IMPPAT Phytochemical information: 
Gossypol
Gossypol
Summary

SMILES: O=Cc1c(O)c(O)c(c2c1c(O)c(c(c2)C)c1c(C)cc2c(c1O)c(C=O)c(c(c2C(C)C)O)O)C(C)C
InChI: InChI=1S/C30H30O8/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36/h7-12,33-38H,1-6H3
InChIKey: QBKSWRVVCFFDOT-UHFFFAOYSA-N
DeepSMILES: O=CccO)cO)ccc6cO)ccc6)C))ccC)cccc6O))cC=O))ccc6CC)C)))O))O))))))))))))CC)C
Scaffold Graph/Node/Bond level: c1ccc2cc(-c3ccc4ccccc4c3)ccc2c1
Scaffold Graph/Node level: C1CCC2CC(C3CCC4CCCCC4C3)CCC2C1
Scaffold Graph level: C1CCC2CC(C3CCC4CCCCC4C3)CCC2C1
Functional groups: cC=O; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Sesquiterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Cadinane sesquiterpenoids
Synonymous chemical names:
Gossypol, Gossypol,(-)-, gossoypol, (+)-gossypol, gossypol
External chemical identifiers:
CID:CID_3503; ChEMBL:CHEMBL51483; ZINC:ZINC000003775575; FDASRS:XNA7DR63CQ; SureChEMBL:SCHEMBL3939; MolPort-003-665-510
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Gossypol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 518.56
Log P RDKit 6.38
Topological polar surface area (Å2) RDKit 155.52
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 38
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
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 22
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.27
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 4
Number of aromatic heterocycles RDKit 0
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
Gossypol
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.131236
Gossypol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -4.54
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
Gossypol
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_000711ENSG00000086696HSD17B23294ChEMBL, NPASS
TAR_EXP_000706ENSG00000291796APEX1328ChEMBL, NPASS
TAR_EXP_000720ENSG00000106211HSPB13315NPASS
TAR_EXP_000701ENSG00000164120HPGD3248ChEMBL, NPASS
TAR_EXP_000773ENSG00000169083AR367BindingDB, ChEMBL, NPASS
TAR_EXP_000709ENSG00000108786HSD17B13292ChEMBL, NPASS
TAR_EXP_000715ENSG00000044574HSPA53309NPASS
TAR_EXP_001680ENSG00000176105YES17525ChEMBL, NPASS
TAR_EXP_001942ENSG00000012504NR1H49971NPASS
TAR_EXP_001900ENSG00000123595RAB9A9367NPASS
TAR_EXP_001868ENSG00000036672USP29099ChEMBL, NPASS
TAR_EXP_000786ENSG00000177606JUN3725NPASS
TAR_EXP_000813ENSG00000138160KIF113832BindingDB, ChEMBL, NPASS
TAR_EXP_001810ENSG00000067955CBFB865NPASS
TAR_EXP_001764ENSG00000165806CASP7840ChEMBL, NPASS
TAR_EXP_001753ENSG00000137752CASP1834BindingDB, ChEMBL, NPASS
TAR_EXP_001728ENSG00000176208ATAD579915ChEMBL, NPASS
TAR_EXP_000687ENSG00000100644HIF1A3091NPASS
TAR_EXP_000818ENSG00000187258NPSR1387129NPASS
TAR_EXP_001665ENSG00000111424VDR7421ChEMBL, NPASS
TAR_EXP_001621ENSG00000141510TP537157ChEMBL, NPASS
TAR_EXP_001259ENSG00000129084PSMA15682ChEMBL
TAR_EXP_001260ENSG00000106588PSMA25683ChEMBL
TAR_EXP_001261ENSG00000100567PSMA35684ChEMBL
TAR_EXP_001262ENSG00000041357PSMA45685ChEMBL
TAR_EXP_001263ENSG00000143106PSMA55686ChEMBL
TAR_EXP_001264ENSG00000100902PSMA65687ChEMBL
TAR_EXP_001265ENSG00000101182PSMA75688ChEMBL
TAR_EXP_001266ENSG00000008018PSMB15689ChEMBL
TAR_EXP_001267ENSG00000126067PSMB25690ChEMBL
TAR_EXP_001269ENSG00000277791PSMB35691ChEMBL
TAR_EXP_001270ENSG00000159377PSMB45692ChEMBL
TAR_EXP_001273ENSG00000100804PSMB55693ChEMBL
TAR_EXP_001274ENSG00000142507PSMB65694ChEMBL
TAR_EXP_001275ENSG00000136930PSMB75695ChEMBL
TAR_EXP_001276ENSG00000235715PSMB85696ChEMBL
TAR_EXP_001277ENSG00000239836PSMB95698ChEMBL
TAR_EXP_001278ENSG00000205220PSMB105699ChEMBL
TAR_EXP_000223ENSG00000154611PSMA8143471ChEMBL
TAR_EXP_000263ENSG00000140505CYP1A21544NPASS
TAR_EXP_000271ENSG00000165841CYP2C191557NPASS
TAR_EXP_000273ENSG00000138109CYP2C91559NPASS
TAR_EXP_000276ENSG00000272532CYP2D61565NPASS
TAR_EXP_000280ENSG00000160868CYP3A41576ChEMBL, NPASS
TAR_EXP_000324ENSG00000184845DRD11812ChEMBL, NPASS
TAR_EXP_000356ENSG00000114867EIF4G11981BindingDB
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL, NPASS
TAR_EXP_000401ENSG00000163631ALB213ChEMBL, NPASS
TAR_EXP_000411ENSG00000165092ALDH1A1216NPASS
TAR_EXP_000433ENSG00000168496FEN12237ChEMBL, NPASS
TAR_EXP_001242ENSG00000034152MAP2K35606ChEMBL
TAR_EXP_001230ENSG00000100030MAPK15594ChEMBL, NPASS
TAR_EXP_001663ENSG00000162607USP17398ChEMBL, NPASS
TAR_EXP_001173ENSG00000196199MPHOSPH854737ChEMBL, NPASS
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000095ENSG00000224143EHMT210919ChEMBL, NPASS
TAR_EXP_000819ENSG00000235268KDM4E390245ChEMBL, NPASS
TAR_EXP_000824ENSG00000134333LDHA3939BindingDB, ChEMBL, NPASS
TAR_EXP_000825ENSG00000111716LDHB3945BindingDB, ChEMBL, NPASS
TAR_EXP_000833ENSG00000160789LMNA4000NPASS
TAR_EXP_000845ENSG00000166949SMAD34088ChEMBL, NPASS
TAR_EXP_000846ENSG00000100299ARSA410ChEMBL, NPASS
TAR_EXP_000853ENSG00000276155MAPT4137ChEMBL, NPASS
TAR_EXP_000860ENSG00000152601MBNL14154NPASS
TAR_EXP_000864ENSG00000143384MCL14170BindingDB, ChEMBL, NPASS
TAR_EXP_000867ENSG00000135679MDM24193BindingDB, ChEMBL, NPASS
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS
TAR_EXP_000456ENSG00000085662AKR1B1231ChEMBL, NPASS
TAR_EXP_000894ENSG00000103152MPG4350ChEMBL, NPASS
TAR_EXP_000918ENSG00000136997MYC4609ChEMBL
TAR_EXP_000966ENSG00000116044NFE2L24780NPASS
TAR_EXP_000968ENSG00000109320NFKB14790NPASS
TAR_EXP_000983ENSG00000141458NPC14864NPASS
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_001059ENSG00000122008POLK51426ChEMBL, NPASS
TAR_EXP_000097ENSG00000108468CBX110951ChEMBL, NPASS
TAR_EXP_000119ENSG00000101751POLI11201ChEMBL, NPASS
TAR_EXP_000174ENSG00000222028PSMB11122706ChEMBL
TAR_EXP_001125ENSG00000127445PIN15300ChEMBL, NPASS
TAR_EXP_001150ENSG00000070501POLB5423ChEMBL, NPASS
TAR_EXP_001166ENSG00000186951PPARA5465NPASS
TAR_EXP_001170ENSG00000112033PPARD5467NPASS
TAR_EXP_001171ENSG00000132170PPARG5468NPASS
TAR_EXP_000901ENSG00000198363ASPH444ChEMBL, NPASS
TAR_EXP_000499ENSG00000108839ALOX12239NPASS
TAR_EXP_001206ENSG00000042088TDP155775ChEMBL, NPASS
TAR_EXP_000503ENSG00000161905ALOX15246NPASS
TAR_EXP_001365ENSG00000129473BCL2L2599BindingDB, ChEMBL, NPASS
TAR_EXP_001364ENSG00000171552BCL2L1598BindingDB, ChEMBL, NPASS
TAR_EXP_001360ENSG00000004700RECQL5965ChEMBL, NPASS
TAR_EXP_001359ENSG00000171791BCL2596ChEMBL, NPASS
TAR_EXP_001341ENSG00000002016RAD525893ChEMBL, NPASS
TAR_EXP_001288ENSG00000002330BAD572BindingDB, ChEMBL
TAR_EXP_000683ENSG00000197386HTT3064NPASS
TAR_EXP_000674ENSG00000123636BAZ2B29994ChEMBL, NPASS
TAR_EXP_000645ENSG00000113580NR3C12908NPASS
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000608ENSG00000115419GLS2744NPASS
TAR_EXP_000572ENSG00000108773KAT2A2648ChEMBL, NPASS
TAR_EXP_000554ENSG00000101347SAMHD125939ChEMBL
TAR_EXP_000676ENSG00000072506HSD17B103028ChEMBL, NPASS
TAR_EXP_000519ENSG00000171298GAA2548ChEMBL, NPASS
TAR_EXP_000545ENSG00000108479GALK12584ChEMBL, NPASS
TAR_EXP_000505ENSG00000198793MTOR2475ChEMBL, NPASS
TAR_EXP_001609ENSG00000151090THRB7068ChEMBL, NPASS
TAR_EXP_001551ENSG00000145335SNCA6622NPASS
TAR_EXP_001547ENSG00000275349SMN16606NPASS
TAR_EXP_001508ENSG00000117394SLC2A16513ChEMBL, NPASS
TAR_EXP_000504ENSG00000179593ALOX15B247ChEMBL, NPASS
TAR_EXP_001477ENSG00000015475BID637ChEMBL
TAR_EXP_001468ENSG00000204842ATXN26311ChEMBL, NPASS
TAR_EXP_001461ENSG00000186350RXRA6256NPASS
TAR_EXP_001366ENSG00000117152RGS45999ChEMBL, NPASS
TAR_EXP_001485ENSG00000197299BLM641ChEMBL, NPASS