Cinegalline



Compound IDCDAMM02588
Common nameCinegalline
IUPAC name(14-oxo-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecan-4-yl) 3,5-dihydroxy-4-methoxybenzoate
Molecular formulaC23H30N2O6

Experimental data

Retention time13.4
Adduct[M+H]+
Actual mz431.217
Theoretical mz431.217
Error1.1
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.4968

Identifiers and class information

Inchi keyWCNNCIUCJFPASX-JCSVEHSYNA-N
SmilesO=C(OC1CCN2CC3CC(CN4C(=O)CCCC43)C2C1)C5=CC(O)=C(OC)C(O)=C5
SuperclassAlkaloids and derivatives
ClassLupin 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)1
Number of rotatable bonds (#rotor)5
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)430.5
Computed dipole moment(dipole)5.861
Total solvent accessible surface area (SASA)704.392
Hydrophobic component of SASA (FOSA)464.236
Hydrophilic component of SASA (FISA)171.569
Pie component of the SASA (PISA)68.587
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1303.11
Number of hydrogen bond donors (donorHB)2
Number of hydrogen bond acceptors (accptHB)9.25
Free energy of solvation of dipole (dip^2/V)0.0263589
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0185713
Globularity descriptor (glob)0.819101
Predicted polarizability in cubic angstroms (QPpolrz)43.441
Predicted hexadecane/gas partition coefficient (QPlogPC16)12.472
Predicted octanol/gas partition coefficient (QPlogPoct)22.57
Predicted water/gas partition coefficient (QPlogPw)16.614
Predicted octanol/water partition coefficient (QPlogPo/w)1.256
Predicted aqueous solubility (QPlogS)-2.566
Conformation-independent predicted aqueous solubility (CIQPlogS)-3.041
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.138
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)30.413
Predicted brain/blood partition coefficient (QPlogBB)-1.044
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)25.364
Predicted skin permeability, log Kp (QPlogKp)-6.022
PM3 calculated ionization potential (IP(ev))9.137
PM3 calculated electron affinity (EA(eV))0.696
Number of likely metabolic reactions (#metab)4
Prediction of binding to human serum albumin (QPlogKhsa)-0.171
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)60.844
Solvent-accessible surface area of fluorine atoms (SAFluorine)0
Solvent-accessible surface area of amide oxygen atoms (SAamideO)35.522
Van der Waals surface area (PSA)118.406
Number of nitrogen and oxygen atoms (#NandO)8
Number of violations of Lipinski’s rule of five (RuleOfFive)0
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
P22303ACHEAcetylcholinesteraseT30082SwissTargetPrediction
Q12809KCNH2HERGT20251SwissTargetPrediction
P29475NOS1Nitric-oxide synthase, brainT16117SwissTargetPrediction
P35228NOS2Nitric oxide synthase, inducibleT02703SwissTargetPrediction
P09874PARP1Poly [ADP-ribose] polymerase-1T06273SwissTargetPrediction
Q99720SIGMAR1Sigma opioid receptorT46360SwissTargetPrediction
Q05586GRIN1Glutamate NMDA receptor; GRIN1/GRIN2BT62276SwissTargetPrediction
O60341KDM1ALysine-specific histone demethylase 1T16739SwissTargetPrediction
P31645SLC6A4Serotonin transporter (by homology)T27812SwissTargetPrediction
Q05940SLC18A2Synaptic vesicular amine transporter (by homology)T48873SwissTargetPrediction
Q01959SLC6A3Dopamine transporterT55959SwissTargetPrediction
O75164KDM4ALysine-specific demethylase 4AT18904SwissTargetPrediction
Q9Y4C1KDM3ALysine-specific demethylase 3AT25362SwissTargetPrediction
P05121SERPINE1Plasminogen activator inhibitor-1T15556SEA
P33527ABCC1Multidrug resistance-associated protein 1T11288SwissTargetPrediction
P08183ABCB1P-glycoprotein 1T25258SwissTargetPrediction and SEA
P53667LIMK1LIM domain kinase 1T70840SwissTargetPrediction
P30291WEE1Serine/threonine-protein kinase WEE1T69991SwissTargetPrediction
Q92847GHSRGhrelin receptorT59604SwissTargetPrediction
P11137MAP2Microtubule-associated protein 2T23276SwissTargetPrediction
O75116ROCK2Rho-associated protein kinase 2T06093SwissTargetPrediction
P41229KDM5CLysine-specific demethylase 5CT85540SwissTargetPrediction
Q9UGN5PARP2Poly [ADP-ribose] polymerase 2T40812SwissTargetPrediction
P47898HTR5ASerotonin 5a (5-HT5a) receptorT15571SwissTargetPrediction
P28482MAPK1MAP kinase ERK2T58970SwissTargetPrediction
Q9UGL1KDM5BLysine-specific demethylase 5BT56871SwissTargetPrediction
Q9Y2K7KDM2ALysine-specific demethylase 2AT71949SwissTargetPrediction
P30968GNRHRGonadotropin-releasing hormone receptorT12475SwissTargetPrediction
P53671LIMK2LIM domain kinase 2T09133SwissTargetPrediction
P22460KCNA5Voltage-gated potassium channel subunit Kv1.5T17569SwissTargetPrediction
P30307CDC25CDual specificity phosphatase Cdc25CT40569SwissTargetPrediction
Q13464ROCK1Rho-associated protein kinase 1T51282SwissTargetPrediction
O76083PDE9APhosphodiesterase 9AT17852SwissTargetPrediction
Q14123PDE1CPhosphodiesterase 1CT92439SwissTargetPrediction
Q13224GRIN2BGlutamate [NMDA] receptor subunit epsilon 2T76414SwissTargetPrediction
O96013PAK4Serine/threonine-protein kinase PAK 4T98293SwissTargetPrediction
P48048KCNJ1ATP-sensitive inward rectifier potassium channel 1T78710SwissTargetPrediction
P12644BMP4Bone morphogenetic protein 4T77410SwissTargetPrediction
O95470SGPL1Sphingosine-1-phosphate lyase 1T01575SwissTargetPrediction

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
T20251DI0175Heart failure[ICD-11: BD10-BD1Z]Q12809KCNH2
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
T06273DI0006Acquired cutaneous blood vessel malformation[ICD-11: EF20]P09874PARP1
T06273DI0143Fallopian tube cancer[ICD-11: 2C74]P09874PARP1
T06273DI0321Ovarian cancer[ICD-11: 2C73]P09874PARP1
T06273DI0334Peritoneal cancer[ICD-11: 2C51]P09874PARP1
T46360DI0105Cough[ICD-11: MD12]Q99720SIGMAR1
T62276DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q05586GRIN1
T62276DI0182HIV-infected patients with tuberculosis[ICD-11: 1B10-1B14]Q05586GRIN1
T16739DI0012Acute myeloid leukaemia[ICD-11: 2A60]O60341KDM1A
T16739DI0025Alzheimer disease[ICD-11: 8A20]O60341KDM1A
T16739DI0138Ewing sarcoma[ICD-11: 2B52]O60341KDM1A
T16739DI0238Lung cancer[ICD-11: 2C25]O60341KDM1A
T16739DI0241Lymphoma[ICD-11: 2A80-2A86]O60341KDM1A
T16739DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]O60341KDM1A
T16739DI0284Myelodysplastic syndrome[ICD-11: 2A37]O60341KDM1A
T16739DI0286Myeloproliferative neoplasm[ICD-11: 2A20]O60341KDM1A
T16739DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O60341KDM1A
T27812DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]P31645SLC6A4
T27812DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P31645SLC6A4
T27812DI0087Chronic pain[ICD-11: MG30]P31645SLC6A4
T27812DI0096concerning food/fluid intake symptom[ICD-11: MG43]P31645SLC6A4
T27812DI0101Corneal disease[ICD-11: 9A76-9A78]P31645SLC6A4
T27812DI0105Cough[ICD-11: MD12]P31645SLC6A4
T27812DI0117Depression[ICD-11: 6A70-6A7Z]P31645SLC6A4
T27812DI0264Migraine[ICD-11: 8A80]P31645SLC6A4
T27812DI0301Nicotine use disorder[ICD-11: 6C4A]P31645SLC6A4
T27812DI0308Obesity[ICD-11: 5B80-5B81]P31645SLC6A4
T27812DI0324Pain[ICD-11: MG30-MG3Z]P31645SLC6A4
T48873DI0079Choreiform disorder[ICD-11: 8A01]Q05940SLC18A2
T48873DI0125Dissociative neurological symptom disorder[ICD-11: 6B60]Q05940SLC18A2
T48873DI0129Dystonic disorder[ICD-11: 8A02]Q05940SLC18A2
T48873DI0137Essential hypertension[ICD-11: BA00]Q05940SLC18A2
T48873DI0190Hypertension[ICD-11: BA00-BA04]Q05940SLC18A2
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
T15556DI0037Asthma[ICD-11: CA23]P05121SERPINE1
T15556DI0405Thrombosis[ICD-11: DB61-GB90]P05121SERPINE1
T11288DI0167Gout[ICD-11: FA25]P33527ABCC1
T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
T69991DI0321Ovarian cancer[ICD-11: 2C73]P30291WEE1
T69991DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P30291WEE1
T69991DI0429Uterine ligament/parametrium/uterine adnexa neoplasm[ICD-11: 2C72]P30291WEE1
T59604DI0087Chronic pain[ICD-11: MG30]Q92847GHSR
T59604DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]Q92847GHSR
T23276DI0036Arteries/arterioles disorder[ICD-11: BD52]P11137MAP2
T23276DI0252Melanoma[ICD-11: 2C30]P11137MAP2
T23276DI0326Pancreatic cancer[ICD-11: 2C10]P11137MAP2
T23276DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11137MAP2
T06093DI0168Graft-versus-host disease[ICD-11: 4B24]O75116ROCK2
T40812DI0321Ovarian cancer[ICD-11: 2C73]Q9UGN5PARP2
T40812DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9UGN5PARP2
T15571DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P47898HTR5A
T58970DI0036Arteries/arterioles disorder[ICD-11: BD52]P28482MAPK1
T58970DI0252Melanoma[ICD-11: 2C30]P28482MAPK1
T58970DI0326Pancreatic cancer[ICD-11: 2C10]P28482MAPK1
T58970DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P28482MAPK1
T12475DI0130Endometriosis[ICD-11: GA10]P30968GNRHR
T12475DI0322Ovarian developmental anomaly[ICD-11: LB45]P30968GNRHR
T12475DI0323Ovarian dysfunction[ICD-11: 5A80]P30968GNRHR
T12475DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P30968GNRHR
T12475DI0346Prostate cancer[ICD-11: 2C82]P30968GNRHR
T12475DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P30968GNRHR
T17569DI0030Angina pectoris[ICD-11: BA40]P22460KCNA5
T51282DI0166Glaucoma[ICD-11: 9C61]Q13464ROCK1
T17852DI0025Alzheimer disease[ICD-11: 8A20]O76083PDE9A
T17852DI0115Dementia[ICD-11: 6D80-6D8Z]O76083PDE9A
T17852DI0165Genitourinary disease[ICD-11: GA0Z-GC8Z]O76083PDE9A
T17852DI0175Heart failure[ICD-11: BD10-BD1Z]O76083PDE9A
T17852DI0256Mental/behavioural/neurodevelopmental disorder[ICD-11: 6E20-6E8Z]O76083PDE9A
T17852DI0331Parkinsonism[ICD-11: 8A00]O76083PDE9A
T17852DI0370Schizophrenia[ICD-11: 6A20]O76083PDE9A
T17852DI0381Sickle-cell disorder[ICD-11: 3A51]O76083PDE9A
T76414DI0024Alpha-1-antitrypsin deficiency[ICD-11: 5C5A]Q13224GRIN2B
T98293DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]O96013PAK4
T98293DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O96013PAK4
T01575DI0098Congenital ichthyosis[ICD-11: EC20]O95470SGPL1
T01575DI0366Rheumatoid arthritis[ICD-11: FA20]O95470SGPL1

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