Orientaloside



Compound IDCDAMM00636
Common nameOrientaloside
IUPAC name1-[8-[3,5-dihydroxy-6-(hydroxymethyl)-4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-1-hydroxy-3-methylnaphthalen-2-yl]ethanone
Molecular formulaC25H32O13

Experimental data

Retention time0.35
Adduct[M+H]+
Actual mz541.188
Theoretical mz541.191
Error6.79
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.9066

Identifiers and class information

Inchi keyPFGAJVHSRWCMOQ-UHFFFAOYNA-N
SmilesO=C(C1=C(O)C=2C(OC3OC(CO)C(O)C(OC4OC(CO)C(O)C(O)C4O)C3O)=CC=CC2C=C1C)C
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds

Plant source

  • Piper longum L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)4
    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)15
    Number of reactive functional groups (#rtvFG)2
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)540.52
    Computed dipole moment(dipole)6.343
    Total solvent accessible surface area (SASA)728.93
    Hydrophobic component of SASA (FOSA)351.082
    Hydrophilic component of SASA (FISA)233.7
    Pie component of the SASA (PISA)144.148
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1446.63
    Number of hydrogen bond donors (donorHB)7
    Number of hydrogen bond acceptors (accptHB)19.5
    Free energy of solvation of dipole (dip^2/V)0.0278079
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0707779
    Globularity descriptor (glob)0.848628
    Predicted polarizability in cubic angstroms (QPpolrz)43.485
    Predicted hexadecane/gas partition coefficient (QPlogPC16)15.795
    Predicted octanol/gas partition coefficient (QPlogPoct)35.693
    Predicted water/gas partition coefficient (QPlogPw)30.194
    Predicted octanol/water partition coefficient (QPlogPo/w)-1.172
    Predicted aqueous solubility (QPlogS)-1.642
    Conformation-independent predicted aqueous solubility (CIQPlogS)-3.078
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.669
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)60.217
    Predicted brain/blood partition coefficient (QPlogBB)-2.504
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)23.734
    Predicted skin permeability, log Kp (QPlogKp)-3.879
    PM3 calculated ionization potential (IP(ev))8.348
    PM3 calculated electron affinity (EA(eV))0.773
    Number of likely metabolic reactions (#metab)9
    Prediction of binding to human serum albumin (QPlogKhsa)-1.259
    Predicted qualitative human oral absorption (HumanOralAbsorption)2
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)13.062
    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)208.164
    Number of nitrogen and oxygen atoms (#NandO)13
    Number of violations of Lipinski’s rule of five (RuleOfFive)3
    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
    P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
    O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction and SEA
    Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction and SEA
    P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
    P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
    P13866SLC5A1Sodium/glucose cotransporter 1T54771SwissTargetPrediction
    P34913EPHX2Epoxide hydrataseT35734SwissTargetPrediction
    Q9ULX7CA14Carbonic anhydrase XIVT31992SwissTargetPrediction and SEA
    P15121AKR1B1Aldose reductaseT26623SwissTargetPrediction
    P29275ADORA2BAdenosine A2b receptorT86679SwissTargetPrediction
    Q9BZP6CHIAAcidic mammalian chitinase (by homology)T51597SwissTargetPrediction and SEA
    P18405SRD5A1Steroid 5-alpha-reductase 1T70309SwissTargetPrediction
    P11511CYP19A1Cytochrome P450 19A1T13260SwissTargetPrediction
    P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction
    P22894MMP8Matrix metalloproteinase 8T08856SwissTargetPrediction
    P03372ESR1Estrogen receptor alphaT02506SwissTargetPrediction
    P03956MMP1Matrix metalloproteinase 1T52450SwissTargetPrediction
    P45452MMP13Matrix metalloproteinase 13T34296SwissTargetPrediction
    P09237MMP7Matrix metalloproteinase 7T73475SwissTargetPrediction
    P15692VEGFAVascular endothelial growth factor AT20761SEA
    P05230FGF1Acidic fibroblast growth factorT18639SEA
    P09038FGF2Basic fibroblast growth factorT31621SEA
    Q9Y251HPSEHeparanaseT47623SEA
    Q99808SLC29A1Equilibrative nucleoside transporter 1T13491SwissTargetPrediction
    Q9NY91SLC5A4Low affinity sodium-glucose cotransporterT22583SwissTargetPrediction
    P31639SLC5A2Sodium/glucose cotransporter 2T30085SwissTargetPrediction
    P01112HRASTransforming protein p21/H-Ras-1T71081SwissTargetPrediction and SEA
    P60568IL2Interleukin-2T61698SEA
    Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SEA
    P17931LGALS3Galectin-3T72038SEA
    P04746AMY2APancreatic alpha-amylaseT86918SEA
    P14679TYRTyrosinaseT97035SwissTargetPrediction and SEA
    P20916MAGMyelin-associated glycoprotein (by homology)T95286SEA
    P63316TNNC1Troponin, cardiac muscleT12966SEA
    P09382LGALS1Galectin-1T09544SEA
    Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
    P05231IL6Interleukin-6T32578SEA
    P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA
    P19429TNNI3Cardiac troponin IT20186SEA
    P45379TNNT2Cardiac muscle troponin TT05887SEA

    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
    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
    T13201DI0166Glaucoma[ICD-11: 9C61]P00915CA1
    T13201DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00915CA1
    T54771DI0120Diabetes mellitus[ICD-11: 5A10]P13866SLC5A1
    T54771DI0175Heart failure[ICD-11: BD10-BD1Z]P13866SLC5A1
    T54771DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P13866SLC5A1
    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
    T26623DI0298Neuropathy[ICD-11: 8C0Z]P15121AKR1B1
    T26623DI0366Rheumatoid arthritis[ICD-11: FA20]P15121AKR1B1
    T86679DI0180Herpes simplex infection[ICD-11: 1F00]P29275ADORA2B
    T86679DI0397Supraventricular tachyarrhythmia[ICD-11: BC81]P29275ADORA2B
    T70309DI0347Prostate disease[ICD-11: GA91]P18405SRD5A1
    T13260DI0062Breast cancer[ICD-11: 2C60-2C6Y]P11511CYP19A1
    T13260DI0108Cushing syndrome[ICD-11: 5A70]P11511CYP19A1
    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
    T02506DI0106COVID-19[ICD-11: 1D6Y]P03372ESR1
    T52450DI0238Lung cancer[ICD-11: 2C25]P03956MMP1
    T34296DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45452MMP13
    T73475DI0238Lung cancer[ICD-11: 2C25]P09237MMP7
    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
    T47623DI0020African trypanosomiasis[ICD-11: 1F51]Q9Y251HPSE
    T47623DI0310Ocular disease[ICD-11: N.A.]Q9Y251HPSE
    T13491DI0030Angina pectoris[ICD-11: BA40]Q99808SLC29A1
    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
    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
    T12966DI0006Acquired cutaneous blood vessel malformation[ICD-11: EF20]P63316TNNC1
    T12966DI0175Heart failure[ICD-11: BD10-BD1Z]P63316TNNC1
    T32578DI0028Anemia[ICD-11: 3A00-3A9Z]P05231IL6
    T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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