(+)-Siddiquine



Compound IDCDAMM00218
Common name(+)-Siddiquine
IUPAC name27-methoxy-22-methyl-15,29,31-trioxa-7,22-diazaoctacyclo[19.9.3.216,19.14,30.110,14.03,8.025,33.028,32]heptatriaconta-1(30),2,4(34),5,7,10(37),11,13,16,18,25(33),26,28(32),35-tetradecaene-13,26-diol
Molecular formulaC34H28N2O6

Experimental data

Retention time33.8
Adduct[M+H]+
Actual mz561.202
Theoretical mz561.202
Error0.17
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.3731

Identifiers and class information

Inchi keyDWAZEYVNMOERBJ-KSYWNVGFNA-N
SmilesCN1CCC2=C3C1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)CC6=NC=CC7=CC8=C(C=C67)OC3=C(O8)C(=C2O)OC)O
SuperclassOrganoheterocyclic compounds
ClassBenzodioxins

Pharmacokinetic properties

Number of descriptor values(#stars)1
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)9
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)1
Molecular weight (mol_MW)560.605
Computed dipole moment(dipole)3.562
Total solvent accessible surface area (SASA)753.565
Hydrophobic component of SASA (FOSA)294.271
Hydrophilic component of SASA (FISA)104.764
Pie component of the SASA (PISA)354.531
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1517.74
Number of hydrogen bond donors (donorHB)2
Number of hydrogen bond acceptors (accptHB)6.75
Free energy of solvation of dipole (dip^2/V)0.0083603
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0126677
Globularity descriptor (glob)0.847569
Predicted polarizability in cubic angstroms (QPpolrz)52.193
Predicted hexadecane/gas partition coefficient (QPlogPC16)15.838
Predicted octanol/gas partition coefficient (QPlogPoct)24.255
Predicted water/gas partition coefficient (QPlogPw)12.249
Predicted octanol/water partition coefficient (QPlogPo/w)5.035
Predicted aqueous solubility (QPlogS)-4.741
Conformation-independent predicted aqueous solubility (CIQPlogS)-8.649
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-6.415
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)250.8
Predicted brain/blood partition coefficient (QPlogBB)-0.553
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)122.736
Predicted skin permeability, log Kp (QPlogKp)-3.4
PM3 calculated ionization potential (IP(ev))8.8
PM3 calculated electron affinity (EA(eV))1.109
Number of likely metabolic reactions (#metab)9
Prediction of binding to human serum albumin (QPlogKhsa)1.016
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)73.452
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)85.293
Number of nitrogen and oxygen atoms (#NandO)8
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
Q15822CHRNA2Neuronal acetylcholine receptor; alpha2/beta2T55815SEA
P54750PDE1APhosphodiesterase 1AT81637SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
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

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