Keioside



Compound IDCDAMM00285
Common nameKeioside
IUPAC name5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-2-yl]oxychromen-4-one
Molecular formulaC28H32O16

Experimental data

Retention time42.592
Adduct[M+H]+
Actual mz625.18
Theoretical mz625.176
Error6.38
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.18

Identifiers and class information

Inchi keyDROLRDZYPMOKLM-BIVLZKPYSA-N
SmilesCC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)OC)O)O)O)O)O)O
SuperclassLipids and lipid-like molecules
ClassPrenol lipids

Plant source

  • Tribulus terrestris L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)7
    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)624.551
    Computed dipole moment(dipole)11.291
    Total solvent accessible surface area (SASA)796.689
    Hydrophobic component of SASA (FOSA)284.247
    Hydrophilic component of SASA (FISA)328.593
    Pie component of the SASA (PISA)183.85
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1577.23
    Number of hydrogen bond donors (donorHB)8
    Number of hydrogen bond acceptors (accptHB)20.55
    Free energy of solvation of dipole (dip^2/V)0.0808264
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0729571
    Globularity descriptor (glob)0.822508
    Predicted polarizability in cubic angstroms (QPpolrz)49.091
    Predicted hexadecane/gas partition coefficient (QPlogPC16)18.168
    Predicted octanol/gas partition coefficient (QPlogPoct)40.884
    Predicted water/gas partition coefficient (QPlogPw)33.772
    Predicted octanol/water partition coefficient (QPlogPo/w)-1.645
    Predicted aqueous solubility (QPlogS)-2.192
    Conformation-independent predicted aqueous solubility (CIQPlogS)-4.47
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.281
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)7.583
    Predicted brain/blood partition coefficient (QPlogBB)-3.579
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)2.528
    Predicted skin permeability, log Kp (QPlogKp)-5.488
    PM3 calculated ionization potential (IP(ev))9.048
    PM3 calculated electron affinity (EA(eV))0.903
    Number of likely metabolic reactions (#metab)10
    Prediction of binding to human serum albumin (QPlogKhsa)-1.251
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)0
    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)253.495
    Number of nitrogen and oxygen atoms (#NandO)16
    Number of violations of Lipinski’s rule of five (RuleOfFive)3
    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
    P22303ACHEAcetylcholinesteraseT30082SwissTargetPrediction
    O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction and SEA
    P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
    P16083NQO2Quinone reductase 2T75498SwissTargetPrediction
    P43166CA7Carbonic anhydrase VIIT37541SwissTargetPrediction and SEA
    P22748CA4Carbonic anhydrase IVT53378SwissTargetPrediction and SEA
    P08913ADRA2AAlpha-2a adrenergic receptorT11448SwissTargetPrediction
    P15121AKR1B1Aldose reductaseT26623SwissTargetPrediction and SEA
    P35354PTGS2Cyclooxygenase-2T66665SwissTargetPrediction
    P09917ALOX5Arachidonate 5-lipoxygenaseT00140SEA
    Q9HC97GPR35G-protein coupled receptor 35T56143SEA
    P18825ADRA2CAdrenergic receptor alpha-2T01777SwissTargetPrediction
    P33527ABCC1Multidrug resistance-associated protein 1T11288SEA
    P08183ABCB1P-glycoprotein 1T25258SEA
    P60568IL2Interleukin-2T61698SEA
    Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SEA
    Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
    P04746AMY2APancreatic alpha-amylaseT86918SEA
    P14679TYRTyrosinaseT97035SEA
    P51812RPS6KA3Ribosomal protein S6 kinase alpha 3T03279SwissTargetPrediction
    Q9NPH5NOX4NADPH oxidase 4T29741SwissTargetPrediction and SEA
    Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SwissTargetPrediction and SEA
    P47989XDHXanthine dehydrogenaseT40954SEA
    Q16678CYP1B1Cytochrome P450 1B1T92521SEA
    Q04760GLO1Glyoxalase IT88285SEA
    Q9HC98NEK6Serine/threonine-protein kinase NEK6T78992SEA
    P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA
    Q13332PTPRSReceptor-type tyrosine-protein phosphatase ST10147SEA
    Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
    Q15717ELAVL1ELAV-like protein 1T78349SEA
    P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA
    Q9UK17KCND3Voltage-gated potassium channel Kv4.3T74500SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T30082DI0025Alzheimer disease[ICD-11: 8A20]P22303ACHE
    T30082DI0166Glaucoma[ICD-11: 9C61]P22303ACHE
    T30082DI0282Myasthenia gravis[ICD-11: 8C6Y]P22303ACHE
    T30082DI0313Oesophageal/gastroduodenal disorder[ICD-11: DD90]P22303ACHE
    T30082DI0332Pediculosis[ICD-11: 1G00]P22303ACHE
    T30082DI0421Unspecific substance harmful effect[ICD-11: NE6Z]P22303ACHE
    T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
    T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
    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
    T75498DI0214Insomnia[ICD-11: 7A00-7A0Z]P16083NQO2
    T53378DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P22748CA4
    T53378DI0166Glaucoma[ICD-11: 9C61]P22748CA4
    T53378DI0372Seborrhoeic dermatitis[ICD-11: EA81]P22748CA4
    T11448DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P08913ADRA2A
    T11448DI0317Opioid use disorder[ICD-11: 6C43]P08913ADRA2A
    T11448DI0396Substance abuse[ICD-11: 6C40]P08913ADRA2A
    T26623DI0298Neuropathy[ICD-11: 8C0Z]P15121AKR1B1
    T26623DI0366Rheumatoid arthritis[ICD-11: FA20]P15121AKR1B1
    T66665DI0087Chronic pain[ICD-11: MG30]P35354PTGS2
    T66665DI0145Female pelvic pain[ICD-11: GA34]P35354PTGS2
    T66665DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]P35354PTGS2
    T66665DI0207Indeterminate colitis[ICD-11: DD72]P35354PTGS2
    T66665DI0227Knee osteoarthritis[ICD-11: FA01]P35354PTGS2
    T66665DI0320Osteoarthritis[ICD-11: FA00-FA05]P35354PTGS2
    T66665DI0324Pain[ICD-11: MG30-MG3Z]P35354PTGS2
    T66665DI0366Rheumatoid arthritis[ICD-11: FA20]P35354PTGS2
    T66665DI0416Tuberculosis[ICD-11: 1B10-1B12]P35354PTGS2
    T00140DI0037Asthma[ICD-11: CA23]P09917ALOX5
    T00140DI0147Filariasis[ICD-11: 1F66]P09917ALOX5
    T00140DI0403Thrombocytopenia[ICD-11: 3B64]P09917ALOX5
    T01777DI0166Glaucoma[ICD-11: 9C61]P18825ADRA2C
    T01777DI0190Hypertension[ICD-11: BA00-BA04]P18825ADRA2C
    T01777DI0196Hypotension[ICD-11: BA20-BA21]P18825ADRA2C
    T01777DI0308Obesity[ICD-11: 5B80-5B81]P18825ADRA2C
    T01777DI0310Ocular disease[ICD-11: N.A.]P18825ADRA2C
    T01777DI0396Substance abuse[ICD-11: 6C40]P18825ADRA2C
    T11288DI0167Gout[ICD-11: FA25]P33527ABCC1
    T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
    T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
    T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
    T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
    T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
    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
    T03279DI0249Mature B-cell leukaemia[ICD-11: 2A82]P51812RPS6KA3
    T29741DI0146Fibrosis[ICD-11: GA14-GC01]Q9NPH5NOX4
    T40954DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]P47989XDH
    T40954DI0266Mineral deficiency[ICD-11: 5B5K]P47989XDH
    T88285DI0210Influenza[ICD-11: 1E30-1E32]Q04760GLO1
    T70518DI0037Asthma[ICD-11: CA23]P16152CBR1
    T10147DI0057Bone paget disease[ICD-11: FB85]Q13332PTPRS
    T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1
    T74500DI0004Acidosis[ICD-11: 5C73]Q9UK17KCND3

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