IMPPAT Phytochemical information: 
Amsacrine

Amsacrine
Summary

SMILES: COc1cc(ccc1Nc1c2ccccc2nc2c1cccc2)NS(=O)(=O)C
InChI: InChI=1S/C21H19N3O3S/c1-27-20-13-14(24-28(2,25)26)11-12-19(20)23-21-15-7-3-5-9-17(15)22-18-10-6-4-8-16(18)21/h3-13,24H,1-2H3,(H,22,23)
InChIKey: XCPGHVQEEXUHNC-UHFFFAOYSA-N
DeepSMILES: COcccccc6Nccccccc6ncc%10cccc6))))))))))))))))))NS=O)=O)C
Scaffold Graph/Node/Bond level: c1ccc(Nc2c3ccccc3nc3ccccc23)cc1
Scaffold Graph/Node level: C1CCC(NC2C3CCCCC3NC3CCCCC32)CC1
Scaffold Graph level: C1CCC(CC2C3CCCCC3CC3CCCCC32)CC1
Functional groups: cNS(C)(=O)=O; cNc; cOC; cnc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Quinolines and derivatives
ClassyFire Subclass: Benzoquinolines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Anthranilic acid alkaloids
NP Classifier Class: Quinazoline alkaloids
Synonymous chemical names:
lamarkine
External chemical identifiers:
CID:2179; ChEMBL:CHEMBL43; ChEBI:2687; ZINC:ZINC000003812923; FDASRS:00DPD30SOY; SureChEMBL:SCHEMBL4047; MolPort-006-129-370
Chemical structure download


Amsacrine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 0
Log P RDKit 0
Topological polar surface area (Å2) RDKit
Number of hydrogen bond acceptors RDKit
Number of hydrogen bond donors RDKit
Number of carbon atoms RDKit
Number of heavy atoms RDKit
Number of heteroatoms RDKit
Number of nitrogen atoms RDKit
Number of sulfur atoms RDKit
Number of chiral carbon atoms RDKit
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit
Number of sp2 hybridized carbon atoms RDKit
Number of sp3 hybridized carbon atoms RDKit
Shape complexity RDKit
Number of rotatable bonds RDKit
Number of aliphatic carbocycles RDKit
Number of aliphatic heterocycles RDKit
Number of aliphatic rings RDKit
Number of aromatic carbocycles RDKit
Number of aromatic heterocycles RDKit
Number of aromatic rings RDKit
Total number of rings RDKit
Number of saturated carbocycles RDKit
Number of saturated heterocycles RDKit
Number of saturated rings RDKit
Number of Smallest Set of Smallest Rings (SSSR) RDKit


Amsacrine
Drug-likeness
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 Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.4877


Amsacrine
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.85
Number of PAINS structural alerts SwissADME 1.0
Number of Brenk structural alerts SwissADME 1.0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No


Amsacrine
Phytochemical - Predicted human target protein associations
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000215659MAPK12700
ENSP00000219070MMP2800
ENSP00000262186KCNH2881
ENSP00000269305TP53938
ENSP00000293288BAX700
ENSP00000298139WRN700
ENSP00000312664CASP2700
ENSP00000329623BCL2700
ENSP00000354522TOP1739
ENSP00000396704TOP2B994
ENSP00000411532TOP2A992
ENSP00000417281MDM2700
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.