IMPPAT Phytochemical information: 
Papaverine

Papaverine
Summary

SMILES: COc1ccc(cc1OC)Cc1nccc2c1cc(OC)c(c2)OC
InChI: InChI=1S/C20H21NO4/c1-22-17-6-5-13(10-18(17)23-2)9-16-15-12-20(25-4)19(24-3)11-14(15)7-8-21-16/h5-8,10-12H,9H2,1-4H3
InChIKey: XQYZDYMELSJDRZ-UHFFFAOYSA-N
DeepSMILES: COcccccc6OC))))Ccncccc6ccOC))cc6)OC
Scaffold Graph/Node/Bond level: c1ccc(Cc2nccc3ccccc23)cc1
Scaffold Graph/Node level: C1CCC(CC2NCCC3CCCCC32)CC1
Scaffold Graph level: C1CCC(CC2CCCC3CCCCC32)CC1
Functional groups: cOC; cnc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Isoquinolines and derivatives
ClassyFire Subclass: Benzylisoquinolines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids|Tetrahydroisoquinoline alkaloids
Synonymous chemical names:
Papaverine, papaverine
External chemical identifiers:
CID:CID_4680; ChEMBL:CHEMBL19224; ChEBI:CHEBI:28241; ZINC:ZINC000000056555; FDASRS:DAA13NKG2Q; SureChEMBL:SCHEMBL34702; MolPort-000-881-409
Chemical structure download


Papaverine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 339.39
Log P RDKit 3.86
Topological polar surface area (Å2) RDKit 49.81
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
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 15
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.25
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 3
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 3


Papaverine
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.682418


Papaverine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.28
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 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 Yes


Papaverine
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_001471ENSG00000136531SCN2A6326ChEMBL
TAR_EXP_001472ENSG00000153253SCN3A6328ChEMBL, NPASS
TAR_EXP_001072ENSG00000123360PDE1B5153BindingDB, ChEMBL
TAR_EXP_001518ENSG00000103546SLC6A26530ChEMBL
TAR_EXP_001519ENSG00000142319SLC6A36531ChEMBL
TAR_EXP_001470ENSG00000144285SCN1A6323ChEMBL
TAR_EXP_001495ENSG00000182199SHMT26472ChEMBL, NPASS
TAR_EXP_001458ENSG00000168398BDKRB2624ChEMBL
TAR_EXP_001190ENSG00000126895AVPR2554ChEMBL
TAR_EXP_001299ENSG00000073756PTGS25743ChEMBL
TAR_EXP_001298ENSG00000095303PTGS15742ChEMBL
TAR_EXP_001289ENSG00000169403PTAFR5724ChEMBL
TAR_EXP_001231ENSG00000102882MAPK35595ChEMBL
TAR_EXP_001230ENSG00000100030MAPK15594ChEMBL, NPASS
TAR_EXP_001207ENSG00000154229PRKCA5578ChEMBL
TAR_EXP_001206ENSG00000042088TDP155775ChEMBL, NPASS
TAR_EXP_001186ENSG00000138814PPP3CA5530ChEMBL
TAR_EXP_001181ENSG00000166148AVPR1A552ChEMBL
TAR_EXP_001105ENSG00000082175PGR5241ChEMBL
TAR_EXP_001320ENSG00000262418PTPRC5788ChEMBL
TAR_EXP_001520ENSG00000108576SLC6A46532ChEMBL
TAR_EXP_001607ENSG00000090534THPO7066ChEMBL, NPASS
TAR_EXP_001547ENSG00000275349SMN16606NPASS
TAR_EXP_001942ENSG00000012504NR1H49971ChEMBL, NPASS
TAR_EXP_001900ENSG00000123595RAB9A9367NPASS
TAR_EXP_001868ENSG00000036672USP29099NPASS
TAR_EXP_001839ENSG00000110148CCKBR887ChEMBL
TAR_EXP_001837ENSG00000163394CCKAR886ChEMBL
TAR_EXP_001836ENSG00000144852NR1I28856ChEMBL
TAR_EXP_001816ENSG00000108846ABCC38714BindingDB, NPASS
TAR_EXP_001811ENSG00000138735PDE5A8654BindingDB, ChEMBL, NPASS
TAR_EXP_001808ENSG00000276582ABCB118647ChEMBL, NPASS
TAR_EXP_001538ENSG00000175003SLC22A16580ChEMBL, NPASS
TAR_EXP_001753ENSG00000137752CASP1834ChEMBL
TAR_EXP_001684ENSG00000104267CA2760ChEMBL
TAR_EXP_001669ENSG00000114812VIPR17433ChEMBL
TAR_EXP_001642ENSG00000121807CCR2729230ChEMBL
TAR_EXP_001631ENSG00000165409TSHR7253ChEMBL, NPASS
TAR_EXP_001592ENSG00000059377TBXAS16916ChEMBL
TAR_EXP_001591ENSG00000006638TBXA2R6915ChEMBL
TAR_EXP_001587ENSG00000115353TACR16869ChEMBL
TAR_EXP_000200ENSG00000163485ADORA1134ChEMBL
TAR_EXP_001549ENSG00000166311SMPD16609ChEMBL, NPASS
TAR_EXP_001727ENSG00000004948CALCR799ChEMBL
TAR_EXP_001061ENSG00000113448PDE4D5144ChEMBL, NPASS
TAR_EXP_000203ENSG00000128271ADORA2A135ChEMBL
TAR_EXP_001059ENSG00000122008POLK51426NPASS
TAR_EXP_000133ENSG00000133019CHRM31131ChEMBL
TAR_EXP_000130ENSG00000181072CHRM21129ChEMBL
TAR_EXP_000127ENSG00000168539CHRM11128ChEMBL
TAR_EXP_000125ENSG00000101180HRH311255ChEMBL
TAR_EXP_000097ENSG00000108468CBX110951ChEMBL, NPASS
TAR_EXP_000095ENSG00000224143EHMT210919ChEMBL, NPASS
TAR_EXP_000085ENSG00000112541PDE10A10846BindingDB, ChEMBL, NPASS
TAR_EXP_000081ENSG00000173198CYSLTR110800ChEMBL
TAR_EXP_000041ENSG00000147955SIGMAR110280ChEMBL
TAR_EXP_000327ENSG00000069696DRD41815ChEMBL
TAR_EXP_000330ENSG00000144891AGTR1185ChEMBL
TAR_EXP_000134ENSG00000180720CHRM41132ChEMBL
TAR_EXP_000332ENSG00000180772AGTR2186ChEMBL
TAR_EXP_001060ENSG00000105650PDE4C5143ChEMBL, NPASS
TAR_EXP_000348ENSG00000146648EGFR1956ChEMBL
TAR_EXP_000357ENSG00000277571ELANE1991ChEMBL
TAR_EXP_000367ENSG00000112759SLC29A12030ChEMBL
TAR_EXP_000387ENSG00000141736ERBB22064ChEMBL
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL
TAR_EXP_000397ENSG00000140009ESR22100ChEMBL
TAR_EXP_000411ENSG00000165092ALDH1A1216NPASS
TAR_EXP_000461ENSG00000102755FLT12321ChEMBL
TAR_EXP_000486ENSG00000159339PADI423569BindingDB
TAR_EXP_000499ENSG00000108839ALOX12239NPASS
TAR_EXP_000339ENSG00000151617EDNRA1909ChEMBL
TAR_EXP_000137ENSG00000184984CHRM51133ChEMBL
TAR_EXP_000144ENSG00000101204CHRNA41137ChEMBL
TAR_EXP_000177ENSG00000183813CCR41233ChEMBL
TAR_EXP_000209ENSG00000005339CREBBP1387ChEMBL, NPASS
TAR_EXP_000214ENSG00000282608ADORA3140ChEMBL
TAR_EXP_000222ENSG00000112062MAPK141432ChEMBL
TAR_EXP_000233ENSG00000171873ADRA1D146ChEMBL
TAR_EXP_000239ENSG00000120907ADRA1A148ChEMBL
TAR_EXP_000243ENSG00000150594ADRA2A150ChEMBL
TAR_EXP_000249ENSG00000274286ADRA2B151ChEMBL
TAR_EXP_000250ENSG00000100448CTSG1511ChEMBL
TAR_EXP_000255ENSG00000184160ADRA2C152ChEMBL
TAR_EXP_000258ENSG00000043591ADRB1153ChEMBL
TAR_EXP_000261ENSG00000169252ADRB2154ChEMBL
TAR_EXP_000263ENSG00000140505CYP1A21544ChEMBL, NPASS
TAR_EXP_000265ENSG00000255974CYP2A61548ChEMBL
TAR_EXP_000267ENSG00000188778ADRB3155ChEMBL
TAR_EXP_000271ENSG00000165841CYP2C191557ChEMBL, NPASS
TAR_EXP_000273ENSG00000138109CYP2C91559ChEMBL, NPASS
TAR_EXP_000276ENSG00000272532CYP2D61565ChEMBL, NPASS
TAR_EXP_000277ENSG00000130649CYP2E11571ChEMBL
TAR_EXP_000280ENSG00000160868CYP3A41576ChEMBL, NPASS
TAR_EXP_000324ENSG00000184845DRD11812ChEMBL
TAR_EXP_000325ENSG00000149295DRD21813ChEMBL
TAR_EXP_000326ENSG00000151577DRD31814ChEMBL
TAR_EXP_000187ENSG00000118432CNR11268ChEMBL
TAR_EXP_000182ENSG00000023839ABCC21244NPASS
TAR_EXP_000178ENSG00000160791CCR51234ChEMBL
TAR_EXP_000503ENSG00000161905ALOX15246NPASS
TAR_EXP_000515ENSG00000010810FYN2534ChEMBL
TAR_EXP_001585ENSG00000075073TACR26865ChEMBL
TAR_EXP_000627ENSG00000102539MLNR2862ChEMBL
TAR_EXP_000968ENSG00000109320NFKB14790NPASS
TAR_EXP_000966ENSG00000116044NFE2L24780ChEMBL, NPASS
TAR_EXP_000888ENSG00000100985MMP94318ChEMBL
TAR_EXP_000883ENSG00000196611MMP14312ChEMBL
TAR_EXP_000578ENSG00000121853GHSR2693ChEMBL
TAR_EXP_000039ENSG00000125257ABCC410257BindingDB, ChEMBL, NPASS
TAR_EXP_000881ENSG00000087085ACHE43BindingDB, ChEMBL, NPASS
TAR_EXP_000987ENSG00000164128NPY1R4886ChEMBL
TAR_EXP_000735ENSG00000166736HTR3A3359ChEMBL
TAR_EXP_000862ENSG00000166603MC4R4160ChEMBL
TAR_EXP_000861ENSG00000124089MC3R4159ChEMBL
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL
TAR_EXP_000833ENSG00000160789LMNA4000NPASS
TAR_EXP_000738ENSG00000158748HTR63362ChEMBL
TAR_EXP_000760ENSG00000163464CXCR13577ChEMBL
TAR_EXP_000761ENSG00000180871CXCR23579ChEMBL
TAR_EXP_000863ENSG00000176136MC5R4161ChEMBL
TAR_EXP_000798ENSG00000055118KCNH23757BindingDB, ChEMBL, NPASS
TAR_EXP_000988ENSG00000185149NPY2R4887ChEMBL
TAR_EXP_001002ENSG00000082556OPRK14986ChEMBL
TAR_EXP_000645ENSG00000113580NR3C12908ChEMBL
TAR_EXP_000687ENSG00000100644HIF1A3091NPASS
TAR_EXP_000692ENSG00000113161HMGCR3156ChEMBL
TAR_EXP_000703ENSG00000196639HRH13269ChEMBL
TAR_EXP_000704ENSG00000113749HRH23274ChEMBL
TAR_EXP_000727ENSG00000178394HTR1A3350ChEMBL
TAR_EXP_000732ENSG00000102468HTR2A3356ChEMBL
TAR_EXP_000733ENSG00000135914HTR2B3357ChEMBL
TAR_EXP_000734ENSG00000147246HTR2C3358ChEMBL
TAR_EXP_001057ENSG00000184588PDE4B5142ChEMBL
TAR_EXP_001056ENSG00000065989PDE4A5141BindingDB, ChEMBL, NPASS
TAR_EXP_001055ENSG00000152270PDE3B5140BindingDB, ChEMBL, NPASS
TAR_EXP_001053ENSG00000172572PDE3A5139BindingDB, ChEMBL, NPASS
TAR_EXP_001052ENSG00000186642PDE2A5138ChEMBL, NPASS
TAR_EXP_001051ENSG00000154678PDE1C5137ChEMBL, NPASS
TAR_EXP_001050ENSG00000115252PDE1A5136ChEMBL
TAR_EXP_001003ENSG00000112038OPRM14988ChEMBL
TAR_EXP_001001ENSG00000116329OPRD14985ChEMBL
TAR_EXP_000822ENSG00000182866LCK3932ChEMBL