Hypochoeroside B



Compound IDCDAMM00621
Common nameHypochoeroside B
IUPAC name[3,6-dimethyl-2,7-dioxo-9-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] 2-methylprop-2-enoate
Molecular formulaC25H32O11

Experimental data

Retention time13.46
Adduct[M+H]+
Actual mz509.207
Theoretical mz509.201
Error12.22
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.988

Identifiers and class information

Inchi keyBOLVUKQTMQVTQI-WPQDXMDZNA-N
SmilesO=C(OC1CC(=C2C(=O)C=C(COC3OC(CO)C(O)C(O)C3O)C2C4OC(=O)C(C)C14)C)C(=C)C
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds

Plant source

  • Piper longum L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)2
    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)10
    Number of reactive functional groups (#rtvFG)3
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)508.521
    Computed dipole moment(dipole)9.469
    Total solvent accessible surface area (SASA)805.346
    Hydrophobic component of SASA (FOSA)432.565
    Hydrophilic component of SASA (FISA)299.762
    Pie component of the SASA (PISA)73.019
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1500.32
    Number of hydrogen bond donors (donorHB)4
    Number of hydrogen bond acceptors (accptHB)17.2
    Free energy of solvation of dipole (dip^2/V)0.0597572
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0427146
    Globularity descriptor (glob)0.786996
    Predicted polarizability in cubic angstroms (QPpolrz)48.165
    Predicted hexadecane/gas partition coefficient (QPlogPC16)15.781
    Predicted octanol/gas partition coefficient (QPlogPoct)32.282
    Predicted water/gas partition coefficient (QPlogPw)24.787
    Predicted octanol/water partition coefficient (QPlogPo/w)-0.587
    Predicted aqueous solubility (QPlogS)-3.508
    Conformation-independent predicted aqueous solubility (CIQPlogS)-2.977
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.327
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)14.232
    Predicted brain/blood partition coefficient (QPlogBB)-3.266
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)4.992
    Predicted skin permeability, log Kp (QPlogKp)-5.827
    PM3 calculated ionization potential (IP(ev))10.236
    PM3 calculated electron affinity (EA(eV))0.846
    Number of likely metabolic reactions (#metab)10
    Prediction of binding to human serum albumin (QPlogKhsa)-0.938
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)18.232
    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)195.541
    Number of nitrogen and oxygen atoms (#NandO)11
    Number of violations of Lipinski’s rule of five (RuleOfFive)2
    Number of violations of Jorgensen’s rule of three (RuleOfThree)2

    Compound-target network

    Cytoscape Graph

    Protein targets associated with phytocompound

    Uniprot ID Gene name Target name TTD_ID Prediction source
    P00533EGFREpidermal growth factor receptor erbB1T59328SwissTargetPrediction
    P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction
    P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
    Q8TDS4HCAR2Hydroxycarboxylic acid receptor 2T88185SwissTargetPrediction
    P00734F2ThrombinT94033SwissTargetPrediction
    P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
    P21917DRD4Dopamine D4 receptorT24983SwissTargetPrediction
    P06239LCKTyrosine-protein kinase LCKT12499SwissTargetPrediction
    P13866SLC5A1Sodium/glucose cotransporter 1T54771SwissTargetPrediction
    P08473MMENeprilysinT05409SwissTargetPrediction
    P17612PRKACAcAMP-dependent protein kinase alpha-catalytic subunitT12808SwissTargetPrediction
    P29275ADORA2BAdenosine A2b receptorT86679SwissTargetPrediction
    P53779MAPK10c-Jun N-terminal kinase 3T85421SwissTargetPrediction
    P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction
    P22894MMP8Matrix metalloproteinase 8T08856SwissTargetPrediction
    Q16539MAPK14MAP kinase p38 alphaT65864SwissTargetPrediction
    Q16831UPP1Uridine phosphorylase 1 (by homology)T97388SwissTargetPrediction
    P45452MMP13Matrix metalloproteinase 13T34296SwissTargetPrediction
    P42575CASP2Caspase-2T09128SwissTargetPrediction
    O14746TERTTelomerase reverse transcriptaseT86052SwissTargetPrediction
    P24723PRKCHProtein kinase C etaT40149SwissTargetPrediction
    Q02156PRKCEProtein kinase C epsilonT00895SwissTargetPrediction
    Q02750MAP2K1Dual specificity mitogen-activated protein kinase kinase 1T99057SwissTargetPrediction
    P53779MAPK10c-Jun N-terminal kinase 3T85421SwissTargetPrediction
    P15692VEGFAVascular endothelial growth factor AT20761SEA
    P05230FGF1Acidic fibroblast growth factorT18639SEA
    P09038FGF2Basic fibroblast growth factorT31621SEA
    P04062GBABeta-glucocerebrosidaseT84173SwissTargetPrediction
    P28482MAPK1MAP kinase ERK2T58970SwissTargetPrediction
    P05556ITGB1Integrin alpha2/beta1T01851SwissTargetPrediction
    P09619PDGFRBPlatelet-derived growth factor receptor betaT59102SwissTargetPrediction
    P11362FGFR1Fibroblast growth factor receptor 1T47101SwissTargetPrediction
    P55263ADKAdenosine kinaseT91661SwissTargetPrediction
    P11142HSPA8Heat shock cognate 71 kDa proteinT12817SwissTargetPrediction
    Q99808SLC29A1Equilibrative nucleoside transporter 1T13491SwissTargetPrediction
    P52789HK2Hexokinase type IIT96685SwissTargetPrediction
    P11021HSPA578 kDa glucose-regulated proteinT77594SwissTargetPrediction
    O43868SLC28A2Sodium/nucleoside cotransporter 2T94627SwissTargetPrediction
    P23415GLRA1Glycine receptor subunit alpha-1T50269SwissTargetPrediction
    P48167GLRBGlycine receptorT55285SwissTargetPrediction
    P31644GABRA5GABA receptor alpha-5 subunitT26368SwissTargetPrediction
    P31639SLC5A2Sodium/glucose cotransporter 2T30085SwissTargetPrediction
    Q15172PPP2R5ASerine/threonine protein phosphatase 2A, 56 kDa regulatory subunit, alpha isoformT57291SwissTargetPrediction
    P42574CASP3Caspase-3T57943SwissTargetPrediction
    P55210CASP7Caspase-7T72252SwissTargetPrediction
    P55212CASP6Caspase-6T20600SwissTargetPrediction
    Q9UQ81MCH5Caspase-8T15700SwissTargetPrediction
    P60568IL2Interleukin-2T61698SEA
    P08151GLI1Zinc finger protein GLI1T40890SwissTargetPrediction
    O14976GAKSerine or threonine-protein kinase GAKT00043SwissTargetPrediction
    P17931LGALS3Galectin-3T72038SwissTargetPrediction
    P04746AMY2APancreatic alpha-amylaseT86918SEA
    P26010ITGB7Integrin alpha-4/beta-7T07403SwissTargetPrediction
    Q9Y2T6GPR55G-protein coupled receptor 55T87670SwissTargetPrediction
    P48730CSNK1DCasein kinase I deltaT87109SwissTargetPrediction
    Q15759MAPK11MAP kinase p38 betaT55729SwissTargetPrediction
    P09382LGALS1Galectin-1T09544SwissTargetPrediction
    P54756EPHA5Ephrin type-A receptor 5T18474SwissTargetPrediction
    Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
    P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T59328DI0030Angina pectoris[ICD-11: BA40]P00533EGFR
    T59328DI0062Breast cancer[ICD-11: 2C60-2C6Y]P00533EGFR
    T59328DI0095Colorectal cancer[ICD-11: 2B91]P00533EGFR
    T59328DI0121Diabetic foot ulcer[ICD-11: BD54]P00533EGFR
    T59328DI0220Ischemia[ICD-11: 8B10-8B11]P00533EGFR
    T59328DI0238Lung cancer[ICD-11: 2C25]P00533EGFR
    T59328DI0303Non-small-cell lung cancer[ICD-11: 2C25]P00533EGFR
    T59328DI0361Renal cell carcinoma[ICD-11: 2C90]P00533EGFR
    T59328DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P00533EGFR
    T59328DI0420Unspecific body region injury[ICD-11: ND56]P00533EGFR
    T77365DI0319Orthostatic hypotension[ICD-11: BA21]P29274ADORA2A
    T77365DI0331Parkinsonism[ICD-11: 8A00]P29274ADORA2A
    T77365DI0359Radionuclide imaging[ICD-11: N.A.]P29274ADORA2A
    T92072DI0319Orthostatic hypotension[ICD-11: BA21]P30542ADORA1
    T88185DI0203Inborn lipid metabolism error[ICD-11: 5C52]Q8TDS4HCAR2
    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
    T36059DI0351Psoriasis[ICD-11: EA90]P0DMS8ADORA3
    T36059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMS8ADORA3
    T24983DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P21917DRD4
    T24983DI0370Schizophrenia[ICD-11: 6A20]P21917DRD4
    T12499DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P06239LCK
    T54771DI0120Diabetes mellitus[ICD-11: 5A10]P13866SLC5A1
    T54771DI0175Heart failure[ICD-11: BD10-BD1Z]P13866SLC5A1
    T54771DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P13866SLC5A1
    T05409DI0175Heart failure[ICD-11: BD10-BD1Z]P08473MME
    T12808DI0279Muscular atrophy[ICD-11: 8B61]P17612PRKACA
    T86679DI0180Herpes simplex infection[ICD-11: 1F00]P29275ADORA2B
    T86679DI0397Supraventricular tachyarrhythmia[ICD-11: BC81]P29275ADORA2B
    T85421DI0125Dissociative neurological symptom disorder[ICD-11: 6B60]P53779MAPK10
    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
    T08856DI0366Rheumatoid arthritis[ICD-11: FA20]P22894MMP8
    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
    T34296DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45452MMP13
    T86052DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]O14746TERT
    T86052DI0284Myelodysplastic syndrome[ICD-11: 2A37]O14746TERT
    T86052DI0326Pancreatic cancer[ICD-11: 2C10]O14746TERT
    T40149DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]P24723PRKCH
    T00895DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]Q02156PRKCE
    T00895DI0243Malaria[ICD-11: 1F40-1F45]Q02156PRKCE
    T99057DI0262Metastatic tumour[ICD-11: 2D50-2E2Z]Q02750MAP2K1
    T99057DI0336Phakomatoses/hamartoneoplastic syndrome[ICD-11: LD2D]Q02750MAP2K1
    T85421DI0125Dissociative neurological symptom disorder[ICD-11: 6B60]P53779MAPK10
    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
    T58970DI0036Arteries/arterioles disorder[ICD-11: BD52]P28482MAPK1
    T58970DI0252Melanoma[ICD-11: 2C30]P28482MAPK1
    T58970DI0326Pancreatic cancer[ICD-11: 2C10]P28482MAPK1
    T58970DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P28482MAPK1
    T01851DI0060Brain cancer[ICD-11: 2A00]P05556ITGB1
    T01851DI0238Lung cancer[ICD-11: 2C25]P05556ITGB1
    T01851DI0365Retinopathy[ICD-11: 9B71]P05556ITGB1
    T59102DI0009Acute diabete complication[ICD-11: 5A2Y]P09619PDGFRB
    T59102DI0361Renal cell carcinoma[ICD-11: 2C90]P09619PDGFRB
    T59102DI0403Thrombocytopenia[ICD-11: 3B64]P09619PDGFRB
    T47101DI0095Colorectal cancer[ICD-11: 2B91]P11362FGFR1
    T47101DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P11362FGFR1
    T47101DI0235Liver cancer[ICD-11: 2C12]P11362FGFR1
    T47101DI0403Thrombocytopenia[ICD-11: 3B64]P11362FGFR1
    T91661DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P55263ADK
    T13491DI0030Angina pectoris[ICD-11: BA40]Q99808SLC29A1
    T96685DI0133Epidermal dysplasias[ICD-11: EK90]P52789HK2
    T77594DI0252Melanoma[ICD-11: 2C30]P11021HSPA5
    T77594DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11021HSPA5
    T50269DI0411Tonus and reflex abnormality[ICD-11: MB47]P23415GLRA1
    T55285DI0411Tonus and reflex abnormality[ICD-11: MB47]P48167GLRB
    T26368DI0216Intentional self-harm[ICD-11: PC91]P31644GABRA5
    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
    T15700DI0120Diabetes mellitus[ICD-11: 5A10]Q9UQ81MCH5
    T15700DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9UQ81MCH5
    T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
    T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
    T00043DI0366Rheumatoid arthritis[ICD-11: FA20]O14976GAK
    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
    T07403DI0107Crohn disease[ICD-11: DD70]P26010ITGB7
    T87670DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]Q9Y2T6GPR55
    T87109DI0249Mature B-cell leukaemia[ICD-11: 2A82]P48730CSNK1D
    T87109DI0326Pancreatic cancer[ICD-11: 2C10]P48730CSNK1D
    T55729DI0025Alzheimer disease[ICD-11: 8A20]Q15759MAPK11
    T55729DI0366Rheumatoid arthritis[ICD-11: FA20]Q15759MAPK11
    T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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