Cyclocalopin D



Compound IDCDAMM00623
Common nameCyclocalopin D
IUPAC name[14-hydroxy-3,9-dimethyl-6-oxo-13-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,8,10-trioxatetracyclo[9.3.1.01,9.02,7]pentadec-12-en-12-yl]methyl acetate
Molecular formulaC23H32O13

Experimental data

Retention time13.46
Adduct[M+H]+
Actual mz517.187
Theoretical mz517.191
Error9.04
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.9618

Identifiers and class information

Inchi keyPDSOUSYYTLHECG-UHFFFAOYNA-N
SmilesO=C(OCC1=C(OC2OC(CO)C(O)C(O)C2O)C(O)C34CC1OC4(OC5C(=O)OCC(C)C53)C)C
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds

Plant source

  • Piper longum L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)1
    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)516.498
    Computed dipole moment(dipole)7.502
    Total solvent accessible surface area (SASA)686.43
    Hydrophobic component of SASA (FOSA)404.661
    Hydrophilic component of SASA (FISA)281.455
    Pie component of the SASA (PISA)0.314
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1353.4
    Number of hydrogen bond donors (donorHB)5
    Number of hydrogen bond acceptors (accptHB)17.45
    Free energy of solvation of dipole (dip^2/V)0.0415855
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.056844
    Globularity descriptor (glob)0.862025
    Predicted polarizability in cubic angstroms (QPpolrz)41.591
    Predicted hexadecane/gas partition coefficient (QPlogPC16)13.852
    Predicted octanol/gas partition coefficient (QPlogPoct)31.385
    Predicted water/gas partition coefficient (QPlogPw)25.593
    Predicted octanol/water partition coefficient (QPlogPo/w)-1.299
    Predicted aqueous solubility (QPlogS)-2.134
    Conformation-independent predicted aqueous solubility (CIQPlogS)-3.123
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-3.766
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)21.226
    Predicted brain/blood partition coefficient (QPlogBB)-2.564
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)7.689
    Predicted skin permeability, log Kp (QPlogKp)-5.746
    PM3 calculated ionization potential (IP(ev))10.244
    PM3 calculated electron affinity (EA(eV))0.224
    Number of likely metabolic reactions (#metab)8
    Prediction of binding to human serum albumin (QPlogKhsa)-1.004
    Predicted qualitative human oral absorption (HumanOralAbsorption)2
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)17.171
    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)208.224
    Number of nitrogen and oxygen atoms (#NandO)13
    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
    O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction
    Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction
    P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
    P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
    P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
    P06239LCKTyrosine-protein kinase LCKT12499SwissTargetPrediction
    P11940PABPC1Polyadenylate-binding protein 1T58679SwissTargetPrediction
    P13866SLC5A1Sodium/glucose cotransporter 1T54771SwissTargetPrediction
    P08473MMENeprilysinT05409SwissTargetPrediction
    Q9ULX7CA14Carbonic anhydrase XIVT31992SwissTargetPrediction
    P29275ADORA2BAdenosine A2b receptorT86679SwissTargetPrediction
    P08253MMP2Matrix metalloproteinase 2T68251SwissTargetPrediction
    P22894MMP8Matrix metalloproteinase 8T08856SwissTargetPrediction
    P03956MMP1Matrix metalloproteinase 1T52450SwissTargetPrediction
    P00519ABL1Tyrosine-protein kinase ABLT63505SwissTargetPrediction
    O14965AURKASerine/threonine-protein kinase Aurora-AT87675SwissTargetPrediction
    P45452MMP13Matrix metalloproteinase 13T34296SwissTargetPrediction
    P09237MMP7Matrix metalloproteinase 7T73475SwissTargetPrediction
    P11387TOP1DNA topoisomerase IT09826SwissTargetPrediction
    P12931SRCTyrosine-protein kinase SRCT85943SwissTargetPrediction
    P11362FGFR1Fibroblast growth factor receptor 1T47101SwissTargetPrediction
    P55263ADKAdenosine kinaseT91661SwissTargetPrediction
    O60502OGABifunctional protein NCOATT19567SwissTargetPrediction
    Q99808SLC29A1Equilibrative nucleoside transporter 1T13491SwissTargetPrediction
    P52789HK2Hexokinase type IIT96685SwissTargetPrediction
    P39900MMP12Matrix metalloproteinase 12T03500SwissTargetPrediction
    Q9NY91SLC5A4Low affinity sodium-glucose cotransporterT22583SwissTargetPrediction
    P31639SLC5A2Sodium/glucose cotransporter 2T30085SwissTargetPrediction
    P60568IL2Interleukin-2T61698SEA
    P20839IMPDH1Inosine-5'-monophosphate dehydrogenase 1T40111SwissTargetPrediction
    Q06187BTKTyrosine-protein kinase BTKT97719SwissTargetPrediction
    P80192MAP3K9Mitogen-activated protein kinase kinase kinase 9T19760SwissTargetPrediction
    P17931LGALS3Galectin-3T72038SwissTargetPrediction
    P29317EPHA2Ephrin type-A receptor 2T57278SwissTargetPrediction
    P20916MAGMyelin-associated glycoprotein (by homology)T95286SEA
    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
    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
    T13201DI0166Glaucoma[ICD-11: 9C61]P00915CA1
    T13201DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00915CA1
    T20401DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P00918CA2
    T20401DI0137Essential hypertension[ICD-11: BA00]P00918CA2
    T20401DI0166Glaucoma[ICD-11: 9C61]P00918CA2
    T20401DI0175Heart failure[ICD-11: BD10-BD1Z]P00918CA2
    T20401DI0214Insomnia[ICD-11: 7A00-7A0Z]P00918CA2
    T20401DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00918CA2
    T12499DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P06239LCK
    T58679DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11940PABPC1
    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
    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
    T63505DI0062Breast cancer[ICD-11: 2C60-2C6Y]P00519ABL1
    T63505DI0220Ischemia[ICD-11: 8B10-8B11]P00519ABL1
    T63505DI0250Mature B-cell lymphoma[ICD-11: 2A85]P00519ABL1
    T63505DI0306Nutritional deficiency[ICD-11: 5B50-5B71]P00519ABL1
    T87675DI0009Acute diabete complication[ICD-11: 5A2Y]O14965AURKA
    T87675DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O14965AURKA
    T34296DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45452MMP13
    T73475DI0238Lung cancer[ICD-11: 2C25]P09237MMP7
    T09826DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P11387TOP1
    T09826DI0095Colorectal cancer[ICD-11: 2B91]P11387TOP1
    T09826DI0238Lung cancer[ICD-11: 2C25]P11387TOP1
    T09826DI0321Ovarian cancer[ICD-11: 2C73]P11387TOP1
    T09826DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11387TOP1
    T85943DI0062Breast cancer[ICD-11: 2C60-2C6Y]P12931SRC
    T85943DI0220Ischemia[ICD-11: 8B10-8B11]P12931SRC
    T85943DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P12931SRC
    T85943DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P12931SRC
    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
    T19567DI0025Alzheimer disease[ICD-11: 8A20]O60502OGA
    T19567DI0331Parkinsonism[ICD-11: 8A00]O60502OGA
    T13491DI0030Angina pectoris[ICD-11: BA40]Q99808SLC29A1
    T96685DI0133Epidermal dysplasias[ICD-11: EK90]P52789HK2
    T03500DI0037Asthma[ICD-11: CA23]P39900MMP12
    T03500DI0238Lung cancer[ICD-11: 2C25]P39900MMP12
    T03500DI0361Renal cell carcinoma[ICD-11: 2C90]P39900MMP12
    T22583DI0009Acute diabete complication[ICD-11: 5A2Y]Q9NY91SLC5A4
    T22583DI0417Type 2 diabetes mellitus[ICD-11: 5A11]Q9NY91SLC5A4
    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
    T40111DI0062Breast cancer[ICD-11: 2C60-2C6Y]P20839IMPDH1
    T40111DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]P20839IMPDH1
    T40111DI0250Mature B-cell lymphoma[ICD-11: 2A85]P20839IMPDH1
    T40111DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P20839IMPDH1
    T40111DI0413Transplant rejection[ICD-11: NE84]P20839IMPDH1
    T97719DI0231Leukaemia[ICD-11: 2A60-2B33]Q06187BTK
    T19760DI0037Asthma[ICD-11: CA23]P80192MAP3K9
    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
    T57278DI0060Brain cancer[ICD-11: 2A00]P29317EPHA2
    T57278DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P29317EPHA2
    T95286DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P20916MAG
    T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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