025Alzheimer disease[ICD-11: 8A20]O60341KDM1A
    T16739DI0138Ewing sarcoma[ICD-11: 2B52]O60341KDM1A
    T16739DI0238Lung cancer[ICD-11: 2C25]O60341KDM1A
    T16739DI0241Lymphoma[ICD-11: 2A80-2A86]O60341KDM1A
    T16739DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]O60341KDM1A
    T16739DI0284Myelodysplastic syndrome[ICD-11: 2A37]O60341KDM1A
    T16739DI0286Myeloproliferative neoplasm[ICD-11: 2A20]O60341KDM1A
    T16739DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O60341KDM1A
    T11211DI0005Acne vulgaris[ICD-11: ED80]P10275AR
    T11211DI0012Acute myeloid leukaemia[ICD-11: 2A60]P10275AR
    T11211DI0021Alcoholic liver disease[ICD-11: DB94]P10275AR
    T11211DI0062Breast cancer[ICD-11: 2C60-2C6Y]P10275AR
    T11211DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P10275AR
    T11211DI0145Female pelvic pain[ICD-11: GA34]P10275AR
    T11211DI0194Hypo-osmolality/hyponatraemia[ICD-11: 5C72]P10275AR
    T11211DI0237Low bone mass disorder[ICD-11: FB83]P10275AR
    T11211DI0247Mammary tumour[ICD-11: 2C60-2C6Z]P10275AR
    T11211DI0346Prostate cancer[ICD-11: 2C82]P10275AR
    T11211DI0401Testicular dysfunction[ICD-11: 5A81]P10275AR
    T40016DI0016Adaptive immunity immunodeficiency[ICD-11: 4A01]P04150NR3C1
    T40016DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P04150NR3C1
    T40016DI0037Asthma[ICD-11: CA23]P04150NR3C1
    T40016DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P04150NR3C1
    T40016DI0108Cushing syndrome[ICD-11: 5A70]P04150NR3C1
    T40016DI0280Muscular dystrophy[ICD-11: 8C70]P04150NR3C1
    T40016DI0314Oesophagitis[ICD-11: DA24]P04150NR3C1
    T40016DI0339Postoperative inflammation[ICD-11: 1A00-CA43]P04150NR3C1
    T40016DI0366Rheumatoid arthritis[ICD-11: FA20]P04150NR3C1
    T40016DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P04150NR3C1
    T40016DI0432Vasomotor/allergic rhinitis[ICD-11: CA08]P04150NR3C1
    T16347DI0009Acute diabete complication[ICD-11: 5A2Y]P18031PTPN1
    T16347DI0062Breast cancer[ICD-11: 2C60-2C6Y]P18031PTPN1
    T16347DI0308Obesity[ICD-11: 5B80-5B81]P18031PTPN1
    T16347DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P18031PTPN1
    T89697DI0117Depression[ICD-11: 6A70-6A7Z]P14902IDO1
    T65200DI0210Influenza[ICD-11: 1E30-1E32]P28845HSD11B1
    T65200DI0239Lupus erythematosus[ICD-11: 4A40]P28845HSD11B1
    T65200DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P28845HSD11B1
    T68251DI0238Lung cancer[ICD-11: 2C25]P08253MMP2
    T86702DI0101Corneal disease[ICD-11: 9A76-9A78]P08254MMP3
    T86702DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]P08254MMP3
    T86702DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P08254MMP3
    T86702DI0275Multiple sclerosis[ICD-11: 8A40]P08254MMP3
    T86702DI0287Myocardial infarction[ICD-11: BA41-BA43]P08254MMP3
    T86702DI0320Osteoarthritis[ICD-11: FA00-FA05]P08254MMP3
    T86702DI0366Rheumatoid arthritis[ICD-11: FA20]P08254MMP3
    T54156DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P14780MMP9
    T54156DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P14780MMP9
    T54156DI0395Stomach cancer[ICD-11: 2B72]P14780MMP9
    T54156DI0419Ulcerative colitis[ICD-11: DD71]P14780MMP9
    T52450DI0238Lung cancer[ICD-11: 2C25]P03956MMP1
    T93344DI0118Dermatophytosis[ICD-11: 1F28]Q14534SQLE
    T93344DI0385Skin fungal infection disorder[ICD-11: EA60]Q14534SQLE
    T50594DI0012Acute myeloid leukaemia[ICD-11: 2A60]P11309PIM1
    T50594DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11309PIM1
    T99799DI0324Pain[ICD-11: MG30-MG3Z]P06276BCHE
    T99799DI0411Tonus and reflex abnormality[ICD-11: MB47]P06276BCHE
    T85435DI0009Acute diabete complication[ICD-11: 5A2Y]P06213INSR
    T85435DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P06213INSR
    T07279DI0274Multiple myeloma[ICD-11: 2A83]Q9P1W9PIM2
    T07279DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9P1W9PIM2
    T34296DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45452MMP13
    T82393DI0062Breast cancer[ICD-11: 2C60-2C6Y]P78536ADAM17
    T82393DI0366Rheumatoid arthritis[ICD-11: FA20]P78536ADAM17
    T73475DI0238Lung cancer[ICD-11: 2C25]P09237MMP7
    T46185DI0037Asthma[ICD-11: CA23]P08172CHRM2
    T46185DI0166Glaucoma[ICD-11: 9C61]P08172CHRM2
    T46185DI0278Muscle disorder[ICD-11: FB32-FB3Z]P08172CHRM2
    T46185DI0333Peptic ulcer[ICD-11: DA61]P08172CHRM2
    T46185DI0362Respiratory system disease[ICD-11: CB40-CB7Z]P08172CHRM2
    T46185DI0371Sebaceous gland disorder[ICD-11: ED91]P08172CHRM2
    T43721DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P80365HSD11B2
    T98269DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P29466CASP1
    T98269DI0146Fibrosis[ICD-11: GA14-GC01]P29466CASP1
    T98269DI0366Rheumatoid arthritis[ICD-11: FA20]P29466CASP1
    T98269DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P29466CASP1
    T81358DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]O00311CDC7
    T81358DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O00311CDC7
    T59845DI0268Molluscum contagiosum[ICD-11: 1E76]P62136PPP1CA
    T56923DI0155Fungal infection[ICD-11: 1F29-1F2F]P25025CXCR2
    T56923DI0324Pain[ICD-11: MG30-MG3Z]P25025CXCR2
    T57943DI0060Brain cancer[ICD-11: 2A00]P42574CASP3
    T72252DI0110Cystic fibrosis[ICD-11: CA25]P55210CASP7
    T15700DI0120Diabetes mellitus[ICD-11: 5A10]Q9UQ81MCH5
    T15700DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9UQ81MCH5
    T89360DI0413Transplant rejection[ICD-11: NE84]P12268IMPDH2
    T02777DI0009Acute diabete complication[ICD-11: 5A2Y]O60706ABCC9
    T02777DI0030Angina pectoris[ICD-11: BA40]O60706ABCC9
    T02777DI0417Type 2 diabetes mellitus[ICD-11: 5A11]O60706ABCC9

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