Lotusanine B



Compound IDCDAMM02901
Common nameLotusanine B
IUPAC nameN-(7-benzyl-5,8-dioxo-3-propan-2-yl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),10,12,15-tetraen-4-yl)-1-(3-phenylprop-2-enoyl)pyrrolidine-2-carboxamide
Molecular formulaC37H40N4O5

Experimental data

Retention time8.12
Adduct[M+H]+
Actual mz621.305
Theoretical mz621.307
Error3.34
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.9235

Identifiers and class information

Inchi keyNYOIXNGBYPQKPL-WIYQFBSONA-N
SmilesO=C(C=CC=1C=CC=CC1)N2CCCC2C(=O)NC3C(=O)NC(C(=O)NC=CC=4C=CC(OC3C(C)C)=CC4)CC=5C=CC=CC5
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives

Pharmacokinetic properties

Number of descriptor values(#stars)3
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)2
Number of rotatable bonds (#rotor)8
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-1
Molecular weight (mol_MW)620.747
Computed dipole moment(dipole)5.036
Total solvent accessible surface area (SASA)962.118
Hydrophobic component of SASA (FOSA)367.169
Hydrophilic component of SASA (FISA)73.658
Pie component of the SASA (PISA)521.291
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1897.31
Number of hydrogen bond donors (donorHB)1.5
Number of hydrogen bond acceptors (accptHB)9.75
Free energy of solvation of dipole (dip^2/V)0.0133646
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0124114
Globularity descriptor (glob)0.770363
Predicted polarizability in cubic angstroms (QPpolrz)69.618
Predicted hexadecane/gas partition coefficient (QPlogPC16)20.429
Predicted octanol/gas partition coefficient (QPlogPoct)31.25
Predicted water/gas partition coefficient (QPlogPw)19.019
Predicted octanol/water partition coefficient (QPlogPo/w)5.875
Predicted aqueous solubility (QPlogS)-7.382
Conformation-independent predicted aqueous solubility (CIQPlogS)-7.54
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.985
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)966.59
Predicted brain/blood partition coefficient (QPlogBB)-0.746
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)1037.07
Predicted skin permeability, log Kp (QPlogKp)-0.273
PM3 calculated ionization potential (IP(ev))9.049
PM3 calculated electron affinity (EA(eV))0.635
Number of likely metabolic reactions (#metab)4
Prediction of binding to human serum albumin (QPlogKhsa)0.796
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)88.859
Solvent-accessible surface area of fluorine atoms (SAFluorine)0
Solvent-accessible surface area of amide oxygen atoms (SAamideO)39.216
Van der Waals surface area (PSA)122.881
Number of nitrogen and oxygen atoms (#NandO)9
Number of violations of Lipinski’s rule of five (RuleOfFive)2
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
P00734F2ThrombinT94033SEA
P98170XIAPInhibitor of apoptosis protein 3T16769SEA
P00747PLGPlasminogenT89034SEA
P12955PEPDXaa-Pro dipeptidaseT94823SEA
P17655CAPN2Calpain 2T86837SEA
P37288AVPR1AVasopressin V1a receptor (by homology)T79232SEA
P30518AVPR2Vasopressin V2 receptor (by homology)T66237SEA
Q9UBU3GHRLAppetite-regulating hormoneT06850SEA
P23946CMA1ChymaseT05114SEA
P62942FKBP1AFK506-binding protein 1AT76059SEA
Q13489BIRC3Baculoviral IAP repeat-containing protein 3T35173SEA
Q13490BIRC2Baculoviral IAP repeat-containing protein 2T84780SEA
P42226STAT6Signal transducer and activator of transcription 6T20585SEA
Q9UNI1CELA1Elastase 1T22839SEA
P47901AVPR1BVasopressin V1b receptorT59881SEA
Q9Y337KLK5Kallikrein 5T11808SEA
P08311CTSGCathepsin GT86385SEA
P15169CPN1Carboxypeptidase N, catalytic subunitT34471SEA
O43895XPNPEP2Xaa-Pro aminopeptidase 2T68320SEA
O60235TMPRSS11DTransmembrane protease serine 11DT00302SEA
P22735TGM1Protein-glutamine gamma-glutamyltransferase KT63217SEA
Q9HAN5TRP1Cationic trypsinogenT27602SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
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
T16769DI0259Metastatic lymph node neoplasm[ICD-11: 2D60]P98170XIAP
T89034DI0030Angina pectoris[ICD-11: BA40]P00747PLG
T89034DI0052Bleeding disorder[ICD-11: GA20-GA21]P00747PLG
T89034DI0254Menopausal disorder[ICD-11: GA30]P00747PLG
T89034DI0287Myocardial infarction[ICD-11: BA41-BA43]P00747PLG
T89034DI0345Procedure injury[ICD-11: NE81]P00747PLG
T89034DI0357Pulmonary thromboembolism[ICD-11: BB00]P00747PLG
T86837DI0106COVID-19[ICD-11: 1D6Y]P17655CAPN2
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
T66237DI0009Acute diabete complication[ICD-11: 5A2Y]P30518AVPR2
T66237DI0041Autism spectrum disorder[ICD-11: 6A02]P30518AVPR2
T66237DI0131Enuresis[ICD-11: 6C00]P30518AVPR2
T66237DI0194Hypo-osmolality/hyponatraemia[ICD-11: 5C72]P30518AVPR2
T66237DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P30518AVPR2
T66237DI0338Polyuria[ICD-11: MF55]P30518AVPR2
T06850DI0120Diabetes mellitus[ICD-11: 5A10]Q9UBU3GHRL
T05114DI0039Atopic eczema[ICD-11: EA80]P23946CMA1
T05114DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P23946CMA1
T05114DI0169Gram-positive bacterial infection[ICD-11: 1B74-1F40]P23946CMA1
T05114DI0175Heart failure[ICD-11: BD10-BD1Z]P23946CMA1
T05114DI0229Left ventricular failure[ICD-11: BD11]P23946CMA1
T05114DI0287Myocardial infarction[ICD-11: BA41-BA43]P23946CMA1
T76059DI0331Parkinsonism[ICD-11: 8A00]P62942FKBP1A
T76059DI0349Pruritus[ICD-11: EC90]P62942FKBP1A
T76059DI0413Transplant rejection[ICD-11: NE84]P62942FKBP1A
T35173DI0259Metastatic lymph node neoplasm[ICD-11: 2D60]Q13489BIRC3
T84780DI0259Metastatic lymph node neoplasm[ICD-11: 2D60]Q13490BIRC2
T22839DI0024Alpha-1-antitrypsin deficiency[ICD-11: 5C5A]Q9UNI1CELA1
T22839DI0065Bronchitis[ICD-11: CA20]Q9UNI1CELA1
T59881DI0009Acute diabete complication[ICD-11: 5A2Y]P47901AVPR1B
T59881DI0041Autism spectrum disorder[ICD-11: 6A02]P47901AVPR1B
T59881DI0194Hypo-osmolality/hyponatraemia[ICD-11: 5C72]P47901AVPR1B
T86385DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P08311CTSG
T63217DI0045Autosomal Recessive Ichthyosis[ICD-11: EC20]P22735TGM1
T27602DI0250Mature B-cell lymphoma[ICD-11: 2A85]Q9HAN5TRP1
T27602DI0274Multiple myeloma[ICD-11: 2A83]Q9HAN5TRP1

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