IMPPAT Phytochemical information: 
Adifoline

Adifoline
Summary

SMILES: COC(=O)C1=CO[C@@H]([C@H]2[C@@H]1Cc1nc(cc3c1n([C@@H]2C)c1c3cc(cc1)O)C(=O)O)O
InChI: InChI=1S/C22H20N2O7/c1-9-18-12(14(21(28)30-2)8-31-22(18)29)6-15-19-13(7-16(23-15)20(26)27)11-5-10(25)3-4-17(11)24(9)19/h3-5,7-9,12,18,22,25,29H,6H2,1-2H3,(H,26,27)/t9-,12-,18-,22+/m1/s1
InChIKey: DJWXVEDJWPDUBQ-DEALGVFLSA-N
DeepSMILES: COC=O)C=CO[C@@H][C@H][C@@H]6Ccncccc6n[C@@H]%11C))cc5cccc6))O)))))))))C=O)O))))))))O
Scaffold Graph/Node/Bond level: C1=CC2Cc3nccc4c5ccccc5n(c34)CC2CO1
Scaffold Graph/Node level: C1CCC2C(C1)C1CCNC3CC4CCOCC4CN2C31
Scaffold Graph level: C1CCC2CC3C4CCCCC4C4CCCC(CC2C1)C43
Functional groups: COC(=O)C1=CO[C@H](O)CC1; cnc; cn(c)C; cO; cC(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Akageran and related alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type
Synonymous chemical names:
adifoline
External chemical identifiers:
CID:CID_441972; ChEBI:CHEBI:2488; ZINC:ZINC000030726744
Chemical structure download


Adifoline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 424.41
Log P RDKit 2.35
Topological polar surface area (Å2) RDKit 131.11
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 9
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 15
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.32
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 3
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


Adifoline
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.534489


Adifoline
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.58
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No