Ipolamiidoside



Compound IDCDAMM00517
Common nameIpolamiidoside
IUPAC namemethyl 7-acetyloxy-4a-hydroxy-7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
Molecular formulaC19H28O12

Experimental data

Retention time13.46
Adduct[M+H]+
Actual mz449.165
Theoretical mz449.165
Error0.61
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.1939

Identifiers and class information

Inchi keyNYOFAHGLZQTUOP-OBSQLXRFNA-N
SmilesO=C(OC)C1=COC(OC2OC(CO)C(O)C(O)C2O)C3C1(O)CCC3(OC(=O)C)C
SuperclassLipids and lipid-like molecules
ClassPrenol lipids

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)10
    Number of reactive functional groups (#rtvFG)4
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)448.423
    Computed dipole moment(dipole)5.902
    Total solvent accessible surface area (SASA)648.453
    Hydrophobic component of SASA (FOSA)380.043
    Hydrophilic component of SASA (FISA)233.153
    Pie component of the SASA (PISA)35.257
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1226.61
    Number of hydrogen bond donors (donorHB)4
    Number of hydrogen bond acceptors (accptHB)15.65
    Free energy of solvation of dipole (dip^2/V)0.0284026
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0482687
    Globularity descriptor (glob)0.854588
    Predicted polarizability in cubic angstroms (QPpolrz)36.85
    Predicted hexadecane/gas partition coefficient (QPlogPC16)12.417
    Predicted octanol/gas partition coefficient (QPlogPoct)26.851
    Predicted water/gas partition coefficient (QPlogPw)22.173
    Predicted octanol/water partition coefficient (QPlogPo/w)-0.955
    Predicted aqueous solubility (QPlogS)-1.902
    Conformation-independent predicted aqueous solubility (CIQPlogS)-2.412
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.053
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)60.941
    Predicted brain/blood partition coefficient (QPlogBB)-2.168
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)24.043
    Predicted skin permeability, log Kp (QPlogKp)-4.732
    PM3 calculated ionization potential (IP(ev))10.137
    PM3 calculated electron affinity (EA(eV))0.247
    Number of likely metabolic reactions (#metab)5
    Prediction of binding to human serum albumin (QPlogKhsa)-1.077
    Predicted qualitative human oral absorption (HumanOralAbsorption)2
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)40.343
    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)188.044
    Number of nitrogen and oxygen atoms (#NandO)12
    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
    P00533EGFREpidermal growth factor receptor erbB1T59328SwissTargetPrediction
    P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction
    P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
    O43570CA12Carbonic anhydrase XIIT16987SEA
    Q16790CA9Carbonic anhydrase IXT64567SEA
    P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
    P13866SLC5A1Sodium/glucose cotransporter 1T54771SwissTargetPrediction
    P08473MMENeprilysinT05409SwissTargetPrediction
    P34913EPHX2Epoxide hydrataseT35734SwissTargetPrediction
    Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
    P29275ADORA2BAdenosine A2b receptorT86679SwissTargetPrediction
    Q9BZP6CHIAAcidic mammalian chitinase (by homology)T51597SEA
    P08253MMP2Matrix metalloproteinase 2T68251SwissTargetPrediction
    P22894MMP8Matrix metalloproteinase 8T08856SwissTargetPrediction
    P03956MMP1Matrix metalloproteinase 1T52450SwissTargetPrediction
    P45452MMP13Matrix metalloproteinase 13T34296SwissTargetPrediction
    P09237MMP7Matrix metalloproteinase 7T73475SwissTargetPrediction
    P07900HSP90AA1Heat shock protein HSP 90-alphaT18477SwissTargetPrediction
    P15692VEGFAVascular endothelial growth factor AT20761SEA
    P05230FGF1Acidic fibroblast growth factorT18639SEA
    P09038FGF2Basic fibroblast growth factorT31621SEA
    P42892ECE1Endothelin-converting enzyme 1T50970SwissTargetPrediction
    P55263ADKAdenosine kinaseT91661SwissTargetPrediction
    O60502OGABifunctional protein NCOATT19567SwissTargetPrediction
    Q99808SLC29A1Equilibrative nucleoside transporter 1T13491SwissTargetPrediction
    P25101EDNRAEndothelin receptor ET-AT23499SwissTargetPrediction
    P39900MMP12Matrix metalloproteinase 12T03500SwissTargetPrediction
    P31639SLC5A2Sodium/glucose cotransporter 2T30085SwissTargetPrediction
    P60568IL2Interleukin-2T61698SEA
    P17931LGALS3Galectin-3T72038SwissTargetPrediction and SEA
    P04746AMY2APancreatic alpha-amylaseT86918SEA
    P14679TYRTyrosinaseT97035SwissTargetPrediction and SEA
    P20916MAGMyelin-associated glycoprotein (by homology)T95286SwissTargetPrediction and SEA
    P17707AMD1S-adenosylmethionine decarboxylase 1T55922SwissTargetPrediction
    Q07108CD69Early activation antigen CD69T48780SEA
    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
    T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
    T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
    T64567DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16790CA9
    T36059DI0351Psoriasis[ICD-11: EA90]P0DMS8ADORA3
    T36059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMS8ADORA3
    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
    T35734DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P34913EPHX2
    T35734DI0190Hypertension[ICD-11: BA00-BA04]P34913EPHX2
    T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
    T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
    T86679DI0180Herpes simplex infection[ICD-11: 1F00]P29275ADORA2B
    T86679DI0397Supraventricular tachyarrhythmia[ICD-11: BC81]P29275ADORA2B
    T68251DI0238Lung cancer[ICD-11: 2C25]P08253MMP2
    T08856DI0366Rheumatoid arthritis[ICD-11: FA20]P22894MMP8
    T52450DI0238Lung cancer[ICD-11: 2C25]P03956MMP1
    T34296DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45452MMP13
    T73475DI0238Lung cancer[ICD-11: 2C25]P09237MMP7
    T18477DI0015Acute upper respiratory infection[ICD-11: CA07]P07900HSP90AA1
    T18477DI0037Asthma[ICD-11: CA23]P07900HSP90AA1
    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
    T91661DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P55263ADK
    T19567DI0025Alzheimer disease[ICD-11: 8A20]O60502OGA
    T19567DI0331Parkinsonism[ICD-11: 8A00]O60502OGA
    T13491DI0030Angina pectoris[ICD-11: BA40]Q99808SLC29A1
    T23499DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P25101EDNRA
    T23499DI0356Pulmonary hypertension[ICD-11: BB01]P25101EDNRA
    T23499DI0425Urinary system clinical symptom[ICD-11: MF8Y]P25101EDNRA
    T03500DI0037Asthma[ICD-11: CA23]P39900MMP12
    T03500DI0238Lung cancer[ICD-11: 2C25]P39900MMP12
    T03500DI0361Renal cell carcinoma[ICD-11: 2C90]P39900MMP12
    T30085DI0120Diabetes mellitus[ICD-11: 5A10]P31639SLC5A2
    T30085DI0175Heart failure[ICD-11: BD10-BD1Z]P31639SLC5A2
    T30085DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P31639SLC5A2
    T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
    T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
    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
    T95286DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P20916MAG
    T55922DI0004Acidosis[ICD-11: 5C73]P17707AMD1
    T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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