N-[[3-(b-D-Glucopyranosyloxy)-2,3-dihydro-2-oxo-1H-indol-3-yl]acetyl]aspartic acid



Compound IDCDAMM02425
Common nameN-[[3-(b-D-Glucopyranosyloxy)-2,3-dihydro-2-oxo-1H-indol-3-yl]acetyl]aspartic acid
IUPAC name2-[[2-[2-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1H-indol-3-yl]acetyl]amino]butanedioic acid
Molecular formulaC20H24N2O12

Experimental data

Retention time12.03
Adduct[M+H]+
Actual mz485.141
Theoretical mz485.14
Error1.9
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.7782

Identifiers and class information

Inchi keyANAVISFXAGVRIA-UHFFFAOYNA-N
SmilesO=C(O)CC(NC(=O)CC1(OC2OC(CO)C(O)C(O)C2O)C(=O)NC=3C=CC=CC31)C(=O)O
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives

Pharmacokinetic properties

Number of descriptor values(#stars)5
Number of non-conjugated amine groups (#amine)0
Number of amidine and guanidine groups (#amidine)0
Number of carboxylic acid groups (#acid)2
Number of non-conjugated amide groups (#amide)1
Number of rotatable bonds (#rotor)13
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)484.416
Computed dipole moment(dipole)4.401
Total solvent accessible surface area (SASA)673.06
Hydrophobic component of SASA (FOSA)179.193
Hydrophilic component of SASA (FISA)359.061
Pie component of the SASA (PISA)134.806
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1286.43
Number of hydrogen bond donors (donorHB)7
Number of hydrogen bond acceptors (accptHB)17.25
Free energy of solvation of dipole (dip^2/V)0.0150531
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0678085
Globularity descriptor (glob)0.849899
Predicted polarizability in cubic angstroms (QPpolrz)38.269
Predicted hexadecane/gas partition coefficient (QPlogPC16)15.219
Predicted octanol/gas partition coefficient (QPlogPoct)33.083
Predicted water/gas partition coefficient (QPlogPw)30.798
Predicted octanol/water partition coefficient (QPlogPo/w)-1.726
Predicted aqueous solubility (QPlogS)-1.019
Conformation-independent predicted aqueous solubility (CIQPlogS)-2.098
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)0.386
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)0.163
Predicted brain/blood partition coefficient (QPlogBB)-3.534
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0.102
Predicted skin permeability, log Kp (QPlogKp)-6.414
PM3 calculated ionization potential (IP(ev))9.08
PM3 calculated electron affinity (EA(eV))0.41
Number of likely metabolic reactions (#metab)7
Prediction of binding to human serum albumin (QPlogKhsa)-1.81
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)23.305
Van der Waals surface area (PSA)264.817
Number of nitrogen and oxygen atoms (#NandO)14
Number of violations of Lipinski’s rule of five (RuleOfFive)2
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
P35968KDRVascular endothelial growth factor receptor 2T80975SwissTargetPrediction
P11387TOP1DNA topoisomerase IT09826SEA
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
P52789HK2Hexokinase type IIT96685SEA
P16109SELPP-selectinT10965SEA
P14151SELLLeukocyte adhesion molecule-1T60526SEA
P01112HRASTransforming protein p21/H-Ras-1T71081SEA
P60568IL2Interleukin-2T61698SEA
P17931LGALS3Galectin-3T72038SEA
P14679TYRTyrosinaseT97035SEA
P09382LGALS1Galectin-1T09544SEA
P01111NRASGTPase NRasT35486SEA
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T80975DI0062Breast cancer[ICD-11: 2C60-2C6Y]P35968KDR
T80975DI0095Colorectal cancer[ICD-11: 2B91]P35968KDR
T80975DI0160Gastrointestinal stromal tumour[ICD-11: 2B5B]P35968KDR
T80975DI0244Malignant digestive organ neoplasm[ICD-11: 2C11]P35968KDR
T80975DI0361Renal cell carcinoma[ICD-11: 2C90]P35968KDR
T80975DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P35968KDR
T80975DI0395Stomach cancer[ICD-11: 2B72]P35968KDR
T80975DI0403Thrombocytopenia[ICD-11: 3B64]P35968KDR
T80975DI0407Thyroid cancer[ICD-11: 2D10]P35968KDR
T09826DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P11387TOP1
T09826DI0095Colorectal cancer[ICD-11: 2B91]P11387TOP1
T09826DI0238Lung cancer[ICD-11: 2C25]P11387TOP1
T09826DI0321Ovarian cancer[ICD-11: 2C73]P11387TOP1
T09826DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11387TOP1
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
T96685DI0133Epidermal dysplasias[ICD-11: EK90]P52789HK2
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
T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
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
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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