(S)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 5-[glucosyl-(1->4)-b-D-glucoside]



Compound IDCDAMM00639
Common name(S)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 5-[glucosyl-(1->4)-b-D-glucoside]
IUPAC name2-[5-[3,4-dihydroxy-6-(hydroxymethyl)-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3-hydroxy-2-oxo-1H-indol-3-yl]acetic acid
Molecular formulaC22H29NO15

Experimental data

Retention time11.5
Adduct[M+H]+
Actual mz548.164
Theoretical mz548.161
Error5.33
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.5714

Identifiers and class information

Inchi keyADONHDUDLSXBIZ-UHFFFAOYNA-N
SmilesO=C(O)CC1(O)C(=O)NC2=CC=C(OC3OC(CO)C(OC4OC(CO)C(O)C(O)C4O)C(O)C3O)C=C21
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds

Plant source

  • Piper longum 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)1
    Number of non-conjugated amide groups (#amide)0
    Number of rotatable bonds (#rotor)16
    Number of reactive functional groups (#rtvFG)2
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)547.469
    Computed dipole moment(dipole)6.928
    Total solvent accessible surface area (SASA)721.161
    Hydrophobic component of SASA (FOSA)186.034
    Hydrophilic component of SASA (FISA)440.913
    Pie component of the SASA (PISA)94.214
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1407.02
    Number of hydrogen bond donors (donorHB)9
    Number of hydrogen bond acceptors (accptHB)22
    Free energy of solvation of dipole (dip^2/V)0.0341143
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0915191
    Globularity descriptor (glob)0.842041
    Predicted polarizability in cubic angstroms (QPpolrz)40.781
    Predicted hexadecane/gas partition coefficient (QPlogPC16)17.028
    Predicted octanol/gas partition coefficient (QPlogPoct)39.957
    Predicted water/gas partition coefficient (QPlogPw)36.416
    Predicted octanol/water partition coefficient (QPlogPo/w)-3.304
    Predicted aqueous solubility (QPlogS)-1.293
    Conformation-independent predicted aqueous solubility (CIQPlogS)-2.145
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-2.73
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)0.165
    Predicted brain/blood partition coefficient (QPlogBB)-4.547
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0.051
    Predicted skin permeability, log Kp (QPlogKp)-7.777
    PM3 calculated ionization potential (IP(ev))9.295
    PM3 calculated electron affinity (EA(eV))0.842
    Number of likely metabolic reactions (#metab)9
    Prediction of binding to human serum albumin (QPlogKhsa)-1.716
    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)282.479
    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
    O43570CA12Carbonic anhydrase XIIT16987SEA
    Q16790CA9Carbonic anhydrase IXT64567SEA
    P00915CA1Carbonic anhydrase IT13201SEA
    Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
    Q9BZP6CHIAAcidic mammalian chitinase (by homology)T51597SEA
    P15692VEGFAVascular endothelial growth factor AT20761SEA
    P05230FGF1Acidic fibroblast growth factorT18639SEA
    P09038FGF2Basic fibroblast growth factorT31621SEA
    Q9Y251HPSEHeparanaseT47623SEA
    P16109SELPP-selectinT10965SEA
    P14151SELLLeukocyte adhesion molecule-1T60526SEA
    P01112HRASTransforming protein p21/H-Ras-1T71081SEA
    P60568IL2Interleukin-2T61698SEA
    P17931LGALS3Galectin-3T72038SEA
    P04746AMY2APancreatic alpha-amylaseT86918SEA
    P14679TYRTyrosinaseT97035SEA
    P20916MAGMyelin-associated glycoprotein (by homology)T95286SEA
    P09382LGALS1Galectin-1T09544SEA
    P01111NRASGTPase NRasT35486SEA
    Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
    Q99417MYCBPMYCBP messenger RNAT37298SEA
    P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA

    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
    T64567DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16790CA9
    T13201DI0166Glaucoma[ICD-11: 9C61]P00915CA1
    T13201DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00915CA1
    T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
    T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
    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
    T47623DI0020African trypanosomiasis[ICD-11: 1F51]Q9Y251HPSE
    T47623DI0310Ocular disease[ICD-11: N.A.]Q9Y251HPSE
    T10965DI0088Circulatory system disease[ICD-11: BE2Z]P16109SELP
    T10965DI0381Sickle-cell disorder[ICD-11: 3A51]P16109SELP
    T60526DI0037Asthma[ICD-11: CA23]P14151SELL
    T60526DI0088Circulatory system disease[ICD-11: BE2Z]P14151SELL
    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
    T95286DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P20916MAG
    T35486DI0095Colorectal cancer[ICD-11: 2B91]P01111NRAS
    T35486DI0172Head and neck cancer[ICD-11: 2D42]P01111NRAS
    T35486DI0238Lung cancer[ICD-11: 2C25]P01111NRAS
    T35486DI0326Pancreatic cancer[ICD-11: 2C10]P01111NRAS
    T35486DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P01111NRAS
    T37298DI0235Liver cancer[ICD-11: 2C12]Q99417MYCBP
    T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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