(+)-3-O-Feruloylcassine



Compound IDCDAMM01210
Common name(+)-3-O-Feruloylcassine
IUPAC name[2-methyl-6-(11-oxododecyl)piperidin-3-yl] 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Molecular formulaC28H43NO5

Experimental data

Retention time14.54
Adduct[M+Na]+
Actual mz496.297
Theoretical mz496.303
Error12.53
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.7596

Identifiers and class information

Inchi keySTSLNURRVKPSHZ-IROJMHOLNA-N
SmilesO=C(OC1CCC(NC1C)CCCCCCCCCCC(=O)C)C=CC2=CC=C(O)C(OC)=C2
SuperclassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives

Pharmacokinetic properties

Number of descriptor values(#stars)3
Number of non-conjugated amine groups (#amine)1
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)473.651
Computed dipole moment(dipole)3.463
Total solvent accessible surface area (SASA)976.966
Hydrophobic component of SASA (FOSA)679.803
Hydrophilic component of SASA (FISA)164.97
Pie component of the SASA (PISA)132.194
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1734.34
Number of hydrogen bond donors (donorHB)2
Number of hydrogen bond acceptors (accptHB)7
Free energy of solvation of dipole (dip^2/V)0.0069139
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0101329
Globularity descriptor (glob)0.714565
Predicted polarizability in cubic angstroms (QPpolrz)53.601
Predicted hexadecane/gas partition coefficient (QPlogPC16)17.7
Predicted octanol/gas partition coefficient (QPlogPoct)23.892
Predicted water/gas partition coefficient (QPlogPw)10.166
Predicted octanol/water partition coefficient (QPlogPo/w)5.537
Predicted aqueous solubility (QPlogS)-7.288
Conformation-independent predicted aqueous solubility (CIQPlogS)-5.333
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-7.507
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)67.359
Predicted brain/blood partition coefficient (QPlogBB)-2.217
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)29.639
Predicted skin permeability, log Kp (QPlogKp)-4.525
PM3 calculated ionization potential (IP(ev))8.919
PM3 calculated electron affinity (EA(eV))0.847
Number of likely metabolic reactions (#metab)3
Prediction of binding to human serum albumin (QPlogKhsa)1.128
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)79.13
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)107.118
Number of nitrogen and oxygen atoms (#NandO)6
Number of violations of Lipinski’s rule of five (RuleOfFive)1
Number of violations of Jorgensen’s rule of three (RuleOfThree)1

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
P02766TTRTransthyretinT86462SEA
P05067APPBeta amyloid A4 proteinT87024SEA
P43166CA7Carbonic anhydrase VIIT37541SEA
P23280CA6Carbonic anhydrase VIT06569SEA
Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
P42330AKR1C3Aldo-keto-reductase family 1 member C3T60857SEA
P11926ODC1Ornithine decarboxylaseT60366SEA
Q8NER1TRPV1Vanilloid receptorT83193SEA
P08183ABCB1P-glycoprotein 1T25258SwissTargetPrediction and SEA
P06276BCHEButyrylcholinesteraseT99799SEA
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
P62942FKBP1AFK506-binding protein 1AT76059SwissTargetPrediction
P11388TOP2ADNA topoisomerase II alphaT17048SEA
Q09472EP300Histone acetyltransferase p300T25956SEA
P08581METHepatocyte growth factor receptorT40474SEA
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
Q9H4B7TUBB1Tubulin beta-1 chainT84397SEA
O43826SLC37A4Glucose-6-phosphate translocaseT47306SEA
P01100FOSProto-oncogene c-FosT28025SEA
Q9NR20DYRK4Dual-specificity tyrosine-phosphorylation regulated kinase 4T20542SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
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
T60857DI0145Female pelvic pain[ICD-11: GA34]P42330AKR1C3
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
T83193DI0163General pain disorder[ICD-11: 8E43]Q8NER1TRPV1
T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
T99799DI0324Pain[ICD-11: MG30-MG3Z]P06276BCHE
T99799DI0411Tonus and reflex abnormality[ICD-11: MB47]P06276BCHE
T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
T76059DI0331Parkinsonism[ICD-11: 8A00]P62942FKBP1A
T76059DI0349Pruritus[ICD-11: EC90]P62942FKBP1A
T76059DI0413Transplant rejection[ICD-11: NE84]P62942FKBP1A
T17048DI0012Acute myeloid leukaemia[ICD-11: 2A60]P11388TOP2A
T17048DI0225Kaposi sarcoma[ICD-11: 2B57]P11388TOP2A
T17048DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11388TOP2A
T25956DI0346Prostate cancer[ICD-11: 2C82]Q09472EP300
T25956DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q09472EP300
T40474DI0238Lung cancer[ICD-11: 2C25]P08581MET
T40474DI0303Non-small-cell lung cancer[ICD-11: 2C25]P08581MET
T40474DI0407Thyroid cancer[ICD-11: 2D10]P08581MET
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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