IMPPAT Phytochemical information: 
brefeldin A
brefeldin A
Summary

SMILES: O[C@@H]1C[C@@H]2[C@@H](C1)/C=C/CCC[C@@H](OC(=O)/C=C/[C@H]2O)C
InChI: InChI=1S/C16H24O4/c1-11-5-3-2-4-6-12-9-13(17)10-14(12)15(18)7-8-16(19)20-11/h4,6-8,11-15,17-18H,2-3,5,9-10H2,1H3/b6-4+,8-7+/t11-,12+,13-,14+,15+/m0/s1
InChIKey: KQNZDYYTLMIZCT-KQPMLPITSA-N
DeepSMILES: O[C@@H]C[C@@H][C@@H]C5)/C=C/CCC[C@@H]OC=O)/C=C/[C@H]%13O))))))C
Scaffold Graph/Node/Bond level: O=C1C=CCC2CCCC2C=CCCCCO1
Scaffold Graph/Node level: OC1CCCC2CCCC2CCCCCCO1
Scaffold Graph level: CC1CCCCCCCC2CCCC2CCC1
Functional groups: CO; C/C=C/C; C/C=C/C(=O)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Macrolides and analogues
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Macrolides
NP Classifier Class: Macrolide lactones
Synonymous chemical names:
brefeldin a
External chemical identifiers:
CID:CID_5287620; ChEMBL:CHEMBL19980; ChEBI:CHEBI:48080; ZINC:ZINC000012371944; FDASRS:XG0D35F9K6; SureChEMBL:SCHEMBL29267; MolPort-003-845-305
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
brefeldin A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 280.36
Log P RDKit 1.96
Topological polar surface area (Å2) RDKit 66.76
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 20
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.31
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.69
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
brefeldin A
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 0.525655
brefeldin A
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.58
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
brefeldin A
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_000095ENSG00000224143EHMT210919NPASS
TAR_EXP_001609ENSG00000151090THRB7068NPASS
TAR_EXP_001663ENSG00000162607USP17398NPASS
TAR_EXP_001705ENSG00000125618PAX87849ChEMBL, NPASS
TAR_EXP_001728ENSG00000176208ATAD579915NPASS
TAR_EXP_001900ENSG00000123595RAB9A9367NPASS
TAR_EXP_000097ENSG00000108468CBX110951NPASS
TAR_EXP_000390ENSG00000142208AKT1207ChEMBL, NPASS
TAR_EXP_000336ENSG00000169297NR0B1190BindingDB, ChEMBL, NPASS
TAR_EXP_001206ENSG00000042088TDP155775ChEMBL, NPASS
TAR_EXP_001031ENSG00000112312GMNN51053ChEMBL, NPASS
TAR_EXP_000983ENSG00000141458NPC14864NPASS
TAR_EXP_000966ENSG00000116044NFE2L24780ChEMBL, NPASS
TAR_EXP_000845ENSG00000166949SMAD34088ChEMBL, NPASS
TAR_EXP_000747ENSG00000138413IDH13417ChEMBL, NPASS
TAR_EXP_000511ENSG00000136931NR5A12516BindingDB
TAR_EXP_001231ENSG00000102882MAPK35595ChEMBL, NPASS
TAR_EXP_001230ENSG00000100030MAPK15594ChEMBL, NPASS
TAR_EXP_001247ENSG00000171867PRNP5621BindingDB, ChEMBL, NPASS
TAR_EXP_001468ENSG00000204842ATXN26311NPASS