Baicalin



Compound IDCDAMM00341
Common nameBaicalin
IUPAC name(2S,3S,4S,5R,6S)-6-(5,6-dihydroxy-4-oxo-2-phenylchromen-7-yl)oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
Molecular formulaC21H18O11

Experimental data

Retention time46.449
Adduct[M+H]+
Actual mz447.093
Theoretical mz447.092
Error2.48
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score8.31

Identifiers and class information

Inchi keyIKIIZLYTISPENI-VAUQHIPYNA-N
SmilesO=C(O)C1OC(OC=2C=C3OC(=CC(=O)C3=C(O)C2O)C=4C=CC=CC4)C(O)C(O)C1O
SuperclassPhenylpropanoids and polyketides
ClassFlavonoids

Plant source

  • Pedalium murex L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)3
    Number of non-conjugated amine groups (#amine)0
    Number of amidine and guanidine groups (#amidine)0
    Number of carboxylic acid groups (#acid)1
    Number of non-conjugated amide groups (#amide)0
    Number of rotatable bonds (#rotor)8
    Number of reactive functional groups (#rtvFG)1
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)446.367
    Computed dipole moment(dipole)6.914
    Total solvent accessible surface area (SASA)691.815
    Hydrophobic component of SASA (FOSA)65.71
    Hydrophilic component of SASA (FISA)355.332
    Pie component of the SASA (PISA)270.774
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1235.79
    Number of hydrogen bond donors (donorHB)4
    Number of hydrogen bond acceptors (accptHB)11.55
    Free energy of solvation of dipole (dip^2/V)0.0386854
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0333904
    Globularity descriptor (glob)0.805017
    Predicted polarizability in cubic angstroms (QPpolrz)40.751
    Predicted hexadecane/gas partition coefficient (QPlogPC16)15.045
    Predicted octanol/gas partition coefficient (QPlogPoct)27.004
    Predicted water/gas partition coefficient (QPlogPw)21.113
    Predicted octanol/water partition coefficient (QPlogPo/w)0.388
    Predicted aqueous solubility (QPlogS)-3.708
    Conformation-independent predicted aqueous solubility (CIQPlogS)-4.635
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.171
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)1.071
    Predicted brain/blood partition coefficient (QPlogBB)-3.574
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0.388
    Predicted skin permeability, log Kp (QPlogKp)-6.346
    PM3 calculated ionization potential (IP(ev))8.982
    PM3 calculated electron affinity (EA(eV))0.811
    Number of likely metabolic reactions (#metab)6
    Prediction of binding to human serum albumin (QPlogKhsa)-0.676
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)3.833
    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)203.772
    Number of nitrogen and oxygen atoms (#NandO)11
    Number of violations of Lipinski’s rule of five (RuleOfFive)2
    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
    P00533EGFREpidermal growth factor receptor erbB1T59328SwissTargetPrediction
    P22303ACHEAcetylcholinesteraseT30082SwissTargetPrediction
    P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
    Q99720SIGMAR1Sigma opioid receptorT46360SEA
    P16083NQO2Quinone reductase 2T75498SwissTargetPrediction
    P43166CA7Carbonic anhydrase VIIT37541SEA
    P22748CA4Carbonic anhydrase IVT53378SEA
    P08913ADRA2AAlpha-2a adrenergic receptorT11448SwissTargetPrediction
    P15121AKR1B1Aldose reductaseT26623SwissTargetPrediction and SEA
    P35354PTGS2Cyclooxygenase-2T66665SwissTargetPrediction
    Q6B0I6KDM4DLysine-specific demethylase 4DT17036SEA
    P11926ODC1Ornithine decarboxylaseT60366SEA
    P18825ADRA2CAdrenergic receptor alpha-2T01777SwissTargetPrediction
    P33527ABCC1Multidrug resistance-associated protein 1T11288SEA
    P08183ABCB1P-glycoprotein 1T25258SEA
    O95271TNKSTankyrase-1T83059SEA
    P01375TNFTNF-alphaT20178SwissTargetPrediction
    P15692VEGFAVascular endothelial growth factor AT20761SEA
    P60568IL2Interleukin-2T61698SwissTargetPrediction and SEA
    P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SwissTargetPrediction
    P49763PGFPlacenta growth factorT70792SEA
    Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
    P51812RPS6KA3Ribosomal protein S6 kinase alpha 3T03279SwissTargetPrediction
    Q9NPH5NOX4NADPH oxidase 4T29741SwissTargetPrediction and SEA
    Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SwissTargetPrediction and SEA
    P47989XDHXanthine dehydrogenaseT40954SwissTargetPrediction and SEA
    Q16678CYP1B1Cytochrome P450 1B1T92521SEA
    P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA
    Q13332PTPRSReceptor-type tyrosine-protein phosphatase ST10147SEA
    Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
    Q99417MYCBPMYCBP messenger RNAT37298SEA
    P16220CREB1Cyclic AMP-responsive element-binding proteinT92098SEA
    P43354NR4A2Orphan nuclear receptor NURR1T67163SEA
    P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA
    Q96HK3CALMCalmodulinT39610SEA
    Q9UK17KCND3Voltage-gated potassium channel Kv4.3T74500SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T59328DI0030Angina pectoris[ICD-11: BA40]P00533EGFR
    T59328DI0062Breast cancer[ICD-11: 2C60-2C6Y]P00533EGFR
    T59328DI0095Colorectal cancer[ICD-11: 2B91]P00533EGFR
    T59328DI0121Diabetic foot ulcer[ICD-11: BD54]P00533EGFR
    T59328DI0220Ischemia[ICD-11: 8B10-8B11]P00533EGFR
    T59328DI0238Lung cancer[ICD-11: 2C25]P00533EGFR
    T59328DI0303Non-small-cell lung cancer[ICD-11: 2C25]P00533EGFR
    T59328DI0361Renal cell carcinoma[ICD-11: 2C90]P00533EGFR
    T59328DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P00533EGFR
    T59328DI0420Unspecific body region injury[ICD-11: ND56]P00533EGFR
    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
    T92072DI0319Orthostatic hypotension[ICD-11: BA21]P30542ADORA1
    T46360DI0105Cough[ICD-11: MD12]Q99720SIGMAR1
    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
    T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
    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
    T83059DI0060Brain cancer[ICD-11: 2A00]O95271TNKS
    T83059DI0062Breast cancer[ICD-11: 2C60-2C6Y]O95271TNKS
    T83059DI0321Ovarian cancer[ICD-11: 2C73]O95271TNKS
    T83059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O95271TNKS
    T20178DI0035Arterial occlusive disease[ICD-11: BD40]P01375TNF
    T20178DI0274Multiple myeloma[ICD-11: 2A83]P01375TNF
    T20178DI0351Psoriasis[ICD-11: EA90]P01375TNF
    T20178DI0366Rheumatoid arthritis[ICD-11: FA20]P01375TNF
    T20761DI0095Colorectal cancer[ICD-11: 2B91]P15692VEGFA
    T20761DI0365Retinopathy[ICD-11: 9B71]P15692VEGFA
    T20761DI0430Vascular system developmental anomaly[ICD-11: LA90]P15692VEGFA
    T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
    T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
    T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1
    T70792DI0095Colorectal cancer[ICD-11: 2B91]P49763PGF
    T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
    T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
    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
    T70518DI0037Asthma[ICD-11: CA23]P16152CBR1
    T10147DI0057Bone paget disease[ICD-11: FB85]Q13332PTPRS
    T37298DI0235Liver cancer[ICD-11: 2C12]Q99417MYCBP
    T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1
    T39610DI0068Cardiac arrhythmia[ICD-11: BC9Z]Q96HK3CALM
    T39610DI0243Malaria[ICD-11: 1F40-1F45]Q96HK3CALM
    T39610DI0370Schizophrenia[ICD-11: 6A20]Q96HK3CALM
    T74500DI0004Acidosis[ICD-11: 5C73]Q9UK17KCND3

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