Frangulanine



Compound IDCDAMM01430
Common nameFrangulanine
IUPAC name2-(dimethylamino)-3-methyl-N-[7-(2-methylpropyl)-5,8-dioxo-3-propan-2-yl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),10,12,15-tetraen-4-yl]pentanamide
Molecular formulaC28H44N4O4

Experimental data

Retention time10.76
Adduct[M+H]+
Actual mz501.348
Theoretical mz501.343
Error9.22
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.5435

Identifiers and class information

Inchi keyULQXKOIGVXLOOC-PFONDFGANA-N
SmilesOC1=NC=CC=2C=CC(OC(C(N=C(O)C(N(C)C)C(C)CC)C(O)=NC1CC(C)C)C(C)C)=CC2
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives

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)2
Number of rotatable bonds (#rotor)8
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)1
Molecular weight (mol_MW)500.68
Computed dipole moment(dipole)4.057
Total solvent accessible surface area (SASA)851.945
Hydrophobic component of SASA (FOSA)663.927
Hydrophilic component of SASA (FISA)56.54
Pie component of the SASA (PISA)131.478
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1663.55
Number of hydrogen bond donors (donorHB)1.5
Number of hydrogen bond acceptors (accptHB)8.75
Free energy of solvation of dipole (dip^2/V)0.0098941
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0125789
Globularity descriptor (glob)0.796973
Predicted polarizability in cubic angstroms (QPpolrz)56.54
Predicted hexadecane/gas partition coefficient (QPlogPC16)15.295
Predicted octanol/gas partition coefficient (QPlogPoct)25.41
Predicted water/gas partition coefficient (QPlogPw)14.604
Predicted octanol/water partition coefficient (QPlogPo/w)3.979
Predicted aqueous solubility (QPlogS)-4.793
Conformation-independent predicted aqueous solubility (CIQPlogS)-3.699
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-3.422
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)386.601
Predicted brain/blood partition coefficient (QPlogBB)-0.114
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)383.06
Predicted skin permeability, log Kp (QPlogKp)-3.393
PM3 calculated ionization potential (IP(ev))9.131
PM3 calculated electron affinity (EA(eV))0.155
Number of likely metabolic reactions (#metab)4
Prediction of binding to human serum albumin (QPlogKhsa)0.392
Predicted qualitative human oral absorption (HumanOralAbsorption)3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)83.595
Solvent-accessible surface area of fluorine atoms (SAFluorine)0
Solvent-accessible surface area of amide oxygen atoms (SAamideO)33.841
Van der Waals surface area (PSA)94.335
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)0

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
Q12809KCNH2HERGT20251SwissTargetPrediction
P30531SLC6A1GABA transporter 1T62184SwissTargetPrediction
P12821ACEAngiotensin-converting enzymeT98311SwissTargetPrediction
P00797RENReninT61622SwissTargetPrediction
P15144ANPEPAminopeptidase NT67272SwissTargetPrediction
P00734F2ThrombinT94033SwissTargetPrediction
P08514ITGA2BIntegrin alpha-IIb/beta-3T50688SwissTargetPrediction
P27487DPP4Dipeptidyl peptidase IVT31391SwissTargetPrediction
P98170XIAPInhibitor of apoptosis protein 3T16769SwissTargetPrediction
P78352DLG4Disks large homolog 4T04507SwissTargetPrediction
P08473MMENeprilysinT05409SwissTargetPrediction
Q96IY4CPB2Carboxypeptidase B2 isoform AT98022SwissTargetPrediction
P35367HRH1Histamine H1 receptorT77913SwissTargetPrediction
P08254MMP3Matrix metalloproteinase 3T86702SwissTargetPrediction
P35372OPRM1Mu opioid receptorT47768SwissTargetPrediction
P41145OPRK1Kappa Opioid receptorT60693SwissTargetPrediction
P35270SPRSubstance-P receptorT47094SwissTargetPrediction
P41143OPRD1Delta opioid receptorT58992SwissTargetPrediction
P00742F10Thrombin and coagulation factor XT84631SwissTargetPrediction
P00750PLATTissue-type plasminogen activatorT45299SwissTargetPrediction
Q9HAN5TRP1Cationic trypsinogenT27602SwissTargetPrediction
Q13489BIRC3Baculoviral IAP repeat-containing protein 3T35173SwissTargetPrediction
Q9Y5Y4PTGDR2G protein-coupled receptor 44T61722SwissTargetPrediction
P49356FNTBFarnesyl protein transferaseT13127SwissTargetPrediction
P29466CASP1Caspase-1T98269SwissTargetPrediction
P06756ITGAVVitronectin receptor alphaT67103SwissTargetPrediction
P17301ITGA2Integrin alpha-2T55293SwissTargetPrediction
P42892ECE1Endothelin-converting enzyme 1T50970SwissTargetPrediction
P05556ITGB1Integrin alpha2/beta1T01851SwissTargetPrediction
P25101EDNRAEndothelin receptor ET-AT23499SwissTargetPrediction
O43174CYP26A1Cytochrome P450 26A1T84634SwissTargetPrediction
Q00987MDM2p53-binding protein Mdm-2T00176SwissTargetPrediction
P41180CASRCalcium sensing receptorT92076SwissTargetPrediction
P24530EDNRBEndothelin receptor ET-BT92828SwissTargetPrediction
P53609PGGT1BGeranylgeranyl transferase type IT76396SwissTargetPrediction
P26010ITGB7Integrin alpha-4/beta-7T07403SwissTargetPrediction
Q9UIQ6LNPEPCystinyl aminopeptidaseT97537SwissTargetPrediction
P49682CXCR3C-X-C chemokine receptor type 3T25315SwissTargetPrediction
Q13822ENPP2AutotaxinT63512SwissTargetPrediction
P13612ITGA4Integrin alpha-4T97587SwissTargetPrediction
Q9H4B7TUBB1Tubulin beta-1 chainT84397SwissTargetPrediction

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T20251DI0175Heart failure[ICD-11: BD10-BD1Z]Q12809KCNH2
T62184DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P30531SLC6A1
T62184DI0274Multiple myeloma[ICD-11: 2A83]P30531SLC6A1
T98311DI0175Heart failure[ICD-11: BD10-BD1Z]P12821ACE
T98311DI0190Hypertension[ICD-11: BA00-BA04]P12821ACE
T61622DI0190Hypertension[ICD-11: BA00-BA04]P00797REN
T67272DI0351Psoriasis[ICD-11: EA90]P15144ANPEP
T94033DI0052Bleeding disorder[ICD-11: GA20-GA21]P00734F2
T94033DI0091Coagulation defect[ICD-11: 3B10]P00734F2
T94033DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P00734F2
T94033DI0275Multiple sclerosis[ICD-11: 8A40]P00734F2
T94033DI0287Myocardial infarction[ICD-11: BA41-BA43]P00734F2
T94033DI0306Nutritional deficiency[ICD-11: 5B50-5B71]P00734F2
T94033DI0403Thrombocytopenia[ICD-11: 3B64]P00734F2
T94033DI0405Thrombosis[ICD-11: DB61-GB90]P00734F2
T50688DI0007Acquired hypermelanosis[ICD-11: ED60]P08514ITGA2B
T50688DI0030Angina pectoris[ICD-11: BA40]P08514ITGA2B
T50688DI0287Myocardial infarction[ICD-11: BA41-BA43]P08514ITGA2B
T31391DI0009Acute diabete complication[ICD-11: 5A2Y]P27487DPP4
T31391DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P27487DPP4
T16769DI0259Metastatic lymph node neoplasm[ICD-11: 2D60]P98170XIAP
T04507DI0073Cerebral ischaemia[ICD-11: 8B1Z]P78352DLG4
T04507DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P78352DLG4
T05409DI0175Heart failure[ICD-11: BD10-BD1Z]P08473MME
T98022DI0073Cerebral ischaemia[ICD-11: 8B1Z]Q96IY4CPB2
T98022DI0074Cerebral ischaemic stroke[ICD-11: 8B11]Q96IY4CPB2
T98022DI0405Thrombosis[ICD-11: DB61-GB90]Q96IY4CPB2
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
T86702DI0101Corneal disease[ICD-11: 9A76-9A78]P08254MMP3
T86702DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]P08254MMP3
T86702DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P08254MMP3
T86702DI0275Multiple sclerosis[ICD-11: 8A40]P08254MMP3
T86702DI0287Myocardial infarction[ICD-11: BA41-BA43]P08254MMP3
T86702DI0320Osteoarthritis[ICD-11: FA00-FA05]P08254MMP3
T86702DI0366Rheumatoid arthritis[ICD-11: FA20]P08254MMP3
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
T60693DI0304Non-specific cutaneous vascular symptom[ICD-11: ME64]P41145OPRK1
T60693DI0324Pain[ICD-11: MG30-MG3Z]P41145OPRK1
T60693DI0349Pruritus[ICD-11: EC90]P41145OPRK1
T47094DI0117Depression[ICD-11: 6A70-6A7Z]P35270SPR
T47094DI0293Nausea/vomiting[ICD-11: MD90]P35270SPR
T58992DI0059Bowel habit change[ICD-11: ME05]P41143OPRD1
T58992DI0218Irritable bowel syndrome[ICD-11: DD91]P41143OPRD1
T58992DI0324Pain[ICD-11: MG30-MG3Z]P41143OPRD1
T84631DI0053Blood-forming organ disease[ICD-11: 3C0Z]P00742F10
T84631DI0080Christmas disease[ICD-11: 3B11]P00742F10
T84631DI0091Coagulation defect[ICD-11: 3B10]P00742F10
T84631DI0103Coronary thrombosis[ICD-11: BA43]P00742F10
T84631DI0114Deep vein thrombosis[ICD-11: BD71]P00742F10
T84631DI0397Supraventricular tachyarrhythmia[ICD-11: BC81]P00742F10
T84631DI0405Thrombosis[ICD-11: DB61-GB90]P00742F10
T84631DI0433Venous thromboembolism[ICD-11: BD72]P00742F10
T45299DI0052Bleeding disorder[ICD-11: GA20-GA21]P00750PLAT
T45299DI0345Procedure injury[ICD-11: NE81]P00750PLAT
T27602DI0250Mature B-cell lymphoma[ICD-11: 2A85]Q9HAN5TRP1
T27602DI0274Multiple myeloma[ICD-11: 2A83]Q9HAN5TRP1
T35173DI0259Metastatic lymph node neoplasm[ICD-11: 2D60]Q13489BIRC3
T61722DI0102Coronary atherosclerosis[ICD-11: BA52]Q9Y5Y4PTGDR2
T13127DI0342Premature ageing appearance[ICD-11: LD2B]P49356FNTB
T98269DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P29466CASP1
T98269DI0146Fibrosis[ICD-11: GA14-GC01]P29466CASP1
T98269DI0366Rheumatoid arthritis[ICD-11: FA20]P29466CASP1
T98269DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P29466CASP1
T67103DI0095Colorectal cancer[ICD-11: 2B91]P06756ITGAV
T67103DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P06756ITGAV
T55293DI0095Colorectal cancer[ICD-11: 2B91]P17301ITGA2
T55293DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P17301ITGA2
T01851DI0060Brain cancer[ICD-11: 2A00]P05556ITGB1
T01851DI0238Lung cancer[ICD-11: 2C25]P05556ITGB1
T01851DI0365Retinopathy[ICD-11: 9B71]P05556ITGB1
T23499DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P25101EDNRA
T23499DI0356Pulmonary hypertension[ICD-11: BB01]P25101EDNRA
T23499DI0425Urinary system clinical symptom[ICD-11: MF8Y]P25101EDNRA
T84634DI0314Oesophagitis[ICD-11: DA24]O43174CYP26A1
T00176DI0012Acute myeloid leukaemia[ICD-11: 2A60]Q00987MDM2
T00176DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q00987MDM2
T92076DI0189Hyper-parathyroidism[ICD-11: 5A51]P41180CASR
T92828DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P24530EDNRB
T92828DI0356Pulmonary hypertension[ICD-11: BB01]P24530EDNRB
T76396DI0241Lymphoma[ICD-11: 2A80-2A86]P53609PGGT1B
T07403DI0107Crohn disease[ICD-11: DD70]P26010ITGB7
T25315DI0178Hepatic fibrosis/cirrhosis[ICD-11: DB93]P49682CXCR3
T25315DI0339Postoperative inflammation[ICD-11: 1A00-CA43]P49682CXCR3
T25315DI0351Psoriasis[ICD-11: EA90]P49682CXCR3
T25315DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P49682CXCR3
T63512DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]Q13822ENPP2
T97587DI0107Crohn disease[ICD-11: DD70]P13612ITGA4
T97587DI0275Multiple sclerosis[ICD-11: 8A40]P13612ITGA4
T97587DI0419Ulcerative colitis[ICD-11: DD71]P13612ITGA4
T84397DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9H4B7TUBB1

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