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: C/C=C/C; C/C=C/C(=O)OC; CO
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:5287620; ChEMBL:CHEMBL19980; 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 properties
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 0.5257
brefeldin A
ADMET 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 0.0
Number of Brenk structural alerts SwissADME 1.0
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
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000003084CFTR728
ENSP00000216037XBP1736
ENSP00000222139EPOR800
ENSP00000258743IL6769
ENSP00000272102ARF1993
ENSP00000311032CASP3943
ENSP00000312664CASP2700
ENSP00000354398CYTH1756
ENSP00000355627AGT786
ENSP00000359000GBF1862
ENSP00000359285CHRNA4800
ENSP00000361125VEGFA700
ENSP00000408236CYTH2969
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.