Capsicoside B2



Compound IDCDAMM00290
Common nameCapsicoside B2
IUPAC name2-[4,5-dihydroxy-2-(hydroxymethyl)-6-(5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl)oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Molecular formulaC39H64O13

Experimental data

Retention time49.51
Adduct[M+H]+
Actual mz741.446
Theoretical mz741.442
Error6.11
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.56

Identifiers and class information

Inchi keyGVRANLUZOJSBTA-ZDOZYXMHSA-N
SmilesCC1CCC2(C(C3C(O2)CC4C3(CCC5C4CCC6C5(CCC(C6)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)CO)O)O)O)O)O)C)C)C)OC1
SuperclassPhenylpropanoids and polyketides
Class2-arylbenzofuran flavonoids

Plant source

  • Tribulus terrestris L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)9
    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)13
    Number of reactive functional groups (#rtvFG)3
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)740.927
    Computed dipole moment(dipole)8.986
    Total solvent accessible surface area (SASA)1026.41
    Hydrophobic component of SASA (FOSA)787.783
    Hydrophilic component of SASA (FISA)238.626
    Pie component of the SASA (PISA)0
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)2103.1
    Number of hydrogen bond donors (donorHB)7
    Number of hydrogen bond acceptors (accptHB)20.2
    Free energy of solvation of dipole (dip^2/V)0.0383936
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0520691
    Globularity descriptor (glob)0.773425
    Predicted polarizability in cubic angstroms (QPpolrz)69.665
    Predicted hexadecane/gas partition coefficient (QPlogPC16)20.86
    Predicted octanol/gas partition coefficient (QPlogPoct)45.179
    Predicted water/gas partition coefficient (QPlogPw)31.094
    Predicted octanol/water partition coefficient (QPlogPo/w)1.737
    Predicted aqueous solubility (QPlogS)-5.368
    Conformation-independent predicted aqueous solubility (CIQPlogS)-5.846
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.198
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)54.077
    Predicted brain/blood partition coefficient (QPlogBB)-2.88
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)21.129
    Predicted skin permeability, log Kp (QPlogKp)-4.669
    PM3 calculated ionization potential (IP(ev))10.374
    PM3 calculated electron affinity (EA(eV))-1.772
    Number of likely metabolic reactions (#metab)7
    Prediction of binding to human serum albumin (QPlogKhsa)-0.267
    Predicted qualitative human oral absorption (HumanOralAbsorption)2
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)29.26
    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)186.549
    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
    Q05586GRIN1Glutamate NMDA receptor; GRIN1/GRIN2BT62276SEA
    P08185SERPINA6Corticosteroid binding globulinT88452SEA
    P11413G6PDGlucose-6-phosphate 1-dehydrogenaseT63484SEA
    P15692VEGFAVascular endothelial growth factor AT20761SwissTargetPrediction and SEA
    P05230FGF1Acidic fibroblast growth factorT18639SwissTargetPrediction and SEA
    P09038FGF2Basic fibroblast growth factorT31621SEA
    P60568IL2Interleukin-2T61698SEA
    P17931LGALS3Galectin-3T72038SEA
    P04746AMY2APancreatic alpha-amylaseT86918SEA
    P14679TYRTyrosinaseT97035SEA
    P60842EIF4A1Eukaryotic initiation factor 4A-IT86805SEA
    Q13224GRIN2BGlutamate [NMDA] receptor subunit epsilon 2T76414SEA
    O15399GRIN2DGlutamate [NMDA] receptor subunit epsilon 4T56588SEA
    Q14957GRIN2CGlutamate receptor ionotropic NMDA 2CT72595SEA
    O14764GABRDGABA(A) receptor deltaT27376SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T62276DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q05586GRIN1
    T62276DI0182HIV-infected patients with tuberculosis[ICD-11: 1B10-1B14]Q05586GRIN1
    T88452DI0037Asthma[ICD-11: CA23]P08185SERPINA6
    T88452DI0339Postoperative inflammation[ICD-11: 1A00-CA43]P08185SERPINA6
    T88452DI0362Respiratory system disease[ICD-11: CB40-CB7Z]P08185SERPINA6
    T63484DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P11413G6PD
    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
    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
    T86805DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P60842EIF4A1
    T76414DI0024Alpha-1-antitrypsin deficiency[ICD-11: 5C5A]Q13224GRIN2B
    T56588DI0296Neurodegenerative disorder[ICD-11: 8A20-8A23]O15399GRIN2D
    T72595DI0296Neurodegenerative disorder[ICD-11: 8A20-8A23]Q14957GRIN2C
    T27376DI0117Depression[ICD-11: 6A70-6A7Z]O14764GABRD
    T27376DI0214Insomnia[ICD-11: 7A00-7A0Z]O14764GABRD
    T27376DI0256Mental/behavioural/neurodevelopmental disorder[ICD-11: 6E20-6E8Z]O14764GABRD

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