Daphnoline



Compound IDCDAMM02599
Common nameDaphnoline
IUPAC name20,25-dimethoxy-15-methyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.29,12.13,7.114,18.027,31.022,33]hexatriaconta-3(36),4,6,9(35),10,12(34),18,20,22(33),24,26,31-dodecaene-6,21-diol
Molecular formulaC35H36N2O6

Experimental data

Retention time17.38
Adduct[2M+K]+
Actual mz1199.49
Theoretical mz1199.48
Error8.21
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.5533

Identifiers and class information

Inchi keyAKGWXHYTRBFUAD-LSFSFQITNA-N
SmilesOC1=CC=C2C=C1OC3=CC=C(C=C3)CC4C5=C(OC=6C=C7C(=CC6OC)CCNC7C2)C(O)=C(OC)C=C5CCN4C
SuperclassLignans, neolignans and related compounds
Class

Pharmacokinetic properties

Number of descriptor values(#stars)1
Number of non-conjugated amine groups (#amine)2
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)12
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)0
Molecular weight (mol_MW)580.679
Computed dipole moment(dipole)6.515
Total solvent accessible surface area (SASA)781.312
Hydrophobic component of SASA (FOSA)452.967
Hydrophilic component of SASA (FISA)95.172
Pie component of the SASA (PISA)233.172
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1619.54
Number of hydrogen bond donors (donorHB)3
Number of hydrogen bond acceptors (accptHB)7.5
Free energy of solvation of dipole (dip^2/V)0.0262076
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0166264
Globularity descriptor (glob)0.853627
Predicted polarizability in cubic angstroms (QPpolrz)53.182
Predicted hexadecane/gas partition coefficient (QPlogPC16)15.968
Predicted octanol/gas partition coefficient (QPlogPoct)26.442
Predicted water/gas partition coefficient (QPlogPw)12.967
Predicted octanol/water partition coefficient (QPlogPo/w)4.607
Predicted aqueous solubility (QPlogS)-3.161
Conformation-independent predicted aqueous solubility (CIQPlogS)-7.29
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-6.465
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)77.123
Predicted brain/blood partition coefficient (QPlogBB)-0.233
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)37.957
Predicted skin permeability, log Kp (QPlogKp)-5.425
PM3 calculated ionization potential (IP(ev))8.746
PM3 calculated electron affinity (EA(eV))-0.035
Number of likely metabolic reactions (#metab)11
Prediction of binding to human serum albumin (QPlogKhsa)0.97
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)74.737
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)85.617
Number of nitrogen and oxygen atoms (#NandO)8
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
P43681CHRNA4Neuronal acetylcholine receptor; alpha4/beta2T70967SwissTargetPrediction
P14416DRD2Dopamine D2 receptorT67162SwissTargetPrediction
Q96FL8SLC47A1Multidrug and toxin extrusion protein 1T39676SwissTargetPrediction
P32297CHRNA3Neuronal acetylcholine receptor; alpha3/beta4T74166SwissTargetPrediction
Q01959SLC6A3Dopamine transporterT55959SwissTargetPrediction
P21728DRD1Dopamine D1 receptorT22118SwissTargetPrediction and SEA
P21918DRD5Dopamine D5 receptorT46828SEA
P06276BCHEButyrylcholinesteraseT99799SwissTargetPrediction
Q92952KCNN1Small conductance calcium-activated potassium channel protein 1T11911SEA
P30926CHRNB4Neuronal acetylcholine receptor; alpha2/beta4T73724SwissTargetPrediction
Q15822CHRNA2Neuronal acetylcholine receptor; alpha2/beta2T55815SEA
Q9H2S1KCNN2Small conductance calcium-activated potassium channel protein 2T86271SEA
P54750PDE1APhosphodiesterase 1AT81637SwissTargetPrediction and SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T70967DI0029Aneurysm/dissection[ICD-11: BD50]P43681CHRNA4
T70967DI0191Hypertensive crisis[ICD-11: BA03]P43681CHRNA4
T70967DI0196Hypotension[ICD-11: BA20-BA21]P43681CHRNA4
T67162DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P14416DRD2
T67162DI0025Alzheimer disease[ICD-11: 8A20]P14416DRD2
T67162DI0037Asthma[ICD-11: CA23]P14416DRD2
T67162DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P14416DRD2
T67162DI0051Bipolar disorder[ICD-11: 6A60]P14416DRD2
T67162DI0063Breathing abnormality[ICD-11: MD11]P14416DRD2
T67162DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P14416DRD2
T67162DI0073Cerebral ischaemia[ICD-11: 8B1Z]P14416DRD2
T67162DI0117Depression[ICD-11: 6A70-6A7Z]P14416DRD2
T67162DI0124Digestive system disease[ICD-11: DE2Z]P14416DRD2
T67162DI0137Essential hypertension[ICD-11: BA00]P14416DRD2
T67162DI0142Faecal incontinence[ICD-11: ME07]P14416DRD2
T67162DI0156Gangrene[ICD-11: MC85]P14416DRD2
T67162DI0166Glaucoma[ICD-11: 9C61]P14416DRD2
T67162DI0175Heart failure[ICD-11: BD10-BD1Z]P14416DRD2
T67162DI0185Hyperaemia[ICD-11: 9A61-9B7Y]P14416DRD2
T67162DI0190Hypertension[ICD-11: BA00-BA04]P14416DRD2
T67162DI0196Hypotension[ICD-11: BA20-BA21]P14416DRD2
T67162DI0205Inborn porphyrin/heme metabolism error[ICD-11: 5C58]P14416DRD2
T67162DI0214Insomnia[ICD-11: 7A00-7A0Z]P14416DRD2
T67162DI0222Itching[ICD-11: 1F28-1G07]P14416DRD2
T67162DI0264Migraine[ICD-11: 8A80]P14416DRD2
T67162DI0293Nausea/vomiting[ICD-11: MD90]P14416DRD2
T67162DI0324Pain[ICD-11: MG30-MG3Z]P14416DRD2
T67162DI0331Parkinsonism[ICD-11: 8A00]P14416DRD2
T67162DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P14416DRD2
T67162DI0340Postpartum haemorrhage[ICD-11: JA43]P14416DRD2
T67162DI0354Psychotic disorder[ICD-11: 6A20-6A25]P14416DRD2
T67162DI0356Pulmonary hypertension[ICD-11: BB01]P14416DRD2
T67162DI0370Schizophrenia[ICD-11: 6A20]P14416DRD2
T67162DI0396Substance abuse[ICD-11: 6C40]P14416DRD2
T67162DI0408Thyrotoxicosis[ICD-11: 5A02]P14416DRD2
T67162DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P14416DRD2
T39676DI0417Type 2 diabetes mellitus[ICD-11: 5A11]Q96FL8SLC47A1
T74166DI0105Cough[ICD-11: MD12]P32297CHRNA3
T55959DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]Q01959SLC6A3
T55959DI0051Bipolar disorder[ICD-11: 6A60]Q01959SLC6A3
T55959DI0101Corneal disease[ICD-11: 9A76-9A78]Q01959SLC6A3
T55959DI0290Narcolepsy[ICD-11: 7A20]Q01959SLC6A3
T55959DI0308Obesity[ICD-11: 5B80-5B81]Q01959SLC6A3
T55959DI0331Parkinsonism[ICD-11: 8A00]Q01959SLC6A3
T22118DI0003Abortion[ICD-11: JA00]P21728DRD1
T22118DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P21728DRD1
T22118DI0190Hypertension[ICD-11: BA00-BA04]P21728DRD1
T22118DI0331Parkinsonism[ICD-11: 8A00]P21728DRD1
T46828DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P21918DRD5
T99799DI0324Pain[ICD-11: MG30-MG3Z]P06276BCHE
T99799DI0411Tonus and reflex abnormality[ICD-11: MB47]P06276BCHE
T11911DI0285Myelopathy[ICD-11: 8B42]Q92952KCNN1
T73724DI0301Nicotine use disorder[ICD-11: 6C4A]P30926CHRNB4
T55815DI0101Corneal disease[ICD-11: 9A76-9A78]Q15822CHRNA2
T55815DI0117Depression[ICD-11: 6A70-6A7Z]Q15822CHRNA2
T55815DI0166Glaucoma[ICD-11: 9C61]Q15822CHRNA2
T55815DI0301Nicotine use disorder[ICD-11: 6C4A]Q15822CHRNA2
T55815DI0411Tonus and reflex abnormality[ICD-11: MB47]Q15822CHRNA2
T86271DI0285Myelopathy[ICD-11: 8B42]Q9H2S1KCNN2

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