Okanin 4-methyl ether 4\'-O-(2\'\'-O-caffeoyl-6\'\'-O-acetylglucoside)



Compound IDCDAMM01646
Common nameOkanin 4-methyl ether 4\'-O-(2\'\'-O-caffeoyl-6\'\'-O-acetylglucoside)
IUPAC name[6-(acetyloxymethyl)-2-[2,3-dihydroxy-4-[3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]phenoxy]-4,5-dihydroxyoxan-3-yl] 3-(3,4-dihydroxyphenyl)prop-2-enoate
Molecular formulaC33H32O15

Experimental data

Retention time22.49
Adduct[M+Na]+
Actual mz691.167
Theoretical mz691.163
Error5.62
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.6077

Identifiers and class information

Inchi keyCXLJITRXRSNEQL-WEHOFHDSNA-N
SmilesO=C(OC1C(OC2=CC=C(C(=O)C=CC3=CC=C(OC)C(O)=C3)C(O)=C2O)OC(COC(=O)C)C(O)C1O)C=CC4=CC=C(O)C(O)=C4
SuperclassPhenylpropanoids and polyketides
ClassFlavonoids

Pharmacokinetic properties

Number of descriptor values(#stars)8
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)20
Number of reactive functional groups (#rtvFG)4
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)668.607
Computed dipole moment(dipole)9.187
Total solvent accessible surface area (SASA)1075.66
Hydrophobic component of SASA (FOSA)304.838
Hydrophilic component of SASA (FISA)435.594
Pie component of the SASA (PISA)335.232
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1955.27
Number of hydrogen bond donors (donorHB)6
Number of hydrogen bond acceptors (accptHB)15.35
Free energy of solvation of dipole (dip^2/V)0.0431676
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0349548
Globularity descriptor (glob)0.703006
Predicted polarizability in cubic angstroms (QPpolrz)62.455
Predicted hexadecane/gas partition coefficient (QPlogPC16)24.223
Predicted octanol/gas partition coefficient (QPlogPoct)39.372
Predicted water/gas partition coefficient (QPlogPw)27.046
Predicted octanol/water partition coefficient (QPlogPo/w)1.705
Predicted aqueous solubility (QPlogS)-6.392
Conformation-independent predicted aqueous solubility (CIQPlogS)-7.41
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-7.936
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)0.733
Predicted brain/blood partition coefficient (QPlogBB)-6.518
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0.202
Predicted skin permeability, log Kp (QPlogKp)-6.446
PM3 calculated ionization potential (IP(ev))8.713
PM3 calculated electron affinity (EA(eV))1.11
Number of likely metabolic reactions (#metab)8
Prediction of binding to human serum albumin (QPlogKhsa)-0.254
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)268.588
Number of nitrogen and oxygen atoms (#NandO)15
Number of violations of Lipinski’s rule of five (RuleOfFive)3
Number of violations of Jorgensen’s rule of three (RuleOfThree)3

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
P02766TTRTransthyretinT86462SEA
P05067APPBeta amyloid A4 proteinT87024SEA
P43166CA7Carbonic anhydrase VIIT37541SEA
P23280CA6Carbonic anhydrase VIT06569SEA
P11926ODC1Ornithine decarboxylaseT60366SEA
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
Q09472EP300Histone acetyltransferase p300T25956SEA
P60568IL2Interleukin-2T61698SEA
Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SEA
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
P10636MAPTMicrotubule-associated protein tauT45593SEA
Q04760GLO1Glyoxalase IT88285SEA
P19438TNFRSF1ATumor necrosis factor receptor R1T86552SEA
Q16236NFE2L2Nuclear factor erythroid 2-related factor 2T88505SEA
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
Q9H4B7TUBB1Tubulin beta-1 chainT84397SEA

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
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
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
T25956DI0346Prostate cancer[ICD-11: 2C82]Q09472EP300
T25956DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q09472EP300
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
T88285DI0210Influenza[ICD-11: 1E30-1E32]Q04760GLO1
T86552DI0060Brain cancer[ICD-11: 2A00]P19438TNFRSF1A
T86552DI0321Ovarian cancer[ICD-11: 2C73]P19438TNFRSF1A
T88505DI0038Ataxic disorder[ICD-11: 8A03]Q16236NFE2L2
T84397DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9H4B7TUBB1

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