(+)-12a-Hydroxyerythynone



Compound IDCDAMM00515
Common name(+)-12a-Hydroxyerythynone
IUPAC name14-hydroxy-10,17,18-trimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.03,12.04,9.015,20]docosa-3,5,9,11,15,17,19-heptaen-13-one
Molecular formulaC24H24O8

Experimental data

Retention time9.65
Adduct[M+H]+
Actual mz441.148
Theoretical mz441.154
Error14
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.2091

Identifiers and class information

Inchi keyVSSFKDAMVNYAEJ-UHFFFAOYNA-N
SmilesO=C1C2=CC(OC)=C3OC(C=CC3=C2OC4COC5=CC(OC)=C(OC)C=C5C14O)(C)C
SuperclassPhenylpropanoids and polyketides
ClassIsoflavonoids

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)4
    Number of reactive functional groups (#rtvFG)0
    Predicted central nervous system activity (CNS)0
    Molecular weight (mol_MW)440.449
    Computed dipole moment(dipole)1.924
    Total solvent accessible surface area (SASA)704.035
    Hydrophobic component of SASA (FOSA)497.172
    Hydrophilic component of SASA (FISA)65.051
    Pie component of the SASA (PISA)141.813
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1287.28
    Number of hydrogen bond donors (donorHB)1
    Number of hydrogen bond acceptors (accptHB)7.25
    Free energy of solvation of dipole (dip^2/V)0.0028753
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0102978
    Globularity descriptor (glob)0.812868
    Predicted polarizability in cubic angstroms (QPpolrz)44.149
    Predicted hexadecane/gas partition coefficient (QPlogPC16)11.876
    Predicted octanol/gas partition coefficient (QPlogPoct)19.554
    Predicted water/gas partition coefficient (QPlogPw)10.544
    Predicted octanol/water partition coefficient (QPlogPo/w)4.035
    Predicted aqueous solubility (QPlogS)-5.739
    Conformation-independent predicted aqueous solubility (CIQPlogS)-6.321
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.236
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)2393.44
    Predicted brain/blood partition coefficient (QPlogBB)-0.334
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)1270.66
    Predicted skin permeability, log Kp (QPlogKp)-1.835
    PM3 calculated ionization potential (IP(ev))8.669
    PM3 calculated electron affinity (EA(eV))0.703
    Number of likely metabolic reactions (#metab)4
    Prediction of binding to human serum albumin (QPlogKhsa)0.508
    Predicted qualitative human oral absorption (HumanOralAbsorption)3
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)100
    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)87.878
    Number of nitrogen and oxygen atoms (#NandO)8
    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
    P17612PRKACAcAMP-dependent protein kinase alpha-catalytic subunitT12808SwissTargetPrediction
    P50406HTR6Serotonin 6 (5-HT6) receptorT16691SwissTargetPrediction
    P11926ODC1Ornithine decarboxylaseT60366SwissTargetPrediction and SEA
    P24941CDK2Cyclin-dependent kinase 2T70176SwissTargetPrediction
    P78536ADAM17ADAM17T82393SwissTargetPrediction
    Q15078CDK5R1Cyclin-dependent kinase 5/CDK5 activator 1T09513SwissTargetPrediction
    P29466CASP1Caspase-1T98269SwissTargetPrediction
    P34998CRHR1Corticotropin releasing factor receptor 1 (by homology)T45262SwissTargetPrediction
    Q9UQ81MCH5Caspase-8T15700SwissTargetPrediction
    Q16584MAP3K11Mitogen-activated protein kinase kinase kinase 11T12126SwissTargetPrediction
    P80192MAP3K9Mitogen-activated protein kinase kinase kinase 9T19760SwissTargetPrediction
    P35557GCKHexokinase type IVT87166SwissTargetPrediction
    P14679TYRTyrosinaseT97035SEA
    Q9Y5X9LIPGEndothelial lipaseT19368SwissTargetPrediction
    O14672ADAM10ADAM10T31902SwissTargetPrediction
    Q02779MAP3K10Mitogen-activated protein kinase kinase kinase 10T89323SwissTargetPrediction
    P00740F9Coagulation factor IXT83369SwissTargetPrediction

    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
    T12808DI0279Muscular atrophy[ICD-11: 8B61]P17612PRKACA
    T16691DI0025Alzheimer disease[ICD-11: 8A20]P50406HTR6
    T16691DI0370Schizophrenia[ICD-11: 6A20]P50406HTR6
    T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
    T70176DI0060Brain cancer[ICD-11: 2A00]P24941CDK2
    T70176DI0062Breast cancer[ICD-11: 2C60-2C6Y]P24941CDK2
    T70176DI0238Lung cancer[ICD-11: 2C25]P24941CDK2
    T70176DI0241Lymphoma[ICD-11: 2A80-2A86]P24941CDK2
    T70176DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P24941CDK2
    T70176DI0303Non-small-cell lung cancer[ICD-11: 2C25]P24941CDK2
    T70176DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P24941CDK2
    T70176DI0406Thymoma[ICD-11: 2C27]P24941CDK2
    T82393DI0062Breast cancer[ICD-11: 2C60-2C6Y]P78536ADAM17
    T82393DI0366Rheumatoid arthritis[ICD-11: FA20]P78536ADAM17
    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
    T45262DI0394Staphylococcal/streptococcal disease[ICD-11: 1B5Y]P34998CRHR1
    T15700DI0120Diabetes mellitus[ICD-11: 5A10]Q9UQ81MCH5
    T15700DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9UQ81MCH5
    T19760DI0037Asthma[ICD-11: CA23]P80192MAP3K9
    T87166DI0009Acute diabete complication[ICD-11: 5A2Y]P35557GCK
    T87166DI0120Diabetes mellitus[ICD-11: 5A10]P35557GCK
    T87166DI0308Obesity[ICD-11: 5B80-5B81]P35557GCK
    T87166DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P35557GCK
    T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
    T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
    T19368DI0081Chronic arterial occlusive disease[ICD-11: BD4Z]Q9Y5X9LIPG
    T19368DI0091Coagulation defect[ICD-11: 3B10]Q9Y5X9LIPG
    T19368DI0102Coronary atherosclerosis[ICD-11: BA52]Q9Y5X9LIPG
    T31902DI0062Breast cancer[ICD-11: 2C60-2C6Y]O14672ADAM10
    T83369DI0052Bleeding disorder[ICD-11: GA20-GA21]P00740F9
    T83369DI0091Coagulation defect[ICD-11: 3B10]P00740F9

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