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: cOC; cNc; cnc; cNS(C)(=O)=O
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:CID_2179; ChEMBL:CHEMBL43; ChEBI: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 393.47
Log P RDKit 4.51
Topological polar surface area (Å2) RDKit 80.32
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 3
Number of sulfur atoms RDKit 1
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 19
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.1
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 4
Total number of rings RDKit 4
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 4


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 0.487708


Amsacrine
ADME 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
Number of Brenk structural alerts SwissADME 1
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 - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_001808ENSG00000276582ABCB118647NPASS
TAR_EXP_001836ENSG00000144852NR1I28856ChEMBL
TAR_EXP_001816ENSG00000108846ABCC38714BindingDB, NPASS
TAR_EXP_001809ENSG00000084676NCOA18648BindingDB
TAR_EXP_001837ENSG00000163394CCKAR886ChEMBL
TAR_EXP_001839ENSG00000110148CCKBR887ChEMBL
TAR_EXP_000987ENSG00000164128NPY1R4886ChEMBL
TAR_EXP_001764ENSG00000165806CASP7840NPASS
TAR_EXP_001002ENSG00000082556OPRK14986ChEMBL
TAR_EXP_001001ENSG00000116329OPRD14985ChEMBL
TAR_EXP_000966ENSG00000116044NFE2L24780NPASS
TAR_EXP_000861ENSG00000124089MC3R4159ChEMBL
TAR_EXP_001900ENSG00000123595RAB9A9367NPASS
TAR_EXP_001753ENSG00000137752CASP1834NPASS
TAR_EXP_000125ENSG00000101180HRH311255ChEMBL
TAR_EXP_001728ENSG00000176208ATAD579915ChEMBL, NPASS
TAR_EXP_001061ENSG00000113448PDE4D5144ChEMBL
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL
TAR_EXP_001105ENSG00000082175PGR5241ChEMBL
TAR_EXP_001106ENSG00000085563ABCB15243ChEMBL
TAR_EXP_001181ENSG00000166148AVPR1A552ChEMBL
TAR_EXP_001190ENSG00000126895AVPR2554ChEMBL
TAR_EXP_001299ENSG00000073756PTGS25743ChEMBL
TAR_EXP_001366ENSG00000117152RGS45999NPASS
TAR_EXP_001458ENSG00000168398BDKRB2624ChEMBL
TAR_EXP_001468ENSG00000204842ATXN26311ChEMBL, NPASS
TAR_EXP_001518ENSG00000103546SLC6A26530ChEMBL
TAR_EXP_001519ENSG00000142319SLC6A36531ChEMBL
TAR_EXP_001520ENSG00000108576SLC6A46532ChEMBL
TAR_EXP_001538ENSG00000175003SLC22A16580BindingDB, ChEMBL, NPASS
TAR_EXP_001570ENSG00000166888STAT66778NPASS
TAR_EXP_001591ENSG00000006638TBXA2R6915ChEMBL
TAR_EXP_001607ENSG00000090534THPO7066NPASS
TAR_EXP_001618ENSG00000198900TOP17150BindingDB, ChEMBL
TAR_EXP_001619ENSG00000131747TOP2A7153BindingDB, ChEMBL, NPASS
TAR_EXP_001620ENSG00000077097TOP2B7155BindingDB, ChEMBL, NPASS
TAR_EXP_001621ENSG00000141510TP537157NPASS
TAR_EXP_001631ENSG00000165409TSHR7253NPASS
TAR_EXP_001663ENSG00000162607USP17398NPASS
TAR_EXP_001747ENSG00000124151NCOA38202BindingDB
TAR_EXP_000798ENSG00000055118KCNH23757BindingDB, ChEMBL, NPASS
TAR_EXP_000243ENSG00000150594ADRA2A150ChEMBL
TAR_EXP_000733ENSG00000135914HTR2B3357ChEMBL
TAR_EXP_000280ENSG00000160868CYP3A41576ChEMBL, NPASS
TAR_EXP_000276ENSG00000272532CYP2D61565ChEMBL, NPASS
TAR_EXP_000273ENSG00000138109CYP2C91559ChEMBL, NPASS
TAR_EXP_000271ENSG00000165841CYP2C191557ChEMBL
TAR_EXP_000263ENSG00000140505CYP1A21544ChEMBL, NPASS
TAR_EXP_000261ENSG00000169252ADRB2154ChEMBL
TAR_EXP_000258ENSG00000043591ADRB1153ChEMBL
TAR_EXP_000255ENSG00000184160ADRA2C152ChEMBL
TAR_EXP_000249ENSG00000274286ADRA2B151ChEMBL
TAR_EXP_000127ENSG00000168539CHRM11128ChEMBL
TAR_EXP_000239ENSG00000120907ADRA1A148ChEMBL
TAR_EXP_000324ENSG00000184845DRD11812ChEMBL, NPASS
TAR_EXP_000214ENSG00000282608ADORA3140ChEMBL
TAR_EXP_000200ENSG00000163485ADORA1134ChEMBL
TAR_EXP_000187ENSG00000118432CNR11268ChEMBL
TAR_EXP_000182ENSG00000023839ABCC21244NPASS
TAR_EXP_000144ENSG00000101204CHRNA41137ChEMBL
TAR_EXP_000133ENSG00000133019CHRM31131ChEMBL
TAR_EXP_000130ENSG00000181072CHRM21129ChEMBL
TAR_EXP_001003ENSG00000112038OPRM14988ChEMBL
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000039ENSG00000125257ABCC410257BindingDB, ChEMBL, NPASS
TAR_EXP_000095ENSG00000224143EHMT210919ChEMBL, NPASS
TAR_EXP_000097ENSG00000108468CBX110951ChEMBL, NPASS
TAR_EXP_000203ENSG00000128271ADORA2A135ChEMBL
TAR_EXP_000325ENSG00000149295DRD21813ChEMBL
TAR_EXP_000326ENSG00000151577DRD31814ChEMBL
TAR_EXP_000330ENSG00000144891AGTR1185ChEMBL
TAR_EXP_000732ENSG00000102468HTR2A3356ChEMBL
TAR_EXP_000727ENSG00000178394HTR1A3350ChEMBL
TAR_EXP_000715ENSG00000044574HSPA53309NPASS
TAR_EXP_000704ENSG00000113749HRH23274ChEMBL
TAR_EXP_000703ENSG00000196639HRH13269ChEMBL
TAR_EXP_000693ENSG00000138356AOX1316BindingDB, ChEMBL, NPASS
TAR_EXP_000687ENSG00000100644HIF1A3091NPASS
TAR_EXP_000676ENSG00000072506HSD17B103028ChEMBL, NPASS
TAR_EXP_000645ENSG00000113580NR3C12908ChEMBL
TAR_EXP_000627ENSG00000102539MLNR2862ChEMBL
TAR_EXP_000593ENSG00000102393GLA2717NPASS
TAR_EXP_000578ENSG00000121853GHSR2693ChEMBL
TAR_EXP_000533ENSG00000113327GABRG22566ChEMBL
TAR_EXP_000528ENSG00000145864GABRB22561ChEMBL
TAR_EXP_000522ENSG00000151834GABRA22555ChEMBL
TAR_EXP_000521ENSG00000022355GABRA12554ChEMBL
TAR_EXP_000505ENSG00000198793MTOR2475ChEMBL, NPASS
TAR_EXP_000450ENSG00000004487KDM1A23028BindingDB, ChEMBL
TAR_EXP_000433ENSG00000168496FEN12237NPASS
TAR_EXP_000367ENSG00000112759SLC29A12030ChEMBL
TAR_EXP_000339ENSG00000151617EDNRA1909ChEMBL
TAR_EXP_000735ENSG00000166736HTR3A3359ChEMBL
TAR_EXP_001053ENSG00000172572PDE3A5139ChEMBL