3'',6''-Di-O-p-coumaroyltrifolin



Compound IDCDAMM00289
Common name3'',6''-Di-O-p-coumaroyltrifolin
IUPAC name[6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-3,5-dihydroxy-4-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Molecular formulaC39H32O15

Experimental data

Retention time56.288
Adduct[M+H]+
Actual mz741.184
Theoretical mz741.181
Error3.78
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.93

Identifiers and class information

Inchi keyMJXRITGQSVKANC-RUGSHEQUSA-N
SmilesC1=CC(=CC=C1C=CC(=O)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)O)O)OC(=O)C=CC6=CC=C(C=C6)O)O)O
SuperclassLipids and lipid-like molecules
ClassPrenol lipids

Plant source

  • Tribulus terrestris L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)10
    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)18
    Number of reactive functional groups (#rtvFG)3
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)740.673
    Computed dipole moment(dipole)11.744
    Total solvent accessible surface area (SASA)1033.59
    Hydrophobic component of SASA (FOSA)129.059
    Hydrophilic component of SASA (FISA)394.923
    Pie component of the SASA (PISA)509.607
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1999.55
    Number of hydrogen bond donors (donorHB)6
    Number of hydrogen bond acceptors (accptHB)15.1
    Free energy of solvation of dipole (dip^2/V)0.0689711
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0357853
    Globularity descriptor (glob)0.742629
    Predicted polarizability in cubic angstroms (QPpolrz)67.177
    Predicted hexadecane/gas partition coefficient (QPlogPC16)24.892
    Predicted octanol/gas partition coefficient (QPlogPoct)41.696
    Predicted water/gas partition coefficient (QPlogPw)28.05
    Predicted octanol/water partition coefficient (QPlogPo/w)2.638
    Predicted aqueous solubility (QPlogS)-6.134
    Conformation-independent predicted aqueous solubility (CIQPlogS)-9.501
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-8.127
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)1.782
    Predicted brain/blood partition coefficient (QPlogBB)-5.295
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0.528
    Predicted skin permeability, log Kp (QPlogKp)-5.275
    PM3 calculated ionization potential (IP(ev))8.975
    PM3 calculated electron affinity (EA(eV))0.897
    Number of likely metabolic reactions (#metab)7
    Prediction of binding to human serum albumin (QPlogKhsa)0.062
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)8.005
    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)260.291
    Number of nitrogen and oxygen atoms (#NandO)15
    Number of violations of Lipinski’s rule of five (RuleOfFive)3
    Number of violations of Jorgensen’s rule of three (RuleOfThree)3

    Compound-target network

    Cytoscape Graph

    Protein targets associated with phytocompound

    Uniprot ID Gene name Target name TTD_ID Prediction source
    O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction and SEA
    P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
    P43166CA7Carbonic anhydrase VIIT37541SwissTargetPrediction and SEA
    P23280CA6Carbonic anhydrase VIT06569SEA
    Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
    P22748CA4Carbonic anhydrase IVT53378SwissTargetPrediction and SEA
    P15121AKR1B1Aldose reductaseT26623SwissTargetPrediction and SEA
    P33527ABCC1Multidrug resistance-associated protein 1T11288SEA
    P60568IL2Interleukin-2T61698SEA
    Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
    Q9NPH5NOX4NADPH oxidase 4T29741SEA
    Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SEA
    P47989XDHXanthine dehydrogenaseT40954SEA
    Q16678CYP1B1Cytochrome P450 1B1T92521SEA
    Q04760GLO1Glyoxalase IT88285SEA
    Q9HC98NEK6Serine/threonine-protein kinase NEK6T78992SEA
    P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA
    Q13332PTPRSReceptor-type tyrosine-protein phosphatase ST10147SEA
    O43826SLC37A4Glucose-6-phosphate translocaseT47306SEA
    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
    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
    T06569DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P23280CA6
    T06569DI0372Seborrhoeic dermatitis[ICD-11: EA81]P23280CA6
    T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
    T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
    T53378DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P22748CA4
    T53378DI0166Glaucoma[ICD-11: 9C61]P22748CA4
    T53378DI0372Seborrhoeic dermatitis[ICD-11: EA81]P22748CA4
    T26623DI0298Neuropathy[ICD-11: 8C0Z]P15121AKR1B1
    T26623DI0366Rheumatoid arthritis[ICD-11: FA20]P15121AKR1B1
    T11288DI0167Gout[ICD-11: FA25]P33527ABCC1
    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
    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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