4,4''-bis(N-feruloyl)serotonin



Compound IDCDAMM01248
Common name4,4''-bis(N-feruloyl)serotonin
IUPAC nameN-[2-[5-hydroxy-4-[5-hydroxy-3-[2-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoylamino]ethyl]-1H-indol-4-yl]-1H-indol-3-yl]ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
Molecular formulaC40H38N4O8

Experimental data

Retention time0.27
Adduct[M+K]+
Actual mz741.232
Theoretical mz741.232
Error0.06
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.9695

Identifiers and class information

Inchi keyURHRFQQPWDNDQE-ACFHMISVSA-N
SmilesO=C(C=CC1=CC=C(O)C(OC)=C1)NCCC2=CNC3=CC=C(O)C(C=4C(O)=CC=C5NC=C(C54)CCNC(=O)C=CC6=CC=C(O)C(OC)=C6)=C32
SuperclassBenzenoids
ClassPhenols

Pharmacokinetic properties

Number of descriptor values(#stars)13
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)19
Number of reactive functional groups (#rtvFG)2
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)702.762
Computed dipole moment(dipole)8.439
Total solvent accessible surface area (SASA)1067.62
Hydrophobic component of SASA (FOSA)300.035
Hydrophilic component of SASA (FISA)308.906
Pie component of the SASA (PISA)458.682
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)2061.8
Number of hydrogen bond donors (donorHB)8
Number of hydrogen bond acceptors (accptHB)9.5
Free energy of solvation of dipole (dip^2/V)0.0345387
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0251681
Globularity descriptor (glob)0.733802
Predicted polarizability in cubic angstroms (QPpolrz)68.54
Predicted hexadecane/gas partition coefficient (QPlogPC16)25.068
Predicted octanol/gas partition coefficient (QPlogPoct)41.009
Predicted water/gas partition coefficient (QPlogPw)24.393
Predicted octanol/water partition coefficient (QPlogPo/w)5.236
Predicted aqueous solubility (QPlogS)-7.684
Conformation-independent predicted aqueous solubility (CIQPlogS)-10.678
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-8.027
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)11.656
Predicted brain/blood partition coefficient (QPlogBB)-4.406
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)4.023
Predicted skin permeability, log Kp (QPlogKp)-3.773
PM3 calculated ionization potential (IP(ev))7.739
PM3 calculated electron affinity (EA(eV))0.619
Number of likely metabolic reactions (#metab)9
Prediction of binding to human serum albumin (QPlogKhsa)0.868
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)24.86
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)205.289
Number of nitrogen and oxygen atoms (#NandO)12
Number of violations of Lipinski’s rule of five (RuleOfFive)4
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
P22303ACHEAcetylcholinesteraseT30082SEA
O15379HDAC3Histone deacetylase 3T05090SEA
P02766TTRTransthyretinT86462SEA
P05067APPBeta amyloid A4 proteinT87024SEA
P16083NQO2Quinone reductase 2T75498SEA
P06280GLAAlpha-galactosidase AT61339SEA
P43166CA7Carbonic anhydrase VIIT37541SEA
P23280CA6Carbonic anhydrase VIT06569SEA
Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
P28566HTR1ESerotonin 1e (5-HT1e) receptorT84117SEA
P05164MPOMyeloperoxidaseT23471SEA
Q92769HDAC2Histone deacetylase 2T51191SEA
P11926ODC1Ornithine decarboxylaseT60366SEA
Q8NER1TRPV1Vanilloid receptorT83193SEA
P08253MMP2Matrix metalloproteinase 2T68251SEA
P14780MMP9Matrix metalloproteinase 9T54156SEA
P03956MMP1Matrix metalloproteinase 1T52450SEA
P35462DRD3Dopamine D3 receptorT02551SEA
P06276BCHEButyrylcholinesteraseT99799SEA
P56817BACE1Beta-secretase 1T79031SEA
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
P43116PTGER2Prostanoid EP2 receptorT38529SEA
P11388TOP2ADNA topoisomerase II alphaT17048SEA
P13500CCL2C-C motif chemokine 2T89988SEA
Q09472EP300Histone acetyltransferase p300T25956SEA
P08581METHepatocyte growth factor receptorT40474SEA
P48039MTNR1AMelatonin receptor 1AT97613SEA
P49286MTNR1BMelatonin receptor 1BT48268SEA
Q9Y251HPSEHeparanaseT47623SEA
P35408PTGER4Prostanoid EP4 receptorT18876SEA
P06737PYGLLiver glycogen phosphorylaseT19184SEA
Q13258PTGDRProstanoid DP receptorT68782SEA
P32239CCKBRCholecystokinin B receptor (by homology)T05849SEA
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
P10636MAPTMicrotubule-associated protein tauT45593SEA
Q04760GLO1Glyoxalase IT88285SEA
P28336NMBRNeuromedin B receptorT68887SEA
P37840SNCAAlpha-synucleinT03644SEA
Q16236NFE2L2Nuclear factor erythroid 2-related factor 2T88505SEA
P28336NMBRNeuromedin B receptorT68887SEA
Q9H2K8TAOK3Serine/threonine-protein kinase TAO3T63682SEA
Q9H4B7TUBB1Tubulin beta-1 chainT84397SEA
P11717IGF2RInsulin-like growth factor II receptorT59550SEA
P01100FOSProto-oncogene c-FosT28025SEA
Q9NR20DYRK4Dual-specificity tyrosine-phosphorylation regulated kinase 4T20542SEA
P35270SPRSubstance-P receptorT47094SEA
Q8TDC3BRSK1BR serine/threonine kinase 1T20053SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T30082DI0025Alzheimer disease[ICD-11: 8A20]P22303ACHE
T30082DI0166Glaucoma[ICD-11: 9C61]P22303ACHE
T30082DI0282Myasthenia gravis[ICD-11: 8C6Y]P22303ACHE
T30082DI0313Oesophageal/gastroduodenal disorder[ICD-11: DD90]P22303ACHE
T30082DI0332Pediculosis[ICD-11: 1G00]P22303ACHE
T30082DI0421Unspecific substance harmful effect[ICD-11: NE6Z]P22303ACHE
T05090DI0241Lymphoma[ICD-11: 2A80-2A86]O15379HDAC3
T05090DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O15379HDAC3
T86462DI0026Amyloidosis[ICD-11: 5D00]P02766TTR
T87024DI0025Alzheimer disease[ICD-11: 8A20]P05067APP
T87024DI0122Diagnostic imaging[ICD-11: N.A.]P05067APP
T75498DI0214Insomnia[ICD-11: 7A00-7A0Z]P16083NQO2
T61339DI0201Inborn carbohydrate metabolism error[ICD-11: 5C51]P06280GLA
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
T84117DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P28566HTR1E
T23471DI0229Left ventricular failure[ICD-11: BD11]P05164MPO
T23471DI0339Postoperative inflammation[ICD-11: 1A00-CA43]P05164MPO
T51191DI0241Lymphoma[ICD-11: 2A80-2A86]Q92769HDAC2
T51191DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q92769HDAC2
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
T83193DI0163General pain disorder[ICD-11: 8E43]Q8NER1TRPV1
T68251DI0238Lung cancer[ICD-11: 2C25]P08253MMP2
T54156DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P14780MMP9
T54156DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P14780MMP9
T54156DI0395Stomach cancer[ICD-11: 2B72]P14780MMP9
T54156DI0419Ulcerative colitis[ICD-11: DD71]P14780MMP9
T52450DI0238Lung cancer[ICD-11: 2C25]P03956MMP1
T02551DI0051Bipolar disorder[ICD-11: 6A60]P35462DRD3
T02551DI0331Parkinsonism[ICD-11: 8A00]P35462DRD3
T99799DI0324Pain[ICD-11: MG30-MG3Z]P06276BCHE
T99799DI0411Tonus and reflex abnormality[ICD-11: MB47]P06276BCHE
T79031DI0025Alzheimer disease[ICD-11: 8A20]P56817BACE1
T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
T38529DI0003Abortion[ICD-11: JA00]P43116PTGER2
T38529DI0102Coronary atherosclerosis[ICD-11: BA52]P43116PTGER2
T38529DI0121Diabetic foot ulcer[ICD-11: BD54]P43116PTGER2
T38529DI0166Glaucoma[ICD-11: 9C61]P43116PTGER2
T38529DI0356Pulmonary hypertension[ICD-11: BB01]P43116PTGER2
T38529DI0378Sexual dysfunction[ICD-11: HA00-HA01]P43116PTGER2
T38529DI0413Transplant rejection[ICD-11: NE84]P43116PTGER2
T17048DI0012Acute myeloid leukaemia[ICD-11: 2A60]P11388TOP2A
T17048DI0225Kaposi sarcoma[ICD-11: 2B57]P11388TOP2A
T17048DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11388TOP2A
T89988DI0083Chronic kidney disease[ICD-11: GB61]P13500CCL2
T89988DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P13500CCL2
T89988DI0087Chronic pain[ICD-11: MG30]P13500CCL2
T89988DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]P13500CCL2
T89988DI0252Melanoma[ICD-11: 2C30]P13500CCL2
T89988DI0262Metastatic tumour[ICD-11: 2D50-2E2Z]P13500CCL2
T89988DI0275Multiple sclerosis[ICD-11: 8A40]P13500CCL2
T89988DI0326Pancreatic cancer[ICD-11: 2C10]P13500CCL2
T89988DI0366Rheumatoid arthritis[ICD-11: FA20]P13500CCL2
T89988DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P13500CCL2
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
T97613DI0214Insomnia[ICD-11: 7A00-7A0Z]P48039MTNR1A
T48268DI0214Insomnia[ICD-11: 7A00-7A0Z]P49286MTNR1B
T47623DI0020African trypanosomiasis[ICD-11: 1F51]Q9Y251HPSE
T47623DI0310Ocular disease[ICD-11: N.A.]Q9Y251HPSE
T18876DI0037Asthma[ICD-11: CA23]P35408PTGER4
T18876DI0175Heart failure[ICD-11: BD10-BD1Z]P35408PTGER4
T18876DI0264Migraine[ICD-11: 8A80]P35408PTGER4
T18876DI0303Non-small-cell lung cancer[ICD-11: 2C25]P35408PTGER4
T18876DI0324Pain[ICD-11: MG30-MG3Z]P35408PTGER4
T18876DI0360Rectum cancer[ICD-11: 2B92]P35408PTGER4
T18876DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P35408PTGER4
T18876DI0414Transplanted organ/tissue[ICD-11: QB63]P35408PTGER4
T68782DI0102Coronary atherosclerosis[ICD-11: BA52]Q13258PTGDR
T05849DI0122Diagnostic imaging[ICD-11: N.A.]P32239CCKBR
T05849DI0327Pancreatic internal secretion disorder[ICD-11: 5A4Y]P32239CCKBR
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
T68887DI0062Breast cancer[ICD-11: 2C60-2C6Y]P28336NMBR
T68887DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P28336NMBR
T03644DI0025Alzheimer disease[ICD-11: 8A20]P37840SNCA
T03644DI0044Autonomic nervous system disorder[ICD-11: 8D87]P37840SNCA
T03644DI0331Parkinsonism[ICD-11: 8A00]P37840SNCA
T88505DI0038Ataxic disorder[ICD-11: 8A03]Q16236NFE2L2
T68887DI0062Breast cancer[ICD-11: 2C60-2C6Y]P28336NMBR
T68887DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P28336NMBR
T84397DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9H4B7TUBB1
T59550DI0146Fibrosis[ICD-11: GA14-GC01]P11717IGF2R
T59550DI0368Sarcoidosis[ICD-11: 4B20]P11717IGF2R
T47094DI0117Depression[ICD-11: 6A70-6A7Z]P35270SPR
T47094DI0293Nausea/vomiting[ICD-11: MD90]P35270SPR

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