Okanin 4\'-O-(2\'\'-O-caffeoyl-6\'\'-O-p-coumaroylglucoside)



Compound IDCDAMM02029
Common nameOkanin 4\'-O-(2\'\'-O-caffeoyl-6\'\'-O-p-coumaroylglucoside)
IUPAC name[6-[4-[3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxyphenoxy]-5-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-3,4-dihydroxyoxan-2-yl]methyl 3-(4-hydroxyphenyl)prop-2-enoate
Molecular formulaC39H34O16

Experimental data

Retention time16.26
Adduct[M+Na]+
Actual mz781.175
Theoretical mz781.174
Error0.75
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.0507

Identifiers and class information

Inchi keyVZXQHTJVWMHMSB-RFGWYJBSNA-N
SmilesO=C(OCC1OC(OC2=CC=C(C(=O)C=CC3=CC=C(O)C(O)=C3)C(O)=C2O)C(OC(=O)C=CC4=CC=C(O)C(O)=C4)C(O)C1O)C=CC5=CC=C(O)C=C5
SuperclassPhenylpropanoids and polyketides
ClassFlavonoids

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)24
Number of reactive functional groups (#rtvFG)4
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)758.688
Computed dipole moment(dipole)6.065
Total solvent accessible surface area (SASA)974.433
Hydrophobic component of SASA (FOSA)136.701
Hydrophilic component of SASA (FISA)447.585
Pie component of the SASA (PISA)390.147
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1986.42
Number of hydrogen bond donors (donorHB)8
Number of hydrogen bond acceptors (accptHB)16.1
Free energy of solvation of dipole (dip^2/V)0.0185158
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0467325
Globularity descriptor (glob)0.78426
Predicted polarizability in cubic angstroms (QPpolrz)61.658
Predicted hexadecane/gas partition coefficient (QPlogPC16)24.208
Predicted octanol/gas partition coefficient (QPlogPoct)42.652
Predicted water/gas partition coefficient (QPlogPw)30.043
Predicted octanol/water partition coefficient (QPlogPo/w)1.447
Predicted aqueous solubility (QPlogS)-3.804
Conformation-independent predicted aqueous solubility (CIQPlogS)-9.016
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-6.884
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)0.564
Predicted brain/blood partition coefficient (QPlogBB)-5.734
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0.152
Predicted skin permeability, log Kp (QPlogKp)-6.09
PM3 calculated ionization potential (IP(ev))8.927
PM3 calculated electron affinity (EA(eV))1.072
Number of likely metabolic reactions (#metab)9
Prediction of binding to human serum albumin (QPlogKhsa)-0.393
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)297.953
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
P02766TTRTransthyretinT86462SEA
P05067APPBeta amyloid A4 proteinT87024SEA
P43166CA7Carbonic anhydrase VIIT37541SEA
P23280CA6Carbonic anhydrase VIT06569SEA
Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
P15121AKR1B1Aldose reductaseT26623SEA
P11926ODC1Ornithine decarboxylaseT60366SEA
P60568IL2Interleukin-2T61698SEA
Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SEA
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
P10636MAPTMicrotubule-associated protein tauT45593SEA
Q9H4B7TUBB1Tubulin beta-1 chainT84397SEA
O43826SLC37A4Glucose-6-phosphate translocaseT47306SEA
P10809HSPD1Mitochondrial matrix protein P1T11283SEA

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
T87024DI0025Alzheimer disease[ICD-11: 8A20]P05067APP
T87024DI0122Diagnostic imaging[ICD-11: N.A.]P05067APP
T06569DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P23280CA6
T06569DI0372Seborrhoeic dermatitis[ICD-11: EA81]P23280CA6
T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
T26623DI0298Neuropathy[ICD-11: 8C0Z]P15121AKR1B1
T26623DI0366Rheumatoid arthritis[ICD-11: FA20]P15121AKR1B1
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
T45593DI0012Acute myeloid leukaemia[ICD-11: 2A60]P10636MAPT
T45593DI0025Alzheimer disease[ICD-11: 8A20]P10636MAPT
T45593DI0265Mild neurocognitive disorder[ICD-11: 6D71]P10636MAPT
T84397DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9H4B7TUBB1
T11283DI0120Diabetes mellitus[ICD-11: 5A10]P10809HSPD1

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