Daphniphylline



Compound IDCDAMM01495
Common nameDaphniphylline
IUPAC name[1-(1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl)-3-(1-methyl-14-propan-2-yl-12-azapentacyclo[8.6.0.02,13.03,7.07,12]hexadecan-2-yl)-1-oxopropan-2-yl] acetate
Molecular formulaC32H49NO5

Experimental data

Retention time15.94
Adduct[M+H]+
Actual mz528.37
Theoretical mz528.368
Error2.7
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.5475

Identifiers and class information

Inchi keyLFLWRPZTBUUBEQ-UHFFFAOYNA-N
SmilesO=C(OC(C(=O)C1(C)COC2(OC1CC2)C)CC34C5N6CC(CCC67CCCC73)C4(C)CCC5C(C)C)C
SuperclassAlkaloids and derivatives
ClassDaphniphylline-type alkaloids

Pharmacokinetic properties

Number of descriptor values(#stars)0
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)6
Number of reactive functional groups (#rtvFG)2
Predicted central nervous system activity (CNS)1
Molecular weight (mol_MW)527.743
Computed dipole moment(dipole)4.568
Total solvent accessible surface area (SASA)772.264
Hydrophobic component of SASA (FOSA)723.918
Hydrophilic component of SASA (FISA)48.346
Pie component of the SASA (PISA)0
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1579.13
Number of hydrogen bond donors (donorHB)0
Number of hydrogen bond acceptors (accptHB)6.5
Free energy of solvation of dipole (dip^2/V)0.0132165
Index of cohesive interaction in solids (ACxDN^.5/SA)0
Globularity descriptor (glob)0.849204
Predicted polarizability in cubic angstroms (QPpolrz)53.19
Predicted hexadecane/gas partition coefficient (QPlogPC16)12.994
Predicted octanol/gas partition coefficient (QPlogPoct)20.913
Predicted water/gas partition coefficient (QPlogPw)6.985
Predicted octanol/water partition coefficient (QPlogPo/w)5.57
Predicted aqueous solubility (QPlogS)-5.252
Conformation-independent predicted aqueous solubility (CIQPlogS)-6.295
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.698
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)859.683
Predicted brain/blood partition coefficient (QPlogBB)0.153
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)464.79
Predicted skin permeability, log Kp (QPlogKp)-3.897
PM3 calculated ionization potential (IP(ev))9.309
PM3 calculated electron affinity (EA(eV))-0.576
Number of likely metabolic reactions (#metab)1
Prediction of binding to human serum albumin (QPlogKhsa)1.209
Predicted qualitative human oral absorption (HumanOralAbsorption)3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)86.163
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)73.019
Number of nitrogen and oxygen atoms (#NandO)6
Number of violations of Lipinski’s rule of five (RuleOfFive)2
Number of violations of Jorgensen’s rule of three (RuleOfThree)0

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
Q9Y5N1HRH3Histamine H3 receptorT64765SwissTargetPrediction
P29475NOS1Nitric-oxide synthase, brainT16117SwissTargetPrediction
P35228NOS2Nitric oxide synthase, inducibleT02703SwissTargetPrediction
P21917DRD4Dopamine D4 receptorT24983SwissTargetPrediction
P98170XIAPInhibitor of apoptosis protein 3T16769SwissTargetPrediction
P28221HTR1DSerotonin 1d (5-HT1d) receptorT11072SwissTargetPrediction
P08908HTR1ASerotonin 1a (5-HT1a) receptorT78709SwissTargetPrediction
P34969HTR7Serotonin 7 (5-HT7) receptorT79062SwissTargetPrediction
Q99705MCHR1Melanin-concentrating hormone receptor 1T09572SwissTargetPrediction
P35354PTGS2Cyclooxygenase-2T66665SwissTargetPrediction
O60885BRD4Bromodomain-containing protein 4T00407SwissTargetPrediction
P51681CCR5C-C chemokine receptor type 5T09960SwissTargetPrediction
P25021HRH2Histamine H2 receptorT30985SwissTargetPrediction
P35367HRH1Histamine H1 receptorT77913SwissTargetPrediction
P21918DRD5Dopamine D5 receptorT46828SwissTargetPrediction
Q13639HTR4Serotonin 4 (5-HT4) receptorT59679SwissTargetPrediction
P35372OPRM1Mu opioid receptorT47768SwissTargetPrediction
P35368ADRA1BAlpha-1b adrenergic receptorT29500SwissTargetPrediction
P41145OPRK1Kappa Opioid receptorT60693SwissTargetPrediction
O60674JAK2Tyrosine-protein kinase JAK2T08391SwissTargetPrediction
P56817BACE1Beta-secretase 1T79031SwissTargetPrediction
Q9Y233PDE10APhosphodiesterase 10A (by homology)T84133SwissTargetPrediction
P49327FASNFatty acid synthaseT16514SwissTargetPrediction
P35270SPRSubstance-P receptorT47094SwissTargetPrediction
P37288AVPR1AVasopressin V1a receptor (by homology)T79232SwissTargetPrediction
P32245MC4RMelanocortin receptor 4T72458SwissTargetPrediction
P41143OPRD1Delta opioid receptorT58992SwissTargetPrediction
O75116ROCK2Rho-associated protein kinase 2T06093SwissTargetPrediction
P23458JAK1Tyrosine-protein kinase JAK1T62460SwissTargetPrediction
P49841GSK3BGlycogen synthase kinase-3 betaT70977SwissTargetPrediction
P25774CTSSCathepsin ST68290SwissTargetPrediction
P47898HTR5ASerotonin 5a (5-HT5a) receptorT15571SwissTargetPrediction
P21730C5AR1C5a anaphylatoxin chemotactic receptorT15439SwissTargetPrediction
P41146OPRL1Nociceptin receptorT52921SwissTargetPrediction
O60658PDE8A3',5'-cyclic phosphodiesteraseT05904SwissTargetPrediction
P34998CRHR1Corticotropin releasing factor receptor 1 (by homology)T45262SwissTargetPrediction
P35346SSTR5Somatostatin receptor 5T64830SwissTargetPrediction
Q99835SMOSmoothened homologT66505SwissTargetPrediction
O00763ACACBAcetyl-CoA carboxylase 2T08922SwissTargetPrediction
P25929NPY1RNeuropeptide Y receptor type 1T89213SwissTargetPrediction
P46098HTR3ASerotonin 3a (5-HT3a) receptorT64591SwissTargetPrediction
Q96LB2MRGPRX1Mas-related G-protein coupled receptor member X1T57253SwissTargetPrediction
Q9Y5Z0BACE2Beta secretase 2T01280SwissTargetPrediction
P49336CDK8Cell division protein kinase 8T10822SwissTargetPrediction
P30874SSTR2Somatostatin receptor 2T53024SwissTargetPrediction
P31391SSTR4Somatostatin receptor 4T62974SwissTargetPrediction
P30872SSTR1Somatostatin receptor 1T16633SwissTargetPrediction
P32745SSTR3Somatostatin receptor 3T13644SwissTargetPrediction

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T64765DI0392Somnolence[ICD-11: MG42]Q9Y5N1HRH3
T16117DI0173Headache[ICD-11: 8A80-8A84]P29475NOS1
T16117DI0264Migraine[ICD-11: 8A80]P29475NOS1
T02703DI0083Chronic kidney disease[ICD-11: GB61]P35228NOS2
T02703DI0320Osteoarthritis[ICD-11: FA00-FA05]P35228NOS2
T02703DI0375Sepsis[ICD-11: 1G40-1G41]P35228NOS2
T02703DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P35228NOS2
T24983DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P21917DRD4
T24983DI0370Schizophrenia[ICD-11: 6A20]P21917DRD4
T16769DI0259Metastatic lymph node neoplasm[ICD-11: 2D60]P98170XIAP
T11072DI0264Migraine[ICD-11: 8A80]P28221HTR1D
T11072DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P28221HTR1D
T78709DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]P08908HTR1A
T78709DI0117Depression[ICD-11: 6A70-6A7Z]P08908HTR1A
T78709DI0190Hypertension[ICD-11: BA00-BA04]P08908HTR1A
T78709DI0264Migraine[ICD-11: 8A80]P08908HTR1A
T78709DI0270Mood disorder[ICD-11: 6A60-6E23]P08908HTR1A
T79062DI0025Alzheimer disease[ICD-11: 8A20]P34969HTR7
T79062DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P34969HTR7
T79062DI0051Bipolar disorder[ICD-11: 6A60]P34969HTR7
T79062DI0117Depression[ICD-11: 6A70-6A7Z]P34969HTR7
T79062DI0265Mild neurocognitive disorder[ICD-11: 6D71]P34969HTR7
T79062DI0331Parkinsonism[ICD-11: 8A00]P34969HTR7
T79062DI0370Schizophrenia[ICD-11: 6A20]P34969HTR7
T09572DI0308Obesity[ICD-11: 5B80-5B81]Q99705MCHR1
T66665DI0087Chronic pain[ICD-11: MG30]P35354PTGS2
T66665DI0145Female pelvic pain[ICD-11: GA34]P35354PTGS2
T66665DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]P35354PTGS2
T66665DI0207Indeterminate colitis[ICD-11: DD72]P35354PTGS2
T66665DI0227Knee osteoarthritis[ICD-11: FA01]P35354PTGS2
T66665DI0320Osteoarthritis[ICD-11: FA00-FA05]P35354PTGS2
T66665DI0324Pain[ICD-11: MG30-MG3Z]P35354PTGS2
T66665DI0366Rheumatoid arthritis[ICD-11: FA20]P35354PTGS2
T66665DI0416Tuberculosis[ICD-11: 1B10-1B12]P35354PTGS2
T09960DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]P51681CCR5
T30985DI0161Gastro-oesophageal reflux disease[ICD-11: DA22]P25021HRH2
T30985DI0313Oesophageal/gastroduodenal disorder[ICD-11: DD90]P25021HRH2
T30985DI0333Peptic ulcer[ICD-11: DA61]P25021HRH2
T77913DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P35367HRH1
T77913DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]P35367HRH1
T77913DI0063Breathing abnormality[ICD-11: MD11]P35367HRH1
T77913DI0099Conjunctiva disorder[ICD-11: 9A60]P35367HRH1
T77913DI0105Cough[ICD-11: MD12]P35367HRH1
T77913DI0117Depression[ICD-11: 6A70-6A7Z]P35367HRH1
T77913DI0136Episodic vestibular syndrome[ICD-11: AB31]P35367HRH1
T77913DI0173Headache[ICD-11: 8A80-8A84]P35367HRH1
T77913DI0214Insomnia[ICD-11: 7A00-7A0Z]P35367HRH1
T77913DI0272Morning sickness disorder[ICD-11: SC00]P35367HRH1
T77913DI0292Nasopharyngitis[ICD-11: CA00]P35367HRH1
T77913DI0293Nausea/vomiting[ICD-11: MD90]P35367HRH1
T77913DI0331Parkinsonism[ICD-11: 8A00]P35367HRH1
T77913DI0349Pruritus[ICD-11: EC90]P35367HRH1
T77913DI0366Rheumatoid arthritis[ICD-11: FA20]P35367HRH1
T77913DI0388Sleep-wake disorder[ICD-11: 7A00-7B2Z]P35367HRH1
T77913DI0432Vasomotor/allergic rhinitis[ICD-11: CA08]P35367HRH1
T46828DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P21918DRD5
T59679DI0161Gastro-oesophageal reflux disease[ICD-11: DA22]Q13639HTR4
T59679DI0218Irritable bowel syndrome[ICD-11: DD91]Q13639HTR4
T47768DI0013Acute pain[ICD-11: MG31]P35372OPRM1
T47768DI0059Bowel habit change[ICD-11: ME05]P35372OPRM1
T47768DI0087Chronic pain[ICD-11: MG30]P35372OPRM1
T47768DI0101Corneal disease[ICD-11: 9A76-9A78]P35372OPRM1
T47768DI0105Cough[ICD-11: MD12]P35372OPRM1
T47768DI0117Depression[ICD-11: 6A70-6A7Z]P35372OPRM1
T47768DI0124Digestive system disease[ICD-11: DE2Z]P35372OPRM1
T47768DI0218Irritable bowel syndrome[ICD-11: DD91]P35372OPRM1
T47768DI0228Large intestine motility disorder[ICD-11: DB32]P35372OPRM1
T47768DI0317Opioid use disorder[ICD-11: 6C43]P35372OPRM1
T47768DI0324Pain[ICD-11: MG30-MG3Z]P35372OPRM1
T47768DI0349Pruritus[ICD-11: EC90]P35372OPRM1
T47768DI0374Sensation disturbance[ICD-11: MB40]P35372OPRM1
T29500DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P35368ADRA1B
T29500DI0190Hypertension[ICD-11: BA00-BA04]P35368ADRA1B
T29500DI0256Mental/behavioural/neurodevelopmental disorder[ICD-11: 6E20-6E8Z]P35368ADRA1B
T29500DI0308Obesity[ICD-11: 5B80-5B81]P35368ADRA1B
T29500DI0324Pain[ICD-11: MG30-MG3Z]P35368ADRA1B
T60693DI0304Non-specific cutaneous vascular symptom[ICD-11: ME64]P41145OPRK1
T60693DI0324Pain[ICD-11: MG30-MG3Z]P41145OPRK1
T60693DI0349Pruritus[ICD-11: EC90]P41145OPRK1
T08391DI0039Atopic eczema[ICD-11: EA80]O60674JAK2
T08391DI0286Myeloproliferative neoplasm[ICD-11: 2A20]O60674JAK2
T08391DI0366Rheumatoid arthritis[ICD-11: FA20]O60674JAK2
T08391DI0404Thrombocytosis[ICD-11: 3B63]O60674JAK2
T79031DI0025Alzheimer disease[ICD-11: 8A20]P56817BACE1
T84133DI0079Choreiform disorder[ICD-11: 8A01]Q9Y233PDE10A
T84133DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]Q9Y233PDE10A
T84133DI0218Irritable bowel syndrome[ICD-11: DD91]Q9Y233PDE10A
T84133DI0370Schizophrenia[ICD-11: 6A20]Q9Y233PDE10A
T84133DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9Y233PDE10A
T16514DI0096concerning food/fluid intake symptom[ICD-11: MG43]P49327FASN
T47094DI0117Depression[ICD-11: 6A70-6A7Z]P35270SPR
T47094DI0293Nausea/vomiting[ICD-11: MD90]P35270SPR
T79232DI0009Acute diabete complication[ICD-11: 5A2Y]P37288AVPR1A
T79232DI0041Autism spectrum disorder[ICD-11: 6A02]P37288AVPR1A
T79232DI0190Hypertension[ICD-11: BA00-BA04]P37288AVPR1A
T79232DI0194Hypo-osmolality/hyponatraemia[ICD-11: 5C72]P37288AVPR1A
T79232DI0236Localisation[ICD-11: N.A.]P37288AVPR1A
T72458DI0192Hypoactive sexual desire dysfunction[ICD-11: HA00]P32245MC4R
T72458DI0228Large intestine motility disorder[ICD-11: DB32]P32245MC4R
T72458DI0308Obesity[ICD-11: 5B80-5B81]P32245MC4R
T58992DI0059Bowel habit change[ICD-11: ME05]P41143OPRD1
T58992DI0218Irritable bowel syndrome[ICD-11: DD91]P41143OPRD1
T58992DI0324Pain[ICD-11: MG30-MG3Z]P41143OPRD1
T06093DI0168Graft-versus-host disease[ICD-11: 4B24]O75116ROCK2
T62460DI0039Atopic eczema[ICD-11: EA80]P23458JAK1
T62460DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P23458JAK1
T62460DI0366Rheumatoid arthritis[ICD-11: FA20]P23458JAK1
T62460DI0404Thrombocytosis[ICD-11: 3B63]P23458JAK1
T70977DI0288Myotonic disorder[ICD-11: 8C71]P49841GSK3B
T68290DI0042Autoimmune disease[ICD-11: 4A40-4A45]P25774CTSS
T68290DI0092Coeliac disease[ICD-11: DA95]P25774CTSS
T68290DI0107Crohn disease[ICD-11: DD70]P25774CTSS
T68290DI0120Diabetes mellitus[ICD-11: 5A10]P25774CTSS
T68290DI0163General pain disorder[ICD-11: 8E43]P25774CTSS
T68290DI0324Pain[ICD-11: MG30-MG3Z]P25774CTSS
T68290DI0382Sjogren syndrome[ICD-11: 4A43]P25774CTSS
T15571DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P47898HTR5A
T15439DI0431Vasculitis[ICD-11: 4A44]P21730C5AR1
T52921DI0039Atopic eczema[ICD-11: EA80]P41146OPRL1
T52921DI0117Depression[ICD-11: 6A70-6A7Z]P41146OPRL1
T52921DI0173Headache[ICD-11: 8A80-8A84]P41146OPRL1
T52921DI0175Heart failure[ICD-11: BD10-BD1Z]P41146OPRL1
T05904DI0222Itching[ICD-11: 1F28-1G07]O60658PDE8A
T05904DI0339Postoperative inflammation[ICD-11: 1A00-CA43]O60658PDE8A
T45262DI0394Staphylococcal/streptococcal disease[ICD-11: 1B5Y]P34998CRHR1
T64830DI0108Cushing syndrome[ICD-11: 5A70]P35346SSTR5
T66505DI0047Basal cell carcinoma[ICD-11: 2C32]Q99835SMO
T66505DI0085Chronic myelomonocytic leukaemia[ICD-11: 2A40]Q99835SMO
T66505DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q99835SMO
T08922DI0417Type 2 diabetes mellitus[ICD-11: 5A11]O00763ACACB
T89213DI0050Binge eating disorder[ICD-11: 6B82]P25929NPY1R
T89213DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P25929NPY1R
T89213DI0174Heart disease[ICD-11: BA41-BA42]P25929NPY1R
T89213DI0190Hypertension[ICD-11: BA00-BA04]P25929NPY1R
T89213DI0308Obesity[ICD-11: 5B80-5B81]P25929NPY1R
T64591DI0087Chronic pain[ICD-11: MG30]P46098HTR3A
T64591DI0101Corneal disease[ICD-11: 9A76-9A78]P46098HTR3A
T64591DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P46098HTR3A
T64591DI0218Irritable bowel syndrome[ICD-11: DD91]P46098HTR3A
T64591DI0293Nausea/vomiting[ICD-11: MD90]P46098HTR3A
T01280DI0425Urinary system clinical symptom[ICD-11: MF8Y]Q9Y5Z0BACE2
T10822DI0012Acute myeloid leukaemia[ICD-11: 2A60]P49336CDK8
T10822DI0284Myelodysplastic syndrome[ICD-11: 2A37]P49336CDK8
T53024DI0108Cushing syndrome[ICD-11: 5A70]P30874SSTR2
T53024DI0122Diagnostic imaging[ICD-11: N.A.]P30874SSTR2
T53024DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P30874SSTR2
T62974DI0087Chronic pain[ICD-11: MG30]P31391SSTR4
T62974DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]P31391SSTR4
T16633DI0108Cushing syndrome[ICD-11: 5A70]P30872SSTR1
T16633DI0395Stomach cancer[ICD-11: 2B72]P30872SSTR1
T13644DI0108Cushing syndrome[ICD-11: 5A70]P32745SSTR3

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