IMPPAT Phytochemical information: 
Picropodophyllin
Picropodophyllin
Summary

SMILES: COc1cc(cc(c1OC)OC)[C@H]1[C@@H]2C(=O)OC[C@@H]2[C@H](c2c1cc1OCOc1c2)O
InChI: InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19+,20-/m0/s1
InChIKey: YJGVMLPVUAXIQN-HAEOHBJNSA-N
DeepSMILES: COcccccc6OC)))OC))))[C@H][C@@H]C=O)OC[C@@H]5[C@H]cc9ccOCOc5c9)))))))))O
Scaffold Graph/Node/Bond level: O=C1OCC2Cc3cc4c(cc3C(c3ccccc3)C12)OCO4
Scaffold Graph/Node level: OC1OCC2CC3CC4OCOC4CC3C(C3CCCCC3)C21
Scaffold Graph level: CC1CCC2CC3CC4CCCC4CC3C(C3CCCCC3)C12
Functional groups: cOC; COC(=O)C; c1cOCO1; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Lignan lactones
ClassyFire Subclass: Podophyllotoxins
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Arylnaphthalene and aryltetralin lignans
Synonymous chemical names:
picropodophyllin, picropodophyllotoxin, picropodophyllotoxi, Picropodophyllin
External chemical identifiers:
CID:CID_72435; ChEMBL:CHEMBL283120; ChEBI:CHEBI:75251; ZINC:ZINC000004098919; FDASRS:0F35AOI227; SureChEMBL:SCHEMBL159598; MolPort-003-665-514
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Picropodophyllin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 414.41
Log P RDKit 2.41
Topological polar surface area (Å2) RDKit 92.68
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
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 13
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.41
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Picropodophyllin
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 Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.762917
Picropodophyllin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.40
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 Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No
Picropodophyllin
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_001781ENSG00000143776CDC42BPA8476NPASS
TAR_EXP_001752ENSG00000278191CARS1833NPASS
TAR_EXP_001751ENSG00000097046CDC78317NPASS
TAR_EXP_001785ENSG00000011566MAP4K38491NPASS
TAR_EXP_001750ENSG00000087008ACOX38310NPASS
TAR_EXP_001796ENSG00000089022MAPKAPK58550NPASS
TAR_EXP_001769ENSG00000102572STK248428NPASS
TAR_EXP_001577ENSG00000118046STK116794NPASS
TAR_EXP_001749ENSG00000072501SMC1A8243NPASS
TAR_EXP_001584ENSG00000165025SYK6850NPASS
TAR_EXP_001593ENSG00000010671BTK695NPASS
TAR_EXP_001594ENSG00000169679BUB1699NPASS
TAR_EXP_001597ENSG00000135605TEC7006NPASS
TAR_EXP_001600ENSG00000107140TESK17016NPASS
TAR_EXP_001603ENSG00000106799TGFBR17046NPASS
TAR_EXP_001604ENSG00000163513TGFBR27048NPASS
TAR_EXP_001619ENSG00000131747TOP2A7153ChEMBL, NPASS
TAR_EXP_001620ENSG00000077097TOP2B7155NPASS
TAR_EXP_001634ENSG00000112742TTK7272NPASS
TAR_EXP_001576ENSG00000072786STK106793NPASS
TAR_EXP_001641ENSG00000178952TUFM7284NPASS
TAR_EXP_001673ENSG00000166483WEE17465NPASS
TAR_EXP_001680ENSG00000176105YES17525NPASS
TAR_EXP_001699ENSG00000137332DDR1780NPASS
TAR_EXP_001717ENSG00000179958DCTPP179077NPASS
TAR_EXP_001721ENSG00000105357MYH1479784NPASS
TAR_EXP_001723ENSG00000166908PIP4K2C79837NPASS
TAR_EXP_001740ENSG00000152495CAMK4814NPASS
TAR_EXP_001744ENSG00000145349CAMK2D817NPASS
TAR_EXP_001745ENSG00000163545NUAK281788NPASS
TAR_EXP_001746ENSG00000148660CAMK2G818NPASS
TAR_EXP_001645ENSG00000105397TYK27297NPASS
TAR_EXP_001797ENSG00000185324CDK108558NPASS
TAR_EXP_001099ENSG00000067057PFKP5214NPASS
TAR_EXP_001799ENSG00000134684YARS18565NPASS
TAR_EXP_001916ENSG00000198752CDC42BPB9578NPASS
TAR_EXP_001922ENSG00000263528IKBKE9641NPASS
TAR_EXP_001927ENSG00000065613SLK9748NPASS
TAR_EXP_001930ENSG00000170312CDK1983NPASS
TAR_EXP_001931ENSG00000165304MELK9833NPASS
TAR_EXP_000062ENSG00000128050PAICS10606NPASS
TAR_EXP_000060ENSG00000134398ERN210595NPASS
TAR_EXP_000059ENSG00000136824SMC210592NPASS
TAR_EXP_000042ENSG00000130669PAK410298NPASS
TAR_EXP_000038ENSG00000136807CDK91025NPASS
TAR_EXP_001911ENSG00000134318ROCK29475NPASS
TAR_EXP_000036ENSG00000277273CDK71022NPASS
TAR_EXP_000032ENSG00000164885CDK51020NPASS
TAR_EXP_000031ENSG00000135446CDK41019NPASS
TAR_EXP_000030ENSG00000061938TNK210188NPASS
TAR_EXP_000029ENSG00000250506CDK31018NPASS
TAR_EXP_000027ENSG00000123374CDK21017NPASS
TAR_EXP_000021ENSG00000138071ACTR210097NPASS
TAR_EXP_000020ENSG00000115091ACTR310096NPASS
TAR_EXP_000013ENSG00000116120FARSB10056NPASS
TAR_EXP_000002ENSG00000117020AKT310000NPASS
TAR_EXP_001574ENSG00000087586AURKA6790NPASS
TAR_EXP_000034ENSG00000105810CDK61021NPASS
TAR_EXP_000091ENSG00000084733RAB1010890NPASS
TAR_EXP_001908ENSG00000071054MAP4K49448NPASS
TAR_EXP_001893ENSG00000114739ACVR2B93NPASS
TAR_EXP_001800ENSG00000160209PDXK8566NPASS
TAR_EXP_001802ENSG00000115661STK168576NPASS
TAR_EXP_001815ENSG00000174292TNK18711NPASS
TAR_EXP_000087ENSG00000101856PGRMC110857NPASS
TAR_EXP_001821ENSG00000104312RIPK28767NPASS
TAR_EXP_001824ENSG00000136143SUCLA28803NPASS
TAR_EXP_001855ENSG00000162302RPS6KA48986NPASS
TAR_EXP_001858ENSG00000115170ACVR190NPASS
TAR_EXP_001866ENSG00000142733MAP3K69064NPASS
TAR_EXP_000082ENSG00000282302SEPTIN910801NPASS
TAR_EXP_001896ENSG00000149930TAOK29344NPASS
TAR_EXP_000074ENSG00000169967MAP3K210746NPASS
TAR_EXP_001867ENSG00000127564PKMYT19088NPASS
TAR_EXP_001869ENSG00000135503ACVR1B91NPASS
TAR_EXP_000064ENSG00000110931CAMKK210645NPASS
TAR_EXP_001870ENSG00000131023LATS19113NPASS
TAR_EXP_001879ENSG00000119638NEK991754NPASS
TAR_EXP_001881ENSG00000140795MYLK391807NPASS
TAR_EXP_001885ENSG00000178999AURKB9212NPASS
TAR_EXP_001886ENSG00000266173STRADA92335NPASS
TAR_EXP_001887ENSG00000100784RPS6KA59252NPASS
TAR_EXP_001889ENSG00000162889MAPKAPK29261NPASS
TAR_EXP_000072ENSG00000142731PLK410733NPASS
TAR_EXP_001573ENSG00000101109STK46789NPASS
TAR_EXP_000598ENSG00000072133RPS6KA627330NPASS
TAR_EXP_001561ENSG00000182934SRPRA6734NPASS
TAR_EXP_000107ENSG00000149554CHEK11111NPASS
TAR_EXP_000509ENSG00000097007ABL125NPASS
TAR_EXP_000515ENSG00000010810FYN2534NPASS
TAR_EXP_000540ENSG00000178950GAK2580NPASS
TAR_EXP_000546ENSG00000105287PRKD225865NPASS
TAR_EXP_000554ENSG00000101347SAMHD125939ChEMBL
TAR_EXP_000557ENSG00000140474ULK325989NPASS
TAR_EXP_000563ENSG00000106105GARS12617NPASS
TAR_EXP_000580ENSG00000143322ABL227NPASS
TAR_EXP_000103ENSG00000111642CHD41108NPASS
TAR_EXP_000587ENSG00000086232EIF2AK127102NPASS
TAR_EXP_000625ENSG00000144840RABL3285282NPASS
TAR_EXP_000647ENSG00000183735TBK129110NPASS
TAR_EXP_000656ENSG00000005022SLC25A5292NPASS
TAR_EXP_000658ENSG00000292334SLC25A6293NPASS
TAR_EXP_000108ENSG00000122966CIT11113NPASS
TAR_EXP_000659ENSG00000105723GSK3A2931NPASS
TAR_EXP_000660ENSG00000082701GSK3B2932NPASS
TAR_EXP_000666ENSG00000138430OLA129789NPASS
TAR_EXP_000680ENSG00000101336HCK3055NPASS
TAR_EXP_000613ENSG00000114353GNAI22771NPASS
TAR_EXP_000502ENSG00000111816FRK2444NPASS
TAR_EXP_000383ENSG00000275482EPHB62051NPASS
TAR_EXP_000496ENSG00000115825PRKD323683NPASS
TAR_EXP_000444ENSG00000112144CILK122858NPASS
TAR_EXP_000449ENSG00000144028SNRNP20023020NPASS
TAR_EXP_000451ENSG00000154310TNIK23043NPASS
TAR_EXP_000460ENSG00000112159MDN123195NPASS
TAR_EXP_000865ENSG00000104738MCM44173NPASS
TAR_EXP_000857ENSG00000168906MAT2A4144NPASS
TAR_EXP_000382ENSG00000196411EPHB42050NPASS
TAR_EXP_000400ENSG00000105379ETFB2109NPASS
TAR_EXP_000394ENSG00000178607ERN12081NPASS
TAR_EXP_000393ENSG00000105221AKT2208NPASS
TAR_EXP_000390ENSG00000142208AKT1207NPASS
TAR_EXP_000462ENSG00000122025FLT32322NPASS
TAR_EXP_000463ENSG00000170145SIK223235NPASS
TAR_EXP_000842ENSG00000254087LYN4067NPASS
TAR_EXP_000097ENSG00000108468CBX110951NPASS
TAR_EXP_000100ENSG00000285379RIPK311035NPASS
TAR_EXP_000101ENSG00000102096PIM211040NPASS
TAR_EXP_000468ENSG00000160584SIK323387NPASS
TAR_EXP_000481ENSG00000039123MTREX23517NPASS
TAR_EXP_000484ENSG00000107937GTPBP423560NPASS
TAR_EXP_000389ENSG00000104884ERCC22068NPASS
TAR_EXP_000694ENSG00000103415HMOX23163NPASS
TAR_EXP_000869ENSG00000095015MAP3K14214NPASS
TAR_EXP_000713ENSG00000086061DNAJA13301NPASS
TAR_EXP_000753ENSG00000198931APRT353NPASS
TAR_EXP_000232ENSG00000070770CSNK2A21459NPASS
TAR_EXP_000260ENSG00000179091CYC11537NPASS
TAR_EXP_000274ENSG00000173020GRK2156NPASS
TAR_EXP_000294ENSG00000156136DCK1633NPASS
TAR_EXP_000300ENSG00000079785DDX11653NPASS
TAR_EXP_001572ENSG00000104375STK36788NPASS
TAR_EXP_000301ENSG00000215301DDX3X1654NPASS
TAR_EXP_000302ENSG00000110367DDX61656NPASS
TAR_EXP_000309ENSG00000116133DHCR241718NPASS
TAR_EXP_000230ENSG00000151292CSNK1G31456NPASS
TAR_EXP_000331ENSG00000157540DYRK1A1859NPASS
TAR_EXP_000353ENSG00000142627EPHA21969NPASS
TAR_EXP_000365ENSG00000072518MARK22011NPASS
TAR_EXP_000371ENSG00000004455AK2204NPASS
TAR_EXP_000372ENSG00000284816EPHA12041NPASS
TAR_EXP_000374ENSG00000116106EPHA42043NPASS
TAR_EXP_000375ENSG00000145242EPHA52044NPASS
TAR_EXP_000376ENSG00000135333EPHA72045NPASS
TAR_EXP_000379ENSG00000133216EPHB22048NPASS
TAR_EXP_000381ENSG00000182580EPHB32049NPASS
TAR_EXP_000348ENSG00000146648EGFR1956NPASS
TAR_EXP_000229ENSG00000133275CSNK1G21455NPASS
TAR_EXP_000228ENSG00000213923CSNK1E1454NPASS
TAR_EXP_000227ENSG00000141551CSNK1D1453NPASS
TAR_EXP_000763ENSG00000166333ILK3611NPASS
TAR_EXP_000114ENSG00000012983MAP4K511183NPASS
TAR_EXP_000115ENSG00000104814MAP4K111184NPASS
TAR_EXP_000119ENSG00000101751POLI11201NPASS
TAR_EXP_000120ENSG00000090376IRAK311213NPASS
TAR_EXP_000129ENSG00000172315TP53RK112858NPASS
TAR_EXP_000765ENSG00000178035IMPDH23615NPASS
TAR_EXP_000770ENSG00000171105INSR3643NPASS
TAR_EXP_000772ENSG00000184216IRAK13654NPASS
TAR_EXP_000779ENSG00000078061ARAF369NPASS
TAR_EXP_000781ENSG00000072778ACADVL37NPASS
TAR_EXP_000783ENSG00000162434JAK13716NPASS
TAR_EXP_000820ENSG00000205940HSP90AB2P391634NPASS
TAR_EXP_000822ENSG00000182866LCK3932NPASS
TAR_EXP_000831ENSG00000106683LIMK13984NPASS
TAR_EXP_000135ENSG00000198231DDX4211325NPASS
TAR_EXP_000136ENSG00000112079STK3811329NPASS
TAR_EXP_000197ENSG00000156110ADK132NPASS
TAR_EXP_000222ENSG00000112062MAPK141432NPASS
TAR_EXP_000225ENSG00000103653CSK1445NPASS
TAR_EXP_000226ENSG00000113712CSNK1A11452NPASS
TAR_EXP_000750ENSG00000140443IGF1R3480NPASS
TAR_EXP_000870ENSG00000198909MAP3K34215NPASS
TAR_EXP_000855ENSG00000075413MARK34140NPASS
TAR_EXP_000872ENSG00000197442MAP3K54217NPASS
TAR_EXP_001242ENSG00000034152MAP2K35606NPASS
TAR_EXP_001241ENSG00000126934MAP2K25605NPASS
TAR_EXP_001240ENSG00000169032MAP2K15604NPASS
TAR_EXP_001238ENSG00000109339MAPK105602NPASS
TAR_EXP_001237ENSG00000050748MAPK95601NPASS
TAR_EXP_001236ENSG00000185386MAPK115600NPASS
TAR_EXP_001235ENSG00000107643MAPK85599NPASS
TAR_EXP_001234ENSG00000166484MAPK75598NPASS
TAR_EXP_001231ENSG00000102882MAPK35595NPASS
TAR_EXP_001243ENSG00000137764MAP2K55607NPASS
TAR_EXP_001230ENSG00000100030MAPK15594NPASS
TAR_EXP_001226ENSG00000065675PRKCQ5588NPASS
TAR_EXP_001220ENSG00000065243PKN25586NPASS
TAR_EXP_001218ENSG00000123143PKN15585NPASS
TAR_EXP_000871ENSG00000085511MAP3K44216NPASS
TAR_EXP_001212ENSG00000163932PRKCD5580NPASS
TAR_EXP_001209ENSG00000166501PRKCB5579NPASS
TAR_EXP_001207ENSG00000154229PRKCA5578NPASS
TAR_EXP_001206ENSG00000042088TDP155775ChEMBL, NPASS
TAR_EXP_001204ENSG00000114302PRKAR2A5576NPASS
TAR_EXP_001229ENSG00000185532PRKG15592NPASS
TAR_EXP_001244ENSG00000108984MAP2K65608NPASS
TAR_EXP_001279ENSG00000163050COQ8A56997NPASS
TAR_EXP_001281ENSG00000281221PSMC45704NPASS
TAR_EXP_001558ENSG00000157764BRAF673NPASS
TAR_EXP_001554ENSG00000291971SRC6714NPASS
TAR_EXP_001543ENSG00000204217BMPR2659NPASS
TAR_EXP_001537ENSG00000138696BMPR1B658NPASS
TAR_EXP_001532ENSG00000107779BMPR1A657NPASS
TAR_EXP_001432ENSG00000108443RPS6KB16198NPASS
TAR_EXP_001431ENSG00000177189RPS6KA36197NPASS
TAR_EXP_001429ENSG00000281877RPS6KA16195NPASS
TAR_EXP_001385ENSG00000186716BCR613NPASS
TAR_EXP_001375ENSG00000067900ROCK16093NPASS
TAR_EXP_001363ENSG00000165731RET5979NPASS
TAR_EXP_001344ENSG00000132341RAN5901NPASS
TAR_EXP_001338ENSG00000069974RAB27A5873NPASS
TAR_EXP_001337ENSG00000168067MAP4K25871NPASS
TAR_EXP_001336ENSG00000175582RAB6A5870NPASS
TAR_EXP_001331ENSG00000100504PYGL5836NPASS
TAR_EXP_001330ENSG00000100994PYGB5834NPASS
TAR_EXP_001304ENSG00000160551TAOK157551NPASS
TAR_EXP_001303ENSG00000101213PTK65753NPASS
TAR_EXP_001301ENSG00000169398PTK25747NPASS
TAR_EXP_001285ENSG00000063761ADCK157143NPASS
TAR_EXP_001203ENSG00000181929PRKAG15571NPASS
TAR_EXP_001202ENSG00000067704IARS255699NPASS
TAR_EXP_001216ENSG00000163558PRKCI5584NPASS
TAR_EXP_001200ENSG00000142875PRKACB5567NPASS
TAR_EXP_001094ENSG00000134602STK2651765NPASS
TAR_EXP_001093ENSG00000167258CDK1251755NPASS
TAR_EXP_001091ENSG00000162368CMPK151727NPASS
TAR_EXP_001089ENSG00000197142ACSL551703NPASS
TAR_EXP_001088ENSG00000087095NLK51701NPASS
TAR_EXP_001078ENSG00000113721PDGFRB5159NPASS
TAR_EXP_001058ENSG00000106617PRKAG251422NPASS
TAR_EXP_001049ENSG00000135090TAOK351347NPASS
TAR_EXP_001046ENSG00000059758CDK175128NPASS
TAR_EXP_001045ENSG00000102225CDK165127NPASS
TAR_EXP_001037ENSG00000198001IRAK451135NPASS
TAR_EXP_001032ENSG00000186010NDUFA1351079NPASS
TAR_EXP_001030ENSG00000161533ACOX151NPASS
TAR_EXP_001095ENSG00000091436MAP3K2051776NPASS
TAR_EXP_001022ENSG00000180370PAK25062NPASS
TAR_EXP_001000ENSG00000198836OPA14976NPASS
TAR_EXP_000994ENSG00000162733DDR24921NPASS
TAR_EXP_000992ENSG00000198400NTRK14914NPASS
TAR_EXP_000975ENSG00000124588NQO24835NPASS
TAR_EXP_000966ENSG00000116044NFE2L24780NPASS
TAR_EXP_000960ENSG00000136098NEK34752NPASS
TAR_EXP_000959ENSG00000117650NEK24751NPASS
TAR_EXP_000958ENSG00000137601NEK14750NPASS
TAR_EXP_000920ENSG00000065534MYLK4638NPASS
TAR_EXP_000919ENSG00000133026MYH104628NPASS
TAR_EXP_000903ENSG00000164078MST1R4486NPASS
TAR_EXP_000879ENSG00000173327MAP3K114296NPASS
TAR_EXP_000874ENSG00000105976MET4233NPASS
TAR_EXP_001014ENSG00000089220PEBP15037NPASS
TAR_EXP_000443ENSG00000115977AAK122848NPASS
TAR_EXP_001113ENSG00000156873PHKG25261NPASS
TAR_EXP_001119ENSG00000137193PIM15292NPASS
TAR_EXP_001198ENSG00000288516PRKACA5566NPASS
TAR_EXP_001194ENSG00000132356PRKAA15562NPASS
TAR_EXP_000422ENSG00000120899PTK2B2185NPASS
TAR_EXP_000432ENSG00000066926FECH2235NPASS
TAR_EXP_000434ENSG00000151422FER2241NPASS
TAR_EXP_000435ENSG00000182511FES2242NPASS
TAR_EXP_000437ENSG00000274205MAPK15225689NPASS
TAR_EXP_000438ENSG00000077782FGFR12260NPASS
TAR_EXP_001201ENSG00000165059PRKACG5568NPASS
TAR_EXP_001193ENSG00000138756BMP2K55589NPASS
TAR_EXP_000832ENSG00000182541LIMK23985NPASS
TAR_EXP_001126ENSG00000150867PIP4K2A5305NPASS
TAR_EXP_001144ENSG00000169118CSNK1G153944NPASS
TAR_EXP_001182ENSG00000135372NAT1055226NPASS
TAR_EXP_001192ENSG00000171219CDC42BPG55561NPASS