IMPPAT Phytochemical information: 
Alstophylline

Alstophylline
Summary

SMILES: COc1ccc2c(c1)n(C)c1c2C[C@@H]2N(C1C[C@@H]1[C@H]2COC=C1C(=O)C)C
InChI: InChI=1S/C22H26N2O3/c1-12(25)17-10-27-11-18-15(17)8-21-22-16(9-20(18)23(21)2)14-6-5-13(26-4)7-19(14)24(22)3/h5-7,10,15,18,20-21H,8-9,11H2,1-4H3/t15-,18+,20-,21?/m0/s1
InChIKey: XFPCHWBAIJUKFN-JQBZYZAUSA-N
DeepSMILES: COcccccc6)nC)cc5C[C@@H]NC6C[C@@H][C@H]6COC=C6C=O)C))))))))))C
Scaffold Graph/Node/Bond level: C1=CC2CC3NC(Cc4c3[nH]c3ccccc43)C2CO1
Scaffold Graph/Node level: C1CCC2C(C1)NC1C3CC4CCOCC4C(CC21)N3
Scaffold Graph level: C1CCC2C(C1)CC1CC2CC2C3CCCCC3CC12
Functional groups: cOC; cn(C)c; CN(C)C; COC=C(C(C)=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Macroline alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Carboline alkaloids
Synonymous chemical names:
alstophylline
External chemical identifiers:
CID:CID_100949563
Chemical structure download


Alstophylline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 366.46
Log P RDKit 3.22
Topological polar surface area (Å2) RDKit 43.7
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.18
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


Alstophylline
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.82


Alstophylline
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.02
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No