IMPPAT Phytochemical information: 
Triacanthine

Triacanthine
Summary

SMILES: CC(=CCn1cnc2c1c(N)ncn2)C
InChI: InChI=1S/C10H13N5/c1-7(2)3-4-15-6-14-10-8(15)9(11)12-5-13-10/h3,5-6H,4H2,1-2H3,(H2,11,12,13)
InChIKey: QMJOEWBOCAQPCN-UHFFFAOYSA-N
DeepSMILES: CC=CCncncc5cN)ncn6)))))))))))C
Scaffold Graph/Node/Bond level: c1ncc2[nH]cnc2n1
Scaffold Graph/Node level: C1NCC2NCNC2N1
Scaffold Graph level: C1CCC2CCCC2C1
Functional groups: CC=C(C)C; cn(C)c; cnc; cN
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Imidazopyrimidines
ClassyFire Subclass: Purines and purine derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Pseudoalkaloids
NP Classifier Class: Purine alkaloids
Synonymous chemical names:
2-(3-methyl-but-2-enyl-amino)-purin-6-one, triacanthine, Triacanthine
External chemical identifiers:
CID:CID_10625; ZINC:ZINC000002036731; FDASRS:299A0P8472; SureChEMBL:SCHEMBL4541360
Chemical structure download


Triacanthine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 203.25
Log P RDKit 1.37
Topological polar surface area (Å2) RDKit 69.62
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 10
Number of heavy atoms RDKit 15
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 5
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.3
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 2
Total number of rings RDKit 2
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 2


Triacanthine
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 0.75


Triacanthine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.47
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No