2,3,4\',5-Tetrahydroxystilbene 2-O-beta-D-(2\'\'-O-galloyl)glucopyranoside



Compound IDCDAMM01826
Common name2,3,4\',5-Tetrahydroxystilbene 2-O-beta-D-(2\'\'-O-galloyl)glucopyranoside
IUPAC name[2-[2,4-dihydroxy-6-[2-(4-hydroxyphenyl)ethenyl]phenoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 3,4,5-trihydroxybenzoate
Molecular formulaC27H26O13

Experimental data

Retention time15.75
Adduct[M+H]+
Actual mz559.15
Theoretical mz559.144
Error10.24
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.9499

Identifiers and class information

Inchi keyHFVXPVDJOMGUNC-UHKUUAOGNA-N
SmilesO=C(OC1C(O)C(O)C(OC1OC=2C(O)=CC(O)=CC2C=CC3=CC=C(O)C=C3)CO)C4=CC(O)=C(O)C(O)=C4
SuperclassPhenylpropanoids and polyketides
ClassStilbenes

Pharmacokinetic properties

Number of descriptor values(#stars)7
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)17
Number of reactive functional groups (#rtvFG)2
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)558.495
Computed dipole moment(dipole)2.98
Total solvent accessible surface area (SASA)712.113
Hydrophobic component of SASA (FOSA)105.192
Hydrophilic component of SASA (FISA)378.285
Pie component of the SASA (PISA)228.636
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1429.08
Number of hydrogen bond donors (donorHB)9
Number of hydrogen bond acceptors (accptHB)14.05
Free energy of solvation of dipole (dip^2/V)0.0062134
Index of cohesive interaction in solids (ACxDN^.5/SA)0.05919
Globularity descriptor (glob)0.861628
Predicted polarizability in cubic angstroms (QPpolrz)42.305
Predicted hexadecane/gas partition coefficient (QPlogPC16)17.698
Predicted octanol/gas partition coefficient (QPlogPoct)35.783
Predicted water/gas partition coefficient (QPlogPw)28.832
Predicted octanol/water partition coefficient (QPlogPo/w)-0.648
Predicted aqueous solubility (QPlogS)-1.89
Conformation-independent predicted aqueous solubility (CIQPlogS)-5.528
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.861
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)2.562
Predicted brain/blood partition coefficient (QPlogBB)-3.858
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0.782
Predicted skin permeability, log Kp (QPlogKp)-6.054
PM3 calculated ionization potential (IP(ev))8.577
PM3 calculated electron affinity (EA(eV))0.593
Number of likely metabolic reactions (#metab)9
Prediction of binding to human serum albumin (QPlogKhsa)-0.809
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)237.001
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)2

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
O43570CA12Carbonic anhydrase XIIT16987SEA
P02766TTRTransthyretinT86462SEA
P43166CA7Carbonic anhydrase VIIT37541SEA
P05121SERPINE1Plasminogen activator inhibitor-1T15556SEA
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
P52789HK2Hexokinase type IIT96685SEA
P60568IL2Interleukin-2T61698SEA
Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SEA
P17931LGALS3Galectin-3T72038SEA
P14679TYRTyrosinaseT97035SEA
P52209PGD6-phosphogluconate dehydrogenaseT76497SEA
P63316TNNC1Troponin, cardiac muscleT12966SEA
P09382LGALS1Galectin-1T09544SEA
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
P05231IL6Interleukin-6T32578SEA
Q99417MYCBPMYCBP messenger RNAT37298SEA
P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA
P19429TNNI3Cardiac troponin IT20186SEA
P45379TNNT2Cardiac muscle troponin TT05887SEA

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
T86462DI0026Amyloidosis[ICD-11: 5D00]P02766TTR
T15556DI0037Asthma[ICD-11: CA23]P05121SERPINE1
T15556DI0405Thrombosis[ICD-11: DB61-GB90]P05121SERPINE1
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
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
T76497DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P52209PGD
T12966DI0006Acquired cutaneous blood vessel malformation[ICD-11: EF20]P63316TNNC1
T12966DI0175Heart failure[ICD-11: BD10-BD1Z]P63316TNNC1
T32578DI0028Anemia[ICD-11: 3A00-3A9Z]P05231IL6
T37298DI0235Liver cancer[ICD-11: 2C12]Q99417MYCBP
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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