Isopetasoside



Compound IDCDAMM01754
Common nameIsopetasoside
IUPAC name4a,5-dimethyl-3-propan-2-ylidene-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,6,7,8-tetrahydro-4H-naphthalen-2-one
Molecular formulaC21H32O7

Experimental data

Retention time3.72
Adduct[M+H]+
Actual mz397.221
Theoretical mz397.222
Error3.21
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.625

Identifiers and class information

Inchi keyAVZCSGMWWXMJEA-UHFFFAOYNA-N
SmilesO=C1C=C2CCC(OC3OC(CO)C(O)C(O)C3O)C(C)C2(C)CC1=C(C)C
SuperclassLipids and lipid-like molecules
ClassPrenol lipids

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)8
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)396.48
Computed dipole moment(dipole)7.752
Total solvent accessible surface area (SASA)670.731
Hydrophobic component of SASA (FOSA)433.182
Hydrophilic component of SASA (FISA)205.455
Pie component of the SASA (PISA)32.095
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1241.93
Number of hydrogen bond donors (donorHB)4
Number of hydrogen bond acceptors (accptHB)12.2
Free energy of solvation of dipole (dip^2/V)0.0483917
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0363782
Globularity descriptor (glob)0.833068
Predicted polarizability in cubic angstroms (QPpolrz)38.718
Predicted hexadecane/gas partition coefficient (QPlogPC16)12.333
Predicted octanol/gas partition coefficient (QPlogPoct)25.763
Predicted water/gas partition coefficient (QPlogPw)19.06
Predicted octanol/water partition coefficient (QPlogPo/w)0.486
Predicted aqueous solubility (QPlogS)-3.267
Conformation-independent predicted aqueous solubility (CIQPlogS)-2.766
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.386
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)111.577
Predicted brain/blood partition coefficient (QPlogBB)-1.892
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)46.226
Predicted skin permeability, log Kp (QPlogKp)-4.425
PM3 calculated ionization potential (IP(ev))9.561
PM3 calculated electron affinity (EA(eV))0.207
Number of likely metabolic reactions (#metab)8
Prediction of binding to human serum albumin (QPlogKhsa)-0.541
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)66.438
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)126.987
Number of nitrogen and oxygen atoms (#NandO)7
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
P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction
Q07820MCL1Induced myeloid leukemia cell differentiation protein Mcl-1T14912SwissTargetPrediction
P00734F2ThrombinT94033SwissTargetPrediction
P13866SLC5A1Sodium/glucose cotransporter 1T54771SwissTargetPrediction
P10275ARAndrogen ReceptorT11211SwissTargetPrediction
P04150NR3C1Glucocorticoid receptorT40016SwissTargetPrediction
P28845HSD11B111-beta-hydroxysteroid dehydrogenase 1T65200SwissTargetPrediction
P14780MMP9Matrix metalloproteinase 9T54156SwissTargetPrediction
P08138NGFRLow affinity neurotrophin receptor p75NTRT50942SwissTargetPrediction
Q07817BCL2L1Apoptosis regulator Bcl-XT56510SwissTargetPrediction
Q16539MAPK14MAP kinase p38 alphaT65864SwissTargetPrediction
Q16831UPP1Uridine phosphorylase 1 (by homology)T97388SwissTargetPrediction
Q16769QPCTGlutaminyl-peptide cyclotransferaseT46245SwissTargetPrediction
P07711CTSLCathepsin LT98691SwissTargetPrediction
P51449RORCNuclear receptor ROR-gammaT25307SwissTargetPrediction
P80365HSD11B211-beta-hydroxysteroid dehydrogenase 2T43721SwissTargetPrediction
Q15858SCN9ASodium channel protein type IX alpha subunitT12119SwissTargetPrediction
Q02750MAP2K1Dual specificity mitogen-activated protein kinase kinase 1T99057SwissTargetPrediction
P19320VCAM1Vascular cell adhesion protein 1T44991SwissTargetPrediction
P41229KDM5CLysine-specific demethylase 5CT85540SwissTargetPrediction
P05362ICAM1Intercellular adhesion molecule-1T26203SwissTargetPrediction
P16581SELESelectin ET72835SwissTargetPrediction
P05186ALPLAlkaline phosphatase, tissue-nonspecific isozymeT09538SwissTargetPrediction
P40763STAT3Signal transducer and activator of transcription 3T29130SwissTargetPrediction
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
P04062GBABeta-glucocerebrosidaseT84173SwissTargetPrediction
Q9UGL1KDM5BLysine-specific demethylase 5BT56871SwissTargetPrediction
P55263ADKAdenosine kinaseT91661SwissTargetPrediction
O60502OGABifunctional protein NCOATT19567SwissTargetPrediction
Q99808SLC29A1Equilibrative nucleoside transporter 1T13491SwissTargetPrediction
P52789HK2Hexokinase type IIT96685SwissTargetPrediction
O43868SLC28A2Sodium/nucleoside cotransporter 2T94627SwissTargetPrediction
P23526AHCYAdenosylhomocysteinaseT68698SwissTargetPrediction
P05023ATP1A1Sodium/potassium-transporting ATPase alpha-1 chainT40800SwissTargetPrediction
Q9NY91SLC5A4Low affinity sodium-glucose cotransporterT22583SwissTargetPrediction
P04629NTRK1Nerve growth factor receptor Trk-AT07173SwissTargetPrediction
P31639SLC5A2Sodium/glucose cotransporter 2T30085SwissTargetPrediction
P06737PYGLLiver glycogen phosphorylaseT19184SwissTargetPrediction
P42574CASP3Caspase-3T57943SwissTargetPrediction
P55210CASP7Caspase-7T72252SwissTargetPrediction
Q02127DHODHDihydroorotate dehydrogenaseT61400SwissTargetPrediction
P60568IL2Interleukin-2T61698SwissTargetPrediction and SEA
P08151GLI1Zinc finger protein GLI1T40890SwissTargetPrediction
Q9H244P2RY12Purinergic receptor P2Y12 (by homology)T46937SwissTargetPrediction
P78527PRKDCDNA-dependent protein kinaseT81735SwissTargetPrediction
O14976GAKSerine or threonine-protein kinase GAKT00043SwissTargetPrediction
Q99683MAP3K5Mitogen-activated protein kinase kinase kinase 5T97589SwissTargetPrediction
P17931LGALS3Galectin-3T72038SEA
P04746AMY2APancreatic alpha-amylaseT86918SEA
P14679TYRTyrosinaseT97035SEA
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T77365DI0319Orthostatic hypotension[ICD-11: BA21]P29274ADORA2A
T77365DI0331Parkinsonism[ICD-11: 8A00]P29274ADORA2A
T77365DI0359Radionuclide imaging[ICD-11: N.A.]P29274ADORA2A
T14912DI0012Acute myeloid leukaemia[ICD-11: 2A60]Q07820MCL1
T14912DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]Q07820MCL1
T14912DI0250Mature B-cell lymphoma[ICD-11: 2A85]Q07820MCL1
T14912DI0252Melanoma[ICD-11: 2C30]Q07820MCL1
T14912DI0274Multiple myeloma[ICD-11: 2A83]Q07820MCL1
T14912DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q07820MCL1
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
T54771DI0120Diabetes mellitus[ICD-11: 5A10]P13866SLC5A1
T54771DI0175Heart failure[ICD-11: BD10-BD1Z]P13866SLC5A1
T54771DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P13866SLC5A1
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
T65200DI0210Influenza[ICD-11: 1E30-1E32]P28845HSD11B1
T65200DI0239Lupus erythematosus[ICD-11: 4A40]P28845HSD11B1
T65200DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P28845HSD11B1
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
T50942DI0299Neurotrophic keratitis[ICD-11: 9A74]P08138NGFR
T56510DI0286Myeloproliferative neoplasm[ICD-11: 2A20]Q07817BCL2L1
T65864DI0102Coronary atherosclerosis[ICD-11: BA52]Q16539MAPK14
T65864DI0287Myocardial infarction[ICD-11: BA41-BA43]Q16539MAPK14
T65864DI0366Rheumatoid arthritis[ICD-11: FA20]Q16539MAPK14
T65864DI0437Vitamin deficiency[ICD-11: 5B55-5B5F]Q16539MAPK14
T97388DI0292Nasopharyngitis[ICD-11: CA00]Q16831UPP1
T46245DI0115Dementia[ICD-11: 6D80-6D8Z]Q16769QPCT
T98691DI0263Middle East Respiratory Syndrome[ICD-11: 1D64]P07711CTSL
T98691DI0376Severe acute respiratory syndrome[ICD-11: 1D65]P07711CTSL
T25307DI0042Autoimmune disease[ICD-11: 4A40-4A45]P51449RORC
T25307DI0107Crohn disease[ICD-11: DD70]P51449RORC
T25307DI0238Lung cancer[ICD-11: 2C25]P51449RORC
T25307DI0275Multiple sclerosis[ICD-11: 8A40]P51449RORC
T25307DI0351Psoriasis[ICD-11: EA90]P51449RORC
T25307DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P51449RORC
T43721DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P80365HSD11B2
T12119DI0051Bipolar disorder[ICD-11: 6A60]Q15858SCN9A
T12119DI0087Chronic pain[ICD-11: MG30]Q15858SCN9A
T12119DI0140Extremities vasodilatation[ICD-11: EG00]Q15858SCN9A
T12119DI0163General pain disorder[ICD-11: 8E43]Q15858SCN9A
T12119DI0320Osteoarthritis[ICD-11: FA00-FA05]Q15858SCN9A
T12119DI0324Pain[ICD-11: MG30-MG3Z]Q15858SCN9A
T12119DI0358Radiculopathy[ICD-11: 8B93]Q15858SCN9A
T12119DI0415Trigeminal nerve disorder[ICD-11: 8B82]Q15858SCN9A
T99057DI0262Metastatic tumour[ICD-11: 2D50-2E2Z]Q02750MAP2K1
T99057DI0336Phakomatoses/hamartoneoplastic syndrome[ICD-11: LD2D]Q02750MAP2K1
T26203DI0436Visual system disease[ICD-11: 9E1Z]P05362ICAM1
T72835DI0012Acute myeloid leukaemia[ICD-11: 2A60]P16581SELE
T72835DI0037Asthma[ICD-11: CA23]P16581SELE
T72835DI0039Atopic eczema[ICD-11: EA80]P16581SELE
T72835DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P16581SELE
T72835DI0088Circulatory system disease[ICD-11: BE2Z]P16581SELE
T72835DI0190Hypertension[ICD-11: BA00-BA04]P16581SELE
T72835DI0351Psoriasis[ICD-11: EA90]P16581SELE
T09538DI0164Genetic prion disease[ICD-11: 8E02]P05186ALPL
T09538DI0330Parasitic infection[ICD-11: 1D0Y-1G2Z]P05186ALPL
T29130DI0351Psoriasis[ICD-11: EA90]P40763STAT3
T20761DI0095Colorectal cancer[ICD-11: 2B91]P15692VEGFA
T20761DI0365Retinopathy[ICD-11: 9B71]P15692VEGFA
T20761DI0430Vascular system developmental anomaly[ICD-11: LA90]P15692VEGFA
T18639DI0081Chronic arterial occlusive disease[ICD-11: BD4Z]P05230FGF1
T18639DI0102Coronary atherosclerosis[ICD-11: BA52]P05230FGF1
T31621DI0005Acne vulgaris[ICD-11: ED80]P09038FGF2
T84173DI0257Metabolic disorder[ICD-11: 5C50-5D2Z]P04062GBA
T91661DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P55263ADK
T19567DI0025Alzheimer disease[ICD-11: 8A20]O60502OGA
T19567DI0331Parkinsonism[ICD-11: 8A00]O60502OGA
T13491DI0030Angina pectoris[ICD-11: BA40]Q99808SLC29A1
T96685DI0133Epidermal dysplasias[ICD-11: EK90]P52789HK2
T40800DI0068Cardiac arrhythmia[ICD-11: BC9Z]P05023ATP1A1
T40800DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P05023ATP1A1
T40800DI0101Corneal disease[ICD-11: 9A76-9A78]P05023ATP1A1
T40800DI0175Heart failure[ICD-11: BD10-BD1Z]P05023ATP1A1
T40800DI0186Hyperhidrosis[ICD-11: EE00]P05023ATP1A1
T40800DI0243Malaria[ICD-11: 1F40-1F45]P05023ATP1A1
T40800DI0397Supraventricular tachyarrhythmia[ICD-11: BC81]P05023ATP1A1
T22583DI0009Acute diabete complication[ICD-11: 5A2Y]Q9NY91SLC5A4
T22583DI0417Type 2 diabetes mellitus[ICD-11: 5A11]Q9NY91SLC5A4
T07173DI0303Non-small-cell lung cancer[ICD-11: 2C25]P04629NTRK1
T07173DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P04629NTRK1
T30085DI0120Diabetes mellitus[ICD-11: 5A10]P31639SLC5A2
T30085DI0175Heart failure[ICD-11: BD10-BD1Z]P31639SLC5A2
T30085DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P31639SLC5A2
T57943DI0060Brain cancer[ICD-11: 2A00]P42574CASP3
T72252DI0110Cystic fibrosis[ICD-11: CA25]P55210CASP7
T61400DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]Q02127DHODH
T61400DI0275Multiple sclerosis[ICD-11: 8A40]Q02127DHODH
T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
T46937DI0287Myocardial infarction[ICD-11: BA41-BA43]Q9H244P2RY12
T46937DI0405Thrombosis[ICD-11: DB61-GB90]Q9H244P2RY12
T81735DI0360Rectum cancer[ICD-11: 2B92]P78527PRKDC
T81735DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P78527PRKDC
T00043DI0366Rheumatoid arthritis[ICD-11: FA20]O14976GAK
T97589DI0083Chronic kidney disease[ICD-11: GB61]Q99683MAP3K5
T97589DI0356Pulmonary hypertension[ICD-11: BB01]Q99683MAP3K5
T72038DI0190Hypertension[ICD-11: BA00-BA04]P17931LGALS3
T72038DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P17931LGALS3
T72038DI0252Melanoma[ICD-11: 2C30]P17931LGALS3
T72038DI0302Non-alcoholic fatty liver disease[ICD-11: DB92]P17931LGALS3
T72038DI0351Psoriasis[ICD-11: EA90]P17931LGALS3
T86918DI0110Cystic fibrosis[ICD-11: CA25]P04746AMY2A
T86918DI0328Pancreatic malfunction[ICD-11: DC30-DC3Z]P04746AMY2A
T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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