Upunaphenol B



Compound IDCDAMM00292
Common nameUpunaphenol B
IUPAC name(9R)-6,12-dihydroxy-8,16-bis(4-hydroxyphenyl)-9-[(1R,8R,9S,16R)-4,6,12-trihydroxy-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.02,7.014,17]heptadeca-2(7),3,5,10(17),11,13-hexaen-9-yl]-15-oxatetracyclo[8.6.1.02,7.014,17]heptadeca-1(16),2,5,7,10(17),11,13-heptaen-4-one
Molecular formulaC56H38O12

Experimental data

Retention time47.803
Adduct[M+H]+
Actual mz903.239
Theoretical mz903.244
Error5.2
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.38

Identifiers and class information

Inchi keyMTGKBWDCQOMOEN-GPKHFHQZSA-N
SmilesC1=CC(=CC=C1C2C(C3=C4C(C(OC4=CC(=C3)O)C5=CC=C(C=C5)O)C6=C2C(=CC(=C6)O)O)C7C8=C9C(=CC(=C8)O)OC(=C9C1=CC(=O)C=C(C1=C7C1=CC=C(C=C1)O)O)C1=CC=C(C=C1)O)O
SuperclassAlkaloids and derivatives
ClassVobasan alkaloids

Plant source

  • Tribulus terrestris L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)14
    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)9
    Number of reactive functional groups (#rtvFG)0
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)902.909
    Computed dipole moment(dipole)6.943
    Total solvent accessible surface area (SASA)1077.53
    Hydrophobic component of SASA (FOSA)6.68
    Hydrophilic component of SASA (FISA)436.595
    Pie component of the SASA (PISA)634.254
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)2312.9
    Number of hydrogen bond donors (donorHB)9
    Number of hydrogen bond acceptors (accptHB)10
    Free energy of solvation of dipole (dip^2/V)0.0208399
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0278415
    Globularity descriptor (glob)0.784947
    Predicted polarizability in cubic angstroms (QPpolrz)86.686
    Predicted hexadecane/gas partition coefficient (QPlogPC16)28.712
    Predicted octanol/gas partition coefficient (QPlogPoct)50.644
    Predicted water/gas partition coefficient (QPlogPw)30.643
    Predicted octanol/water partition coefficient (QPlogPo/w)5.771
    Predicted aqueous solubility (QPlogS)-9.104
    Conformation-independent predicted aqueous solubility (CIQPlogS)-15.482
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-8.037
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)0.717
    Predicted brain/blood partition coefficient (QPlogBB)-4.703
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0.198
    Predicted skin permeability, log Kp (QPlogKp)-6.468
    PM3 calculated ionization potential (IP(ev))8.337
    PM3 calculated electron affinity (EA(eV))1.122
    Number of likely metabolic reactions (#metab)18
    Prediction of binding to human serum albumin (QPlogKhsa)1.819
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)6.321
    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)242.956
    Number of nitrogen and oxygen atoms (#NandO)12
    Number of violations of Lipinski’s rule of five (RuleOfFive)4
    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
    P20151KLK2Kallikrein 2T01908SEA
    P15692VEGFAVascular endothelial growth factor AT20761SEA
    P49763PGFPlacenta growth factorT70792SEA
    P47989XDHXanthine dehydrogenaseT40954SEA
    Q16678CYP1B1Cytochrome P450 1B1T92521SEA
    P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA
    Q9UK17KCND3Voltage-gated potassium channel Kv4.3T74500SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T01908DI0213Innate/adaptive immunodeficiency[ICD-11: 4A00]P20151KLK2
    T20761DI0095Colorectal cancer[ICD-11: 2B91]P15692VEGFA
    T20761DI0365Retinopathy[ICD-11: 9B71]P15692VEGFA
    T20761DI0430Vascular system developmental anomaly[ICD-11: LA90]P15692VEGFA
    T70792DI0095Colorectal cancer[ICD-11: 2B91]P49763PGF
    T40954DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]P47989XDH
    T40954DI0266Mineral deficiency[ICD-11: 5B5K]P47989XDH
    T70518DI0037Asthma[ICD-11: CA23]P16152CBR1
    T74500DI0004Acidosis[ICD-11: 5C73]Q9UK17KCND3

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